She Built a Business After Being Stood Up Abroad with Ally Pintucci
What if the trip you keep waiting to take is exactly what you need?
We are all guilty of it. Waiting for the right timing, the right stage of life, the right circle of friends, while the months quietly pass and the vaca never leaves the group chat.
In this episode, we have Ally Pintucci, founder of The Girls Trip Series, a community of 37,000-plus women built on small, curated trips for women who hate tours. After nearly a decade in travel sales and operations, a layoff at 23, and being stood up in Portugal, Ally landed in a surf town that changed everything and launched her first trip, which sold out in 24 hours. She joins us to talk about the real cost of running trips, where pricing meets integrity, and why you should stop waiting to go.
What does it actually cost to run a group trip? More than people assume. Between scouting a destination and running it, Ally can spend 10 to 15,000 dollars of her own money before a single traveler pays. The margin is not in packing people in, it is in the experience, which is why she keeps her groups small on purpose.
Where does pricing meet integrity in the travel world? Ally is candid that the industry is murky. Some influencers white-label a trip that costs 2,500 to run and resell it for 6,800. She prices to reflect real value and real community, not to become the biggest travel company in the room.
What money decisions do women forget when booking a trip? The ones that hit late: visas, vaccinations, currency conversion, and tipping the local team. Ally sets those expectations up front, often a year out, so there are no painful surprises at the destination.
Should you wait for friends before you travel? No. 99% of the women who come do not book with a friend, and they arrive just as nervous as you would. As Ally says, not all friends are compatible to travel, and time stops for no one.
00:00 An anxious start and nearly a decade in travel.
10:30 Everything happens for a reason.
13:00 The real cost of getting a trip off the ground.
19:00 The application form that turns people away.
32:30 Scouting a brand-new destination.
36:30 The money decisions women forget.
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YouTubeAbout the Hosts
Barbara Provost, EdD and Maggie Nielsen, MBA are the co-founders of Purse Strings, a national platform helping women make confident financial decisions by connecting them with vetted financial professionals who truly understand women’s lives and money needs. Purse Strings connects women across the U.S. with vetted financial professionals who specialize in supporting women through divorce, money transitions, and financial independence.
Full Episode Transcript
(This transcript was generated using AI, so please excuse any misspellings or errors)
PS: Ally (Girls Trip Series) MP3
[00:00:00] I don’t know about my listeners, but I am personally loving these conversations about travel. We’ve had conversations about solo travel. We’ve had them about having a travel planner. And this one I was just most excited about because there’s so many places in the world that I wanna go see, and it’s kinda like, I’m gonna be honest, I don’t wanna go alone.
I don’t wanna go alone. It’s not just like sitting out at a cafe. It’s really just exploring these towns. Whether this is in Egypt or it’s going, to a, a [00:00:30] desert or it’s going somewhere in India. I mean, Whatever it may be. It’s just something like sometimes you’re at a place and you’re like, “Wow, I’d really love to be here with a really good friend or a partner,” and something like that.
And making all those timelines work together can stop us from traveling, and I don’t like that. I don’t wanna wait on somebody else to hold me back. So I’m excited to share Ally with all of you guys today because she really sets up the Girls Trip series. And so a group of women can go on these amazing [00:01:00] trips that she curates to go see some different amazing parts of the world and really connect with other women who have that value of traveling, want to go now.
And even like we talk about in this podcast, sometimes if you could get all your friends or whoever it may be, on the timeline with the budget, the time off, the childcare taken care of, not all of your friends are friends you wanna travel with and that’s okay too. And so really having that community around you who wants to do those similar things is so important, especially when you’re [00:01:30] spending that money to go on a great vacation.
The last thing you wanna do is, just do things that you don’t wanna do after spending all that money. So I’m so excited to have Ally on for this conversation and would love to hear from you guys what kind of trips you have planned soon or where you would love to go or how this podcast resonates with you.
So we do have a new feature. If you look on our podcast show notes, there’s a way that you can send in a voice note. So if you wanna share what your thoughts are, what questions you might [00:02:00] have, what you wanna talk about we might feature some of those voice notes if you allow it on our podcast as well ’cause we would love to hear from the community.
So send in your notes after you listen and I will see you on the other side of the episode.
[00:02:30]
Maggie: Welcome to Women & Money, the sh*t we don’t talk about. I am so excited to have Ally Pintucci on today, and she runs many things, but what we’re gonna talk about today is the Girl Trip [00:03:00] series. So before we dive into all of that, Ally, can you share a little bit about who you are and what you do and kind of how you got to building this community specifically about women traveling together?
Ally: Yeah. First of all, thank you so much for having me on. I haven’t been on a podcast in a while, and I’m excited to feel like I’m back. This is gonna be a bit of a long-winded story, so bear with me, and I promise I’ll bring you back to how the Girls Trip series started. But going back to when I left high school, I was one of those people that wanted to do so many [00:03:30] different things, and it made me very anxious to choose one specific thing going into university, ’cause I was like, “What if I choose the wrong thing?”
Ally: And it was like international development and relations, and like physical therapy, and working with athletes, and marketing, and I’m like, “I genuinely don’t know how to pick.” So I decided to take a stereotypical eye roll gap year. And then just as I was about to book a trip, I got contacted from a student travel company that was based in Toronto at the time, and I was like, [00:04:00] “Well, this is kinda cool.
Ally: Like, what if I just worked for a year, and worked in travel, and Figure it out from there. That gap year turned into the first almost 10 years of my career. I ended up landing in the travel industry doing sales and operations for almost four companies, like three and a half companies. I had a couple contracts.
Ally: And it was incredible because never in a million years did I think that was the industry that I would land in. I think a lot of people [00:04:30] think like, “Oh, how can I work and travel?” And you think travel agent. And that’s not really anything I ever wanted to be at the time. But it was so cool because I got to live and work and travel and experience all of these incredible countries at such a young age.
Ally: And then on my time off or during my time off, I would also use that time to travel on my own. So from like 18 to 23, 24, I got to work in the travel industry, and I got to experience a lot of countries on my own. [00:05:00] And to be honest, towards the end of it, I realized I hated working in sales. I, you know, at a young age, got into a really cool role of being director of sales and operations, and when you’re 23, like, that’s pretty exciting.
Ally: But I got put into that role when I was very sick of being in sales. It was … And anyone who’s in sales knows that you’re chasing money in a cycle, and you can’t really leave because when you think, “Okay, I’m [00:05:30] gonna quit now,” well, then I don’t get my back end commission. And so you wait for your back end commission, and then you’re like, “Well, I just sold the front end of this, so if I wait for that,” and, you know, you’re in these cycles just constantly chasing money.
Ally: And I had been mentally checked out for, you know, a couple years at that point, and I got fired from my job. And at the time, you know, 23, it’s very devastating, and looking back at it now, it makes so much sense. But, you know, when you’re a director, you don’t [00:06:00] really have room for mediocrity. You have to lead and plan, and you can’t coast.
Ally: And I was kind of I guess at the time, if I’m being honest now and taking accountability I didn’t, my heart wasn’t fully in it. And that firing was probably one of the best things that happened to me. I was 23, living in a brand-new city across the country at the time, and I had to decide what I was going to do from there.
Ally: The side stories of when that was all happening was like, I call it the good old [00:06:30] days of Instagram. You know, when you could like post at 7:30 PM with three hashtags, and then boom, like you’d get like 3,000 likes. And I was new to Vancouver in the Pacific Northwest, and new to hiking, and spent so much time outdoors, and started a personal Instagram page that got a lot of traction.
Ally: And at the time, like there weren’t social media managers at companies. There were no such thing as influencers. You were just genuinely posting about doing things and building community, and like meeting [00:07:00] other people doing the same thing and having so much fun. So I guess, you know, at that time in 2013, 2014, I understood Instagram very well, and I moved into the creative industry and social media marketing industry. And I worked on freelance projects. I worked on brand teams. I was taking courses. And I did this whole shift of now working in the creative industry, and I loved it until I didn’t, and I realized that the common- denominator in a lot [00:07:30] of these things was maybe I don’t want a boss.
Maggie: Vibes. I get it. I hear you
Ally: And keep in mind, like now I’m 28, so like I’m still a baby. Now in the story 28, not 28 talking to you now, I wish. And so I left that industry. So I left the creative industry to to basically go freelance. After I worked in an agency, I was like, “Agency life was not for me.” But everything I had done at that point was such a massive stepping stone and a, a very important [00:08:00] part to who I am today and how I got here today, because I don’t think I could be here if I didn’t have sales.
Ally: I don’t think I could manage clients the way I did without working at an agency, and it helped me with pitching. Like, every single role that I had really became like an integral part of who I am today. So I started freelancing, and anyone listening to this that freelances knows, you’re like, “I’m gonna be my own boss.”
Ally: Congratulations, you now have 25 [00:08:30] bosses. And freelancing was amazing. I focused a lot on doing commercial photography, and I was very blessed and grateful to travel the world and work for incredible brands like Air Canada, and The Four Seasons, and tourism boards. And I also shoot a lot of portraits and brand photos here for like entrepreneurs, and lifestyle brands, and people who need content for website.
Ally: And so, All while freelancing, I was still traveling quite a bit, and I would always continue to post about my travel even though my page wasn’t very active [00:09:00] as like a quote-unquote “influencer page.” And back in 2023 I had been dating someone in Europe for a few years. At that point, I was doing like a cute long-distance relationship.
Ally: It did not end cute, by the way. Basically it ended up with me being stood up in Portugal at like two and a half years into my relationship, and I mean, it was super traumatic, but you’re right. I was in Portugal, and it happened very close to the beginning of my three months that I was spending there.
Ally: And I couldn’t leave [00:09:30] because I was, like, shooting something for the Four Seasons. I had a wedding, so I was kinda trapped, and I’m like, “Okay, what am I gonna do?” So I heard of this small surf town called Ericeira, and I’m like, “Okay, I’m gonna go to Ericeira. I’m gonna just, like, hang out here, and while I’m in Ericeira for a few days, I’m going to plan a trip to Italy because, like, Italy’s gonna make everyone feel better.”
Ally: And I always wanted to learn how to surf, so I was like, “Okay, I’m gonna book a surf camp, and for three days, and then I’ll get the hell out of here.” And so I get to Ericeira. [00:10:00] Again, everyone raves about this town. And I get there and I’m like, “This place fucking sucks.”
Ally: And I think after realizing, you know, after a few days of being there, it, the place didn’t suck. It was just so quiet that I actually had to sit with everything going on in my life at the time. And the reality was I was going through a breakup. I was on the other side of the world. I was alone. A lot of things that I had been void- avoiding talking about in therapy [00:10:30] were coming up for me.
Ally: I wasn’t feeling fulfilled in my business, and it just kinda realized, “Okay, I’m at this crossroad, and now I’m in a very quiet place that’s very confronting, and now I have to feel it.” And I started connecting and working with an energy coach there that was recommended to me through a friend, and after my session with her, I felt like there was a weight lifted off of my chest, and I was sitting on my surfboard one day, and I’m looking at this coastline, and I’m like, from the water, I’m like, “This is [00:11:00] one of the most beautiful places I’ve ever been.”
Ally: And I’m like, “Wait, I love this place.” And my three days in Ericeira turned into five days, turned into seven days, turned into nine days. And as I was posting authentically about this experience, even though I had posted about hundreds of trips prior to this, the amount of women that started messaging me saying like, “I don’t know what it is that you’re doing on this trip, but I’m into it.
Ally: Can you share the details?” And back [00:11:30] in the original influencer days, I had an old blog called The Staycation Series, where I worked with clients to visit their tourism– like work with their tourism board to put together a staycation itinerary for people to experience here in BC. And then it spun off into the Girls Trip series, where I would go to cities and create like girls trips itineraries for people to do with their friends.
Ally: So my brain started like you know, swirling a little bit, and I was like… It was the first time in my life that I ever heard my intuition [00:12:00] say, “Go home.” And I didn’t go to Italy. I went home. I built a webpage, and I launched a 10-day trip back to Ericeira, Portugal, that was gonna take place a couple months later, and I was gonna call it the Girls Trip series.
Ally: It was going to be a series of trips that women could connect with like-minded women on and really just take time for themselves to experience travel in a different way than they– the different way that they haven’t experienced before, maybe that they were craving. [00:12:30] And so I just went for it. I launched it.
Ally: The trip sold out in 24 hours. That was September 2023, and we… And I say we, but it’s me. But it’s also we, ’cause like the girls that come on the trip, I– now I have women coming on their third, fourth trip with me. Yeah, I’ve done 11 trips so far. I have five upcoming. We’re– I’m launching so many more. And that was my 27-minute introduction of how I got to the Girls Trip series.
Ally: But [00:13:00] yeah, it has been the most fulfilling thing I have ever done, and it was just a very big lesson that everything does happen for a reason, and to really take advantage of the skill set that you have in front of you, because everything in your life, whether you realize it or not, really does play an important role for building your toolbox.
Maggie: There’s so much I wanna say to all of this.
Ally: I know. Sorry, I might derail this whole episode now.
Maggie: It’s okay. I mean, it’s just like clearly everything always happens for [00:13:30] a reason. And in that time we never know why, but it’s almost like thank you for firing me. Thank you for this not working out. And it’s funny how you still did all these different kind of categories of work without getting a degree or going back to school or all this stuff.
Maggie: You still were able to do all that and get to travel, which I feel like is every woman’s dream, especially while we’re younger, while we’re single. You know, it’s this newer thing of like, we’re not waiting until we’re 65 and retired. Like, I can’t learn how to surf then, you know? I’m gonna learn how to surf now when I’m physically capable, all these different things.
Maggie: [00:14:00] I also feel like I should go to an energy coach. I could really use that right now.
Ally: I can give you guys a plug for one that changed my life, but
Maggie: Yeah, I’m gonna need that name. Does she work?
Ally: She works virtually and she has containers for women from all over the world can work with her, and it’s fantastic.
Maggie: Yeah, when I came across your page and saw… Well, first let me throw it back and say I used to love the old Instagram days when things were so much simpler, and now it’s not the same. It’s just not the same. That’s all I have to say about it.
Ally: Yeah, it’s really not
Maggie: but there’s so much, I think, you [00:14:30] know, women, we are kind of afraid.
Maggie: Some of these places, you know, oh, it’s not safe to go as a single woman by yourself. You know, you wanna have these different things. We’ve had a couple other podcasters on share about how to do these solo trips and how to travel the world alone, which is fabulous. We’ve had travel planners so you can help and do some creative and unique things, and that’s what I was afraid you were gonna say about at your trip at first.
Maggie: It was just like an Instagram famous place, and that’s why it wasn’t as exciting. But it’s amazing to have these other women to connect with because sometimes, like, your friends don’t either have the budget, have the [00:15:00] time, they have kids. You know, like, we’re all in different stages of life, and so it is that commonality to really pull together, which is exciting.
Maggie: I saw your trip about Egypt and I was, like, checking my budget to see how I get on that one. But so you’ve now built this community that’s, you know, over 37,000 followers on socials. But I just kinda wanna talk behind the scenes. You got this calling to go home and to kind of start building this.
Maggie: What did it kind of cost you, like financially, logistically, emotionally to get this off the ground?
Ally: [00:15:30] Yeah. Well, the one thing I think that sparked it all, also just to note, is I built something for me. And I don’t mean for me to make money. I don’t mean to fulfill me. I built something for me, Ally, the consumer, the traveler. And I think going into that with that mindset really helped with problem-solving to understand who I [00:16:00] was actually looking for and who I was building for.
Ally: And I think that really helped me make decisions early on. Financially It’s different for every trip, ’cause at the beginning I, I looked at doing it, what is the least risk possible? So I look at accommodation first. I have to build my trip out of like, what’s it gonna be for the net cost per person to run this trip? And I have to look at things where it’s like, how do I do this in the [00:16:30] least risk possible?
Ally: Okay, I’m gonna find a hotel that it can allow me to make a reservation where I don’t have to pay until I get there. So right away now I’m putting something on hold, but I’m not spending $17,000 to hold that in case that trip doesn’t run. So for me at the beginning as this, that first trial trip, my upfront cost was actually quite low.
Ally: If anything minimal, because I built my website myself, I did my branding myself. I didn’t [00:17:00] actually have to hire anyone until it came to the actual trip of like, who are the suppliers that I wanted to hire to be a part of the trip that would feel like family and really make that trip very special.
Ally: And that’s an integral part of every trip that we run, and we can talk about that later. But things that you definitely have to look into is like, aside from what the net cost is per person and how much you as a business want to make, there’s a fine line of like making money and being in integrity.
Ally: I know that this industry is very murky. I see a lot of [00:17:30] influencers running influencer trips where they’re just white labeling an existing trip that costs, let’s say, 2500 USD to run, and then they’ll put their price of 6800 USD. And they can do whatever they want and that’s fine. I mean, is it? But,
Maggie: That’s a different conversation
Ally: That’s a different conversation. But no, for me it was like I didn’t have to put a lot of investment in at the beginning, but I did look into when building on top of my net price, what my cost would be to actually be there to run the trip. So if I’m there for two weeks, [00:18:00] outside from my flight, what are my food expenses?
Ally: What are additional expenses that I have to take on? If I’m there for two weeks and I’m literally on running this trip, well, I’m not working with any clients back home. I can’t take on any photo shoot gigs because I’m a commercial photographer on the side of this, or I should say simultaneously. So it just came down to, as any freelancer would kind of quote their business and their time, what is the cost of my time to be there?
Ally: And also where does that meet integrity, [00:18:30] where I feel like I’m charging a very fair price because I want people to actually see the value in traveling with me and build a community out of this. And this might sound like make me a horrible business person. I’m not looking to be the largest female travel company in the world.
Ally: I’m not. I set out with a mission and that was to build community and offer experiences to women and, yeah, trying to have fun doing it
Maggie: And there’s a point where it’s like, well, really in life I kinda wanna travel, and so if I get to [00:19:00] travel and make some money and, you know, pay my rent I feel pretty satisfied, you know? Do you feel like you’re still a, a traveler when you’re hosting these, or do you feel like I’m really on and this is, like, a lot of work?
Maggie: I mean, I know we enjoy our work, but Cause I know, like, hosting an event, they’re fun, but, like, events by the end I just need to, like, lay down and breathe, you know? And so I can see how it is not as just relaxing as maybe, like, oh, well Ally, you get to go on the trip. It’s like, yes, [00:19:30] and you know, I’m taking care of everyone, I’m making sure every, all I’s are dotted, T’s are crossed, all the things, so it can be exhausting as well
Ally: Totally. I think You nailed it in the sense where when you’re hosting something, you are always on. So like energetically, when that trip leaves Some- I will even go as far as to say sometimes I’m, like, depleted energetically. And, but at the same time, I’m so overwhelmed with, like, happiness and gratitude because the women [00:20:00] that come on these trips are unbelievable.
Ally: But you’re always… Like, we joke because I feel like when I come on the trip, I participate as a traveler because I never wanted to be like, “I’m your tour guide.”
Maggie: Right. Follow my flag
Ally: yeah, like we’re anti-tour. Like, my brand statement is, like, small curated experiences for women who hate tours. So I’m not like, “Hey, I’m your tour guide.
Ally: I’m the boss.” I try and simultaneously put myself as a traveler where I’m connecting with all of the [00:20:30] women and participating in everything I possibly can, while also making it very known, “Hey I’m here working. I’m here to serve you. I’m here to make this the absolute best experience I can for you.
Ally: So whatever you need and however I can do that on top of what’s laid out, you just let me know.” So yeah. Is it a dream? Absolutely. Am, am I tired after the trip when you’re just like, “Okay, now I have a chance to, like, breathe?” Yeah, because, like, you’re always the first one up. You’re the last one to go to bed.
Ally: You’re checking on it. And I become such good friends with the women [00:21:00] that come on each of the trips, and they always jo- I have this, like, joke where I’m like, “Are you guys mad at me?” Like, when I can see everyone’s, like, tired, I’m like, “Are you guys mad? We have, like, a long drive today.” And they’re like, “No.”
Ally: But everyone that’s come on the trip’s been amazing. And I think, too, having an application form is such an important part just to ensure the right women are coming on this trip. And speaking about money, travel is a massive investment. So, like, forget my business. Again, it’s like me, let’s put my consumer hat on.
Ally: [00:21:30] It is such an investment to decide to take a trip. And so it is… You need to make a decision on, like, am I choosing the best trip and the best experience for me? And I know I’m offering something and creating something that’s very different from a lot of other experiences out there. So I don’t wanna take someone and essentially take their money if I don’t think, like, energetically they’re gonna be a good fit for this type of travel.
Ally: That doesn’t mean, like, sign up this form. I wanna, like, see your Instagram and make sure you’re cool. Like, we don’t, I don’t run [00:22:00] influencer trips. It’s just, like, I look for the people that have traveled really well solo. And we talked about solo travel a little bit at the beginning. But when you’re younger, solo travel was so much fun because you would just meet people in hostels, and you would go to bars, and we’re not staying in hostels anymore.
Ally: Like, at least I’m not. I’m not as social as I used to be, and I’ve built something for women, I, I say, like, 30-somethings to 50-ish because it is energetic. But I want the girls that, like, when I [00:22:30] go on solo trips now, I’m kinda sad. Like, I wanna go to nicer places, and, like, I’m not meeting people the same way.
Ally: And I’m, like, experiencing these beautiful things wishing that I was experiencing it- Like, doing it with other people. So to find those women that are also, like, very self-sufficient and enjoy free time and want the ability to kinda wander off, but always knowing that, like, the activities we do are very intentional and, like, knowing that there’s always someone to have, like, dinner and drinks with or coffee with.
Ally: Like, that’s really special. Whereas, like, other travelers might [00:23:00] want, like, a crazy strict itinerary, a bit more hand-holding guidance, and that’s okay. But I wanna make sure that, like, you’re investing in the, the travel that’s going to change your life versus just taking anyone’s money
Maggie: And that’s what drew me in too. It’s like, it’s not all these tours, but it’s also not like, yeah, this full agenda. And as much as I love group things, like I need that introvert time to just be me, do me whether that’s just like walking by myself or whatever. So it’s not like you have to be with a group for 11 days straight.
Maggie: Like, absolutely [00:23:30] not. You don’t want me with a group for 11 days straight. Like, that’s not gonna happen. And so like, yeah, and you mentioned it is a big financial thing. So for women listening who wanna say yes but keep talking themselves out of it, what’s typically stopping them and what do you tell them?
Maggie: Do you find that’s usually like the money aspect, or is it more of like a, a fear or tell us what you get from the community. Yeah
Ally: I think a fear when you see a price tag is always scary. Like, let’s keep it real. Even if you weren’t coming on a trip with me and you wanted to [00:24:00] have a Euro summer, you’re spending thousands of dollars. It is a luxury and a privilege to be able to travel these days, so let’s just be transparent and, like, acknowledge that.
Ally: So is the price tag a, an issue or a hurdle or a, a sticker shock for some people? Absolutely. It’s gonna be with a lot of trips. So I think, like, one, finding something, knowing your budget for travel and finding something that’s going to fulfill you in that budget. Anything is possible. [00:24:30] And I’m taking off my girls trip series hat, and I’m coming to you from, like, a travel planner now, ’cause I, I have so many people come to me, men and women, families, corporate, and they’re like, “Hey, we wanna do a safari,” or like, “We wanna go to Europe.”
Ally: I can plan individual trips for people, and that’s the first thing. What’s your top? Like, what’s your line?
Maggie: Because it all adds up, those little things. I mean, I think about like, ” Oh, we got the flight and the hotels.” I’m like, great, that’s… Yeah, it’s a good chunk of it, but like all those excursions, all those meals, all the wine, all the [00:25:00] everything
Ally: I’m assuming majority of your listeners are American. I’m Canadian. I don’t know if you guys have ever converted to the Canadian dollar, but you, when you convert to the Canadian dollars you must be like, “Oh my God, that’s so cheap.”
Maggie: That’s exactly what I did when I looked at that on that trip. I was like, “Oh, 6,000 Canadian, that’s 4,700
Ally: Hair flip. Yeah. I need to find more Americans and Europeans to come on our trips because I– that was a [00:25:30] big thing for me when doing my girls trips.
Ally: Again, put on my consumer hat. As a Canadian, I cannot stand looking at like, “Oh, I’m gonna work with this coach. I’m gonna go to this retreat. It’s in USD. It’s 5,000 USD.” Great, that’s 8,500 Canadian. I’m out. So for me, I’m like, I’m gonna always price myself in Canadian, even if I have to pay suppliers in euros, in Moroccan dirhams, in USD.
Ally: I take all my pricing, and it’s usually USD around the world. [00:26:00] I take all my pricing, I put it together, I convert it to Canadian, and then I work in Canadian dollars. So yeah, pricing was like a big… I think like, I mean, it could be a hurdle for people, absolutely. It’s travel. Think another thing is like, yeah, how am I gonna…
Ally: Like, what’s the group gonna be like? How am I gonna be on this group? This is scary. What are the what are they like? What if we don’t get along? Girls always think too like, “Oh, girls trips, like they’re, it’s dramatic. Girls are gonna fight.” [00:26:30] And when I built this, I’m like, I wanna take the best parts on girls trips and put it into one.
Ally: Because when you talk about let’s go like to the drama of girls trips, well, let’s go to the root of that. Not all friends are compatible to travel And that’s not, like, a bad thing to say. That’s not subject to just women. That’s literally everyone. Not all friends are compatible to travel. I have friends that I would consider some of my best friends.
Ally: I love you. I’m not going on [00:27:00] a trip with you. I’m not doing it. We do completely different things. You’re gonna get mad at me if I don’t wanna do everything with you, and I’m telling you right now, if I’m spending $8,000 to go to Mexico, I’m not sitting on a resort. I’m renting a car. I’m driving around. I want to experience where I’m going.
Ally: So I think, you know, when people look at like, “Oh my God, what’s it gonna be like traveling with 12 other women? This must be the worst,” again, that’s why we have the application form. [00:27:30] 99% of women that come on this trip do not book with a friend, and they’re coming in feeling the exact same way that you are, scared sh*tless.
Ally: But I’ve tailored the application form to turn people away, if that makes sense. If you’re getting anxiety answering these questions of like, what would you do in situation X, awesome. Don’t come. There’s so many other tour companies out there that I think would be better suited to you, and I want you to be happy.
Ally: So yeah, I would say the [00:28:00] hurdle for people would definitely, one, be like, what is the price tag, and two, what am I getting myself into by signing up for a trip in like Morocco with 15
Maggie: And I think, you know, when you know somebody right away, you can’t start a fight with them that much. Like, what is there to fight about, right? But you all are all coming from this like, “I don’t know. Let’s see. I wanna have the best trip I can.” And so if everyone’s coming like, “I wanna make the best out of it,” it seems like all boats then will go in the same direction of just trying to make the [00:28:30] best, wanna have a good time, wanna travel and explore.
Maggie: I mean, it is pulling those like-mindedness together,
Ally: Yeah. And like when you’re on a safari in the Serengeti, how are you having a bad time? You’re experiencing very wow moments. You’re bonding people. And let me tell you, like I think at the beginning you asked something, you asked a question, something about like how grateful do I feel that this is my job or I was gonna say something at the time.
Ally: Like I’ve been traveling [00:29:00] for work, for pleasure for more than 50% of my life. And I have, like my first trip I ever did solo, I was 18. I bush camped in six countries in Southern Africa. And that, like we had a truck, and then our hotels at night were like the side of the road. We would put our tents up. And I was 18 or 19 when I did that trip.
Ally: That trip changed my life. That was the trip where I’m like, “Yeah, [00:29:30] I’m gonna do this for the rest of my life.” And being able to share so many of those moments with other people, like it’s incredible. The downside of it, and I try and like pinch myself a little bit to be like, “Hey, snap, like change your mindset.”
Ally: Do you remember how excited you were when you, like, went on your first solo trip or your first big trip, and like a week before you’re like, “Should I start packing?” And then you’re so excited to go to the airport, and everything is wowing you because you’re seeing [00:30:00] something for the first time. That novelty, sadly, I catch myself wearing off.
Ally: And I hate that. I hate that I catch myself, like, not being, like, blown away sometimes, and I’m like, “No, you have to reel that back in,” because that is the magic of being out there. So going… Like, putting together these trips for women I feel like has energized me, because to see those moments, going back to, like, what you said of, like, we don’t wanna wait for [00:30:30] other people to travel anymore.
Ally: And women are coming on these trips single, women are coming on these trips married, in committed relationships. Women are coming on these trips as moms. I’m telling you, the 30-somethings to 50-ish, it is the best group because you’re either going through something in your life that someone is simultaneously going through it with you, they’ve either just gone through it, or they went through it 15 years ago, and let me tell you, they have some advice for you.
Ally: And when you’re pulling together this [00:31:00] magical age range of women, and some people are like, “Well, how are you excluding everyone?” It’s like, I’m not excluding. There’s trips for 18 to 30s. There’s trips for seniors. It is actually okay to offer someone something exactly, like, that they’re looking for, that I felt was missing.
Ally: And to get this magical group of women together in, in such an important age, yeah, are we seeing incredible things? For sure. But, like, the bonding’s happening when people are in the kitchen at night, like, drinking wine. [00:31:30] Or when, like, the three girls that are up super early in the morning are having their morning coffee together in Portugal, like, sitting in the Atlantic, like at, looking at the sun come over the Atlantic Ocean.
Ally: Or when we’re in the middle of the fucking Sahara Desert, and, like, we’re in luxury tents in this, like, glamping thing, and there’s, like, these soaring dunes around you, and people are just, like, crying because they’re just like, “Where the fuck am I?” And we hit this age group, [00:32:00] and you said it yourself people are moms, people have careers, people are freelancing, people can’t.
Ally: PTO, vacation time, children. How do you get your friends together to do these adventures?
Maggie: Much less all those friends that you could travel with, you know? Then it just keeps getting smaller.
Ally: Totally. So that’s exactly what it is. You’ve hit this point in your life where you’re it’s… No, I’m not saying it’s impossible, but I think it’s more common than not for women to be like, “I don’t [00:32:30] have the friends that wanna do this.”
Ally: And even if you do, then you’re getting into, again, time of year, budget, can’t get the… It’s like there’s memes about it. Can’t get the trip out of the group chat. That is, is so common. Or like for me, you know, I just came out of a relationship. Like, I loved my boyfriend, my ex-partner to death, but like, we couldn’t get experiences together.
Ally: And like, that was such a big thing for me, is like I still want to experience things and I’m not [00:33:00] gonna not go. Why, I’m just gonna not experience my life because like I can’t find someone else to go with? And so like, fuck it, we’re going. I’m gonna plan the trip for us and I’m gonna find the girls that are like, “Yeah, I don’t wanna wait anymore.
Ally: I do wanna do this. I’m not getting any younger.” Time literally stops for no one. Okay, I’m gonna go on the trip. And so my trips kind of have transformed. They were very like loosey-goosey at the beginning in terms of like flow of the trip. Lot, not a lot of [00:33:30] structure. As the trips became a bit more bucket list, they became…
Ally: I don’t like to call them tours, ’cause I was like anti-tours, but I call them my more structured trips. So like those are the overland trips when you’re going through Egypt or Morocco or like I’m about to launch a Sri Lanka Maldives trip
Maggie: I need a tour if I’m going through Egypt. I can’t lead myself through the dunes.
Ally: But we can like make it a cool like a cool tour, you know? But yeah, I call them my structured trips. And strangely enough, but not so strangely, those are the ones that have been the absolute [00:34:00] bestsellers. And because they are at a higher price point, I just launch them earlier in advance and give women the opportunity to do a payment plan to make it more accessible, and launch it without, “Hey, we’re going to the Maldives in three months.”
Ally: It’s like, “No, we’re gonna go next year. So take the year to save and pay it off.”
Maggie: Yeah. And I mean, you’re also paying for, like, you to curate the whole trip and plan the whole trip. I mean, that’s half the battle, right? And so having someone do that, do the research, do the stuff for you, I mean,
Ally: And people don’t realize what it costs for [00:34:30] me to run these trips. We touched on it a little bit, but like, yeah, it’s fine when I’m running them in a, in Portugal or my costs are pretty low. I have a flight and, like, my time and my you know, spending while I’m there. But, like, let’s look at developing a new destination.
Ally: Okay. Well, I launched a Tanzania trip two months ago. At the end, prior to me going, I went to Tanzania
Maggie: Oh, so do you always go before you host a trip?
Ally: Usually, so at the beginning, all of these trips [00:35:00] were based off of my favorite solo travel experiences. So I knew a destination really well. But I can only do the same trip so much.
Ally: And there are some trips that, like, I’m not going to be… Like, respectfully, I’m not gonna be like a white girl taking a bunch of girls to Morocco being like, “I’m the expert.” I’m not. What makes my trips so special is the local team that I hire that become our family. Like, we call… it’s all, I try and hire women where I can, but for the most part, when I’m abroad, a lot of these, in some of these countries the teams are men.
Ally: [00:35:30] And like, I call them, we call them our trip dads. And like, when I talk about Yusuf in Morocco, I, he feels like family to me. And like the best part about Morocco is like Yusuf showing us his home. And we’re, us getting to see a different part of Morocco that you wouldn’t see if you were just flying to Marrakech and like taking a bus to the Agafay desert to ATV.
Ally: Great. If you have seven days and that’s all you can do, fine. But like the magic is like meeting a local family and going to a market with them and cooking dinner in their home. And [00:36:00] you know, hearing stories that, you know, from locals when we’re doing experiences and not booking through like a third-party DMC that like has their office in London, England.
Ally: So when I talk about the cost of running these trips, I had been to Tanzania before, but I also can’t just go to these trips and open a business there. Like there’s visas, you have to, like I have to hire a local company. So it’s like who is that company? And what are they about? And who am I supporting?
Ally: And I wanna make sure I’m [00:36:30] grassroots and as local as possible when I’m building these trips. So I got contacted by a guy who owns a safari company in Tanzania, and he was absolutely incredible. And he’s young as well, and he’s out there doing what I’m trying to do and build an incredible business.
Ally: And yeah, I went over to… we spent time on Zoom and built this incredible trip together and then he was like, “Okay, I’ll host you. Come, come run through the itinerary. We’ll we’ll make sure it’s good.” But like it still cost [00:37:00] me 6,000 to fly there. It still was two weeks that I couldn’t work and take on photo shoots.
Ally: It was still all my spending money while I was there. So let’s say that trip cost me $8,500. That’s $8,500 before that trip even runs next year. So that comes out of your profit. And like not to mention it’s gonna cost me another 5,000 to like fly back out there. So just for that trip alone people are like, “Oh, you must make so much money.”
Ally: Well [00:37:30] no, I’m gonna spend between the scouting and running it 10 to $15,000 just my expenses. So it’s not like… Trust me, if I was a millionaire doing these trips
Maggie: Life
Ally: wouldn’t be selling for what they’re selling.
Maggie: And you keep them small, which is great, but some of those prices can only be divided so far between, you know, it’s not being divided between 45 people. Thank God, ’cause I wouldn’t wanna come with 45 people.
Ally: You… when you see [00:38:00] these other tour groups where it’s like, “Yeah, you’ll be with 25 to 30 people,” it’s like, well, that’s why you’re making money because your money is in the volume. And same with the trips, the other travel companies that I worked with.
Ally: All of our money came through volume. And again, there’s nothing wrong with it, but I just didn’t wanna be what was already out there
Maggie: Yeah. No, that makes a ton of sense. Putting on more of your, like, consumer hat, when women come to these trips that you plan, are there, like, financial decisions most of them are not thinking about until it’s too late? Do you find [00:38:30] anything similar come up there?
Ally: Yes and no. I think I try and get ahead of that where because they are booking a year in advance, I kinda just say like, “Here’s what to expect. Here’s when…” You know, if you’re booking, for example, our Tanzania trip for 2027, travels end of May 2027. I launched it two months ago, so they have one full year until departure.
Ally: That’s a really long time. So the benefit to it is if you don’t wanna pay in full, that’s great. There’s a payment plan that allows them to [00:39:00] slowly pay their trip off. And then I kinda just say, “Here are other things you can expect while you’re on the trip. You know, this trip is great because you have your room and board included.
Ally: You’re really not spending a lot of money on the ground there unless you’re gonna add an extra excursion,” and I can list those out for them in advance, so they’re like, “Okay, I wanna do that.” If they don’t book an upgraded photo package, but, like, I’m a photographer, so that’s amazing thing is that I can offer photos to the women on the trip.
Ally: If they don’t wanna book a full upgraded package, I’m like, “Okay, if last minute you [00:39:30] wanna book a photo package as, like, memories, this is what it will cost you.” Other things, you’re gonna need to do a visa. You’re gonna probably have to go to a travel clinic to get your shots. You know, I recommend setting aside 20 to 30 US dollar per day, and if you’re there for nine days, that’s 30 times nine.
Ally: Like, that should be your tip that you’re giving at the end. Not to me. I never take tips from any of my travelers. That’s to, like, the local team. And your driver’s with you literally 24/7. Unless you’re at the lodge, like, [00:40:00] they’re just taking care of you, and our driver and our guide, I couldn’t imagine our trip without him.
Ally: Again, these people become family to us, so that’s what I… I try and list everything that I can in advance so there’s no surprises last minute where women are like, “Oh, fuck I shouldn’t have…” You know? And that’s, that is a big thing. You spend so much money when doing any trip that you think, “Okay, so many of my costs are up front,” which they are.
Ally: But, like, again, what are you what’s the cur- currency conversion for [00:40:30] you? How much are you gonna wanna spend? What activities are you doing when you get there? Are you a partier? Are you a drinker? Are you… Again, these are to generic to all travels, not just my trip. What excursions are you gonna do?
Ally: Do you like to shop? Like, these are all kind of things that are like, what am I going to want to do when I travel, and how much should I set as- should I be setting aside for that as well?
Maggie: Yeah, I think all those great things are, yeah, they’re easy to forget and then later, yeah, you need that cash, which none of it [00:41:00] adds up to as much as you probably paid for the trip. But like those people who you are with every day, who are the boots on the ground people, I mean, those are the ones you want to ensure that you’re tipping, that, you know, are really seen and valued.
Maggie: I mean, yeah, the flight’s the flight and it’s the cost of the flight, but like these people who you’re with who are making and breaking your trip, like you want to make sure that they feel seen as well, which is really important. And then, yeah, those visas, which is a great thing about you booking those out a bit more in advance is that time to file for those visas, passports, shots, all those things, [00:41:30] because not every place is just like going to Portugal for 10 days or something where it’s not as necessary, and changing political climates, you never know what you’ll need these days, so just kinda being prepared there.
Maggie: Before we ask our final question, do you wanna share like some trips that you have coming up that maybe people in our community can join or where they can learn more about it?
Ally: Yeah. So again, the company is called The Girls Trip Series, and I’m sure you’ll link all of the stuff for people to follow. I won’t spell it out. But yeah, for [00:42:00] 2026, for the rest of this year aside from Egypt, all of our trips are sold out, which is sad for new listeners, but also exciting for me. So if you do have some time and you wanna travel at the end of November this year, we have two spots available for Egypt.
Ally: And then in 2027, I’m going to be launching a bunch of new trips. So all of our current 2027 trips are sold out, but at the end of September, I’m gonna be launching a Sri Lanka Maldives experience, which I’m very excited for because Sri Lanka [00:42:30] is just a beautiful country with so much to offer from small surf towns and incredible coastline to safaris to see elephants and leopards to, like, tea farms and misty mountains and train rides and incredible food and people.
Ally: It’s such an amazing destination, and the fact that it’s only an hour-and-a-half flight from the Maldives, I think, like, most women listening probably think, like… I know it’s the same. Like, Maldives to me is, like, romantic, so unless I’m going on some, like, honeymoon with a cute boy, like, probably not ever gonna go.
Ally: [00:43:00] And again, same mentality. I’ll plan it for us. The girls are going to the Maldives. So that’s actually gonna launch at the end of September, early October for 2027, if women are interested in learning more about that. And then we’ll also probably relaunch trips for, like, the gorilla… hiking to see the gorillas, another Morocco adventure.
Ally: Yeah, there’s so much coming up in the pipeline, and I just kind of, like, post as we go. So if you check out our Instagram, and obviously the link in our bio will kinda show what’s available and what’s coming [00:43:30] up.
Maggie: Yeah I love going through your Instagram. I mean, of course it helps that you’re a photographer, but everything is so great and just like, I’m like, “Oh, wow, these trips just look fabulous.” So Ally, there is a question we like to ask all of our guests on here, and with all of your experience from your different jobs, traveling the world, what does financial freedom look like to you?
Ally: You know, that’s a really hard question because I feel like that answer evolves so much over time. And I think when I was younger, I’m like, “I wanna be rich enough to do anything.” But I think [00:44:00] the older I get, it means freedom. And I think I like the answer freedom because freedom can mean something completely different to anybody.
Ally: And, you know, freedom could be like, I’d love to pay all my bills and not feel, like, strapped about it. I’d love to, like, be able to pick up the dinner tab for my girlfriends when we’re out and not sweat about it. I’d like to be able to take a few days off and, like, do a trip when I want to be able to do a trip.
Ally: And [00:44:30] yeah, so I think for me, like, financial, like, being able to breathe, you know, and not feel stressed when making decisions in my wallet
Maggie: I love it. I love it. Well, I thank you for coming on, sharing your expertise, making this amazing community so the girls can get out there and get traveling. I hope to see you on one of your trips soon. And until next time, be financially fearless.
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