Out-of-town bachelor and bachelorette parties are one of the biggest trends in travel right now. Many betrothed couples plan getaways as elaborate as honeymoons for their bridesmaids and groomsmen.
To talk about the how-tos of planning these shindigs, we turned to Avery Singer and Jolie Golub on a recent episode of the Frommer’s Travel Podcast. The pair are best friends and the founders of BachBoss, a travel agency that specializes in bachelor and bachelorette parties.
The following is a transcript of our conversation, edited for length and clarity.
Pauline Frommer: How did you get the idea to start this business?
Avery Singer: Jolie and I were co–maid of honors planning our mutual best friend's bachelorette [party]. I whipped out an Excel spreadsheet of options (having a finance background), dividing costs per person. And I said to her, "Wow, Jolie, we are so good at this. Can you imagine how many people struggle?" And she replied, "Yeah, Avery, should we maybe make this a business?”
So I researched companies and competition, [but we didn’t do anything until] I ended up getting laid off from my tech job when all of tech was getting laid off at the end of 2022. And I was like, “Jolie, I think I'm going to start this business that you thought of with me. Are you in?”
We launched [BachBoss in] February 2023. It's been our full-time job and we've never looked back.
Frommer: When I was getting married, people didn't travel [for bachelor parties]. This seems to be a pretty new trend. Do you have any kind of stats either about your own business or about the industry in general, about what percentage of brides and grooms in the United States are doing this?
Singer: I would say about 80% [of couples] right now are traveling to do these 3-day long weekends, either by train or plane or car.
We're seeing that most of our clients are getting on a plane. They are also going international. They are flying to Cabo, to Tulum, even Mykonos and Ibiza. Really nothing is off the table.
It’s a great way for the group to come together from different walks of life, because not everyone [in the wedding party] knows each other. [This is a way to] celebrate the bride or the groom and get to spend some time to get to know each other before the wedding week or weekend.
Frommer: Are [the above places] your most popular destinations?
Jolie Golub: Yes. Our clients tend not to go to the most overall popular bachelor/bachelorette destinations. I believe Nashville is one of those. We personally don't plan that many Nashville trips. Our clients tend to lean more towards Miami, Las Vegas, Cabo, and Tulum. Those are our "Big Four."
Frommer: Are those four more popular with the men or the women?
Golub: Totally equal.
It’s interesting because when you think Vegas, a lot of times you think men. We definitely do a lot of Vegas bachelor parties.
But honestly, a lot of trips we're doing now are joint, as in joint bachelor/bachelorette parties, where the guys and the girls are going together.
Mexico is a great destination for that because we rent a lot of big villas. So sometimes we'll do a guy villa, a girl villa, and then they'll do activities together. Separate stays, but their dinners are together or their yacht day is together.
Frommer: So I guess if they're doing it together, they are not getting strippers and they are not doing the stuff that became infamous in the film The Hangover.
Golub: You might be surprised. I would say the joint ones, not so much. But the purely bachelor [parties] lean into some of the naughtier activities. I think it really depends on [the group].
Singer: I would say [our offerings are] luxury trips. People are taking vacation days, time off of work, [so] it's really not just about partying 24/7. Even in Vegas, the guys are doing a round of golf. They're doing some type of different excursion. Similarly in Cabo. The girls are doing spa days. They are doing yoga. It’s definitely a balance between partying and that type of vacation where it's not go, go, go.
Frommer: Okay, Jolie, I gotta ask you, when you mention naughty stuff, have you ever gotten a request that you've thought, Ooh, I can't do this. I can't set this up for them.
Golub: The answer is no.
We definitely have had some raunchy requests, but we are a professional company and we are absolutely happy to set up anything our clients request. So nothing is too out there for us. We have connections everywhere. We have contacts everywhere, and we can really make anything happen.
Frommer: What are some of the most over-the-top bachelor parties or bachelorette parties that you've planned?
Singer: We had a very over-the-top bachelor party in Tulum last year. We were working with the older brother, and he had some very creative requests. ... He wanted to have fire dancers. He wanted to have mermaids. So we literally got mermaids [to swim] in the [rental] villa’s pool. And there was a DJ club room downstairs with windows that could look into the pool.
We also love doing luxury beach picnics. Boat days are also superfun.
We love when clients get creative, especially with custom swag and welcome bags.
Golub: One of our most famous clients is Olivia Culpo, and she did her bachelorette in Cabo. When we worked with her and her team, they were extremely creative.
They wanted to set the tone [for the weekend] with the approach to the private plane. So we hired shirtless models that served drinks [on the runway]. We had a balloon arch that said "Olivia Land." We had her whole private plane decked out in custom swag and welcome bags.
When people kind of look through our Instagram, they'll say, "We want this, we want that." We really do set a lot of trends that people want.
Frommer: What do you think the biggest mistakes are that bachelorettes and bachelors make when they're planning these events?
Golub: There's quite a lot of mistakes that can be made. The first is not hiring us and trying to plan it on your own [laughs].
But I would say that what tends to come up a lot as an issue are budgets. It's a mistake not being upfront with the group about what things may or may not cost, especially if the person throwing the trip is not planning to subsidize anything.
Budgets are definitely a common issue. Same thing goes, I think, for guest lists. Women in particular feel more pressure around inviting family members—cousins or sisters-in-law or whatever that looks like. And that can be a sticky issue as well.
Frommer: I noticed on your website you have different levels of planning, and some of them include spreadsheets or sign-up sheets for how much people will pay. Do folks ever do tiered payments? So the maid of honor pays the most, the bridesmaids pay second most, and the second cousins maybe pay just a little bit? Or is it usually even-steven?
Singer: I would say normally it's split evenly. When we do send those custom surveys, we write in the survey, How much do you feel comfortable spending on accommodations per night? Give ranges. And: How much do you feel comfortable spending on meals and activities?
This is something that the bride or groom can review ... and decide what they want to subsidize. If someone can't afford to come, we've seen the bride or groom help pay for that one person. But that's not publicly known. Money can be a sensitive subject. That's part of the reason why we created this business—to just have transparency and be that third party that can defuse any situation, talk through what's realistic, and just get all the planning as seamless as possible.
Frommer: Is a lot of your job being a consigliere? Are you the person who has to deal with negotiations among the groups? Because group travel is always tricky.
Golub: We normally work with one or two people—the bride, groom, maid of honor, sister, or mom. We don't really like getting a bunch of opinions and talking to the 15 people who are attending. We don't need the peanut gallery.
When we do send that survey, that's really just to get intake and information that whoever we're working with can take into consideration. At the end of the day, the people that we're working with—they will make the decisions. And we will never book or do anything without their approval.
In terms of payments, we have a bunch of vendors that we work with over and over again. All payments are done in house. So if we book a boat or a chef, the client can pay us and then we'll pay the vendors directly.
We can also collect money from the group and say, "Hey, we're planning to do so-and-so's bachelorette, the villa, transportation, and the chefs are going to be this much. We'll do two installments. Please send the first batch by this date."
Frommer: Is the way you make your money by taking a percentage of what the chef makes, what the boat makes, all of that? Or do you make money by charging a planning fee?
Singer: [We have] tiers of service and each tier builds on each other. We have four packages: Bronze, Silver, Gold, Platinum. It’s a flat fee, not per person, and this covers our time and services.
So Bronze is an intro where we will propose your accommodations, we will book your [restaurant] reservations and activities, create an aesthetic itinerary and mood boards, and then we leave the rest to you.
Our most popular is a step up, which is Silver, where we will do everything that I just said, plus go ahead and book the accommodations because we work a lot with partners directly that are kind of off-listed. So we can save you money, get involved in transportation, get involved in the custom decor, swag, balloons, and do a lot.
Frommer: What surprised me in looking at your site is sometimes you take over creating social media content for your brides and grooms. I guess showing the world what you've done on social media is a huge part of this event, right, Jolie?
Golub: Yes and no.
We do have clients where content is extremely important. They want Reels and TikToks and recap videos and all of that good stuff.
But we do have clients that are also very private. Not only do they not want the world to see—they might not want their wives to see or vice versa.
Frommer: And you also sometimes make sure that they look good. I was interested to see that you offer photo sessions for these parties. How popular are those?
Singer: Very. Photo sessions are super-, superpopular. More amongst the women, especially if they're getting dressed up for a specific theme night. That is something that they'll want captured and documented. So professional photos are a must.
Frommer: Is there anything I haven’t asked you that I should have?
Singer: I would say it's very important to start planning early. Especially now. A lot of people are doing destination bachelor, bachelorettes, and potentially destination weddings. So peoples’ calendars are filling up. If you definitely want to go to a certain place and want to get the best accommodations and have as many of your friends come, we recommend getting started ASAP.