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How to Plan a Group Trip with Friends

Stephanie Bragdon
Stephanie Bragdon
7 min read
planning a group trip - Dubrovnik

So where to begin… my best friend (let’s call her Jordyn) and I have always talked about going abroad for a girl’s trip. We imagined England or France – somewhere that seemed accessible. At the time, she had more experience traveling abroad with her, and her now-husband (we’ll call him Greek Guy – he’s Greek, and a guy…thus an inside joke was born) spent a month hopping around Italy, France, and Portugal, so I trusted her to guide us. Little did I know that she hates planning, does not like looking things up, and refuses to ask for help. Inevitably, the girl's trip turned into a group trip with the boys.

In the summer of 2018, we started planning our trip. We wrote out dates and picked locations. She’s part Czech, so we knew Prague was going on the list. We then decided to add Vienna and Cinque Terre – some advice my dad gave was to pick places with different architecture so it all doesn’t blend together. Being an artist, it made sense to trust his opinion.

So there we were three countries in 10 days. We waited until January of 2019 to start planning our May trip. At that point, I was in a new relationship with Skylar – an avid traveler himself. Greek Guy was interested in coming. There were also some legitimate concerns about our ability to navigate the world alone. Though Jordyn and I still fully believe it would have worked out in the end…. There just might have been some mishaps along the way.

After a lengthy discussion period, we decided to invite the boys on our girls-only trip. I should also mention this 10-day trip was the first time Skylar met Greek Guy, and the second time he saw Jordyn. Maybe it would have been fun to make a proper girl’s trip, but we made it clear the boys couldn’t hijack anything. This was our trip, they had to go and do what we wanted.

That’s easier said than done.

While in the planning stages, the boys pointed out that three countries might be a lot (Skylar has a thing about slow travel), so we started to think of a plan. Still, Jordyn and I knew two things: we didn’t want to re-visit a country we had already been to, and we wanted to go to Prague. After a lot of searching, Greek Guy suggested Dubrovnik. We were hesitant at first – after all, it was a girls’ trip, so suggestions from the boys were immediately suspect – but after some searching, we agreed. Coincidentally, this trip coincided with the Game of Thrones finale, so it almost seemed like destiny.

A view from the city walls in Dubrovnik, Croatia
A view from the city walls in Dubrovnik, Croatia

The hardest part of planning a group trip is trying to avoid stepping on other people’s toes. Oh, and budgets. It’s hard when there is a significant wage gap within the group (I can say that because I was making by far the least and had minor panic attacks whenever I started doing the mental math of how much this trip would cost). It’s essential to be honest and open with each other, so everyone feels heard. Likely it isn’t as big of a deal as it is in your head, so just be sure to communicate.

One of the more natural parts of trip planning is deciding where to stay (though again, the prices can cause some sensitivity). I found a cute apartment in Prague while Greek Guy found the perfect place in Dubrovnik. Looking back, it felt easy, but at the time, I remember long FaceTime calls filled with Airbnb links and my constant concern that the place wasn’t in a great area. Those concerns went unfounded though, we had some of the best Airbnb travel experiences (which seem to be a rarity nowadays).

Skylar and I are more the planning type. I created a spreadsheet of restaurants to visit, bars to try, and top attractions in each city. Skylar is an excellent researcher. He directed us to some of the most amazing meals we had on the trip (having been to Prague before). But planning for a group is a tricky thing. Skylar is willing to wait a little longer and walk a bit farther for a great meal; others might not be so willing (I won’t lie, sometimes I just want to eat – but the wait is usually worth it). If everyone isn’t on the same page, there’s an opportunity for hanger to set in. There’s a learning curve and a balance that has to happen.

Fortunately, it worked out. Jordyn and Greek Guy were happy to explore and find perfect places, leaving Skylar to his own devices (check out the Prague map for inspiration). Still, sometimes it’s hard not to feel as though you’re monopolizing others’ time or plans.

jet ski in the adriatic sea
You can't be sad on a jet ski

A friend of mine who studied abroad in Prague told me to check out this bar on the outskirts of town. We had no idea what to expect, oddly no research was done ahead of time; we just got in an Uber and went for it. The bar looked like it was plucked straight from Burning Man; there were staircases and scaffolding made of metal pipes, a stage where a metal band was playing, at least two different bar areas, and outside seating where drunk conversations were ensuing. We also spent a good hour talking to a drunk guy who didn’t speak any English and seemed indifferent to the fact that we didn’t speak Czech. It is still one of the weirdest bars (for lack of a better word) I’ve ever been to. After the fact, when I told my friend I went, he laughed at me and walked away.

We tried to keep it even, so everyone got to pick something to do. But I’m not going to lie, Jordyn and Greek Guy are up for anything, which leads to some fun adventures trying out scooters and jet skis in Croatia.

The one thing I did push was for us to leave the major cities (Prague and Dubrovnik) and head to a nearby small town to explore. I highly recommend getting out of the central city and finding smaller places to explore. It allows you to see some of the cultures of the country and is usually cheaper. The lunch in Kutná Hora was probably the least planned meal of our entire trip. It resulted in perusing Yelp (to Skylar’s horror) to find a highly-rated eatery near us. Having misjudged the distance from the Bone Church, we’d been walking a couple of miles. We were hot and hungry, but the restaurant turned out to be beautiful, overlooking a beautiful valley and a castle. So sometimes spontaneity works out!

A creepy bone church outside of Prague
A creepy bone church outside of Prague

In the end, we’re lucky that our dynamic worked out. The way we travel is similar – wander around, find cool places to eat and drink and see some cool shit. It also helped that we were a mix of planners. If everyone tried to take control of our daily plans, it would have become a headache.

Tips for Your Group Trip


Talk to your friends about what they want to do and see on the trip. It might take some compromises or concessions, but that’s ok. Even when you’re actually on the group trip, be open about how you’re feeling.

Be open about budgets.

Money is a sensitive thing. It can be awkward if not everyone is on the same page about how much the trip will cost. For some, its budget eats, for others, it’s crushing bottles of wine with dinner. So just be honest about what your price point realistically is. It might be awkward at first, but after that, it’ll make for a much smoother trip. Setting the expectation up front goes a long way.

Recognize your own travel style.

Everyone has a travel style. There’s the planner. The go-with-the-flow type. The museum-goer. The foodie. All of these are essential aspects of a trip; one is not more important than the other. So recognizing those preferences is important. Most of the time, your friends will be more than happy to accommodate anything. If not, get new friends.

You don’t have to do everything together.

If you can’t get new friends, then it’s ok to not be tied to the hip during every point of the trip. Does everyone want to go to the Kafka museum in Prague? Probably not. I mean, I don’t really want to. But what about the Sex Machine Museum? If you are genuinely interested in both, you seem like an exciting person, and I’d like to meet you. Jokes aside, each person has different interests and paces. Think about scheduling a half-day or so doing your own thing and meeting up for happy hour drinks. Plus, it’ll give you some potentially needed time apart after living in the small spaces of planes and Airbnbs.

At the end of the day, some of the most fun and rewarding trips I’ve ever taken are with friends. No matter what ends up happening during a trip, nothing can beat sharing a new experience or meal with those you care about.

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