How to Travel With a Group

End of the Inca Trail
Machu Picchu

I was going to write a post filled with adventures of my Travel Club.  Stories like the time we hired someone to drive us from Puno to Arequipa, Peru, not realizing until partway through the 8 hour drive (it should have taken 5), that technically our driver needed a permit to be accepting money from us and that we could have been stranded at any of the number of checkpoints along the way.

Or the kindness of strangers every time we had a flat tire in Baja.


Or how when we travel with Tim, he likes to go around the table each night at dinner and talk about everyone’s favorite moment of the day.

That’s Tim there giving the thumbs up. I love this picture! We had all been traveling together for almost three weeks. Here we had rented a place in Paracas, Peru so we could take a boat tour of the Ballestas Islands. We were exhausted and getting frustrated with each other but still having so much fun. It was Thanksgiving Day in the states, so we decided to put together a meal with what we could find at the local market.

But then I realized, that this post should be about how to travel with a group.  Because I love traveling with my friends.  We always come home with so many great memories, and it’s cool to bring so many perspectives into the experience.

Biking the Danube River
Biking the Danube, Austria
Canon de la Zorra, Baja

Over the years, I’ve learned that the single most important thing you can do while traveling with a group is to discuss expectations ahead of time.


If you’ve booked a place in advance, talk about sleeping arrangements, because if you’re going to rent a house or cram into a hotel room, someone will inevitably have to take the couch.  Who gets the amazing master bedroom?  Who gets the private deck?  When you have eight people in a place with two bathrooms, are the couple with the private bathroom willing to share?  (Hotel rooms/suites are definitely designed for families, not groups of friends.)

Arequipa, Peru
La Casa de Melgar, Arequipa, Peru

If you book your accommodations in advance, especially with a bigger group, it can ease the stress level and save a bunch of time. However, not having a planned itinerary can be really exciting.  In most cases, I prefer the places we book on the fly rather than the ones in advance.  They always have more character and are in the preferred location.


If you want to eat out the entire time, do it!  Try as much of the local cuisine as possible.

Taco Stand
Taco truck near Playa Chileno, Los Cabos

We often rent places with kitchens and take one trip to a large grocery chain for the bulk of the food and then fill in with local markets during the week.  It’s also much easier for people with food allergies to acquire what they need.  Making a master list of groceries ahead of time is helpful too.  When I was in college and we took a road trip to Florida every spring break, we would all contribute equally to the gas and food fund before we even left town, and when the trip was over, if there was anything left, we’d split it.  That was a good system.

And of course, you have to include meals using the fresh, local ingredients.

Fish market in Todos Santos

This is obvious, but very important: Don’t forget to alternate cooking and cleaning.

A thought about all-inclusive resorts: They’re extremely convenient for a group, but I’m certain that we’ve never come close to consuming our daily rate, no matter how much booze we drink.  Also, while all-inclusive resorts can be fun, that daily rate can keep you locked in to eating all your meals in-house instead of exploring the country that you spent all that money on airfare to get to…  and that’s pretty lame.


This is huge, this is the whole reason we travel. Everyone should vocalize the things they want to do ahead of time.  No one wants to deal with disappointment and resentment, especially if it can be easily be avoided.  Many activities/cultural sites/places to eat will overlap, but some may not.  It’s not a bad idea to pre-plan the timing and transportation (if you’re renting a vehicle) for the people who want to do different things.

Hellbrunn Palace, Salzburg

In my experience, we’ve pretty much stuck together the entire time. Despite the fact that we might not have the same interests.

Brian Hates Birds
Brian hates birding.

What I love about this is I get to do things that I never would’ve discovered on my own, like touring a monastery of nuns in Arequipa, Peru or participating in a sea turtle release in Baja.

Clockwise: Ice Caves in Werfen, Austria, Cayo Santiago or Monkey Island, Puerto Rico, Grand Cenote, Mayan Riviera, Olive Ridley Sea Turtle, Las Tunas, Monasterio de Santa Catalina in Arequipa, Peru
Cabo Pulmo

Basically, the key to having an amazing trip while traveling with a group is communication.  During the planning process, everyone should bring their thoughts to the table.  Leave room for spontaneity, of course, just make sure everyone knows what they’re getting into.  It’s that simple.

If you liked this post, check out our group travels to Peru, Europe, and Mexico.

2 thoughts

  1. Great tips! When you travel in a group, does one person seem to take the lead on planning the time schedule for activities each day or is it a group effort?


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