Last updated October 2026

I started hosting group trips because I got tired of waiting on friends to commit to the trips I wanted to take. Five trips later, I’m convinced: the right group trip beats planning it yourself almost every time. Here’s why.

1. You stop waiting on flaky friends
No more “we should totally go!” group chats that die in a week. A hosted trip has dates, a plan, and people who actually booked. If you want to go, you go.

2. Someone else handles the logistics
Accommodations, transfers, reservations, timing: the host handles it. You don’t have to be the friend who plans everything and gets blamed when the restaurant’s mid.

3. A built-in crew of like-minded people
Everyone on the trip chose this experience on purpose, so you’re starting with something in common. On my trips, that means fun, drama-free people who are there to enjoy it.

4. Small group, not a tour bus
Group trip doesn’t have to mean 40 strangers following a flag. I keep my trips intentionally small, so it feels like traveling with friends, not a field trip.

5. Experiences that are hard to pull off alone
Some of the best things to do are a pain to arrange for one or two people: a private villa, your own catamaran day, Carnival costumes and parade access. A group makes them possible and a lot more fun.

6. Someone in your corner on the ground
When something goes sideways, like a delayed flight or a missing transfer, you’re not figuring it out alone in a foreign airport. Your host is right there.

7. Structure plus free time
A good group trip isn’t scheduled down to the minute. The big stuff is planned and handled, and there’s still time to nap, explore, or do your own thing.

8. Great if you’re traveling solo
You can show up on your own without actually being alone. Group trips are one of the easiest ways to take a big trip solo and still have people to share it with.

9. No awkward money math
What’s included is spelled out up front. No splitting the dinner bill five ways, no “I’ll Venmo you later,” no figuring out who owes what for the boat.

10. Friendships that outlast the trip
The inside jokes, the group photos, the “remember when” texts months later. Some of the best people you’ll meet, you’ll meet on a trip.

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Want to see what that looks like? My next trip is The Jaunt: Revel & Restore, a women-only trip to Sint Maarten Carnival in April 2027. Join the waitlist to get first access.

Planning a group trip of your own (friends, family, a milestone birthday)? Let’s plan it together.