zoom chat

Start a zoom group chats before you go. It’s easiest to have one designated text chain where you can firm up airport transfers, potential excursions, and the breakdown of the bedrooms — together. “The best way to go into a group trip is with everyone feeling like they’re in the loop,” It’s a great way to build excitement, too: In the weeks before your trip, shared articles, Instagram screenshots, and the sunny forecast among our traveling party group.

Travel Budget

Be clear about costs. “It’s better to talk about how expenses will be shared before the awkward moments when the bills arrive. Decide how costs will be split — for the short-term rental, for groceries, for dining out meals, and for transportation. Will someone put the deposit on a credit card and you’ll all Venmo?

Appoint a treasurer

Appoint a treasurer. Someone in the group who is good at figuring out tips and keeping track of who owes what to whom. Use Notes on your Phone. At the end of the trip you should have things like, “James paid $20 for a taxi to Grand Anse Beach, Lydia paid out $60 cash for Cultural Tours in Grand Anse‎, Lisa bought a round of Carib beer for $40.

vacation room assignments

Be strategic with the room assignments. Our listings include photos so you can scope out the pad, but you won’t definitively know where everyone should go until you get there. You’ll set yourself up for a smoother trip if you take a tour of the house and make suggestions for who should bunk where based on the personalities and needs of the guests. If someone is known to get up to use the bathroom a lot, offer them the room with the en-suite bath. Figuring out who gets the master is probably the most significant decision, so “to avoid arguments and set expectations you may want to have this conversation about it ahead of time.

sleeping habits

Disclose any sleeping habits. If you’re sharing a room with your friend and she doesn’t know you snore, speak up so there are no surprises. If you’d like privacy while in a shared room, ask for 20 minutes to get ready and offer to give that in return. Communication is the key to a successful shared rooming situation.”


Set some house rules. If you’re going to have kids with you, it may be a good idea to suggest a vacation family meeting where you can ask if there are any rules anyone wants to propose. When parents go on vacation, we’re looking for downtime, but kids need supervision, especially in the beginning. Giving them guidelines to follow will help things run smoothly.

schedule alone time

Schedule alone time. Just because you’re in a group doesn’t mean you should never get to be alone. Taking an hour a day to unwind alone will help keep the energy in the group positive.” If you’re traveling with little kids, take turns watching each other’s children so you can do an activity on your own.

don’t judge

If you didn’t plan for it, don’t judge. Every trip has bumps in the road, and those things don’t always need pointing out. “You don’t want to be the one toxic person who turns the whole trip into a complain-a-thon. You can gripe when you get home.

Wait before snapping. If someone gets snippy, take a moment to breathe before saying something you might regret. Step away from the situation and remind yourself that if someone does something to upset or annoy you, it’s probably not done maliciously or personally. By letting it go, you’ll make sure you don’t escalate the situation any further.