Group Vacations for Dummies: A How-to Guide
curating group hangs, bonding experiences, and bringing people together, with close-to zero effort
Now more than ever before, Americans are gathering together less frequently – no longer hosting dinner parties1, nor having regularly scheduled social hangs. Bowling leagues have all but died. It’s impossible to find a Canasta group anymore! To make matters worse, many of our nearest and dearest are spread hither and yon, from coast to coast, all over the continental United States. Our group hangouts now feature flights, hotels, and Ubers. We’re in the era of the Great Coordination.
To that end – and for those of us who are Tired [read: everyone] but need to see our people [ditto] – we’ve compiled a short guide for how to pull together a group vacation without feeling like a tour guide, a chaperone, or everyone's mom.
Be Unilateral: Decide the specifics.
So you want to go somewhere? Instead of wrapping everyone into the initial planning process, first choose the destination, time period, and lodging. Then, when the basics are decided and mostly booked, share the news of the fabulous vacation that you hope your friends can make time for. This eliminates not only the hassle of decision-by-consensus, but also the pressure for your friends to agree to a plan before understanding what the costs might be for them (see more about Money below).
Yes, this carries the potential of upsetting some, but, in truth, the people who get their panties in a wad during the planning process are the same people who get upset by every unforeseen inconvenience. These people are not group travel people. Don’t say it in those words, because that’s rude. But it’s true.
Example message to friends:
“Hi! We’re going to fabulous Omaha from June 12-17. Flights are cheap. Renting a big Airbnb. Plans are to see the rodeo and to toilet-paper Warren Buffet’s fabulously modest home.”
You Are Not HR: Don’t curate who will be there.
Yes, unfortunately, that includes your friend’s terrible boyfriend. It doesn’t matter whether it’s a mix of old friends, new friends, boos, cousins, sisters, and assorted children. Trust people to enjoy one another and make new connections. You are not responsible for anyone else’s fun. You are not responsible for everyone’s damage, either. Your friend may spend the trip fighting with her boyfriend. Your other friend’s child may get sick. In these circumstances, you should count your blessings, put on some sunscreen, and see “Do Your Own Thing” below.
TIP
Start a group chat, so that, for example, you too can vicariously enjoy the hijinks of three people who had never met before, becoming immediate besties and going on a Harold-and-Kumar level all-night adventure montage.
Do Your Own Thing: Abandon the idea of excessive group activities.
Once on-site, create the space for possibility and then let all your expectations go. On a vacation, the only “must-do” activity is the one that calls to you most in the moment.
The number of full group activities should be non-zero, but should also be capped. A single, nice dinner during the course of a weeklong trip is sufficient. Sightseeing excursions are ALWAYS optional. Otherwise, you will be treated as the cruise ship director and you will resent it.
Group chats beginning with “Where should we go for…” and “What are we doing?” are to be avoided - let the group splinter into smaller, mutable groups. Accept that FOMO may be a part of this approach - you cannot be with everyone at every moment, and that is great. Forcing yourself (or anyone else) to do the activity you “should” be doing leads to communal strife on a group vacation, and doesn’t enrich you.
Be Older
When cohabitating on vacation, be in your 30s or above. This is not a requirement, but will ease the way considerably. This was something we first noticed in our late-20s on one of our weeklong summer trips to Cherry Grove, Fire Island: once our friend group began to encompass folks who were a bit older than us, things just chugged along so beautifully in the rental house.
Someone notices the dishes need to be done and just…does them. Someone notices we are running low on produce in the fridge and strolls off to the Pines Pantry to buy $11 apples. Someone sweeps up the sand from the gritty living room floors. Someone sees it’s getting to be about that time, and starts to mix up a big salad and a cheese board to eat by the pool. No questions, no chore allocations, just taking it upon oneself to quietly do the thing.2
People often think of group vacations as the domain of the young and single and freewheeling; increasingly difficult to pull off when you are older, married, parenting, with other demands on your time. But older group vacations can also come with additional resources, financial freedoms, thoughtfulness, and communal care. If this quality of tacit, grown-ass-adult responsibility isn’t the friend dynamic you have, know that you can get there with time. Being in your early 20s is not an immediately-avoidable condition, but it will pass.
Money
This one is controversial and causes some stress among our friends; money being one of the final friend taboos.3 But here goes:
Don’t worry so much about who spent what. DON'T use those infernal money apps that track your spending to make sure everyone is settled up to the dime. Treat people to a round. Allow someone to buy you a meal. The worst part about venmo-culture is being accosted by a $8.65 payment notification when you’re just trying to treat your friend to a goddamned sandwich.
This mindset has worked for us – both when we were on a shoestring budget, and when we are on a longer-shoestring budget. Our conscious choice to live as artists and sybarites means we are STILL the least financially-resourced people on the trip. You can treat, and be treated, regardless of the wide(ning) class divides between you and your friends. [Hello, up there, friends!]
Rather than tracking to the penny, why not be more more attuned to the tides of debt and repayment. If you feel that you’re in the red, make an offering (not necessarily financial!) and get into the black. If you feel you’re too-often in the black, be vulnerable enough to ask from others what you need. Trust your friends to do the same. What a gift it is to be bound together that way.4
If you still feel weird, ask yourself why it matters to be “square” with your friends and try again.
VOILA
And that, friends, is how less planning, less consensus, and less insistence on togetherness leads to more relaxation, more trust and more deep connectedness. Cheers!
Fair; I didn’t have space in my apartment for a dining table until I relocated towards the end of a subway line. [grumbles and harumphs in NYC]
NOTE: It doesn’t work if only one person (woman) is the quiet labor person. Everyone has to be the quiet labor person. Except for that one friend whose executive functioning prevents her from anticipating the group’s needs in advance, and who will instead contribute richly in curating the playlists, distributing weed gummies, and offering everyone a fabulous sun hat. We all have our roles.
I know infinitely, exquisitely, more detail of my friends’ sexual proclivities and escapades than their bank accounts.
That’s that Debt-Gratitude cycle at work, baby!
Let me know if you end up in Omaha in June;)