How to plan trips with friends?
This advice column is a public service by me, Kat Vellos, author of We Should Get Together: The Secret to Cultivating Better Friendships. I’m a certified connection coach and have been facilitating community groups for almost twenty years. I regularly speak and lead workshops on the topics of adult friendship and cultivating healthy work teams. If you’d like to work with me, reach out on my booking contact form. If you have a question that you’d like answered in a future blog post or newsletter, instructions are at the bottom of this post.
Q: Travel is so (so!) important to me, and I really want to understand how better to plan short trips with friends. I’m single right now, and going away solo is a big investment — a solo retreat for $500 can be cool, but I’ve definitely had my share of them. I really wanted to do a weekend trip to experience summer before the fires, but everyone I asked was already booked out for the next 4-6 weeks — sometimes even already having group trips planned with a fixed number of people.
Or alternatively, other folks don’t like to make a plan in advance. But I notice some people can get this done within their friend group. One friend mentioned that she multiplies the number of people involved times the number of weeks or months, and that’s how far ahead she needs to get everyone’s calendar coordinated. Still, I was a little at a loss when coordinating with just one person has led to so many dead ends. I’m curious what insight you might have from your research!
A: You have a lot of options here! I’ll dig into each of them below…
Option 1: Treat it like a VIP area with limited spots and firm RSVPs
This is your chance to live out your alternate life in which you’re a travel agent. You come up with a full itinerary with dates, locations, and prices locked in. You float that to your peeps as an enticing invitation (dreamy brochure with gorgeous photography optional). Then people either sign up or they don't — there's no crazymaking Jenga of trying to make decisions incorporating everyone's calendars.
There are a few places in life that demand clarity about the number of spots available and your commitment to claiming one of them: flights, VIP tickets, and dinner reservations at shmancy restaurants. You totally have the right to use this approach to make trip-planning less wishy-washy.
A great way to initiate this kind of trip-planning is to invite friends to a dinner or happy hour and use the Better than Small Talk: Travel deck to get people talking about what kind of traveler they are, what they value and prioritize the most when traveling, what kind of travel memories they cherish the most.
Even if you don’t take a trip together, that kind of conversation will help you feel closer to your friends right at home. But if you’re ready for the next step — moving inspiration into action — here’s what to do:
1. Decide exactly how many spaces you’re making available on this trip.
2. Create an event invitation.
3. Over-invite. Share the invitation with 2-3X the number of people than you have spaces for, letting people know that they need to opt-in first-come, first-served, to save their spot on the trip.
4. Include a deadline for replies so you get a firm Yes or No that leaves ample time for finalizing a plan. It’s important here to not allow Maybes, and it you do, to set a deadline for Maybes to give you a firm answer. It’s ok to ask that people be clear and committed with their decision to join or not especially when reservations (that require $$ deposits) are being made.
Option 2: Make it a surprise party for everyone, including you
Take an experimental approach, like Logan Rockmore does. He described in The Atlantic that twice a year he books a vacation rental and invites a list of 30+ people to jump into it with him. They're a mix of friends and former colleagues and he is fine with whoever comes and whoever sits out. They figure out sleeping arrangements based on whoever shows up — if it’s crowded or sparsely attended, so be it.
Logan’s open-door attitude towards planning results in a twice-annual reunion made of a constantly shifting and growing community of friends and partners. For many of them, this getaway is sacred time since it's the only time they get to really talk to each other. And with back-to-back days together, they have the time to go deep in their conversations because they don’t feel rushed to wrap things up quickly.
Something like this works especially well if you're open to mixing friends from different groups and if you’re cool to roll with the spontaneity of a surprise assortment of final attendees.
If you’re going to try this, I recommend letting people know something about the other folks you invited because that will reduce their hesitancy to go on a trip with other folks they don't know well. If you do this in a super fun way, like a Hall of Fame Mega Email-Introduction that’s playful, fun, and flattering to everyone, it’ll make everyone excited to meet everyone else, which makes them more likely to say yes. You can also create a fun video where you show a picture of each person and say what you love about each of the people you’ve invited. This will make each person feel special and get everyone stoked about the new friends they’ll meet during the trip.
Option 3: Outsource all of it
If you don’t want to play the role of travel agent, nor deal with the anxiety of not really knowing who’s coming, and you’re ready to drop some coins on a luxurious, zero-stress travel indulgence, outsource ALL of it. Here’s how:
Find an existing retreat and invite your friend(s) to come with you. You get to offload all the planning work to the retreat organizers. Then you get to visit an exciting new destination with your pals, deepening your friendship while you’re there and potentially even making new friends along the way.
Built-in Bonus: The new friends you make during the retreat are almost guaranteed to be the kind of people who love to travel with friends, so hang on to those new travel-lovers and plan some future trips with them too. Maybe you can pencil in plans with your new friends for a future adventure before you even fly home?! ;)
Option 4: Go small
If trying to organize a huge friend group vacation has you pulling your hair out, consider taking your goals down a notch and focus on creating an exceptional experience for a party of two.
Roll like Heather and Catherine, friends who have never lived in the same city but who take 1-on-1 vacations together every year. They’ve gone to Iceland, the Caribbean, and the red rock country of the American Southwest.
It works because they each are willing to jump into a new experience and travel just about anywhere — and most of all, because the reason they go on the trip is just to spend time with each other. Sock away some money in a separate “Travel Fun(d)” bank account, and invite a friend to sign up for a flight deal newsletter like going.com with you.
When you see a flight deal that looks awesome to you both, jump at it using that cash you stashed. Split up the tasks like booking a place to stay or a rental car. If you remember to keep things simple, and focus on enjoying each other’s company, you’ll avoid the stress that can come with wrangling a big group of wily humans into a single cohesive action.
Retreats, camps, and organizations to check out
Here are a few retreats, camps, and getaway organizations that bring people together for friendship and community. They give you the chance to travel or yo hang out in a retreat or camp-like setting.
OmNoire for BIPOC women
Remote Year for mini digital-nomad-and-make-friends trips
Plastic-free wellness retreats
Hollyhock personal growth retreats
Kripalu Yoga and Healing Center
Camp Grounded Summer Camp for Adults
If you care about social justice, you might want to check out Ruckus Society’s Action Camp — a week-long intensive training program designed to unite community members, students, organizers, and other people interested in learning more about campaign development and expanding their nonviolent direct action skills.
And here are 20 exuberantly interesting sleep-away camps for grown-ups, including Zombie Survival Camp, Space Camp, Nerd Camp, Circus Camp, Music Camps for adults, and more.
That oughta keep you busy for the next 17 summers, but if you still have questions or need more help, reach out below!
XO,
Kat Vellos, author of We Should Get Together: The Secret to Cultivating Better Friendships