I've discovered a group trip format that I really love, and I wanted to share it with others because (a) you might find it fun to host or join something like this in the future and (b) selfishly, I would like more people to organize trips like this so that I can join them!

The basic idea simple: live in an interesting new place for a few days or weeks with friends in walking distance, as if we were neighbors. I pick a walkable neighborhood in a city, tell friends what dates I will be there, and then draw a circle of a 5-minute walk from my AirBNB and recommend to friends that they book within it. I've now organized half a dozen of these trips to places like Chautauqua, Buenos Aires, Las Catalinas, and beyond with groups of 8-40 people each time. It's a blast and I can't wait to do more.

I love these trips because they are a way to explore the world while staying connected to friends. In some ways it's even better than living in the same city as a friend, because the intensive nature of an extended trip with a small group gives you focused time to see the same people every day or at least multiple times a week. This builds friendships quickly, compared to the typical rhythm that happens when you live in the same city as a friend, where you might see each other for dinner once a month but never really build up that velocity of the friendship.

An important aspect of this format is that it is very much "choose-your-own-adventure". Here is the basic recipe:
  • Throughout the year, I tell friends that I'll be in X city (e.g. Buenos Aires) for a particular timeframe (e.g. the last three weeks of November) and that if they happen to be free, I'd love to see them there. If they seem interested, I send them an email with some basic details about the trip and a spreadsheet for them to sign up if they're interested.
  • It's very low-key. Basically I just put a pin on a map saying, "Here's where I'll be staying. You should book an AirBNB within a 5 min walk".
  • I create a simple spreadsheet where everyone puts the dates they plan to be in Buenos Aires, so they can coordinate with each other. Some folks choose to book together in group houses, some do not.
  • Everyone comes for different lengths of time – some for the whole month, some for less then a week, and everything in between.
  • Most people work remotely from Buenos Aires over the course of the month, though some folks take the time off to explore the city. It's very much choose-your-own adventure.
  • We join up for meals most nights, and everyone is welcome to coordinate their own activities together throughout the days, but there's no expectation that everyone hangs out all the time.
  • It's very low-commitment. Lots of people show up last-minute, and other people drop out last-minute. Think of it more as a transient neighborhood rather than a big group tour.

I've now hosted a bunch of these and have learned a lot about how to make them fun. Here are some of the tactics I've learned over the years:
  • Chat group as the primary coordinating mechanism: Telegram with channels + viewable history
    • Viewable history is important because people join at different times, and they often have questions that have already been asked. Unfortunately Telegram is the only chat app I've found that has this feature.
    • Once you get past ~10 people, channels are important because they reduce the amount of noise people have to deal with from irrelevant messages.
  • Share the list of people who are coming ahead of time: When inviting someone, it's helpful to give them a curated list of others who will be coming so that they get excited to see them. This becomes less important for folks who've joined on one of these trips in the past, but for folks who don't really understand the format yet, it's especially helpful.
  • Curation is key: At this size (10-20 people at any given time in the city), it's really important to curate the group. People often ask me if they can bring people they don't know, and I've found that it can really bring down the vibe, because it's hard for me to tell if they will jive. It's a bit uncomfortable to say no to your friend asking if they can bring someone you haven't met, but I can assure you it's much more uncomfortable to spend days/weeks with someone you haven't met who turns out to be difficult or unpleasant. (I have learned this lesson the hard way.)
  • Group size: I'm considering doing a larger size so that it would actually feel more like a neighborhood. The 10-15 in the neighborhood at a time is a bit of an odd number because it's too large for 1 dinner table but too small to feel like everyone can genuinely break off and not get to know everyone on the trip.
  • Decoupled bookings: It's important that everyone books on their own rather than you booking accommodation for everyone, because otherwise you (a) bear a lot of risk and (b) are stuck in the middle of people's preferences, which is a surprisingly unpleasant place to be. (The alternative to this is to be extremely hardline about what dates everyone needs to be there, more like a wedding, and try to do something like book a hotel block. But that still creates a lot of work for you and not necessarily much benefit.) If people want to share AirBNBs or something like that, you can still put them in touch with each other, but I don't recommend getting in the middle of the transaction because it likely won't contribute much and it'll get messy quickly. (Again, a lesson I've learned the hard way. If things go well, people don't really notice all the work you put in; if they go poorly, they get angry at you.)
  • Light structure: I've found the trips are even more fun and special if you add some optional structure around them to nudge people to share what they are working on or thinking about. My friends tend to be people who care deeply about their work, and I love learning from their expertise. Here are a few things I've tried, and I plan to experiment with other ideas too in future trips:
    • Dinner leads: One of my goals for this trip is for its organization to be fairly decentralized. There are two reasons for this: (1) it makes it more interesting if different people provide their ideas and energy to plan how we spend our time, rather than me doing all the central planning, and (2) it takes some of the coordination load off my shoulders, which allows me to not spend 100% of my energy planning and allows me to have more fun. One way I achieve this is by asking people to volunteer to organize at least one of the nightly dinners during the trip. They are responsible for picking the restaurant and getting a reservation, which means we end up going to a broader diversity of restaurants than if I were to pick all of them. The organizer also has the opportunity to bring something extra to the dinner, e.g. start the meal with a prompt for everyone to discuss to make the conversation go a little deeper than it otherwise would. The organizer is encouraged to get creative to make it interesting for everyone!
    • Lightning talks: Fun opportunity for everybody to show off their expertise in a particular area, and I ended up learning interesting things about everybody. One thing I've experimented with is having an evening where everyone gives a lightning talk, but after a few of them it gets a little boring to sit still like that, so in the future I'm going to experiment with doing 1 lightning talk over dessert each night instead.
    • Group workouts & sports: On one of the recent trips, a friend suggested that we all go play Padel, which was something I never would've thought to suggest to the group. It was the highlight of the trip for me! I'm so glad he recommended it, and it was a great instance of how having the schedule emerge rather than being planned centrally by me makes the trip way more fun.

  • Group dinner size: Group dinners are a bit unwieldy. Natural instinct is for everyone to gather together each night, but dinners of >6 people are not so fun in my experience. Ideally we'd find a natural way for people to break off in groups more often. This is one downside to me being the primary hub of the group rather than everyone individually having relationships ahead of time, although many of these people do know each other from other contexts too.
  • Effectively signaling that the invite is very low-key: Most people have never participated in trips with this format before, so when I invite them, it's hard to credibly signal that it's totally fine if they don't come. This has gotten easier though as these trips are getting better known in my social circle, since they have more context for it.
  • Remember you're not a tour guide company: It's sometimes hard for me not to feel really responsible for everyone's experience, which is a bit stressful especially as the group gets large and the problems people bump into grows with the number of people, but it's critical for me to make it as decoupled as possible and not play "tour guide", because otherwise I will not have fun. Plus a big part of the purpose of these trips is to experience what it's like to live together in a place, and they're grown adults who can take care of themselves. I'm not getting paid, so if I let myself get sucked into playing tour guide, it can really ruin it for me

If you're interested in organizing a trip like this, I'm happy to share the materials I've created over time as a starting point for how to explain and coordinate a trip of this sort!

As my friends are more and more scattered across the globe in different cities, finding ways to be together has become more important for cultivating those friendships. These "traveling neighborhoods" have been an incredible way to not only stay in touch with people I care about but also get to know them much more deeply than before, and I hope to see more people organizing trips like this that I can join too!
One of our upcoming trips is to Seabrook, Washington
The most recent traveling neighborhood I organized was to Las Catalinas, Costa Rica