The Art and Zen of Group Travel

How to get the most from it? Go with the flow—for the most part.

Solo travel has its rewards: freedom, spontaneity, adventure. Point your nose in one direction and follow it.

Group travel doesn’t work like that.

Point your nose in one direction—and chances are that a half-dozen other noses will be pointed at an art museum, a mall, a McDonald’s, an organic grocery store, a bookstore and a NASCAR track. Whether you’re traveling with high-school buddies, an adventure-minded book club or more in-laws than you actually knew you had, group travel can be messy. It is usually complicated.

But it is, perhaps paradoxically, often more permissive of magic and the truly unexpected than solo trips. Interesting things can happen when our natural inclinations are challenged—even when your natural inclinations would happily lead you to a pottery exhibition and your father-in-law wants to spend the afternoon diving with sharks. It might, in fact, turn out that sharks were the better bet all along. And while solo travel is often exceptionally safe, there’s truth to the idea of safety in numbers: A pack of old field hockey teammates may, in some circumstances, actually have more freedom than that team’s goalie traveling on her own.

Be firm; be free

So how to handle the inevitable aggravations? Look for the balance between firm and free. Figure out, early, what everyone must do—say, land at the destination airport in time to travel onward together—and realize that there are probably fewer things that fit on that list than you might think. (If the worst thing that happens following a late arrival is that someone has to take a cab, that is … not a big problem.)

It’s also crucial to accept that your must-do might not be the group’s must-do—and that is OK. Maybe the dissenters are at a point in their lives when flexibility feels like failure—and you can head off to the seashell museum solo. Maybe they can dip into your store of excitement for conchs and whelks and come along. But even if someone opts to sack out on a couch to watch baseball rather than accompany you, that could just be their vacation mode. Strive not to take demurrals to heart.

Schedule your dreams in

Along those lines, compromise has a place—a key place—in any group trip. A destination and time frame must be agreed on; a general vibe—party, family, spa, activity—should be determined. Constant compromise, though, wears on the soul, so incorporate it judiciously. The perfect trip, in fact, may be a series of solo or small-group adventures within the context of a bigger experience. It is smart, not selfish, to schedule time within a group trip to indulge your own interests without apology. And when you do it, do it right: If your true heart’s desire is to explore an Irish distillery, don’t settle for a quick look at the gift shop. If you want to climb an Icelandic glacier, do it, whether your trip mates want to come along or not.

This isn’t an excuse to be unpleasant—if you’d rather not invite members of your group to a special-to-you expedition, it might be fair to ask if you’re traveling with the right people. Just be sure that your own vacation needs are tended to: The biggest risk of group travel—besides the tantrums and disagreements that might in fact be the natural occurrence of any group of human beings in roughly the same place throughout history—is feeling like you never got to do anything for “yourself.” It’s fair to say that there are situations that can make this impossible—traveling with the very small or very old, for example. But otherwise, don’t be that person—know what you want and do it.

And just remember: The best thing about group trips is that most of the time even the most spectacular flameouts are funny in retrospect and an expedition shared with friends and family tends to deepen bonds, regardless of the setbacks encountered along the way. In other words, sometimes a spat in company is better than a solo selfie.

Make group travel a breeze

Here are 10 resources for making group travel eaiser—and fun.

1. If your travel mates are anything like ours, the hardest aspect of planning a group trip will be settling on dates. Rather than spend weeks talking through school vacations and family commitments, try Doodle: Come up with some options, share them and let all-comers pick the ones that work. This also ensures that the pushier types in your group don’t drown out the preferences of everyone else.

2. Veteran group-trip planners say this site, rather than Airbnb, is their go-to for vacation rentals with 10-plus bedrooms.

3. Parcel out bills for accommodations, rental cars, groceries and the like with the Splittr app. Made for traveling groups, it accepts multiple currencies and works offline, which saves on data charges.

4. Imagine shepherding a dozen people, with different interests and walking speeds, through the Louvre, the Grand Canyon or even an airport: The FriendLynk app can handle this logistical nightmare, providing a map with all their locations and easy messaging options when it’s time to round them up.

5. Whatever its political profile at the moment, Facebook offers group travelers a top resource: a private group page, with varying levels of privacy. There’s no easier way to share and store documents, updates and photos in one place.

6. At least one person on the trip should have a Project Fi phone, the telephony brand from Google. For years, T-Mobile was the go-to U.S. carrier for frequent international travelers, thanks to its no-added-cost data roaming in most countries. Project Fi, though, does T-Mobile one better: Its international data is charged at the same rate whether in the U.S. or most other countries—but unlike T-Mobile, which offers free 2G service overseas, Project Fi’s roaming data is full speed.

7. A free version of the pro travel planning system Travefy allows users to make and share itineraries, chat about them and work out common expenses (though we prefer a dedicated app like Splittr, above, for this last job.)

8. While there are dedicated apps for this, we find that the easiest way to share photos is whatever you’re using to store images. For us, that’s Google Photos, which allows users to create an album of images and then share that album with all interested parties. For a more expansive affair, try Cluster, through which you can set up a group of friends with whom photos are instantly shared.

9. For glam city breaks with friends, the Velocity app makes booking tables at hot restaurants (The Lambs Club in Manhattan, Birch in Hollywood) easy, with integrated bill-splitting options. One issue: It’s limited to the cities above as well as Miami and London, with more reportedly on the way.

10. An easy way to share ideas about how to spend your days, TripHugger allows users to create an itinerary, share it with friends and then edit that itinerary together—changing the order of events, for example. Users can edit offline, and if you are democratically minded, set up polls to gauge your group’s level of interest in various attractions.

Photography: Jovo Jovanovic/Stocksy, Adobe Stock; JackF, Adobe Stock; Rawpixel, Thinkstock; Gregory Lee, Adobe Stock; Andrey Pavlov, Stocksy