How to Plan a Group Trip

Traveling in a group can be…challenging, but where’s the fun if there’s not a little bit of a challenge?

Travel inspiration typically arrives in some organic way—you read an article online (like, say, this one on fishing off the coast of Baja, Mexico), catch a clip of a place on TV or YouTube, or tour vicariously via Instagram before a locale graduates to your must-visit list. And once that seed has been planted, one of the best ways to let it grow is to recruit a few like-minded participants—friends, family—to join you. With that comes companionship…and complexity.

But we’ve got you covered with this, our guide to best plan an activity-centric group trip:

Choose a Place

“We should go somewhere together,” is a common friendship refrain. But defining that “somewhere” will make it tangible, and it will also help you start to unravel how long you plan to escape. If you choose a place that’s relatively close to all the intended adventurers, then you can easily swing a long weekend without swallowing anyone’s vacation time. But if you’re going further afield—to South America, say, or Europe or even Asia—you should bake in more time. No one wants to spend as much time on the ground as they did in an airplane. A good rule of thumb: plan to spend at least a day per flight hour. It ain’t an exact ratio, but it’s a good ballpark.

A good rule of thumb: plan to spend at least a day per flight hour. It ain’t an exact ratio, but it’s a good ballpark.

Beyond that, define the “what” first as that will help you highlight where is the ideal spot to visit. Fishing? Baja beckons, as does Florida, Montana, Idaho, Central America, and the Caribbean. Diving? Belize, Honduras, Bonaire, and the Caymans are all within striking distance. And as you narrow down to a shortlist of locations, consider the overall skill set of your potential group and make sure you find a place that can accommodate all activity levels. Don’t pull the equivalent of dropping a first-time skier at the top of a double-black diamond.

Choose a Crew

This one should be easy—create a list of friends that view the active world the way you do. But think a bit about lodging. If you invite everyone in your contact list, lodging costs and logistics may prove challenging (more on that below). A group between three and eight might be the ideal sweet spot, especially if your logistics includes on-the-ground transportation.

Plan Ahead—Way Ahead

After you’ve got your shortlist of dream participants and a place picked out, hone in on when everyone can attend. First, pay attention to any seasonal shifts like hurricane or rainy seasons to help avoid any climate catastrophes. Then survey the crew, using some sort of digital solution like a Google Doodle, which can allow you poll your friends on potential dates. Then you can narrow it down a few dates that work for everyone. And get ahead of the curve. Family, work, kids, and 1,001 other obligations make everyone’s lives a chaotic jumble of competing obligations. The more in advance you plan everything out, the better the chance of everyone attending. And you’ll also probably get better deals on airfare.

The more in advance you plan everything out, the better the chance of everyone attending.

Lock Down Airfare

After you’ve got the dates and a tentative list of attendees, the group organizer should dive into booking airfare. You don’t have to buy tickets for everyone and wrestle with reimbursement. Start by getting your own airfare squared and circulating that info to the wider group. Think of it as establishing a beach head—others might be flying from different cities (or different airports within the same city), so if you book first, you provide a general timeline for others to follow.

That said, if you want to score the credit card points or airline miles, you can always buy tickets for the entire crew; online payment options like PayPal or Venmo can help you square what you’re owed long before the trip.

RELATED: Deep Sea Fishing in Baja

Secure Lodging

Once you’ve got your head count and have your airfare, it’s time to secure the base camp. For larger groups, Airbnb and VRBO offer smart, cheaper options, rather than booking a handful of hotel rooms—and it also offers the ability to cook in, rather than always eating out. Some destinations also have hotels with options that have more than one room, ideal for smaller groups.

Also pay attention to the property’s proximity to where you’re going to play. And more often than not, certain properties cater to particular activities. Think such amenities as easy access to a guide and a boat for deep-sea fishing or diving, or easy bike rental and quick access to the singletrack. Choosing these spots also means the hotel staff will share your appetite for the outdoors, and you’ll never stand out, covered in mud or smeared with the aftermath of a deep-sea fishing adventure.

What to Bring

For active-centric trips, most likely the crew in attendance will have their own kit—mountain bike clothes, say, or what they need to thrive during a day-long deep-sea fishing excursion. But it’s always a good idea to draw a boilerplate packing list about a month before departing. That way everyone’s on the same page, and can either arrange to borrow items or buy them to address any gaps. It’s also a good idea to volunteer to bring a few common-use items. No group staying in the same house needs five Bluetooth speakers.

Sweat (Some of) the Small Stuff

It’s a good idea to source a local outfitter that’s close to where you’ll be staying. For guided trips, this is essential, and often the guides and at least a small support shop will be part of an all-inclusive sport-centric hotel or lodge. But even for more DIY projects, a local outfitter can provide beta on where to go, when to go, and how to avoid the crowds. And they’ll also sell whatever small stuff you forgot—stuff like spare tubes, sun block, or an additional layer of protection against the elements.

It’s a good idea to source a local outfitter that’s close to where you’ll be staying.

If you’re visiting during peak season and have crowds larger than four, it’s a good idea to secure at least one or two dinner reservations before you get there, just so you don’t face a two-hour wait or cram yourselves onto a four-top at the bar. The last night is often a great night to splurge. But as it relates to other meals—and other non-sport activities—allow a degree of flexibility.

You’ll probably all be departing at the same time to start biking or hiking or fishing or skiing or whatever. But some like a lazy morning, while others can roll out of the bed and hit the ground running. Post-event, some will want to go right to après, while others might want coffee, the sauna, or (gasp) a bit of solo time to check in with their 9-to-5 gig. Keeping the wider itinerary loose will make everyone more comfortable, afford more spontaneity, and putting everyone’s spirits and attitudes on an even keel.