8 Tips for Planning a Trip with Friends

Read these 8 tips for planning a trip with friends.

When planning a trip, I’m scrupulous about the details. I keep track of everything from the walking distances between must-see spots to restaurant phone numbers to museum hours. I map out itineraries and, sometimes, alternate itineraries. You know, to keep our options open.

My best friend couldn’t be more different. Planning stresses her out. She’s the spontaneous kind, a firm believer that the best moments aren’t the ones we plan. When I start to think about what’s next, she keeps me grounded in the present.

Our other bestie (and fellow traveler) falls somewhere in the middle. She’s a planner, to be sure, but she doesn’t get as bogged down in the details as I do. She lets me take charge, but she’s glad to talk about logistics or call the shots when I’m feeling conflicted.

The three of us have been planning trips together for close to a decade, and we’re still learning to accommodate each of our personalities and preferences. We complement each other well, but our quirks and differences can bring out a lot of friction.

Traveling can be as much about navigating relationships as it is about navigating a new place. If you’re planning a trip with friends, follow these tips from the get-go to avoid bumps on the proverbial road later on.

1. The art of compromise

Group travel is all about compromise. But in order for compromise to happen, communication has to happen. Just because one person’s a natural planner doesn’t mean he or she can (or should) make all decisions for the group. Decisions like where to go, when to go, how long you’ll be gone for, and how much you’re willing to spend have to be made together. This takes honest, open communication.

Each person should both state his or her preferences and listen to other points of view. Sure, you’d rather go to Montreal in the fall for its gorgeous foliage, but if your friends who work in schools are pulling for a summer vacation, something’s gotta give. Boarding a train to Machu Picchu is the stuff of bucket lists, but the time it takes to travel to and from the ruins could well ruin those plans if you can’t take off for more than a long weekend. Practicing the art of compromise from the start prevents conflict later on.

That said, pre-trip planning and stressful, spur-of-the-moment decisions (like what to do when a flight gets canceled) can heighten tensions fast. If you’re thinking about planning a trip with someone who’s difficult to deal with on the reg, traveling together could do the friendship more harm than good.

2. Talk about #travelgoals

If you’re planning a trip with friends, chances are you’re compatible and have some shared interests. Even so, people have different expectations when it comes to travel. Is your goal to be on the go, or are you looking for leisure? Do you all but live for nightlife, or is waking up at dawn for a run more your speed?

Discuss what everyone wants out of the trip, including each person’s must-sees. Chances are, there will be some overlap here. But if someone’s must-see spot is less of a landmark and more of a monument to a niche interest, decide whether to stick together or split up. Leaving some room in the schedule for alone time can ensure that each person can set out to pursue their interests without feeling rushed.

3. Divide and conquer

Decisions like travel dates and a budget have to be made together. Moving forward, figure out whether you’re planning all aspects of the trip together or delegating the planning to certain people.

If you’re traveling with people who live near you, consider designating some time to get together so that everyone can hash out ideas in person. I have a friend who takes this approach, and she’s been able to plan the bulk of each of her trips in a single, albeit several-hours-long, meetup. Sure, this method’s a bit of a marathon, but there’s no need to finish in one sitting. In fact, she and her friends continue planning through a shared Google doc, adding to it whenever a good idea comes up.

Sometimes, though, people want to take charge of certain aspects of the trip, whether it’s logistics, dining, or itineraries. If you’re a natural planner, remember to keep in mind each person’s preferences as much as possible, and be sure to check with the others before booking something like a flight or hotel, which can be non-refundable. If you’re not a natural planner, be careful not to let the weight of these decisions fall onto one person. Offer to help, even it’s as simple as booking reservations at the restaurants a friend found. It’s appreciated.

Of course, before getting started with either approach, you’ll want to discuss how to divide the budget. No need to plan it all out to the dollar, but you’ll keep costs (and tensions!) down if you hammer out a general idea of how much should go toward transportation, accommodations, and entertainment. (More on that below.)

4. Getting there

If you’re not sure how much of the budget should go to what, start with researching flights or other forms of transportation, such as train tickets or car rentals. Transportation (along with accommodations) can be a big chunk of the budget, so having these plans in place will let you know how much will be left over.

Remember, too, that your group needs to get there and get around once you’re there, whether that’s via car, public transportation, walking, etc. This begs the question: Who’s going to be in charge of navigation? That is, will just one person pull up walking directions or enter an address into the Uber app each time each time you’re going somewhere? Will you need to coordinate flight times with a bus or ferry schedule? Who will look into that? Talk about all of this before going for smoother sailing once you’re there.

5. Making accommodations

One of the perks of traveling with friends is that you’re able to split the cost of a room. Once you’re able to estimate how much to spend on accommodations, narrowing down hotels or Airbnbs to a price range and geographical area can make finding (and agreeing on) a place a lot easier. Reading reviews will help to narrow it down even more.

6. Have reservations?

You’ll also have to decide whether to book tables, show tickets, walking tours, and the like before the trip. I find that booking at least a few reservations and activities beforehand eliminates the guesswork of what to do and when once you’re there — and guarantees your group a spot.

In some cases, however, waiting to book a reservation could make more sense. You may want to know the weather will be pleasant before booking that non-refundable sunset cruise, for example, or wait till the last minute to score discounted Broadway tickets. But if something tops your must-see list, it’s a good idea to book it ahead of time rather than leaving it up to chance.

Sometimes, no reservations are needed. For example, I never book reservations for lunch. Instead, I’ll make a list of restaurants in each neighborhood we plan to explore so that, come lunchtime, we’ll have some places in mind wherever we are. You don’t even need to research this beforehand, though. Getting recommendations from a local right before lunchtime has introduced me to some real gems.

7. Pay, don’t delay

Shared expenses are often part of traveling with friends. Waiting to divide costs can lead to confusion over who owes whom. You’ll want to reimburse others ASAP, even if it’s just for the cost of ice cream. The Venmo app makes this super simple. If you have to wait till you’re connected to Wi-Fi to use Venmo, just take photos of receipts for reference.

8. Continue to communicate

Traveling with friends all but guarantees that someone will get irritated with someone after a while. Knowing how to overcome communication pitfalls will keep the trip as drama-free as possible.

First, be self-aware, which can prevent conflict before it starts. Here’s what I mean. If you tend to get hangry, bring a snack wherever you go. If you’re tired and about to snap, choose a power nap over more sightseeing. If you’ve become hyper-aware of everyone’s quirks and are feeling hyper-annoyed, seek out some alone time. Just be sure to let the others know where you’re going and about how long you’ll be.

Second, along those lines, don’t forget about self-care. Rest, exercise, meditation, and prayer are all techniques that can help you feel more balanced, not to mention more equipped to deal with your travel companions.

Third, address conflicts sooner than later. Even being on the same page while planning doesn’t prevent conflicts of interest during the trip. Talk about an issue before it boils over into a fight. If a fight happens, take some time to cool off, but don’t wait too long to apologize and talk about what happened. Tactics like passive-aggressive behavior or the silent treatment will make a trip real awkward, real fast. Instead, take this chance to work through a solution to prevent similar conflicts in the future. Be honest but diplomatic!

Fourth, be positive. Plans get derailed. Thunderstorms come up. Restaurants look better on Instagram. Phones die mid-selfie in spite of the excellent photo op. Just move forward, focusing on the good. If someone starts to mope, help him or her put the situation into perspective. Maybe it’s not that big of a deal. Maybe it’ll make a great story one day. Optimism goes far.

Grotto quote graphic about planning a trip with friends: "Be positive...Optimism goes far."

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