The Ultimate Guide to Planning a Group Trip

Not everyone travels in the same way. Some like to relax and take it slow, some want to hit the ground running, and others fall somewhere in between.

If you want to invite others on a trip you've already planned, be clear about what the itinerary entails and set expectations so invitees can opt in or out. Not everyone will want to spend ten days hiking the Appalachian trail, and that's okay—just make sure they don't find out after they arrive. If the group is planning a trip together, be prepared to compromise. It's perfectly possible to satisfy everyone's vacation style (more on this later) for a trip everyone will treasure.

The 'travel style' discussion is also the time to consider other lifestyle factors. Make sure the early risers aren't sharing a room with the night owls, and the light sleepers aren't stuck with someone who snores like a chainsaw. Be honest now about your daily needs and routines to avoid resentment at the end of the trip.

The time to get transparent about money is before the trip, not after the expenses start rolling in. If inviting friends to join you on a pre-planned trip, be upfront about the cost, what’s included, and what expenses they will be expected to cover. If planning a trip collaboratively, budget may be a limiting factor when deciding on the destination, trip length, activities, and accommodations.

Once you’ve discussed budgets, create a priorities list to decide where to focus your group funds. If everyone in the group values privacy, put more money towards accommodations. If your friends are all foodies, you may decide to hack it in a hostel to dedicate more of the budget to group dinners. Agreeing on your collective priorities will make planning an itinerary that much easier.

This step gets more complicated as more people are added to the group. Coordinating everyone's can't-miss spots into one itinerary is bound to leave at least a few people bored or unsatisfied. The key to avoiding a grumpy group is to occasionally break up the group. Rather than stick to a rigid group itinerary, select a few tentpole events that everyone agrees to attend. The rest of the time is theirs to spend as they wish.

For example, during a weeklong trip to New York City, the group is expected to meet for dinner on Tuesday, brunch on Wednesday, and a Broadway show on Friday. The rest of the time, breakout groups can wander as they please. Structuring the trip in such a way can also resolve any lingering budget or travel-style tension, as not everyone will feel obligated to participate in every activity.

Tip: It helps to schedule one of these "mandatory" group events directly before departure to ensure everyone is gathered and ready to leave together.

Don't let the travel stress fall on the most responsible friend. Be intentional about delegating responsibilities to share the load.

Before the trip, divide up planning responsibilities like booking accommodations and travel. Assign a leader for each task and agree on a due date. For any Type B travelers, partner up to conquer tasks like booking a hotel. Working in teams keeps everyone accountable and makes the process more fun.

During the trip, divide logistical responsibilities. For example, assign a point person to make restaurant reservations, another to book event tickets, and another to send out group chat reminders to keep everyone on schedule. If everyone has a small task, it lightens the load on any one traveler and ensures nothing slips through the cracks.

Money may be the top cause of tension on group trips, so decide how you'll handle it well ahead of time. Before your trip, agree on which expenses will be shared and which will be individual—for example, whether you'll split group meals evenly or each pay for what you ordered. For shared expenses, keep track of what each person owes and decide ahead of time whether you'll settle up at the end of each day or the end of the trip. Apps like Tab make it easy to split expenses and avoid squabbling over the bill.

Tensions can run high when planning a trip, and there's potential for butting heads. The number one key to group travel is to keep cool, take a step back, and remember that your goal is to have a memorable experience with your friends and family. Be honest about your budget and expectations, know when to schedule some alone time to unwind, and focus on being in the moment with the people you want to share it with.