Planning a vacation can be taxing, but planning a group vacation can be a nightmare. Coordinating with numerous people makes agreeing on a destination, budgeting, booking accommodations, and every other aspect of traveling that much tougher.
But group trips can be splendid with the right companions and mindset. We have some tips to help your group vacation go as smoothly as possible, ensuring everyone can have a good time, and no one goes home feeling sour.
1. Set a Clear and Considerate Budget
Before we go any further, we want to say one thing: it’s almost always best to travel with people in a similar economic position as you. If you make low five figures and your best friends make comfy six figures, a trip together might not be ideal.
The person with more money will feel stifled or frustrated by either paying more than their fair share or having to skipout on things to stay within a budget. The person with less money may feel less or embarrassed that they can’t spend as much. Before booking anything, set a detailed budget for the accommodations, travel, excursion, dining, and other expenses. If you can’t agree, reconsider the trip.
2. Choose a Low-Effort Trip
One of our best tips for planning a successful group trip is to make the vacation as easy as possible to plan and enjoy. Some of the easiest options are all-inclusive resorts, road trips, beach-focused vacations, and camping trips.
These kinds of vacations either offer everything in one convenient location (cruise ship, resort, etc.) or offer limited activities, making it easier to stay together and limiting disagreements on what to do (camping, beaching, etc.).
3. Require a Commitment From Everyone
We hate flaky friends. To ensure your money isn’t wasted, make everyone pay for flights and accommodations before anything is booked. This way, if people want to back out at the last second, you won’t be forced to eat the share of the cost.
Also, if you're not booking together, make sure everyone books flights at the same time. This also reduces the odds of someone canceling after the Airbnb is already booked or the scuba diving is paid for. We also suggest reminding—and maybe pressuring a little—everyone to take off work, call their dog sitter, cancel other plans, etc.
4. Delegate Responsibilities
How you delegate responsibilities depends heavily on your group dynamic. Many groups have a leader or “mom” who tends to be the most organized. One might use the term “control freak.” If everyone agrees, this person can take the lead in scheduling and booking flights, accommodations, excursions, etc.
Otherwise, it’s best to give each person a responsibility, such as booking the flights, finding restaurants, making reservations, choosing a hotel, etc. If you don’t address who should take care of what, something may get missed and the trip falls apart.
5. Respect Everyone’s Boundaries and Limitations
Just because you’re willing to take a 10-hour redeye and stay in a sketchy hotel doesn’t mean all your travel companions are cool with it. Just because you love skydiving doesn’t mean everyone else is up for the thrill.
If someone says they get seasick, don’t plan a boat ride. If someone says they’re too tired, don’t pressure them to go to a nightclub. It is even more important to consider if one or more of your companions have a condition that requires more resting time. Ultimately, if someone’s boundaries and limitations will ruin your trip, don’t go with them.
6. Make a List of Priorities
Long before the trip, but perhaps after flights and accommodations are booked, have everyone make a list of their vacation priorities. One person might want one whole day on the beach, while someone else has a museum they’re dying to visit.
People must be reasonable — no one can make a list of a dozen effortful priorities and expect the group to adhere to them. Have people pick three to five, and then narrow it down based on vacation length and overlapping priorities.Ideally, everyone should have at least one priority fulfilled.
7. Lay Down Some “Rules”
Okay, please don’t set any annoying rules. Rules like “no drinking before 5 PM” or “no talking to strangers” are not in the spirit of vacation.
However, some rules, like “always meet back in this spot,” “if you’re alone check-in every two hours,” or “don’t bring strangers back to the hotel” are more reasonable. Every group will need to communicate what kind of rules they’d like to have in place, but it might be best not to refer to them as “rules.”
8. Keep the Schedule Loose
We recommend keeping the schedule on the looser side but still planning activities. Maybe one activity a day is sufficient, ensuring everyone gets out and about without shackling them to a minute-by-minute itinerary.
Depending on how everyone feels, you may want to make time for people to go off and do their own thing. Your group may also like to see where the day brings you all, rather than having a locked-in plan.
9. Discuss Expectations
This discussion can be rolled into the talk of priorities. However, this is about more general vacation expectations and styles. Everyone in the group should explain what they expect this vacation to look like before planning everything to avoid disappointment or arguments.
Some people like to do as little as possible on vacation, meaning no museum visits, guided tours, whitewater rafting, ziplining, and so on. Others want to cram it all in, going from an art gallery to a Broadway show to dinner to a nightclub and ten other places the night takes them.
10. Go With the Flow
Try to go with the flow. Keep an open mind and be fluid with your plans. We’re not saying to let all your wants take a backseat, but the more easygoing you (and everyone else) can be, the more enjoyable the trip will be for all.
This is also why it’s best to let everyone choose one priority the group can fulfill. If everyone can do at least one thing they’re excited about, it’s easier to go with the flow for the rest of the trip. Even if you wouldn't choose a certainactivity for yourself, you might wind up having a blast and discovering something new about yourself.
11. Foster Consistent Communication
Make sure everyone stays in the loop about everything at all times. This communication keeps everyone on the same page and enhances safety.
You just booked the hotel? Awesome, let your travel buddies know and send them the reservation details. You just found out it’s going to be rainy the whole time you’re at this destination? Alert everyone so they can prepare and pack accordingly. Have you decided to go for a solo walk through this new city? Tell everyone where you’re going.
12. Designate a Daily Time to Be Together
To ensure the trip retains a group vibe, have at least one time each day that everyone spends time together. This could mean you always have breakfast together, or dinner, or maybe everyone goes out to party as a group each night.
As mentioned, people can split up and go solo, but to keep things convivial, at least do one thing together each day.
13. To Share or Not Share Rooms
Sharing rooms comes down to budget and people’s boundaries. For very close groups, sharing rooms may be a no-brainer, which is great because you’ll save money. But if people want their privacy, it might cost more.
Our opinion on this is that if someone isn’t comfortable sharing a room, but everyone else is, that person needs to be responsible for the extra cost of a private room. If sharing rooms is a no-go, a homestay is usually the better option, as you can rent a house. But if you are sharing, hotels are typically more affordable.
14. Download Splitwise (Seriously)
Splitwise is a blessing for group trips, and roommates, friends, couples, and everyone. This app makes it a breeze to keep track of who paid for what and who owes what, without having to send Venmo requests or text one another asking for money.
The app can actively show you where everyone in the group stands, making it easy to decide who pays for tomorrow morning’s coffee or who doesn’t have to pay for dinner one night. If you use it wisely, you may not even have to settle up after the trip. (We swear this isn’t a Splitwise ad; we’re just fans.)
15. Don’t Go With a Group If You Can’t Compromise
While researching group trips and considering personal experiences while writing this guide, we encountered many people who seem to be allergic to them. If you need to spend every second of your vacation doing exactly what you want to do, a group trip may not be for you. Compromise is the key here, so you can’t be selfish or stubborn.
While you might not be thrilled with every single second, traveling with close ones can make for treasured memories and tighter bonds. In our opinion, sacrificing some of your freedom and control on vacation is worth it to share these experiences.