If you enjoy trips with lots of walking or hiking, but your friend would rather lounge by a pool all day, consider how much you’ll both be willing to compromise and if it’s worth it to invite them or not. Also consider whether a friend is an early riser or prefers to go to sleep late, and how high-maintenance they tend to be.
If one or two people simply aren’t available, tell them that you’re sorry it didn’t work out for this trip and that you’ll let them know when you’re planning your next holiday with friends.
For example, you could say, “I know it’s awkward, but we should talk about a budget before we start planning everything. I know I’d like to keep the full cost of the trip under $2,000, if we can!” If it starts getting too expensive for any of your friends, let them know that you understand if they’re not able to splurge for this trip, and that you’re excited to travel with them at a time that’s better for them.
Choose friends who aren’t afraid to try new things and who won’t be too grumpy in the face of jet lag or long days of walking.
This is a great choice for a larger group of five people or more, because there’s something for everyone and the group can easily split up if some of the group can lay in the sun all day, while more active friends can rent jet skis or go snorkeling.
Ask your friends to take turns driving, so one person isn’t behind the wheel the whole time.
Use online documents to share ideas as you create the itinerary, and send out a final version when it’s all done.
Let your group know early on if you’ll be sharing rooms, so they can choose roommates and work out any issues.
If some activities are similar, like boating and snorkeling, try to merge them. For example, you can rent a boat for the day and bring snorkeling equipment for those who want to swim.
Plan for downtime in the afternoon, especially after lunch when the group may be full and sleepy or as a quick pick-me-up before dinner.
Plan a meetup spot and time, especially if you’re in a foreign country where not everyone has phone service.
Remind your friends that you won’t be able to accommodate everyone at every restaurant. If your group has widely varying tastes, compromise: choose a burger place one night, and go out for sushi the next. Not everyone will get their favorite food every night, but they’ll be happier to compromise knowing that their voice was heard.
Remind your group to bring any IDs necessary for traveling. If you’re going abroad, you’ll need your passport. If you’re staying in the country, make sure to bring your driver’s license or another government-issued ID card.
Share luggage space and items like toothpaste, shampoo or camping tents.
