5 Tips For Planning a Group Trip

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Traveling as a group (and doing it well) is a fine art. It sounds incredible to go on vacation with a big group of friends, but once you arrive and everyone has their own interests and needs, it can get stressful. How do you plan a trip for a group of friends without feeling responsible for everyone else? Well, here are our five tips for planning group travel:

#1 Choose the Destination Wisely

When you’re trying to decide where to go on a trip, pick your destination wisely. It’s all fun and games until you can’t find a place to eat because no restaurant can accommodate your group size or you have to order three Ubers to get anywhere. When thinking about where to go, consider somewhere small and easy to navigate. It’s hard to transport a group of people from one place to another, so the more you can walk the better. If you’re staying in a city, pick a neighborhood that you want to explore and try to keep most of your activities within a few blocks of where you’re staying. When you are picking your Airbnb or hotel, try to find a place that has something for everyone to do in their downtime. You might want to go somewhere near the beach or with a pool so that people can lounge around when they aren’t on an excursion. Or rent a cabin near lots of hiking trails so that friends can go on a hike when there’s nothing else going on. Really think about where people can spend their time—look for hammocks to hang in or beach chairs to lounge in.

#2 Structured and Unstructured

The key to creating the perfect itinerary for your group vacation is having time for both structured things, like a wine tasting, and unstructured things, like lounging by the beach. If it’s all structured, everyone will feel like they are on a tight schedule. If it’s all unstructured, it will be really tough to wrangle the group. Try to plan one structured thing to do every day of your trip. Rent kayaks, reserve an Airbnb Experience, go snorkeling, get massages, go on a hike, swim with dolphins, etc. Have all of the logistics for that activity figured out and have people pay you for their reservations ahead of time. Then, the rest of the day can be unstructured time. This is when the destination really matters. If you’ve picked a good spot, people can fill their time with lounging by the pool, laying on the beach, going on a hike, whipping up dinner, or something else that they want to do. Put all of the activities and times in an email and, if you really wanna step up your planning game, print them out and give them to everyone on the first day.

#3 Set Expectations

Not to pat ourselves on the back, but this is an awesome piece of advice: on the first day of your trip, have a group meeting. It might sound annoying or unnecessary because you know everyone in your group, but it really helps make the trip run smoothly. In your quick huddle, find out what everyone is excited for. Have people share what they most want to do and see. It’s a great way to make sure you are all on the same page. Then, share information with the group. Give them the itinerary you’ve been working on, let them know what time dinner will be every night, hand out the keys to the Airbnb, and share the wifi password. The goal of this chat is to get everyone on the same page to avoid any miscommunications. This is also the time to let everyone know that you are handing over the torch of organizer to everyone else. You’ve done your job: you did the research and you got everyone there. Now the entire group is responsible for the vacation. It’s important that they have all the same information you do, so give them the itinerary, the Google Map, and any other resources you have so that they can find out information for themselves.

#4 Plan Your Meals

The only thing worse than being hangry is traveling with people who are hangry. Hanger leads to frustration, disappointment, fights, and rumbling stomachs. Planning your meals for the day will make your trip run smoothly and ensure nobody is getting fussy. Here’s our suggestion: have groceries in your fridge for breakfast, find something easy to do for lunch, and make a reservation for dinner. On the first day of your trip, stock the fridge with basics. Get your alcohol, your snacks, and your breakfast goods. Get stuff that people can bring along with them when they are out for the day, too (granola bars, apples, cheese sticks, whatever does it for you). For lunch, try not to do the whole sit down thing. Find something super easy—head to a cafe where everyone can order their own food at the counter or go to a grocery store and buy a few things for a picnic. Have an idea of what you want to do for lunch before you head out. Finally, for dinner, make reservations. Before you even go on your trip, find the spots you wanna eat for dinner and, if they take them, make a reservation for the same time every night. This way everyone knows what time dinner will be and you don’t have to stress about where to eat. You can include your dinner time and reservations in the group email, too.

#5 Hard Times and Soft Times

So, there are two types of times on a trip. There are soft times and there are hard times. Hard times are things like dinner reservations and activities. It’s something where everyone needs to be on time for the benefit of the group. Nothing is worse than trying to corral your friends out of the Airbnb to get to your dinner reservation on time. So, when you’re saying that dinner is at 7:00 p.m. at Creme Brule, you’d say “and that’s a hard time.” That way everyone knows to get their butt out the door. It’s a friendly way to keep your friends in check. Soft times are for things that don’t require people to be prompt. Perhaps you’re playing frisbee on the beach at 3:00 p.m. You’d say “We’re playing frisbee at 3:00 —that’s a soft time.” That way people know they are invited along, but nobody feels pressure to be anywhere at a given time.

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