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If you’ve ever been tasked with planning a group outing—be it a guy’s weekend in Vegas, a gal pal gathering in South Beach or a weekend camping excursion with your old college besties—you know that it’s preferable to having a root canal while being forced to watch Kirk Cameron’s Saving Christmas on continuous loop. Fear not. Next time you’re tasked with heading up a group getaway, here are the answers to your most vexing group-travel planning challenges.

ALSO: The 7 best trips to take as soon as you graduate

camping, woods, nature, group, vacation

Q: Where to go?

A: Cabin in the woods
UPSIDE A gathering in the woods is a mythologized U.S. tradition—think Big Chill—and can perfectly bring together a large group for an intimate weekend of cooking meals, playing charades and trading stories while connecting with Mother Nature.
DOWNSIDE Before booking a Big Sur escape, find out: Does the cabin have WiFi? Will people have to share rooms? Who’s going to cook meals? How far away is the nearest airport? Most importantly, will your dedicated city dwellers be bitching the entire time?

A: Beach getaway
UPSIDE An option that gives groups a much-needed dose of vitamin D without the risk of mosquito bites is a beach vacation. Beaches are often clustered near resorts—especially in popular spots like Punta Cana—and resorts are designed to do the work for you. Even better, those resorts usually have swimming pools.
DOWNSIDE Of course, if you have that one friend who cringes like a vampire every time she steps into the sun, a resort-based vacay may not work. Also, ask yourself this: Is a beach getaway such a novelty for invitees who are already living on one of the coasts?

A: The big city
Big cities like Chicago, LA or New York make for ideal group outings because there’s always a major airport nearby, everyone can pretty much get around on their own, and numerous culinary and cultural options will please even the most finicky among the group—and also guarantee alternative activities when the weather turns sour.
DOWNSIDE Cities also have disadvantages. They tend to be expensive, unfit for unwinding (Houston’s sprawl hardly screams relaxation) and if your crew is already scattered across all the major metropolises, it might be hard finding just the perfect place.

money jar, money

Q: How do we divide up costs?

A: Pick a hotel with lots of room options
Your investment banker friends can rent a poolside suite on their own while the penny pinchers in the group can share an interior double room with no view. Unlike restaurant tabs, hotel bills tend to divide neatly among a group of four sharing a single room. As for airline tickets, if you’re booking together (which is helpful if you plan on getting seats together), sites like now offer Affirm, an online payment option that allows you to pay in installments, so the sucker charged with buying all the tickets doesn’t have to pony up until all group members pony up.

A: Estimate a budget in advance
This one actually works. Plan out ancillary expenses (dining, ride shares, admission prices, etc.) and build that into the per person cost of the trip. For example, if the estimated daily cost for a resort weekend is an additional $100 per person, then simply have everyone pay the group leader that amount in advance so that nobody but the leader has to take out money during the entire trip. Leftover funds can be returned via Venmo later.

A: Choose an all-inclusive
Ahh, the benefits of booking a stay at an all-inclusive resort where the cocktails flow freely and money never once needs to change hands. Another route is to rent a condo or cabin where cooking is encouraged and thus the headache of adding up a bill at the end of every meal is ditched in favor of splitting a onetime grocery tab.

vacation, beach, group, men

Q: When should we go?

A: Determine schedules first
This is often the hardest part. Are there teachers in the group? They tend to have summers off while anyone working in retail is going to be slammed during the holidays. Figure out whose schedules need to be the most tended to and ask your work-from-home or flex schedule friends to bend to the needs of those with stricter time off.

A: Think about where your squad resides
Does the group primarily live in a cold weather climate? If that’s the case then January through March is usually the perfect time for a winter thaw. Conversely, it can be a novelty for folks living in the sunbelt to experience autumn in New York, a winter wonderland in the Rocky Mountains or a cold summer weekend in San Francisco.

Q: What kind of lodging should we choose?

A: A hotel
Big hotels are great because they offer privacy, terrific amenities, a variety of room options and default dining choices.
DOWNSIDE In large hotels, groups can sometimes be separated by multiple floors. (Think a sprawling resort in Las Vegas.)

A: Vacation rentals
Vacation rentals are intimate, often infinitely more charming and usually cheaper than a traditional hotel.

DOWNSIDE Most rentals put a strict limit on how many guests in total are allowed and often these cozy quarters mean guests will be in each other’s grill at all times, so you’d better really like each other.

family, vacation, kids

Q: What if there are children involved?

A: That’s called a family vacation. Leave the little ones at home.

dining, group, friends, travel

Q: Where will we eat?

A: Dine out
UPSIDE Restaurants are great because they allow for a variety of choice and, importantly, others are doing all the work for you.
DOWNSIDE Ask in advance about everyone’s dietary restrictions. Food sensitivities are part of the world we live in and the last thing you want is to book a table at a low country boil only to find that half your group is allergic to shellfish. Also, restaurants are pricey.

A: Eat in
UPSIDE Cooking meals at your condo or cabin inspires bonding and is ideal for finicky friends since supermarkets offer endless food options and all you have to do as leader is pick up whatever your allergy-prone companions want to meet their dietary needs.
DOWNSIDE Who will cook? Who will set the table? Who will clean up? Assign out these responsibilities in advance of traveling. You don’t want to be miserable because you’re doing all the work.

seniors, travel, group, activities

Q: Who will lead group activities?

A: If you’re traveling with a crew of type B peeps, you’re in luck. You have complete control over the vacation’s itinerary and if everyone is willing to blindly follow along, this is where leadership pays off.

A: If you’re traveling with a pack of alpha dogs, consider putting each one in charge of planning a different day. This establishes fairness and gives control freaks little to complain about when it’s not their turn.

A: Gently remind everyone that it’s okay for folks to go their own way. You may suggest that everyone has the afternoon to themselves, but have the gang circle back for dinner and drinks later that night. If your squad is large, this may be your best bet.


Tagged: Tips & advice

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