Plan the perfect friendcation

Smiling man taking group selfie on mobile phone at dinner party

Vacationing with friends — the friendcation — can be exciting and refreshing. Here’s what to know to help make your trip a success.

If you’re considering a special vacation for you and your friends to reconnect, the following guidance can help make it a trip you’ll never forget, for all the right reasons.

Friendcations for urban adventurers

Cities are smart choices if your friend group is made up of high-energy people who love exploring new places. (And if you need a break, cities offer lots of opportunities for downtime or exploring on your own, and you can reunite as a group for evening fun.)

If a day of wine tastings, museums, and shopping followed by a group dinner in a hot new restaurant and drinks in one of the world’s top 50 bars sounds like a perfect mix, you might consider an international cultural hotspot like Lisbon, Melbourne, or Milan.

The Cathedral of Milan on a sunny winter morning

Friendcations for chill-out types

If your group is more focused on relaxing and recharging, a more scenic and rural locale might be the ticket. One great example: Parts of Montana have accommodations to suit groups (you can rent rooms in a lodge, an entire house, or individual cabins, depending on preference), stunning scenery, and lots of dark sky for stargazing. Days can be spent hiking, nights around the campfire … and there won’t be so many “must dos” that everyone feels guilty for just wanting to relax.

Friendcations with something for everyone

Higher-end outdoorsy locations can fill the bill if your friend group is looking for a mix of the adventurous and restful. Two examples:

  • Mountain towns like Vail or Santa Fe, New Mexico, have a wide range of activities for those who like to be on the move all day and great accommodation options for large parties. Those who want to can ski or hike from sunrise to sunset, or do a little of either followed by a leisurely nap, while the most sedentary can admire the scenery from a sofa in front of the fire.
  • Towns with lively water sports scenes — Puerto Escondido on Mexico’s western coast, for example, or San Diego or Hawaii (all three have a good stock of multiple-bedroom rentals) — mean that the energetic can fill their days with kitesurfing lessons while others read their novels by a peaceful pool.

Luxurious Hawaiian 5-star resort with pool view toward ocean and mountains.

The key to success: Planning ahead

Planning this kind of vacation can require some delicate maneuvering to strike the right balance for everyone involved. After all, some people expect a vacation with friends to be packed full of activities, while others are looking for slow-paced afternoons spent catching up over coffee.

To get a sense of your group’s interests in a way that’s more manageable than group chats or ongoing email threads, consider using an online tool to create a short survey that you can email to your group.

As part of that survey, have everyone note their preferences for dates, for budget, and for location. Other questions to ask:

  • Do they have dietary restrictions?
  • Do they want to bring children?
  • What kind of vacation are they looking for: city or outdoorsy, action-packed or relaxing by the pool?

Communication now may mean fewer problems down the line.

Remember: Flexibility will make it fun

No matter which kind of group you’re with, a few simple strategies can help ensure that all friendships are still intact at the end of the vacation.

  • Establish ground rules before anyone puts money down on reservations. Are there expectations and agreement on the price range of lodging, transportation, meals, and entertainment? And if sharing expenses, is it clear who pays for what? Make sure you all agree before moving forward.
  • Don’t completely fill your schedule. Consider sticking to no more than three activities each day, or the agenda might be so packed that people stress about getting to the next event when they should be enjoying the moment. But make sure there’s at least one group activity per day — after all, that’s why you’re together.
  • Be flexible. Plans change, people get sick, the person who booked the all-day spa experience suddenly decides they’d rather go on a vineyard tour instead. Don’t sweat the small stuff and you’ll likely end the vacation better friends than when you started.

A few additional tips

  • Consider adding travel insurance when you book your trip. Check that your travel insurance plan includes some level of reimbursement in the event you need to cancel or alter your travel plans before or during your vacation. The cost of the insurance is a percentage of the larger costs you might incur if you suddenly encounter a medical issue or other disruption during your trip.
  • Notify your bank or credit card provider that you will be traveling. To help prevent disruption to your credit or debit card use and to help you prevent fraudulent activity on your card, let your bank know that you will be traveling. Typically your mobile app allows you to easily provide this notification.