Bachelor/bachelorette parties, birthdays vacations, destination weddings, vow renewals, large family getaways…group trips can be tricky to plan, but extremely rewarding when planned correctly.

Don’t believe me? I just returned from 5 days in Jamaica with 18 of our close friends, and everything went off without a hitch! Click here to watch a few highlights of the trip.

Over the course of the last 6 years, we have worked with many to plan a variety of group vacations, including our very own. The one thing I have learned is that there is a method to the madness when trying to get any amount of people to one destination.

Below are the top tips for organizing a group vacation in a manner that gets everyone to the destination safely (and on time) and also, how you (the organizer!) can enjoy it, too!

  1. Choose ONE chief! Too many Indians means too many opinions. Too many opinions means you’re going to be running in circles to come to decisions. Pick one person in the group to head up the trip and make all final decisions.
  2. The chief establishes the travel dates, the destination and the resort. If it’s your birthday trip, you call the shots! For example: May 5-9 in Cabo at Marquis Los Cabos. Those that can/want to make it, will. Those that cannot/do not want to make it, won’t. Not everyone is going to be able to attend and that is okay. It is impossible to please everyone and at the end of the day, it’s your birthday!
  3. Choose a destination with a short flight. Longer flight times mean pricier flights, longer time in the air versus in your destination and more days required. Always shoot for a destination with a nonstop flight. Some of my go-to destinations for group trips are: Cancun/Riviera Maya, Cabo, Montego Bay, Nassau. These destinations are closest to the US, which means there are usually nonstop or short flights available no matter where you’re flying from.
  4. Make it a short/quick trip: 3-5 nights max. Most of your guests have families, pets and jobs and it can be rather difficult to pull away from those for an extended amount of time. For the best attendance, keep the trip short. You’ll not only have a better turn out, but your guests will appreciate it as well. If you want to stay longer, go for it! It’s your birthday, remember?! 
  5. Invite your people, but not all your people. Keep the invite list to those who are closest to you: best friends, their significant others, close family members (who you travel well with). The more you invite, the more out of hand it can get, and the more stressed you are going to feel. If you truly want to enjoy your vacation, keep the guest count to less than 30.
  6. Work with an experienced group travel expert. (Ahem…it’s me.) The chief (that’s you) will work directly with me throughout the entire planning process to make sure all i’s are dotted, t’s are crossed and everyone gets to and from the destination safe and sound. As your travel advisor, I always assist in all room bookings, transportation, group events, dining, tours, payment plans, itinerary planning and so much more! 
  7. Take advantage of group benefits. Did you know you can qualify for FREE rooms, FREE upgrades, FREE private dinners and check ins and so much more, when you book a group?! This is why working with an experienced travel advisor is so crucial because only your travel advisor will know to set up your group and group incentives with the resort. For example, I personally & recently qualified for a free vow renewal, as well as a free cocktail reception and a free room. I have recently had clients qualify for multiple free room upgrades, free private check-ins for their group and…wait for it…over $8000 in cash back! Yes….you read that correctly…literally FREE money for the chiefs who organized the entire group. This not only paid for their portion of their vacation, but covered their flights, their family member’s room and then some. (Disclaimer: group benefits differ at each resort.)

At the end of the day, you want your crew to get together to celebrate…whether it be a birthday, a small intimate wedding or just a fun social getaway. But, you also want to enjoy it yourself. It is possible to accomplish both and we’d love nothing more than to partner with you (the chief!) to do just that!

Looking to plan a group vacation? Click here and let’s start planning today!