Travel Tips: How to Plan a Group Vacation

How To Book a group vacation w%2Fo losing your mind


As a vacation rental villa specialist for TC Villas for the past 4 years, I have helped countless guests plan their vacations. I have seen it all!  Some groups plan their trips quickly with little fuss, but more often travel plans can be difficult for a group to decide. Many times a ring-leader can feel as if they were herding cats as their party members find trouble committing to dates! Here are 5 tips to follow as you take on planning a trip for multiple families.

  1. Smile and Keep it Positive: I cannot tell you how many times I have had guests call in terrible moods…and I get it. The pressure is on as you attempt to plan the perfect vacation for a group. As you go online, there are thousands of choices and it can be so overwhelming! On top of that, you have opinions, schedules and requests coming from all directions.

Breathe….you can do this. We have a list to follow here and step one is realizing that the vacation will end up great.

You’re planning a vacation, so go ahead and start the relaxation now! Believe me, if you try to bring a fun, laid back attitude into finding a rental, the whole process will go so much better 🙂

Let’s get organized.

2) Travel Dates: This is where it can get difficult. I suggest sending a group email or Facebook message to ask your party what dates would work for each family or individual. Many villas have weekly schedules, so having your party stick to Saturday-Saturday is a great idea and narrows it down to finding a week. Be sure you remind your party to check their schedules for the following:

School/Sports Calendars

Work commitments/meetings/busy weeks for their jobs

Family Birthdays/Obligations


Church or Club Events

Once you have a general month or season your party had discussed, I suggest sending an message with three possible weeks and asking your group to rate each week:


I can do it but not ideal

Cannot Travel

That way you can see what weeks cancel out due to your party’s schedules. Keep in mind that you may have to select a week that is “I can do it but not ideal” for a group.

Once you have your dates, celebrate the hardest step with a small dance and send an email out thanking everyone and announcing the winning week! Keep it positive and upbeat so everyone feels good.

3) Destination: Most parties have a region in mind of where they would like to go. Should your party agree on “Caribbean Beach Vacation”, you then have tons of islands to choose from! We may be a bit biased (we only offer beachfront villas on Providenciales, Turks and Caicos) to recommend TCI, but it is one of the safest islands in the Caribbean with tons of water activities and some of the clearest turquoise water in the world 🙂

If you don’t want to take our word for it, TripAdvisor Just named Grace Bay Beach in TCI the #2 beach in the world for their 2017 Traveler’s Choice Awards!

4) Pick the Villa: Things to keep in mind here:

Proximity to beach.

Is a rental car necessary?

Is there enough space, bathrooms and bedrooms for everyone? (Occupancy typically goes 2 guests per bedroom including children)

Is it available for the dates you selected?

It may be great to send a few links out to your party and have each family discuss and vote.

Tip: Don’t send out every villa you find, too many choices may overwhelm the party. Pick 2-4 villas of different styles for the party to choose from.

5) Talk to Someone who has been to the Villa: A phone conversation with a villa booking specialist who knows the island and villa can make your trip so much better! They can answer your questions/doubts, make recommendations that you may have never thought of, and offer helpful advice that could save you time and energy in research.


My colleagues and I have seen each villa on our site and know Provo like our own hometowns! Call us to ask your questions and let us help you find the perfect villa! Here are a few great 5-7 bedroom villas perfect for larger Groups:


c hammock


Conched Out Villa on Long Bay Beach, a 7 bedroom spacious villa great for pool time and star gazing!


Oceanus 01


Beach Villa Oceanus on Grace Bay Beach, a 6 bedroom modern villa with amazing snorkeling and two pools!




Cascade, a 6 bedroom beachfront villa with staff and amazing turquoise views as far as the eye can see!

You can find our villas at TC Villas. Contact TC Villas at or by phone from 9-5 EST at 1.877.467.4858 to book your perfect beachfront vacation rental villa!

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