Take a Flotilla Sailing Holiday – Sail with All Your Friends

flotilla sailing holiday

The flotilla sailing holiday is probably the best thing that ever happened to group travel.

Imagine you and all your friends (or extended family) together, exploring new destinations, experiencing new things, enjoying gorgeous weather and good food and just being on vacation — without the logistical nightmare of arranging multiple flights and hotels, and without the risk of driving one another crazy by being constantly together.

That’s what you get with a flotilla sailing holiday.

Flottilla Sunsail
Coppyright: Sunsail

What exactly is a flotilla sailing holiday?

A flotilla sailing holiday is a larger group of people all on vacation together, sailing on a fleet of up to 12 or so chartered yachts.

What are the benefits?

  • Travel easily with more people: Book the number of boats to perfectly fit your group size.
  • Choose your route: Your holiday, your friends, your call on where you want the fleet to sail to (hint: a flotilla sailing holiday is a great for island hopping and visiting many destinations on a single trip).
  • It’s perfect for both novice and skilled sailors: You can arrange your flotilla experience to fit your group’s level of sailing skills (or lack thereof).
  • More privacy, even in a big group: More boats means more personal space for everyone. The last thing you want is for all your friends to get sick of one another by the end of the trip!
  • Enjoy group activities: You may be split up when sailing and sleeping. However, when it comes swimming, snorkeling, barbecuing on the beach, exploring your destinations and whatever else your group wants to do, you’ll get to enjoy doing it together.

Bottom line: A flotilla sailing vacation offers all the excitement, novelty, and independence of a classic boat holiday, PLUS you get to relax like you’re alone but have fun like you’re with all your favorite people.

Sunsail Flottilla Croatia
Copyright: Sunsail

What’s a good charter company that offers group sailing holidays?

Sunsail is definitely a charter we can recommend for a flotilla sailing holiday. Additionally, they’ve also got a wonderful selection of flotilla holidays and offer special kinds of flotilla experiences.

Sunsail flotilla highlights

  • Lead crew support: With a skipper, a technician, and a host on board the lead boat, you’ll have all the support you need. You will get help from casting off to recommendations on where to find the best local spots to visit.
  • Food and wine flotillas: The ideal holiday for a bunch of foodies who love to dive into the local cuisine when traveling.
  • Learn to sail: Sunsail offers courses for anyone looking to learn the ropes of sailing while on their group vacation.
  • The right trip based on sailing experience: Choose between a more laid-back “level 1” holiday or a more sailing intense “level 2” experience.
Copyright: Sunsail

What destinations does Sunsail offer flotilla sailing holidays in?

You can charter a flotilla to explore several locations on routes in some top sailing destinations, including:

sail in Croatia


Discover the gems of this beloved sailing destination, including Dubrovnik and Marina Agana.

Book a flotilla in Croatia

sailing in Greece


Go island hopping from Lekfas and explore the best of the Ionian Sea, such as Ithaka and Kefalonia.

Book a flotilla in Greece

Sailing in Italy


Enjoy southern Italy on a flotilla sailing trip off the coast of Naples, Sicily, or Sardinia (and visit Corsica on your trip as well!).

Book a flotilla in Italy

soggy dollar bay, jost van dyke BVI

British Virgin Islands

Set sail in the Caribbean with visits to Virgin Gorda and Jost Van Dyke.

Book a flotilla in the British Virgin Islands

Make your group’s flotilla sailing holiday a truly unique experience

In conclusion, as you and your friends all sail from one destination to another, you’re free to stop as you like. Together or in smaller groups, you can swim, search for the perfect hidden beach, or simply explore along the way. This is what makes slow travel in general — and flotillas in particular — such an amazing friends’ vacation.

Looking for destination inspiration on where to go for a flotilla sailing holiday with your friends? Our 2021 sailing calendar guide offers boat holiday suggestions for every month of the year.

Want to find out what makes the boat holiday the best way to see the world? Check out our article on 10 reasons to charter a boat.