
First things first: What is a flotilla?
Think of a flotilla as the best parts of sailing combined with a friendly support network. It’s a small fleet of yachts cruising together, guided by an experienced crew on a lead boat. You get your own yacht, freedom, and privacy, but with the bonus of a structured itinerary, daily assistance, insider tips, and a group of fellow sailors to share the journey.
Whether you’re brand new to sailing, recently qualified, or a seasoned skipper, flotillas are easy-going, hassle-free, and simply more enjoyable. Perfect for families, couples, solo sailors, or groups of friends, flotillas offer a vacation option that’s anything but ordinary.
Back in the 1970s, Eric Richardson started it all with Sunsail’s original brand, the Yacht Cruising Association (YCA). Today, Sunsail keeps the spirit alive, blending independence with community, all under the watchful eye of your expert lead crew, including a skipper, mechanic, and host ready 24/7.
Curious? We answer common questions to show you why flotilla sailing might just be your next favorite vacation style.
Do I need a sailing qualification?
You’ll need the same qualifications as a bareboat charter, but don’t stress if you’re newer to sailing. Sunsail offers skippers to sail your yacht for you, or courses, like Flotilla Starter and Flotilla Hero in Greece and Croatia, so you can learn as you go. Check out our detailed sailing qualification guide.

A day in the life of a flotilla sailor
Every morning, your lead crew provides weather updates and a daily itinerary briefing via a private VHF channel. They know the best restaurants, secluded beaches, and hidden gems, and they’ll help you set off smoothly each day and safely dock at night.
Then, you’re free to set your own pace. Chase the breeze, drop anchor at a secluded cove, or explore bustling harbors—you’re in control, with peace of mind knowing assistance is always within reach.
In the evenings, you’ll often dock at charming local villages and harbors. Connect with fellow sailors over dinner or wander off on your own—the choice is always yours.

Where can I sail on a flotilla?
Flotilla vacations are very popular with our European guests, allowing you to meet sailors from around the world and share your common passion for the sea. Explore three of the Mediterranean’s most amazing sailing regions with your flotilla friends:
- Greece: Crystal-clear waters, unbeatable sunsets, and a perfect spot for water sports.
- Croatia: Ancient towns, vibrant culture, and hundreds of islands begging to be explored.
- Italy: Indulge in spectacular coastal towns, world-famous cuisine, and our special Food & Wine Flotillas in Procida and Sicily.
Rest easy knowing your vacation is fully protected as Sunsail is a proud member of ABTA and ATOL.
Can I go off on my own?
Absolutely. Flotillas are flexible. If you spot a destination off-route, just tell your lead crew you’re going solo for a night or two. They’ll always be just a radio call away if you need them.

Don’t just sail, Sunsail
Ready to experience sailing differently? Sunsail makes booking your next flotilla sailing vacation simple and stress-free. Choose your route, gather with fellow adventurers, and let the Mediterranean become your playground.
Author Name:
Sunsail
Contributor
Ian Pedersen
Step Aboard Here
Start your experience with Sunsail on land and sign up to receive e-mails from us about yachts, offers and destinations.
By clicking 'Sign up' you confirm that you have read and understood our Privacy Policy and consent to our use of your information.