50+ Years of Flotilla Expertise
We pioneered the flotilla experience and continue to lead with expert crews, tried-and-tested routes, and world-renowned service.
Swap the Daily Commute for a 2026 Flotilla Holiday
Set sail on an unforgettable journey across some of the world’s premier cruising grounds, with expert support and like-minded company every nautical mile.
Great for solo sailors, groups, couples, and families, flotillas are the way to go for social sailing. Whether you are unqualified, a new skipper, or an old hand, there’s a flotilla sailing holiday for you.
A flotilla is a group of yachts sailing together on a shared route, with support from a professional lead crew. It’s the ideal balance of independence and guidance, perfect for new and seasoned sailors alike.
Whether you’re navigating solo, with family, or a group of friends, a flotilla gives you the freedom to sail with peace of mind, discover new places, and meet fellow travellers along the way.
Hear from Claire, one of our experienced base managers, and get a feel for what makes flotilla holidays with Sunsail so special.
We pioneered the flotilla experience and continue to lead with expert crews, tried-and-tested routes, and world-renowned service.
Enjoy comfort and performance on board our fleet of monohulls and catamarans, ideal for all levels of experience.
Sail to a mix of iconic islands and hidden coves, carefully curated for every flotilla itinerary.
Your lead crew handles moorings, briefings, and daily logistics—so you can focus on the sailing, not the stress. Curious what that looks like in action? Meet the Sunsail Flotilla Lead Crew
Flotilla holidays are as social—or as independent—as you like. Make memories with other guests at beach barbecues and snorkelling stops, or sail at your own pace with the comfort of support nearby.
Discover Mediterranean gems on a serene flotilla sailing holiday. Each destination offers something special – from historical sites and gourmet delights to breathtaking beaches. With six stunning sailing grounds across Greece (Lefkas), Croatia (Dubrovnik and Agana) and Italy (Procida, Sardinia and Sicily), adventure awaits. Each offers incredible sailing conditions, breathtaking landscapes, historical sites, authentic culinary delights and beautiful beaches.
New for 2025 – We’re always looking for new ways to explore world-class sailing destinations and we’re delighted to be expanding our Dubrovnik offering in 2025 with our Libertas flotilla itinerary. Ideal for budding adventurers, you’ll have the opportunity to sail along rugged coastlines, discover hidden coves, admire picturesque harbours and enjoy some of the best swimming, snorkelling and scuba diving in Dubrovnik.
Find out more about each destination and book your flotilla sailing holiday today:
Food and Wine Flotilla
If exploring the world of local wines and traditional culinary treats is your passion, these unique flotillas are perfect for you. They combine some of the best sailing in the Mediterranean with tastings of local produce and the chance to meet the artisans who make it.
Whether you want to immerse yourself in Italian culture or experience the wonders of Croatian cuisine, take a look at our Food and Wine sailing flotilla holidays:
Flotilla Sailing Holiday FAQs
Ready to catch the wind? Browse our bareboat, skippered, and flotilla sailing holidays today and start planning an unforgettable escape on the seas. Your next adventure awaits!
*Fuel is not included on our specialist flotillas in Italy
**In place of Flotilla Punch Party will be a Gin and Tonic party. Lead crew consists of a Skipper and Technician.
No, the only people you will share your yacht with are the people in your party and a skipper if you choose to hire one. All the other sailors in your flotilla will have their respective yachts, ensuring you have a sociable yet still private holiday.
The cost of your flotilla sailing holiday will depend on a number of factors, and can start from around £1,775 for two people. Factors may include:
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