Why you should book a holiday with Sailsquare?
The leading sailing holiday marketplace
25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.
Get onboard solo, with your family, or your friends
Reserve a single spot, a cabin, or a whole boat just for you and your friends or family.
Discover who’s already onboard
Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.
Sailing holidays that suit all budgets
Rumour has it that sailing holidays are only for the rich or well-connected. With Sailsquare, that's no longer true. Come and discover a world you never thought was accessible!
Reviews - Flotilla sailing holidays2463 reviews
Would you like some support using the platform? We've (almost) always got the answers!
Can't find the perfect holiday for you?
Use our free holiday concierge tool - and let us find your dream sailing experience for you!Let's find it together!
5 reasons to choose a flotilla experience for your next holiday:
- Flotillas are perfect for both those who travel alone and in groups: meet new people, share new experiences
- The perfect atmosphere for a party - several boats moored together, a little music, perhaps a guitar, the sunset hitting the sea, everything needed for a beautiful evening.
- Much more than a group holiday: during a flotilla holiday, water tribes are formed, made up of people who love the sea, and the beautiful life on a sailboat.
- There is room for everyone: those who simply want to relax on a sailboat, those who like to cook, those who want to learn to sail - a flotilla experience allows everyone to find their place.
- Your skipper is responsible for the organisation and safety, so that you can relax and have piece of mind about your holiday!
Flotilla holidays: the beauty of group sailing
A flotilla trip allows you to move to a new place everyday to discover the most beautiful spots, from breathtaking bays to crystal clear waters - a complete adventure.
The social nature and fun of flotilla holidays
Learn the basics of sailing, relax on deck, play games with your new friends, and dance until dawn. Bath in the beautiful waters of your choosing, learn more about your crew members and the destination you are exploring, and for those who which, you will have the opportunity to go ashore to explore the local day and nightlife. Flotilla sailing experiences offering endless opportunities to have fun with your holidays.
Making new friends
There is often the freedom to enjoy time on other boats that are part of the flotilla, this makes for a truly rich social experience, and allows you to interact with each of the different travellers. Many travellers that choose to partake in a sailing holiday forge long-lasting friendships.
Tips to help you to better plan for your next flotilla sailing holiday:
All you need to know about your next flotilla cruise.
When is best to set sail on a flotilla holiday?
Many flotillas take place throughout the Mediterannean in the summer months - including throughout Greece, Croatia, Italy, the Balearics, and more. However, throughout the winter months you can find beautiful flotilla experiences around the Caribbean and East Asia - popular destinations include the Seychelles, Guadeloupe, and Thailand.
How much do flotilla holidays cost?
Types of flotilla holidays can vary quite significantly in price, with variety in types of boats, location, date, and whether they have onboard staff including hostesses and chefs onboard. You can find flotilla sailing experiences starting from €600.
What is the age range for flotillas?
Group sailing trips are distinguished by age and type of activity, so that you can find the best solution for you and your desires. Whether you want to dance all night or simply enjoy the relaxation of the sailboat in good company, there are flotillas for all ages and tastes.
- Fleets in Croatia combine the exploration of this sailing paradise with the pleasure of sailing with other boats.
- Flotillas in Greece are perfect for enjoying the blazing sunsets over the white villages, a glass of wine in hand, next to your new friends.
- Flotillas in the Balearics, the festival islands, to alternate between sailing holidays and parties in the best parties in the world.
- Flotillas in the Aeolian Islands to explore the 7 sisters of Sicily, make friends and share experiences.
- Exotic flotillas across the Caribean and East Asia allow you to spend the winter in the sun, they are often on catamarans to make the most of the shallow waters.