Flotillas holidays: Sail as a group, in one of the world’s best travel destinations.

Flotillas holidays: Sail as a group, in one of the world’s best travel destinations.

A flotilla sailing holiday means sharing your experience with others.

Flotilla holidays consist of between 2 and 10 sailboats coming together to form a fleet of holidaying fun. This means that for activities and parties you can have a group of between 20 and 100 travellers uniting to enjoy the local beauty and blissful environment.

Some refer to flotilla cruises as the brief creation of a water tribe - whereby the shared unique experiences on and off the deck bring a free, collectivist atmosphere and, with that, many new friends.

Flotillas are lead by a group of pro-skippers, who design and coordinate a smooth and coherent itinerary - this allows a high level of freedom in doing with your time as you wish - bask in the sun and cruise on the water with your new crew-mates. All you need to do is ready up for some unforgettable holidaying!

Bath morning and evening, in the exoctic waters of your choosing.

So, what does a flotilla sailing holiday actually mean? It means waking up everyday in a new cove, in a new part of the sea. It means discovering the beautiful treasures of a destination, that can only be seen on a sailboat or catamaran. It means floating on the crystal waters of your choosing. It means all of the above - but, with your crew.

With a dash of curiosity, you can help your skipper in the navigation, manoeuvring, and steering aboard - taking some time to learn from a veteran of the sea.

In the evenings, when the sails have been stored, you will either be at anchor in a cove of your skipper’s fancy, where you will toast to the day and prepare for an evening with the crew of your fleet - or, you will be setup in a local harbour, where you will venture into the town for dinner and entertainment.

Looking for a flotilla experience? On Sailsquare, find holidays for all tastes, styles, and budgets.

Sounds good? But what about X, Y and Z? On Sailsquare, you can find flotillas for a host of tastes and interests!

Whether you are looking for a grand summer flotilla adventure, or a winter flotilla getaway - with Sailsquare, you’re covered.

Whether it is exploring the Ionian Islands or the Cyclades in Greece, discovering the beauty of the Kornati Islands in Croatia, touring the Balearics Islands in Spain, or escaping further afield to the Caribbean or Indian Ocean - here you can find the right flotilla experience to match those of your dreams.

Travel with people who’s wants match yours.

Looking for a weekend trip on a budget? Or, want to sail off the popular routes for a couple of weeks? Flotilla sailing trips are generally designed with specific ages, activities, and budget in mind.

Whatever your travel desires are, make sure to reach out to the organising skipper with any of your questions, who will be more than happy to offer additional information about the trip - and what you can expect from the voyage!