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Flotilla sailing holidays & skippered cruises

In a flotilla holiday, you are sharing your sailing holiday with a bigger group of travellers. By sailing alongside numerous other boats, from 2 to more than 10, you combine the great experience of being at sea with a social diversity, that makes for a unique sailing experience.

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The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Flotilla sailing holidays & skippered cruises

3212 reviews

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Emerald Flotilla: La Maddalena Archipelago with Velasquez

08/19/2025

Giuseppina B.

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Italy

Great boat holiday in one of the most beautiful places.... crystal clear sea white beaches surrounded by nature.... but above all so many beautiful people met .... Sailing is the best way to enjoy the sea. ... The only thing to improve is greater aggregation to be created among the group with more activities to organize all together. This is not my first experience in the flotilla and compared to the others perhaps you need an entertainment staff to organize evenings together. Congratulations to the legendary tireless Claudio and to the whole team. To the px
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The Wild Flotilla: dive into the wild nature of Tuscany and Corsica

08/19/2025

Fredi S.

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Italy

I realize that the Elba Capraia Corsica tour includes more hours of navigation than others, but there was a lack of organization on the part of the flotilla leader, not so much of our skipper who was not in charge of making decisions, it must be said that he did not even become the spokesperson for the ideas of our crew in contrast with the programs and organization. So many sparses in places where it was not very pleasant to stay, take a bath... Then in the morning we almost always left without the possibility of taking a dip and having breakfast still. Surely there will have been more beautiful beaches to see with a minimum of planning. Moreover, it did not even seem to be in a flotilla, the package must have been made twice and for a short time. The buoy docking in Capraia, we arrived first and all the other boats set off on their own despite being able to stand next to us. We went sailing half a time approximately.. I don't know, we could have done better! Absurdly, last but certainly not least, a 52-foot boat without music speakers in the cockpit has never been seen, but even a dinghy has a stereo.
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The Wild Flotilla: dive into the wild nature of Tuscany and Corsica

08/19/2025

Francesco M.

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Italy

The holiday went well, which is why the evaluation is positive overall. It is an itinerary that I recommend but there are some details of the organization that could have been improved. The main problem of this round was the composition of the boats. Out of 40 participants (20 men and 20 women) there were boats that were too unbalanced (mine 7 men and 3 women, others with too many women, in one case 3 girls and 1 boy put together with three elderly couples). In general, too many couples (5, therefore 10 participants) who had to be put all on the same boat, having partly different needs than the other participants. Another problem was that, apart from a party on a deserted beach, no activities were done/booked together... Is it possible that out of four dinners made on land, the organization did not have the idea or the ability to book a restaurant for everyone? or a place for an aperitif? not even the last evening in Scarlino? Don't tell me that the week of August is impossible because otherwise I recommend a basic negotiation course... The head skipper traveled seemed to us to be a particularly suitable person to facilitate relationships/activities between groups. I won't go into the indisputable technical skills but considering that people choose the flotilla mode also to meet other people, maybe I would choose skippers with more organizational skills (and, since they are working, I would avoid skippers traveling in pairs). Finally, the boats had no crates outside. It can be okay but then notify the skippers and advise everyone to bring Bluetooth speakers .... A holiday without music is not the best.
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Different Flotilla: Party and new friends in the Aeolian Islands

08/19/2025

Giulia B.

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Italy

An unforgettable experience! The organization was impeccable: the staff puts energy and passion into every detail, offering original and super fun activities. Every day was a party, with music, smiles and moments of sharing with special people, all immersed in the wonderful setting of the Aeolian Islands: crystal clear sea, breathtaking sunsets and views that will remain in the heart. The flotilla formula is truly unique, because it allows you to meet many people and create authentic bonds thanks to the many moments of common life. I started with high expectations, but reality far exceeded them. I can't wait to leave with you again!

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6 reasons to take part in a sea crossing or deep-sea sailing

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  • Learn to sail in the company of professional skippers who will pass on their passion for the open sea.
  • .
  • Experience the magic of night sailing: sailing accompanied by silence and the stars is an unparalleled experience.
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  • Experience the magic of real sailing: discover routes that are less common and far from mass tourism to experience a unique adventure!
Be aware of the magic of real sailing: discover routes that are less common and far from mass tourism to experience a unique adventure!
  • Test yourself sailing long distances in the open sea.
  • Sail in the company of dolphins and whales: starting from Liguria and from South of France , cross the Cetacean Sanctuary to reach Corsica .
  • Experience the feeling of absolute freedom . The days will be free of any haste and the times will be marked by alternating between the sun and starry skies.

The best itineraries for sailing on the open sea

Are you interested in sailing away from the coast, surrounded only by the open sea? Embarking in the company of a passionate skipper for a crossing, including ocean, is the ideal experience for those who love long voyages and for those who want to experience a unique adventure by enriching their nautical knowledge.

From Liguria to Corsica: crossing the Mediterranean on a sailing boat

One of the most fascinating routes for offshore sailing is right behind the house: the Mediterranean triangle enclosed between the Liguria , the Côte d'Azur , the Tuscany and the Corsica is known as the Cetacean Sanctuary . It is a marine protected area where you can sail in the open sea in the company of dolphins and whales. The departure is generally from one of the ports of west of the Ligurian Riviera or from the French Riviera.

Some skippers choose to set sail in the evening, carry out a night navigation with shifts and land on the coasts of Corsica at dawn. Another possibility is to leave Liguria or the south of France at dawn to fully enjoy offshore sailing during the day. In this way your skipper can pass on his seafaring knowledge and you can test yourself at the helm or adjusting the sails. During the day someone will be able to practice trolling, to have lunch with fresh fish.

For those who are just starting out with offshore navigation, we suggest the route departing from Tuscany, which often sees an intermediate stop in Capraia, before reaching the mythical rock of Giraglia in Corsica. The Giraglia is famous for being one of the stops of sailing regattas in the Mediterranean, including the Giraglia Rolex Cup , departing from Saint Tropez, and the 151 Miles departing from Livorno.
Are you a group of friends? This route is perfect for you, whether you want to try your hand at sailing, or experience a long weekend on a sailing boat in company: rent a whole boat with skipper to live an exciting experience starting from the comfortable ports of Tuscan coast .

Atlantic crossing on a sailing boat

The crossing of the Atlantic Ocean to reach the turquoise Caribbean seas is the best known ocean route. This long experience on a sailing boat consists of two sections. The first route lasts a week, departing from Balearic Islands or from south of Spain to reach Tenerife or Gran Canaria < / a>, passing through Gibraltar. Once you have landed in the Canary Islands it is time to wait for the ideal weather window to head to the Caribbean . When the winds are favorable your unforgettable adventure in the blue of the Atlantic will begin!

Generally the crossing of the Atlantic Ocean by sailing boat lasts at least 20 days ; the stages and the navigation rhythms depend on the winds and the weather. On board a sailboat, everyone always has a specific role, but in this case it is even more important that each crew member respects the sailing shifts and is always vigilant. For this reason, most skippers require their travel companions to have a minimum of experience in offshore sailing.

After the long Atlantic voyage you wish to relax for a week in the crystal clear waters of the Caribbean Sea, soaking up the sun aboard a catamaran or of a sailing boat ? You are in the right place and you will be spoiled for choice: Martinique , Guadelupa , St. Vincent and the Grenadines and St. Lucia await you!

Offshore navigation in the North Sea

Cold? I'm not afraid of you! When we talk about offshore sailing, we must also think of routes less traveled by mass tourism . Starting from the coasts of the Basque Country in Spain, sailing in the Bay of Biscay, or Bay of Biscay, is the ideal experience for those who want to learn the fundamentals of offshore navigation and have a period of less than 2 weeks.

For the more adventurous, Iceland and the great north are certainly a essential destination ; we suggest the departure from the port of Reykjavik with a stop at the Faroe Islands, characterized by steep cliffs and home to sea birds. Once you have landed on the coast of Scotland, you can reward yourself with an excellent glass of scotch like a real sea dog!

If you are looking for breathtaking landscapes and unspoiled nature, you absolutely cannot miss the magic of the midnight sun , sailing through the waters of a Norwegian fjord . Stop among the fishing villages that populate the Lofoten islands in Norway is a unique adventure.
On the opposite side of the Atlantic ocean , in Canada , you will instead admire the green of the coniferous forests that is reflected on the blue of the sea. Along the canal that will take you to Québec-City you can take part in a sailing course with professional skippers.

Crossing the English Channel on a sailboat

The north fascinates you but you still don't feel ready for such a challenging navigation? Crossing the Manche is the perfect adventure to get closer to offshore sailing in small doses.
Setting sail from one of the ports of Brittany near Calais, in a few hours you will find yourself enjoying an excellent Fish & Chips in the Southern England . Do you think this is a less adventurous sailing experience? Far from it! The English Channel is known for the strongest tides and currents in Europe, which is why after this 3-day adventure you will be ready to tackle even the most demanding voyages.

Crossing the Pacific Ocean: from Panama to the Hawaiian Islands to Alaska

If your dream is to spend as much time as possible on board a sailboat sailing the Pacific Ocean, we suggest the longest route ever : from Panama Canal to Honolulu Your adventure will last at least 4 weeks and you will sail for almost 5000 miles : a long journey during which you will have the opportunity to deepen your seafaring knowledge and discover all the secrets of life on board during a ocean crossing.

Another less traveled route suitable for lovers of the sea and nature is certainly the one to the north: starting from Hawaiian Islands awaits you one of the most exciting crossings passing through different climates, until you reach the coasts of Alaska .

Everything you need to know to go deep-sea sailing or a crossing

When is the best time to sail across the Mediterranean?

In addition to being an excellent experience to enrich your seafaring knowledge, sailing in the sea triangle between Liguria , Corse and Côte d'Azur is the perfect opportunity to spot whales. The best time for sightings is between mid-April and late October . On the way back, always keep an eye on the bow: it will be easy to see a group of dolphins playing in the waves created by your sailing boat.

What is the best time to sail across the Atlantic?

Most skippers organize the crossing from east to west between October and November and sail back to the Mediterranean between April and May. If you want to escape from the cold of winter, we advise you to leave during the autumn to enjoy the best weather conditions while sailing and the tropical climate once you reach the Caribbean.

What experience do you need to participate in offshore sailing?

No nautical license is required to book an offshore sailing experience. Depending on the duration of the crossing and its difficulty, the skippers will be able to ask you a minimum of experience at sea in order to guarantee shifts during navigation. If you want to experience the adrenaline of sailing in the open sea for the first time, we recommend that you always ask the skipper for the level of difficulty of the chosen route.

How long does it take to have an offshore sailing experience?

It depends on the course you choose and the winds blowing on your sails. A long weekend is enough to sail from Liguria to Corsica, with return, or to cross the English Channel.
Generally the Atlantic crossing from east to west lasts a total of 3 weeks : a week to sail from the south of Spain to the Canary Islands, while the second leg from Gran Canaria to the French Antilles two weeks. The Pacific Ocean crossing will certainly be longer, lasting an average of 4 weeks.

How much does an offshore sailing cost?

The prices of a sailing trip vary according to the duration and the route of the trip. In general, prices start from € 500 per week for offshore navigation routes in the Mediterranean up to € 1,000 per week to cross the Atlantic or the Pacific. A offshore weekend in the English Channel offers very affordable prices, starting from € 200 per person .

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