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Flotilla sailing holidays & skippered cruises

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.

  • Sailing Holidays
  • Flotilla

FLEXIBLE CANCELLATION.

Stress-free booking: you can cancel up to 24 hours before departure!

  • 99+ reviews
    confirmed

    "Different" flotilla of 3 boats in the Aeolian Islands: splendid sea, party and new friends - week 4

    from 20 August - 7 nights
    Aeolian Islands Italy
    1 person
    is on board
    976€ Per person
  • 6 reviews
    confirmed

    Flotilla in the Aeolian Islands: Exciting sunsets and new friends - week 3

    from 20 August - 7 nights
    Aeolian Islands Italy
    7 people interested
    in this holiday
    991€ Per person
  • 99+ reviews
    confirmed

    CRAZYSAIL CROATIA - 5 boats in the Split Archipelago

    from 20 August - 7 nights
    Split Archipelago Croatia
    6 people
    are onboard
    798€ Per person
  • 6 reviews
    confirmed

    Flotilla between the Gulf of Naples and the Pontine Islands - week 3

    from 20 August - 7 nights
    Pontine Islands Italy
    3 people
    are onboard
    1.080€ Per person
  • 99+ reviews
    confirmed

    Flotilla of 3 sailboats to Sardinia, La Maddalena and Corsica

    from 21 August - 7 nights
    Northern Sardinia Italy
    3 people
    are onboard
    1.082€ Per person
  • 21 reviews
    6 discounted
    spots

    It's time to Sail! 4 boats to the Pontine and Flegree islands!

    from 27 August - 7 nights
    Pontine Islands Italy
    4 people
    are onboard
    731 710€ Per person
  • 99+ reviews
    confirmed

    Flotilla of 3 sailboats to Sardinia, La Maddalena and Corsica

    from 28 August - 7 nights
    Northern Sardinia Italy
    6 people interested
    in this holiday
    901€ Per person
  • 99+ reviews
    confirmed

    Flotilla of 3 sailboats to Sardinia, La Maddalena and Corsica

    from 4 September - 7 nights
    Northern Sardinia Italy
    1 person interested
    in this holiday
    901€ Per person
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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.

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Discover who’s already onboard

Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.

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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 holidays & skippered cruises

2826 reviews
20 / 10
Leo L.

Leo L.

review about In the sea of Ulysses with the sport you want! August 2021

10 / 10
Expert skipper, great historical, political and social culture of Greece. He knows all the excellences present in the territory, a great connoisseur of wines and typical foods. Great cook and organizer. He was a great colleague for organizing holidays out of standard.
Ylenia P.

Ylenia P.

review about Drop the moorings: explore the Aeolian Islands in a flotilla of 3 boats July 2021

10 / 10
My week on a sailing boat in the Aeolian Islands was crazy. I traveled in a flotilla with three captains, Alessio, Lorenzo and Antonello, completely exceptional, attentive, strict, patient and welcoming. As for Alessio, well, you should know him! He tells you improbable stories and never avoids exposing/imposing his outlook on life. His visceral voice pierces your meninges but you can't stop being in a good mood in his presence. He is the captain of all captains and traveling with him was just fabulous; I couldn't imagine going to sea with anyone else. I loved everything about that week and if I close my eyes I can still see myself there, sitting at the stern watching the sun set the horizon line on fire.
Jacopo R.

Jacopo R.

review about CRAZYSAIL CROATIA - 6 boats in the Split Archipelago August 2021

10 / 10
The official videomaker of the holiday ! A wonderful person, always available, with a smile and precise. Thanks for everything! We will miss your coffees! We look forward to your video!
Piero G.

Piero G.

review about In the sea of Ulysses with the sport you want! August 2021

10 / 10
Leo was a skipper available from the beginning to facilitate the organization of the trip and during the holiday he showed us his competence and perfect knowledge of the places. Then the sympathy and the feeling did the rest... (also good food). great experience, which I recommend.
Marco S.

Marco S.

review about Sailing week in the Tuscan Archipelago: relaxing bays and beautiful islands! August 2021

8 / 10
Alessandro is a skipper with experience and competence as well as being very sociable and nice to review some functional things on the ?...
Pietro S.

Pietro S.

review about 3 boats from Genoa to Rome: Cinque Terre, Porto Venere, Capraia, Elba, Giglio, Argentario July 2021

10 / 10
Young, fun and helpful. Wonderful holiday
Federico C.

Federico C.

review about CRAZYSAIL CROATIA - 6 boats in the Split Archipelago August 2021

10 / 10
Grandeeeee..!!!! Seba and an incredible person.. organize every evening with the team for many people is not an easy job! However they made this holiday an unforgettable experience! Great Seba! Ask Him: "What time is it?" and you would be surprised every day! heheh
Margherita O.

Margherita O.

review about CRAZYSAIL ORIGINAL - 4 boats in the Split Archipelago August 2020

10 / 10
super attentive skipper, patient, and great person!! really recommended!!!
Davide C.

Davide C.

review about CRAZYSAIL ORIGINAL - 4 boats in the Split Archipelago August 2020

10 / 10
Gianluca was our holiday DJ, but first of all an integral and fundamental member of the crew. Fantastic! Always available and ready to lend a hand and put the right sound at any time of the day! TOP
Fabio Z.

Fabio Z.

review about CRAZYSAIL ORIGINAL - 4 boats in the Split Archipelago August 2020

10 / 10
now in her 4th year with her as Staff Director, a woman full of energy!! knows how to create together with the Staff a strong bond with all the Crew trying to satisfy the requests and filling the days with joy and activities. never unprepared!!
Fabio Z.

Fabio Z.

review about CRAZYSAIL ORIGINAL - 4 boats in the Split Archipelago August 2020

10 / 10
Passed from passenger to staff she managed with her joy together with Lucrezia and Ariele to manage situations that were not always simple given the period. My Crew recognizes in her a great desire to do. Thank you
Fabio Z.

Fabio Z.

review about CRAZYSAIL ORIGINAL - 4 boats in the Split Archipelago August 2020

8 / 10
She was at her first experience as Staff of our holiday, always ready with a smile to involve all the Crew of the holiday! together with Silvia and Ariele they managed situations that were not always simple... I am very happy to have had her in our group, I do not give the 5 stars since her training must be completed
Massimiliano M.

Massimiliano M.

review about 2 boats in the Kornati and southern Croatia: a dream trip for sailing lovers August 2020

8 / 10
Very pleasant holiday in the company of equally pleasant people who made the holiday fun, carefree and full of anecdotes to tell. Marco is a capable and empathetic skipper, assisted by Roberto who has shown the exact same skills, even in situations dictated by unfavorable weather. The places allow numerous nights at anchor and the possibility of sailing, the true essence of the sailing holiday. It could have been 5 stars of appreciation if only there had been more prior communication from Marco, depriving me in fact of choosing what was right for me. My flexibility has allowed this not to affect my stay and I am equally convinced that others would not have liked it. It is a piece of advice that I would like to give for the future. Ad maiora. Ps sabbbinooooo????????????????
Federica G.

Federica G.

review about Flotilla on the Aeolian islands: young and experienced skippers, guaranteed fun :) - week 1 August 2020

10 / 10
Lorenzo is a young guy with a lot of passion for the sea and a lot of professionalism that has helped to create a nice group.
Cristina F.

Cristina F.

review about Discovering the Grenadines by catamaran December 2019

10 / 10
Perfect organizer, very prepared and precise... as always, a guarantee!
Alessandro P.

Alessandro P.

review about Discovering the Grenadines by catamaran December 2019

10 / 10
Massimo is an exceptional person, able with his professionalism and passion to make the boat holiday a beautiful experience and always safe. Available to involve the crew in the maneuvers on board.
ANTONELLA G.

ANTONELLA G.

review about Sun & Fun Marmaglia Flotilla August 2019

10 / 10
Thanks for your availability and sympathy
ANTONELLA G.

ANTONELLA G.

review about Sun & Fun Marmaglia Flotilla August 2019

10 / 10
Angelo is always exquisite and very kind ...
Giuditta I.

Giuditta I.

review about Overwhelmed by an Unusual Destiny ... In the Flotilla! August 2019

10 / 10
Girvano is not simply a great skipper; Girvano is a master of navigation, windsurfing, sup, cooking and.... of life! Thanks to his skilful guide I had my fill of new experiences and spent a fun and super exciting week!
MICHELA B.

MICHELA B.

review about Flotilla of 3 sailboats to Sardinia, La Maddalena and Corsica August 2019

10 / 10
This holiday would not have been the same without Francesca: perfect in organization and boat, an inexhaustible source of charge and positive energy. Great!
MICHELA B.

MICHELA B.

review about Flotilla of 3 sailboats to Sardinia, La Maddalena and Corsica August 2019

10 / 10
Davide is just amazing! Very good captain, precise, present and attentive to the needs of his crew. I wish I could be on board even now!
Barbara D.

Barbara D.

review about Greece - International Flotilla 2019 August 2019

10 / 10
super, we enjoy too much and Eliot ws wonderfull.
Filippo P.

Filippo P.

review about Flotilla on the routes of Ulysses in Ionian Greece - 2nd week August 2019

10 / 10
With his hand-rolled cigarette... his ugly sailor's glove... a love for the sea that exudes from every pore... the attention of the perfectionist A true sailor but with a kind soul, ready to listen to everyone's needs and to make himself in 4 to support them; clearly master of his boat in all conditions; ad majora commander
Stefano M.

Stefano M.

review about Flotilla on the routes of Ulysses in Ionian Greece - 2nd week August 2019

10 / 10
Well what about Laura is the best skipper ever!! She is a beautiful nice and decisive girl!! Thank you for this week boss!!!
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6 reasons to take part in a sea crossing or deep-sea sailing

.
  • 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.
  • .
  • 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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