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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

    Marmaglia flotilla in the Seychelles by Catamaran

    from 22 April - 7 nights
    Seychelles Indian Ocean
    18 people
    are onboard
    1.599€ Per person
  • 99+ reviews
    Discounted
    spots until 28 Feb.

    Mini Flotilla Rabble Sail & Friends - Ionian Greece

    from 29 July - 7 nights
    Ionian Islands Greece
    1 person interested
    in this holiday
    850 800€ Per person
  • 99+ reviews
    Discounted
    spots until 17 Mar.

    CRAZYSAIL CROATIA - Adventure Edition at the Split Archipelago

    from 29 July - 7 nights
    Split Archipelago Croatia
    1 person interested
    in this holiday
    999 899€ Per person
  • 14 reviews
    Discounted
    spots until 15 Feb.
    Flotilla

    Velasquez flotilla of 3 boats in Sardinia

    from 5 August - 7 nights
    Northern Sardinia Italy
    2 people
    are onboard
    1.101 990€ Per person
  • 14 reviews
    Discounted
    spots until 15 Feb.

    Relaxation and fun in Flotilla in Ionian Greece

    from 5 August - 7 nights
    Ionian Islands Greece
    1 person
    is on board
    1.101 990€ Per person
  • 99+ reviews
    Discounted
    spots until 28 Feb.

    Sun & Fun Rabble Flotilla - Ionian Greece

    from 5 August - 7 nights
    Ionian Islands Greece
    2 people interested
    in this holiday
    940 865€ Per person
  • 99+ reviews
    Discounted
    spots until 17 Mar.

    CRAZYSAIL CROATIA - Adventure Edition at the Split Archipelago

    from 5 August - 7 nights
    Split Archipelago Croatia
    Join in on this experience!
    999 899€ Per person
  • 99+ reviews
    Discounted
    spots until 17 Mar.

    CRAZYSAIL CROATIA - Flotilla Festival in the Split Archipelago

    from 5 August - 7 nights
    Split Archipelago Croatia
    2 people interested
    in this holiday
    999 899€ Per person
  • 99+ reviews
    Discounted
    spots until 17 Mar.

    CRAZYSAIL GREECE - Adventure Edition to the Saronic islands

    from 5 August - 7 nights
    Saronic Islands and Athens area Greece
    1 person
    is on board
    999 899€ Per person
  • 14 reviews
    Discounted
    spots until 15 Feb.

    Relaxation and fun in Flotilla in Ionian Greece

    from 12 August - 7 nights
    Ionian Islands Greece
    1 person
    is on board
    1.191 1.072€ Per person
  • 14 reviews
    Discounted
    spots until 15 Feb.

    Velasquez flotilla of 5 boats in Sardinia

    from 12 August - 7 nights
    Northern Sardinia Italy
    2 people
    are onboard
    1.191 1.072€ Per person
  • 99+ reviews
    Discounted
    spots until 28 Feb.

    Sun & Fun Rabble Flotilla - Ionian Greece

    from 12 August - 7 nights
    Ionian Islands Greece
    1 person
    is on board
    940 865€ Per person
  • 1
  • 2

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Reviews - Flotilla sailing holidays & skippered cruises

3069 reviews
20 / 10
Maria Luisa G.

Maria Luisa G.

review about CRAZYSAIL CROATIA - 10 boats in the Split Archipelago August 2022

10 / 10
For those who love sailing, adventure, fun Elia is the right skipper! Tireless, fun and very smart. I can't wait to work together again!
Anna G.

Anna G.

review about LAST MINUTE! CRAZYSAIL GREECE - 7 boats to the Saronic Islands - LAST PLACES FOR WOMEN August 2022

10 / 10
Agata was the skipper of my first sailing holiday and I couldn't get better, passionate, professional and full of energy, a wonderful soul!
Matteo Q.

Matteo Q.

review about LAST MINUTE OFFER! - CRAZYSAIL GREECE - 4 boats to the Saronic islands August 2022

10 / 10
I had sensed Luca's potential as a skipper already at the Academy and the first week of the CrazySail Greece sailing experience was the confirmation I was waiting for. I am extremely proud to be part of the path luca has made and the results he has achieved. Despite various difficulties that he had to face, starting from the aftermath of Meltemi, up to the broken anchor sail, he managed not only to get out of it with his head held high at a technical level, but also not to make his crew weigh the unexpected situations, keeping morale high, the smile on everyone's lips and a strong desire to sail and party. Luca deserves a special mention for landing in Hydra, a very busy and difficult port, which often even the most prepared skippers avoid like the plague. He managed the mooring masterfully, giving his crew the opportunity to enjoy a fantastic day on the island. Great job, Luca and good wind for the future!
Matteo Q.

Matteo Q.

review about LAST MINUTE OFFER! - CRAZYSAIL GREECE - 4 boats to the Saronic islands August 2022

10 / 10
Isa is definitely the skipper for whom I have the most esteem and admiration of the whole CrazySail flotilla. She had already distinguished herself during the Academy, but it was during the first week of CrazySail Greece that she really showed her qualities. Despite my young age, I don't know any other person I would blindly rely on for technical skills and crew management. He led his crew during a week-long sailing experience in the Saronic Islands, with Meltemi aftermath, wind at 28-30 knots, gusty 35. Impeccable both in sailing and in port and raft maneuvers, having Isa as a skipper is an opportunity for all those who want to approach sailing and also for those more experienced. I am obliged to a special mention for how he managed the mooring in the port of Hydra, a well-known marina very busy and very difficult to approach, which many skippers even with more experience, avoid like the plague. Good wind, Isa!
Matteo Q.

Matteo Q.

review about LAST MINUTE! CRAZYSAIL GREECE - 7 boats to the Saronic Islands - LAST PLACES FOR WOMEN August 2022

10 / 10
I met Simone on a sailing boat and immediately there was a great understanding between us, which led us to consolidate a strong friendship, born from the common passion for the sea and sailing, as well as from the sharing of the same ideals. Simone is an excellent skipper, capable both at a technical level and at the level of crew management. You spend completely to give your crew strong emotions, as only sailing can do. In navigation with him you will feel safe in all weather and even where many skippers tend to "slip", that is, the maneuvers in port, Simone knows how to face them calmly and lucidly, thanks to the years of experience gained. I would like to recommend it to the entire Sailsquare Community; having him as a skipper will be an honor and a privilege and you will not regret it.
Maria Luisa G.

Maria Luisa G.

review about CRAZYSAIL CROATIA - 10 boats in the Split Archipelago August 2022

10 / 10
Vico is a talented young skipper. He combines sailing experience with great human skills, which make him a perfect captain for a cruise full of fun and relaxation. Working together at Crazysail has been really fun and his constant availability is a guarantee in teamwork. I can't wait to sail together again in the flotilla!
Maria Luisa G.

Maria Luisa G.

review about CRAZYSAIL CROATIA - 10 boats in the Split Archipelago August 2022

10 / 10
The solidity of Marco's sailing experience is perceived from the first moments and it is a pleasure to work with him in the flotilla. Experienced skipper, solid and reliable, manages to combine fun and safety for a dream holiday! Those who get on the boat with him can enjoy a wonderful experience in total relaxation.
Maria Luisa G.

Maria Luisa G.

review about CRAZYSAIL CROATIA - 7 boats in the Split Archipelago August 2022

10 / 10
I shared with Luca the experience in the flotilla of Croatia and we often found ourselves collaborating and discussing maneuvers and navigation. Great teammate, competent and reliable skipper, it is a real pleasure to work together!
Maria Luisa G.

Maria Luisa G.

review about CRAZYSAIL CROATIA - 10 boats in the Split Archipelago August 2022

10 / 10
Federico is an enthusiastic and experienced skipper. Always ready to fulfill the demands of his crew, keeping safety first. It's a pleasure to work together and I can't wait to set sail for the next sail.
Luca M.

Luca M.

review about CRAZYSAIL CROATIA - 7 boats in the Split Archipelago August 2022

10 / 10
I had the opportunity to work together with Milù in the flotilla, I found myself really well both personally and technically. Those who go by boat with her find a competent Skipper, available and able to entertain!
Davide G.

Davide G.

review about Maddalena Park and Costa Smeralda in premium catamaran and sailing boat - WEEK 1 August 2022

8 / 10
Unforgettable holiday, to be repeated definitely! Prepared and sociable skipper. Inspiration for improvement: more formalism in the checkin process of the boat (which was rented and not 100%).
Matteo Q.

Matteo Q.

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

10 / 10
Valeria proved to be both an excellent member of the boat crew, and an excellent member of the Staff in coordinating two crews during crazySail Croatia 2021. She is a sunny girl, always smiling and with a great desire to have fun and entertain the other participants in the holidays. Should you receive a boarding request from you, do not hesitate to confirm it! You won't regret it... word of Skipper!
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!!!
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????????????????
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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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Top Destinations

  • Italy
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  • Aeolian Islands
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  • Northern Sardinia
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  • Venice and the Gulf of Trieste
  • Gulf of Naples
  • Amalfi Coast
  • Dodecanese
  • Canary Islands
  • Sicily
  • Corsica

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