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Flotilla yacht sailing holidays & tours in Italy

Flotilla yacht sailing holidays & tours in Italy

Discover the magic of flotilla sailing holidays in Italy! A new way of traveling with your loved one, your friends or your family. Find your dream adventure among hundreds of holidays organised by local skippers.

  • Sailing Holidays
  • Italy
  • Flotilla

FLEXIBLE CANCELLATION.

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

  • 99+ reviews

    Easter in a flotilla of two comfortable boats in Elba and Capraia

    from 7 April - 3 nights
    Tuscany Italy
    1 person interested
    in this holiday
    297€ Per person
  • 99+ reviews

    1st May Elba Capraia in 2 boats: How do you explain a sunset on a boat in words?

    from 28 April - 3 nights
    Tuscany Italy
    4 people interested
    in this holiday
    371€ Per person
  • 99+ reviews
    Discounted
    spots until 31 Mar.

    WINDART FESTIVAL: a weekend of pure fun!

    from 19 May - 2 nights
    Tuscany Italy
    43 people
    are onboard
    98 79€ Per person
  • 20 reviews
    confirmed

    Cilento on a sailing boat with skipper, staff and galley service

    from 31 May - 4 nights
    Campania Italy
    9 people
    are onboard
    650€ Per person
  • 99+ reviews
    confirmed

    Rabble Boat Party - Early Summer Flotilla

    from 16 June - 2 nights
    Liguria Italy
    20 people
    are onboard
    270€ Per person
  • 32 reviews
    confirmed

    San Pietro e Paolo in Ponza: 5 boats in the flotilla

    from 28 June - 4 nights
    Pontine Islands Italy
    9 people interested
    in this holiday
    591€ Per person
  • 99+ reviews
    confirmed

    Different cruise to the Aeolian Islands: Party and new friends on a Luxury Catamaran

    from 29 July - 7 nights
    Aeolian Islands Italy
    1 person interested
    in this holiday
    1.399€ Per person
  • 14 reviews
    confirmed
    Flotilla

    Velasquez flotilla of 3 boats in Sardinia

    from 5 August - 7 nights
    Northern Sardinia Italy
    2 people
    are onboard
    1.101€ Per person
  • 99+ reviews
    confirmed

    Flotilla Different: Party and new friends on the Aeolian Islands

    from 5 August - 7 nights
    Aeolian Islands Italy
    2 people
    are onboard
    1.099€ Per person
  • 32 reviews
    Discounted
    spots until 1 Apr.

    Flotilla to the Aeolian Islands: Exciting sunsets in good company

    from 5 August - 7 nights
    Aeolian Islands Italy
    Join in on this experience!
    1.280 1.174€ Per person
  • 32 reviews
    confirmed

    Flotilla of 3 boats between Tuscany and Corsica

    from 5 August - 7 nights
    Tuscany Italy
    Join in on this experience!
    1.280€ Per person
  • 32 reviews
    confirmed

    Flotilla between the Gulf of Naples and the Pontine Islands

    from 5 August - 7 nights
    Pontine Islands Italy
    Join in on this experience!
    1.280€ Per person
  • 1
  • 2

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Get onboard solo, with your family, or your friends

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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 yacht sailing holidays & tours in Italy

1412 reviews
18 / 10
Elisabetta T.

Elisabetta T.

review about A journey in the name of nature, fun and lots of relaxation! August 2022

10 / 10
Professional skipper, prepared, attentive to the needs of all the crew, fun. Along the coasts of the islands made us discover wonderful coves!!!!! What about holiday to repeat! Good wind Ale!!! You're the top!!
Fabio S.

Fabio S.

review about Maddalena Park and Costa Smeralda in premium catamaran and sailing boat - WEEK 2 August 2022

10 / 10
One of the most ingamba skippers I have known in my life. A person of heart and very technically prepared... always available and ready to help you in your time of need. A great man and a great skipper.
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%).
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.
Nicola S.

Nicola S.

review about Maddalena Park and Costa Smeralda in premium catamaran and sailing boat in Flotilla! - WEEK 1 August 2021

8 / 10
Boat: a truly spectacular and comfortable Bali catamaran for 10 people with plenty of space, even if you want to be alone. Massimo the skipper: always quiet, never intrusive, he always facilitated our holiday. Also called aggressive valet parking for positioning at anchor super strategic. :-) Perfect group, but it's a matter of luck. I give only 4 stars for my accommodation in the single bow with entrance from porthole. I thought I would find a bed but it wasn't, only 30cm wide at the feet, I slept very badly. I am of small stature, a man older than me would have had difficulty even to enter. In addition, the single uses the captain's shared bathroom, which I thought was accessible, instead it was right inside his room. At night it was unthinkable to access it and even during the day you seem to invade a private space, so it is almost like not having a bathroom. Overall, it was a major inconvenience. The double cabins were great and comfortable.
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
Moira L.

Moira L.

review about Egadi and the coast of Sicily - sailing by boat and catamaran July 2021

10 / 10
Very nice holiday, magnificent places and very nice travel companions with whom I spent very fun days. Catamaran nice and comfortable in the spaces, but a little neglected (it was not really spotless on our arrival especially in the interior spaces). Skipper extremely competent, tireless and very helpful towards guests, careful to always take into consideration the requests of all. Nice to travel in a flotilla for the chance to meet more people.
Alessio  R.

Alessio R.

review about Sailing holiday to the Aeolian Islands in mini Flotilla: Sea, Sailing, Relaxation and Fun August 2019

10 / 10
Excellent organization both for careful choice of boats, and for care and selection of participants. Marianna is a sailing instructor with a lot of passion for the sea, the same that she puts for all her secretarial work. It is a pleasure to both work with her and to have her crews.... Rely on her and safely you will make an unforgettable experience in total safety and in the hands of experienced people and with many miles of navigation behind them. Thank you Mary of all and honored to be of yours for more than fifteen years.
Alessandro S.

Alessandro S.

review about Flotilla of 5 Boats to the Aeolian Islands: young and experienced skipper, fun guaranteed :) August 2019

10 / 10
Daniele has all the qualities you can ask of a skipper. Attentive to the safety and needs of his crew, he loves to sail and teach. It's brilliant and fun. A pleasure to be on the boat with him and once on land you can not be friends
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.
Francesco G.

Francesco G.

review about Marmaglia Flotilla Sun & Fun Maddalena and Southern Corsica August 2019

10 / 10
I sailed a lot with Arturo and I can tell you that it could not happen better! He is a sea wolf, competent and available to the crew and other skippers, he does not miss an opportunity to share his passion and experience with lightness and sympathy making the stay on board pleasant. You are always sure that you can count on a friend, a companion of adventures. He is a skipper who fully embraces the philosophy "mi casa es tu casa", what more could you want? Hello commander, to the next adventure!!
Maria D.

Maria D.

review about Late Summer Flotilla 2019 - Anonymous Skipper September 2019

10 / 10
When you have a Bolognese on the boat you have everything. Oli is a fantastic person with immense sympathy that makes you feel immediately at home. Wonderful skipper . Rating 100
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!
Daniela M.

Daniela M.

review about Flotilla Sardegna 2019, new encounters and fun - 5 boats August 2019

10 / 10
Unforgettable holiday. Absolutely to be redone ... sympathy, fun, safety. Unfortunately the 40 knots of mistral forced us to change course abandoning the idea of Corsica but We still visited wonderful coves and beaches with turquoise and calm waters. Absolutely recommended !
Veronica C.

Veronica C.

review about 3 Catamarans for 2 Weeks in Flottiglia in the Wonderful Maddalena - South Corsica August 2019

10 / 10
What can I say... an unforgettable holiday like the whole crew! Thank you all for this beautiful experience that I will carry forever with me! Thank you Skipper and thank you guys!!!!!
Federica F.

Federica F.

review about Egadi Islands: sun and relaxation in the Mediterranean August 2019

10 / 10
Francesco is a man of experience, not only at sea. Sailor, chef, masseur, kitesurfing master, traveler and I could go on.... It is able to put the crew at ease and to read the needs of the group. He also tries to fulfill everyone's wishes, taking advantage of all his skills and knowledge on the spot. He's a great person! Thanks Ciccio!
Simona P.

Simona P.

review about In the Pontine flotilla August 2019

10 / 10
First sailing holiday for me, and I must say that I found myself very well! Luca is a very professional skipper, he immediately put us in a position to understand how it is possible to enjoy maximum freedom in complete safety! Excellent cook, he delighted us with his delicacies, he always tried to meet the needs of guests and also taught us some rudiment of sailing. Big!
Marco R.

Marco R.

review about 100% AEOLIAN ISLANDS - 9 nights in flotilla between ALL the islands August 2019

10 / 10
Thank you Antonio for your skills and for everything!!! I hope to be able to sail with you again!! Thanks also to Irma for the wonderful collaboration! Good wind!
Marco R.

Marco R.

review about 100% AEOLIAN ISLANDS - 9 nights in flotilla between ALL the islands August 2019

10 / 10
With Antonio, Irma and Gabriella everything was great. Thank you very much to everyone and good wind!!!
Roberta L.

Roberta L.

review about Egadi and Coast of Sicily - Flottiglia in Boat for Sailing, Sea and Fun! August 2019

10 / 10
Giusto is very professional and elastic at the same time! Highly recommended
Marta M.

Marta M.

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

10 / 10
Angelo welcomed us on his Lulù impeccably. 5 star cook and 10 star skipper. His lectures on the rudiments of sailing proved to be very useful during navigation. Tips on where to eat on the ground, a real treat. Thank you for this wonderful experience! See you soon to Angelo, Valeria and Lulù.
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Top Destinations

  • Italy
  • Greece
  • Tuscany
  • Aeolian Islands
  • Northern Sardinia
  • Ionian Islands
  • France
  • Caribbean
  • Pontine Islands
  • Aegadian islands
  • Lake Garda
  • Cyclades
  • Croatia
  • Liguria
  • Spain
  • The Balearic Islands
  • French Riviera and Porquerolles
  • Sicily
  • Gulf of Naples
  • Amalfi Coast
  • Split Archipelago
  • Grenadines & Martinique
  • French Polynesia
  • Dodecanese
  • Brittany and Normandy
  • The Maldives
  • Saronic Islands and Athens area
  • Guadeloupe
  • Corsica
  • Canary Islands

Top Travel Ideas

  • Adventure
  • Catamaran
  • Courses & regatta
  • Day trips
  • Flotilla
  • Gulet and sailing ship
  • Monohull
  • Offshore
  • Sport & wellness
  • Whole boat with skipper
  • All inclusive
  • Crewed
  • WWF Sailing Cruises
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