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Crewed yacht sailing holidays & tours in Tuscany

Crewed yacht sailing holidays & tours in Tuscany

Get on board on a crewed sailing holiday in Tuscany for the most relaxed time ever.

  • Sailing Holidays
  • Italy
  • Tuscany
  • Crewed

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
  • 12 reviews
    confirmed

    1st May - Sailing and trekking on the Island of Elba

    from 28 April - 3 nights
    Tuscany Italy
    2 people
    are onboard
    371€ Per person
  • 13 reviews

    Weekend to discover Elba - Hostess on board - All Inclusive

    from 5 May - 2 nights
    Tuscany Italy
    1 person interested
    in this holiday
    467€ Per person
  • 13 reviews

    Super weekend to discover Elba - Hostess on board - All Inclusive

    from 12 May - 2 nights
    Tuscany Italy
    Join in on this experience!
    509€ Per person
  • 13 reviews

    Super weekend to discover Elba - Hostess on board - All Inclusive

    from 19 May - 2 nights
    Tuscany Italy
    Join in on this experience!
    509€ Per person
  • 25 reviews
    confirmed

    Elba: spring of emotions - Hostess on board! (Cabins with bathroom)

    from 1 June - 3 nights
    Tuscany Italy
    4 people interested
    in this holiday
    376€ Per person
  • 25 reviews
    confirmed

    Elba, all the colors of the big blue - Hostess on board! (3 cabins with bathroom)

    from 4 June - 6 nights
    Tuscany Italy
    Join in on this experience!
    599€ Per person
  • 25 reviews
    confirmed

    The sunsets of the Tyrrhenian - Hostess on board

    from 11 June - 6 nights
    Tuscany Italy
    Join in on this experience!
    599€ Per person
  • 25 reviews
    confirmed

    Elba, all the colors of the big blue - Hostess on board! (3 cabins with bathroom)

    from 18 June - 6 nights
    Tuscany Italy
    Join in on this experience!
    599€ Per person
  • 25 reviews
    confirmed

    Elba, all the colors of the big blue - Hostess on board! (3 cabins with bathroom)

    from 25 June - 6 nights
    Tuscany Italy
    2 people
    are onboard
    599€ Per person
  • 23 reviews
    almost
    confirmed

    Sailing between Capraia and Northern Corsica

    from 26 June - 5 nights
    Tuscany Italy
    Join in on this experience!
    658€ Per person
  • 23 reviews
    almost
    confirmed

    Sailing between Capraia and Northern Corsica

    from 2 July - 6 nights
    Tuscany Italy
    Join in on this experience!
    742€ 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 - Crewed yacht sailing holidays & tours in Tuscany

93 reviews
20 / 10
Elisa V.

Elisa V.

review about Between Tuscany and Corsica: infinite well-being - cook on board! July 2022

10 / 10
It was an unforgettable week aboard Kikko, a wonderful boat, very spacious and kept like a jewel, which exudes the passion for the sea that only three fantastic people like Daniele, Mariapia and Andrea can infuse. Daniele is an excellent captain, with him you always feel in good hands, thanks to his experience and his ability to keep the situation under control with a smile on his face. Mariapia is an exceptional cook, she delighted us throughout the week with dishes that are always different and able to satisfy everyone's tastes. Andrea is a very nice guy who at sea, despite his young age, has experience to sell. Together, they make an exceptional trio but above all a sweet family that makes all guests feel at home and in total relaxation. For lovers of water sports, the boat is super equipped and you can experience wonderful places in an even more adventurous way. Thank you for this wonderful experience! Elisa and Michele
Stefania C.

Stefania C.

review about Northern Corsica and Capraia ... Hostess on board July 2022

10 / 10
Unforgettable holiday! Giulia and Vittorio are a perfect team, they make you feel at home. Giulia, in addition to being an excellent cook, is attentive to every need and involves with her sympathy; Vittorio is a skipper of great experience, with him on sails in perfect safety and transmits the passion he has for his work. I thank them both for the experience they made me live and I hope to be able to travel with them again. Angela
Elena S.

Elena S.

review about Weekend among the pearls of the archipelago with hostess on board June 2022

10 / 10
Fantastic experience, what to say elba always beautiful but this time in particular, the skipper Edoardo and his partner Irene were very good I dare say of the travel companions albeit short. Edoardo very good and self-confident in steering the boat and Irene an excellent assistant but above all cook. Experience to be redone as soon as possible Everything above all expectations
Daniela D.

Daniela D.

review about For a day feel like a pirate of the Caribbean aboard the catamaran, Captain Marco's sailing ship May 2022

10 / 10
What can I say! A very pleasant first experience in the company of Marco and his wife!! My husband and I should have had travel companions but at the last we found ourselves exclusive guests of the tour ... We sailed, chatted, laughed, sunbathed and slept in absolute freedom. We were greeted by a good aperitif which was then followed by an excellent lunch and also a good snack. We felt pampered until sunset and to conclude this beautiful adventure we also thought of the dolphins spotted in packs along the way back ... Thanks Marco!! Good wind and to the next adventure!
ELENA L.

ELENA L.

review about experience the sea on a sailboat with hostess September 2021

10 / 10
Fantastic holiday, exquisite people! We can't wait to start again!
Heiner R.

Heiner R.

review about All-Inclusive holiday with Chef on board in the enchanting setting of the Tuscan Archipelago July 2021

10 / 10
Tommaso perfect skipper and Anton cooks really well. I had fun and rested. 100% successful holiday thanks to the attention to detail and the All-inclusive formula for the lazy like me. To recommend.
Luca C.

Luca C.

review about Between Elba and Corsica-Boat 14 meters exclusively for 4 guests-Hostess on board. July 2021

10 / 10
Ganzissimi: Cinzia, Michel, the boat. Excellent holiday with exceptional skipper and hostess. Cinzia is very nice, always attentive and cooks divinely. Michael is a professional who knows the best places in the area, and is calm and always available. The boat is comfortable and impeccably clean. Return! Luca, Tracy, David, Maria Claudia
Andrea Q.

Andrea Q.

review about Cruise between Capraia and Corsica with professional skipper and hostess cook. Pamper yourself in the waves! July 2020

10 / 10
WONDERFUL holiday ! I was at the first experience of a week on a sailing boat, the Skipper Riccardo and Giulia guided us in numerous coves and their passion was seen right away. Professional, nice and attentive to every need of the customer, a truly unforgettable holiday together with other wonderful people, you can not ask for better. Meals on board are never trivial, Giulia is very good in the kitchen as Riccardo is a skipper with great experience.
Francesca R.

Francesca R.

review about Charter with KITCHEN SERVICE between the islands of the Tuscan Archipelago July 2020

10 / 10
Wonderful week from all points of view. Ale very good skipper and Mara perfect collaborator ... as soon as we got on board they immediately made us feel "old friends" rather than "guests". The boat is extremely comfortable, in excellent condition and always impeccably clean. Mara's kitchen and Alessandro's cellar delighted us all the time, what else to say if not.... when do you start again? Francesca & c.
Ivan A.

Ivan A.

review about Elba and Capraia on 18m maxi sailing yachts with Skipper and Hostess, what more could you want? June 2020

10 / 10
Fabio and Marino made me feel part of the crew, taught a lot and amused ... you can't ask for more!!!
Enrico S.

Enrico S.

review about Elba and Capraia the first week of September between the turquoise bays and the beautiful colorful villages September 2019

10 / 10
This fantastic experience allowed me to know not only an excellent commander, scrupulous, attentive to the needs of his guests, an expert connoisseur of the sea and navigation, capable in the difficult role of creating amalgam between the crew, but also an exquisite, friendly, nice person, with a great dose of common sense, with whom it is really pleasant to spend your time. I am thrilled with the experience that my wife and son and I have had. Surely it will be the first of many other holidays. I must also praise Luca, Paolo's son who, despite his young age, has proved to be a great connoisseur of the weather, boats, the sea and spearfishing.
Margherita D.

Margherita D.

review about Elba galeotta and the Tuscan pearls - Hostess on board August 2019

10 / 10
Competence, kindness and a lot of sympathy on board the Allegra! Fabio, experienced and charismatic sea lion, sweet our Angela! Good wind guys! See you soon! Daisy????
Debora B.

Debora B.

review about CATAMARAN, LUXURY AND RELAXATION August 2019

10 / 10
Beautiful holiday, Stefano a perfect Skipper, safety and precision in navigation and maneuvers, on a catamaran in which nothing is really missing!! Kira and her kitchen the extra touch... or maybe the real extra touch was Giotto, the dachshund??? Absolutely to be repeated
Deborah D.

Deborah D.

review about Exclusive Cruise on Regatta Boat, with Hostess on Board! August 2018

10 / 10
Pleasant holiday and definitely to be redone. Group immediately close-knit, skipper available, professional and fun, boat flying over the water. The days are spent between baths in turquoise waters, exciting and even instructive sailing, spritz at sunset and chatter under the stars. All unforgettable.
Edoardo C.

Edoardo C.

review about Gennakerata between the islands June 2018

10 / 10
Stefano is a Skipper of great experience and great patience, you can perceive not only his ability to lead the boat, but also his experience as an instructor. The man you would like by your side in a storm in the open sea.
Edoardo C.

Edoardo C.

review about Gennakerata between the islands June 2018

10 / 10
Massimiliano is a concentrate of love for sailing; Toned skipper in navigation, relaxation companion at anchor, glides on the water like a hawk. You learn a lot from him, and I'm not just talking about technique.
Alfonso C.

Alfonso C.

review about Gennakerata between the islands June 2018

8 / 10
Great instructor.great character that always puts you at ease . Staying on the boat must be pleasure .on Marco is assured
Marco G.

Marco G.

review about Saleccia Forever! April 2018

10 / 10
Enrico and his beautiful boat welcomed us and made us spend 5 pleasant days we hope to meet again soon good wind!!!
Paola A.

Paola A.

review about ONE WAY - From Sardinia to Tuscany, sailing and relaxation September 2017

8 / 10
Nice boat, good captain
Ana Maria  P.

Ana Maria P.

review about Capraia, Elba, North Corsica sailing! August 2017

10 / 10
Holiday from 110 and praise! Richard... he is simply a No. 1 because he loves his work that he does with full dedication. Very professional, kind and careful to never miss anything. I hope to relive other fun moments and still steer, under his watchful eye, his beautiful and comfortable boat, Mr. Hood.... maybe with the same crew of beautiful people! Good wind to all ?
Stefania B.

Stefania B.

review about Tuscan Archipelago and Corsica cruise on a beautiful 15 meters 5 cabins 5 bathrooms !! August 2017

10 / 10
Very experienced, safe, fun, helpful
Francesco S.

Francesco S.

review about Bridge of June 2 on the Tuscan archipelago June 2017

10 / 10
Marino is really Skipper with a capital S... great professionalism but at the same time always cheerful and helpful. Boat level of absolute comfort. As a good sea wolf he prefers to stay 24 hours a day on a boat, so if you want to make a bet on land, you have to warn him ... :) Until next time!!
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