header cover
sailsquare logo

Crewed yacht sailing holidays & tours in Tuscany

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

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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 - Crewed yacht sailing holidays & tours in Tuscany

167 reviews

avatar placeholder

Elba, all the colors of the big blue - Stewardess on board - 3 Cab/ 3 Bathrooms

07/18/2025

Maurizio M.

-

Italy

Fabio and Angela are two excellent hosts. Of those who make the boat completely available to guests, to the point of making them the real owners by placing themselves at their complete disposal. Our desire - expressed from the beginning - was to "go sailing", carrying the boat and actively participating in the maneuvers. A will fully supported and guaranteed by Fabio, purist of sailing and good Master advocate of practice and putting himself to the test! We learned so much and had a lot of fun. Added to this is the good company, the beautiful (many) chats in the evening in the cockpit in the roadstead, with Angela's good food and a good glass of wine resulting from a careful and complete galley. We will definitely return to sail with them and [hidden], a boat that really knows how to give great emotions. Too bad only a day and a half lost for a great libecciata that forced us into port, ruining the initial intentions but allowing, thanks to Fabio, a nice complete circumnavigation of the island of Elba, wonderful even in its most hidden coves. Thanks guys.
avatar image

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

07/14/2025

Alberto M.

-

Italy

Riccardo proved to be an excellent Skipper, a true professional, always ready to take advantage of any gust of wind to unfurl the sails. Great cook and great company. A boat experience with Riccardo is highly recommended.
avatar image

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

07/13/2025

Ruben R.

-

Italy

It was a unique experience! Riccardo is an exceptional person, as well as a skipper: helpful, serious, willing and nice. He tries to create cohesion in the group, he loves to sail as soon as the conditions allow it, he is an excellent cook, a very good guide and a skipper of great experience and safety. The boat is very comfortable and well maintained. The places and bays visited were all wonderful, real pearls of unspoiled nature and landscapes that we will always carry with us. Thank you and see you soon! Ruben and Francesca
avatar placeholder

Week of sailing and sea between the Tuscan Archipelago and Corsica with Hostess

07/8/2025

sonia s.

-

Italy

-I spent a wonderful holiday with Paolo and Bianca. They are very kind, very nice, Bianca is a very good cook. They are very helpful . My first experience on a sailing boat was very pleasant. I saw beautiful places, coves that otherwise I could not have seen except by boat. I highly recommend a holiday with Paolo and Bianca

Customer Support

nightLifeGeneralInfo

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

search

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964