header cover
logo

Log in

Yacht sailing holidays & skippered tours in Tuscany

Discover the magic of sailing holidays in Tuscany! Get onboard with a local skipper and live a unique adventure with your crew: learn to sail, explore incredible places, recharge your batteries and experience the local culture & gastronomy.

Why book a holiday with Sailsquare?

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

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 more about the skipper and travellers who have already booked the holiday, to find out more about the

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 - Yacht sailing holidays & skippered tours in Tuscany

4111 reviews

avatar image

Wind, sea and freedom: a week between Corsica and the Tuscan archipelago

09/8/2026

matteo l.

A week at sea simply fantastic! Joshua is an exceptional skipper: knowledgeable, patient and always available. A truly unforgettable experience!
avatar image

Mini-cruise with WWF guide in the heart of the Tuscan Archipelago

09/8/2026

Simone M.

-

IT

an experience that far exceeded expectations!! the skipper, Nico Pente, proved to be really good, helpful, easy-going, nice and able to bring a neophyte closer to sailing, the WWF guide Joelle Montesano was very good!! super prepared, passionate, engaging, enthusiastic!! And then the group, 6 people who in 4 days and 4 nights have been able to create a close-knit group capable of creating and sharing special moments, moments of light fun and deep reflections, laughter and confidences! I wished it would never end!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

09/8/2026

Paolo P.

-

IT

Interesting tour in very nice places, for the amount spent (which is in the high end of the market) I found the boat a bit dated. Competent skipper but on some occasions he lost his patience a little too much

Wind, sea and freedom: a week between Corsica and the Tuscan archipelago

09/7/2026

Giulia F.

-

IT

A beautiful week between islands and the sea of the most beautiful colors. A very good skipper capable of involving young and old guests with enthusiasm and patience!

Customer Support

customer support

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!

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!

Guides & tips


Italy

Tuscany, Sardinia, the Aeolian Islands and Liguria are just some of the most beautiful destinations for a sailing or catamaran holiday, let's discover them all!
Guide to Italy on a sailing boat

Tuscany

The island of Elba, Capraia, Il Giglio and Giannutri are just some of the best destinations for a sailing or catamaran vacation in Tuscany.
Guide to the Tuscany on a sailing boat

WWF Whale watching cruises

A close-to-nature sailing cruise that integrates unrepeatable emotions and new scientific knowledge, perfect for true lovers of the sea, ready to have fun, wonder and delve into the magical world of cetaceans.
Guide to the WWF Cruises

Catamaran vacations

An alternative to the sailboat, the catamaran is an ideal choice for those who do not want to give up comfort and convenience and for a first vacation at sea.
Guide to the catamaran vacations

Flotilla holiday

A perfect vacation for singles (and others) to experience sailing, meet new friends and multiply the fun.
Guide to the flotilla holidays

Singles and solo travellers

Set out alone and return enriched by an unparalleled baggage of freedom, new friendships and lasting bonds. It is on a sailboat that an adventure as a solo traveler turns into a unique sharing experience.
Guide to solo travellers sailing holidays

Sailing vacations for families

To leave with one's family and return home enriched by an unparalleled baggage of adventure, bonds and indelible memories.
What to know before you go sailing with your family?

Sailing with children

Have you ever wondered if there is a vacation that is both the best for children and parents? The answer is yes, and it is indeed on a sailboat!
uide to sailing vacations with children

Tuscany: the best travel ideas

Other travel ideas

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

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