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.
25
experiences
25
experiences
4.8
Italy: Tuscany
4 days - 3 nights
One departure available
September
€450
Per person
4.8
Italy: Tuscany
3 days - 2 nights
One departure available
September - October
€240
Per person
4.9
Italy: Tuscany
4 days - 3 nights
One departure available
September
€283
Per person
4.8
Italy: Tuscany
2 days - 2 nights
2 departures available
September - October
Starting from
€240
Per person
Italy: Tuscany
1 day - 0 nights
29 departures available
September - November
Starting from
€115
Per person
4.8
Italy: Tuscany
7 days - 7 nights
One departure available
September
€590
Per person
4.0
Italy: Tuscany
2 days - 2 nights
One departure available
September
€240
Per person
4.9
Italy: Tuscany
3 days - 2 nights
2 departures available
September
€200
Per person
4.9
Italy: Tuscany
2 days - 2 nights
2 departures available
September - October
€250
Per person
4.6
Italy: Tuscany
3 days - 2 nights
One departure available
October - November
€350
Per person
5.0
Italy: Tuscany
3 days - 2 nights
One departure available
October
€390
€362
Per person
5.0
Italy: Tuscany
1 day - 0 nights
2 departures available
October
Starting from
€97
Per person
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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
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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
3714 reviews
Midweek special on the island of Elba, 2 nights
09/18/2025
Roberta Anna P.
-
Italy
Week-end all'Elba - Hostess a bordo
09/17/2025
Riccardo A.
-
Italy
Long weekend of whale watching with WWF guide on an 18-meter schooner
09/16/2025
Paolo S.
-
Italy
Trekking and sailing weekend on the island of Elba
09/16/2025
Fabio B.
-
Italy
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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
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
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
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
A perfect vacation for singles (and others) to experience sailing, meet new friends and multiply the fun.
Guide to the flotilla holidays
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
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?
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
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