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.
87
experiences
4.9
Super!
Italy: Tuscany
4 days - 4 nights
One departure available
August
€750
Per person
New
Italy: Tuscany
7 days - 7 nights
2 departures available
July - August
Starting from
€835
€752
Per person
4.8
Super!
Italy: Tuscany
6 days - 6 nights
8 departures available
July - September
Starting from
€980
Per person
4.9
Super!
Italy: Tuscany
4 days - 5 nights
One departure available
August
€800
Per person
4.8
Super!
Italy: Tuscany
7 days - 7 nights
One departure available
September
€750
Per person
4.8
Super!
Italy: Tuscany
3 days - 2 nights
2 departures available
September
€260
€234
Per person
4.8
Super!
Italy: Tuscany
5 days - 4 nights
3 departures available
September
€490
Per person
4.9
Super!
Italy: Tuscany
2 days - 2 nights
2 departures available
September
€280
Per person
4.9
Super!
Italy: Tuscany
3 days - 3 nights
One departure available
September
€280
Per person
4.9
Italy: Tuscany
7 days - 7 nights
One departure available
August
€995
Per person
4.9
Italy: Tuscany
3 days - 3 nights
2 departures available
September
€390
€351
Per person
4.8
Italy: Tuscany
3 days - 3 nights
One departure available
September
€380
€361
Per person
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Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.
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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
3892 reviews
All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company
07/18/2026
Elisa A.
-
IT
Tuscany and Corsica: sailing sun adventure good food energy and well-being
07/17/2026
chiara s.
-
IT
Wind, sea and freedom: a week between Corsica and the Tuscan archipelago
07/16/2026
Carlotta P.
-
IT
Magnificent weekend of approach to sailing on the island of Elba
07/16/2026
Alfredo M.
-
IT
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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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