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.
114
experiences
4.8
Italy: Tuscany
3 days - 3 nights
2 departures available
July - August
Starting from
€370
€352
Per person
New
Italy: Tuscany
2 days - 2 nights
6 departures available
July - November
€250
Per person
4.8
Italy: Tuscany
3 days - 3 nights
5 departures available
July - September
Starting from
€410
€369
Per person
5.0
Italy: Tuscany
4 days - 3 nights
2 departures available
June
€300
Per person
4.8
Italy: Tuscany
7 days - 6 nights
2 departures available
August - September
Starting from
€750
€713
Per person
4.8
Italy: Tuscany
7 days - 6 nights
One departure available
August
€801
€721
Per person
4.8
Italy: Tuscany
7 days - 6 nights
One departure available
August
€890
€801
Per person
4.9
Italy: Tuscany
3 days - 2 nights
One departure available
September
€390
€351
Per person
4.9
Italy: Tuscany
4 days - 3 nights
4 departures available
June - September
€317
Per person
4.0
Italy: Tuscany
2 days - 2 nights
One departure available
July
€400
Per person
5.0
Italy: Tuscany
6 days - 6 nights
4 departures available
July - August
Starting from
€850
Per person
4.9
Italy: Tuscany
3 days - 2 nights
3 departures available
June - September
€250
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
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
3799 reviews
Long weekend of June 2nd to discover the coves of the islands of Elba
06/10/2026
Riccardo C.
-
IT
Long weekend of June 2 with WWF guide in the heart of the Tuscan Archipelago
06/10/2026
Enrica Caterina B.
-
IT
Weekend Elba or Capraia
06/10/2026
Gloria F.
-
IT
2 June 2026 long weekend between Tuscany and Corsica
06/10/2026
Giacomo D.
-
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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