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.
90
experiences
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
4.8
Italy: Tuscany
7 days - 6 nights
One departure available
August
€780
€741
Per person
4.9
Italy: Tuscany
2 days - 2 nights
2 departures available
July
€320
Per person
Italy: Tuscany
7 days - 7 nights
One departure available
August
€1,299
Per person
4.7
Italy: Tuscany
4 days - 4 nights
One departure available
September
€567
Per person
5.0
Italy: Tuscany
6 days - 6 nights
3 departures available
July - August
Starting from
€950
Per person
4.7
Italy: Tuscany
2 days - 3 nights
One departure available
July
€390
Per person
5.0
Italy: Tuscany
3 days - 3 nights
3 departures available
July - September
Starting from
€350
Per person
New
Italy: Tuscany
2 days - 1 night
One departure available
August
€160
Per person
5.0
Italy: Tuscany
4 days - 3 nights
2 departures available
August
Starting from
€320
€288
Per person
4.9
Italy: Tuscany
4 days - 3 nights
One departure available
August
€510
€459
Per person
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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
3887 reviews
Long weekend among the queens of the archipelago - Elba and Capraia
07/14/2026
CHIARA A.
-
IT
Long weekend among the queens of the archipelago - Elba and Capraia
07/14/2026
Alessia B.
-
IT
Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company
07/14/2026
Luca S.
-
IT
Weekend among the most beautiful coves of Elba
07/14/2026
andrea t.
-
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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