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.
108
experiences
4.8
Super!
Italy: Tuscany
10 days - 10 nights
One departure available
June - July
€1,200
Per person
4.8
Super!
Italy: Tuscany
2 days - 2 nights
6 departures available
July - September
Starting from
€200
Per person
4.9
Super!
Italy: Tuscany
3 days - 3 nights
One departure available
September
€280
Per person
4.9
Italy: Tuscany
4 days - 3 nights
2 departures available
August
€510
€459
Per person
5.0
New
Italy: Tuscany
6 days - 6 nights
One departure available
July
€900
€810
Per person
4.7
Italy: Tuscany
1 day - 0 nights
One departure available
July
€90
Per person
4.6
Italy: Tuscany
7 days - 6 nights
7 departures available
July - September
Starting from
€700
Per person
4.4
Italy: Tuscany
2 days - 2 nights
3 departures available
July
€250
Per person
4.8
Italy: Tuscany
3 days - 3 nights
2 departures available
July - August
Starting from
€370
€352
Per person
4.9
Italy: Tuscany
2 days - 2 nights
2 departures available
July
€320
Per person
4.8
Italy: Tuscany
3 days - 3 nights
5 departures available
July - September
Starting from
€410
€369
Per person
4.8
Italy: Tuscany
7 days - 6 nights
2 departures available
August - September
Starting from
€580
€551
Per person
Why book a holiday with Sailsquare?
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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
3804 reviews
A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia
06/16/2026
Alessandro L.
-
IT
Giglio or Elba the pearls of the Tuscan archipelago
06/16/2026
Moira C.
-
IT
A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia
06/15/2026
SILVIA C.
-
IT
Weekend among the most beautiful coves of Elba
06/14/2026
Roberto L.
-
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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