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.
97
experiences
97
experiences
4.7
Duration:
6 days - 5 nights
Italy:
Tuscany
2 travellers
Starting from
€638
€750
Per person
Duration:
6 days - 5 nights
Italy:
Tuscany
Give this experience a try!
Starting from
€850
€1,000
Per person
4.9
Super!
Duration:
3 days - 3 nights
Italy:
Tuscany
18 travellers
Starting from
€342
€380
Per person
4.9
Super!
Duration:
3 days - 3 nights
Italy:
Tuscany
23 travellers
Starting from
€356
€395
Per person
5.0
Duration:
3 days - 2 nights
Italy:
Tuscany
Give this experience a try!
€405
€450
Per person
4.8
Duration:
2 days - 2 nights
Italy:
Tuscany
29 travellers
Starting from
€225
€250
Per person
4.9
Super!
Duration:
3 days - 2 nights
Italy:
Tuscany
32 travellers
Starting from
€275
€305
Per person
4.9
Super!
Duration:
7 days - 6 nights
Italy:
Tuscany
9 travellers
Starting from
€630
€700
Per person
5.0
Super!
Duration:
2 days - 2 nights
Italy:
Tuscany
34 travellers
Starting from
€264
€293
Per person
5.0
Duration:
3 days - 2 nights
Italy:
Tuscany
2 travellers
Starting from
€261
€290
Per person
4.8
Duration:
7 days - 6 nights
Italy:
Tuscany
Give this experience a try!
€855
€950
Per person
5.0
Super!
Duration:
6 days - 7 nights
Italy:
Tuscany
115 travellers
Starting from
€714
€793
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
3361 reviews
1 May long weekend sailing with RICCARDO PROFESSIONAL SKIPPER COOK
05/8/2025
Maria Pia D.
-
Italy
A long weekend of sea and freedom from Argentario to Elba
05/7/2025
RAFFAELE L.
-
Italy
Weekend in Capraia, the island with timeless sunsets
05/7/2025
Leonardo R.
-
Italy
Weekend in Capraia, the island with timeless sunsets
05/7/2025
Simone S.
-
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
Let's talk Sailsquare!
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