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.
110
experiences
110
experiences
5.0
Duration:
3 days - 3 nights
Italy:
Tuscany
+35 travellers
have booked
Starting from
€370
Per person
5.0
Duration:
7 days - 6 nights
Italy:
Tuscany
Give this experience a try!
€800
Per person
5.0
Duration:
7 days - 6 nights
Italy:
Tuscany
+4 travellers
have booked
Starting from
€790
Per person
5.0
Duration:
6 days - 7 nights
Italy:
Tuscany
+13 travellers
have booked
Starting from
€662
Per person
5.0
Duration:
6 days - 7 nights
Italy:
Tuscany
Give this experience a try!
€1,350
Per person
5.0
Duration:
6 days - 7 nights
Italy:
Tuscany
+3 travellers
have booked
Starting from
€638
€750
Per person
4.9
Duration:
3 days - 3 nights
Italy:
Tuscany
+22 travellers
have booked
€333
€350
Per person
4.3
Duration:
4 days - 5 nights
Italy:
Tuscany
Give this experience a try!
€429
Per person
4.8
Duration:
3 days - 2 nights
Italy:
Tuscany
Give this experience a try!
€290
Per person
5.0
Duration:
2 days - 2 nights
Italy:
Tuscany
Give this experience a try!
€315
Per person
4.5
Duration:
7 days - 7 nights
Italy:
Tuscany
Give this experience a try!
€980
Per person
5.0
Duration:
6 days - 6 nights
Italy:
Tuscany
+3 travellers
have booked
Starting from
€711
€790
Per person
Why book a holiday with Sailsquare?
The world's largest marketplace for sailing holidays
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
3009 reviews
May 1st on Elba - Stewardess on board -3 Cab./ 3 Bathrooms
05/2/2024
susanna s.
-
Italy
LONG WEEKEND 25 April barefoot: 4 days between Capraia and the island of Elba
05/1/2024
Simone D.
-
Switzerland
Long weekend in Capraia and North Corsica
04/30/2024
Licio M.
-
Italy
Long weekend in Capraia and North Corsica
04/30/2024
Marcello O.
-
Italy
Customer Support
Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!
Call us at
+44 2035144220Read our
Contact & Support
Can't find the perfect holiday for you?
Tell us what you are looking for and let our team find the right solution for you!
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!
Sailsquare
Follow us on
Secure payments
© 2023 Sailsquare Srl SB • All rights reserved - VAT IT07860990964
