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.
65
experiences
4.8
Super!
Italy: Tuscany
6 days - 7 nights
2 departures available
August - September
Starting from
€900
Per person
4.7
Italy: Tuscany
6 days - 6 nights
One departure available
August - September
€1,041
Per person
4.7
Italy: Tuscany
3 days - 3 nights
2 departures available
September
Starting from
€441
Per person
4.1
Italy: Tuscany
2 days - 2 nights
30 departures available
January - December
€300
€270
Per person
5.0
Super!
Italy: Tuscany
6 days - 7 nights
2 departures available
August - September
€1,150
€1,035
Per person
4.9
Italy: Tuscany
7 days - 6 nights
3 departures available
August - September
Starting from
€650
Per person
4.9
Super!
Italy: Tuscany
4 days - 3 nights
4 departures available
August - September
Starting from
€400
€360
Per person
5.0
Super!
Italy: Tuscany
4 days - 3 nights
One departure available
September
€530
€477
Per person
4.9
Super!
Italy: Tuscany
7 days - 6 nights
One departure available
August
€890
Per person
4.8
Super!
Italy: Tuscany
2 days - 2 nights
2 departures available
September
€200
Per person
4.8
Super!
Italy: Tuscany
7 days - 7 nights
4 departures available
August - October
€650
Per person
4.7
Italy: Tuscany
7 days - 6 nights
4 departures available
August - September
Starting from
€700
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
3956 reviews
Midweek getaway between Elba and Capraia
08/2/2026
Barbara B.
-
IT
Leave everything for the Island of Elba
08/2/2026
Gianmarco N.
-
IT
Week between the Tuscan Islands and Northern Corsica
08/2/2026
maria vittoria l.
-
IT
Whale watching cruise with WWF guide between Northern Corsica and the Tuscan Archipelago
08/2/2026
silvia r.
-
IT
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 20 3514 4220Read our
Contact & SupportCan'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!
Follow us on
Secure payments
© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964
