header cover
logo

Log in

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.

cover image
avatar image

5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

4 departures available

June - September

Starting from

€950

€855

Per person

cover image
avatar image

4.7

Whale watching cruise with WWF guide for children 14-17 on an 18-meter schooner

Italy: Tuscany

6 days - 6 nights

One departure available

July

Starting from

€1,052

Per person

cover image
avatar image

4.9

Super!

Sailing holiday in the turquoise blue waters of Corsica

Italy: Tuscany

7 days - 7 nights

One departure available

August

€890

Per person

cover image
avatar image

4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

3 departures available

August - September

Starting from

€1,041

Per person

cover image
avatar image

4.7

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

36 departures available

January - December

Starting from

€300

€270

Per person

cover image
avatar image

4.8

Super!

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

8 departures available

June - September

Starting from

€490

€466

Per person

cover image
avatar image

4.7

Whale watching cruise with WWF guide between Northern Corsica and the Tuscan Archipelago

Italy: Tuscany

6 days - 7 nights

4 departures available

July - August

Starting from

€1,052

Per person

cover image
avatar image

4.8

Super!

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

10 departures available

July - October

Starting from

€230

Per person

cover image
avatar image

4.8

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

9 departures available

July - October

Starting from

€230

Per person

cover image
avatar image

4.8

Super!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

Italy: Tuscany

6 days - 7 nights

6 departures available

July - September

Starting from

€900

Per person

cover image
avatar image

4.7

Youth cruise (18-23 years): whale watching with WWF between the Tuscan Archipelago and Northern Corsica

Italy: Tuscany

6 days - 7 nights

2 departures available

July - August

€999

Per person

cover image
avatar image

4.8

Super!

Elba, Tuscan archipelago or Corsica aboard a full opt catamaran.

Italy: Tuscany

7 days - 7 nights

5 departures available

August - September

Starting from

€850

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

3795 reviews

Weekend on Elba, sea, colors and scents.

06/9/2026

Martina N.

-

IT

Ivo is a real sea dog, with his fantastic experience he welcomed my family on his boat and safely gave us a nice experience despite the possible unforeseen events. Thank you
avatar image

A bridge in the blue - June 2 on a sailing boat

06/9/2026

Sara M.

-

IT

Although I have often been on a boat, traveling aboard [hidden] has been a unique experience! Not only is the boat beautiful and well maintained (clean and with all the comforts, like at home!), Max transmits his great passion for the sea and, in addition to accompanying you to the most beautiful and unspoiled places, he transmits the beauty of living the boat and the sea, you can only come out fascinated. He is also very good at uniting and involving the whole group. We sailed as soon as there was the opportunity to do so and for some newly licensed drivers on board he was a fantastic instructor, dedicating a lot of time that was not taken for granted. Beautiful Capraia and Corsica a wonderful discovery! I hope to be back on board soon!
avatar image

Midweek special between Capraia and Northern Corsica

06/7/2026

DANIELA C.

-

IT

Thank you very much, Marco! You are an attentive, kind and always available skipper. From the first moment you manage to make everyone feel welcomed and at ease, sharing your beautiful boat with great generosity. Your experience and expertise convey safety and serenity, allowing everyone to fully enjoy every moment of navigation. The boat is perfect, spotless and equipped with every comfort. You know how to choose the best routes and spectacular destinations. Thanks also to my travel companions for the pleasant company.

Midweek special between Capraia and Northern Corsica

06/7/2026

Silvia G.

-

IT

Thank you Marco, you were an excellent skipper, you told us so many interesting things, you led us safely to beautiful places.,Waking up in the morning and swimming in an emerald bay, all for us, is an unforgettable experience! Thanks also to all the travel companions who helped make this trip magical.....and thanks especially to [hidden]!

Customer Support

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 4220

Read 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!

Guides & tips


Italy

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

Tuscany

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

WWF Whale watching cruises

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

Catamaran vacations

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

Flotilla holiday

A perfect vacation for singles (and others) to experience sailing, meet new friends and multiply the fun.
Guide to the flotilla holidays

Singles and solo travellers

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

Sailing vacations for families

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?

Sailing with children

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

Sailboat (560)Whole boat with skipper (385)Cooking service onboard (75)Family sailing cruises (70)WWF Sailing Cruises (40)Courses & regatta (35)Catamaran (30)Sport & wellness (15)Day trips (15)Gulet and sailing ship (5)

Other travel ideas

Sailboat (613)Whole boat with skipper (476)Cooking service onboard (121)Catamaran (92)All inclusive (46)Family sailing cruises (33)Courses & regatta (29)Exotic destinations (26)Day trips (21)Offshore (21)

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Sailsquare

Travellers

Providers

Follow us on

FB IconIG IconYT Icon

Secure payments

MastercardVisaGoogle PayApple Pay

Top Destinations

Top Travel Ideas

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964