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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.

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New

Cruise for young people, from Piombino to Cannigione

Italy: Tuscany

7 days - 7 nights

One departure available

July - August

€980

Per person

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New

Educational cruise between Tuscany and Corsica

Italy: Tuscany

14 days - 14 nights

One departure available

August

€1,700

Per person

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5.0

Capraia and Elba Island - Sun, Sea and Fun!

Italy: Tuscany

4 days - 3 nights

4 departures available

September - October

Starting from

€400

Per person

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4.9

Between sunsets and aperitifs on a sailing boat

Italy: Tuscany

7 days - 6 nights

6 departures available

July - September

Starting from

€617

Per person

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5.0

Sailing adventures: summer sailing camps IN ENGLISH - for children from 9 to 14 years old

Italy: Tuscany

5 days - 5 nights

One departure available

July

€660

Per person

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4.9

6 days of Elba, Capraia and Corsica

Italy: Tuscany

6 days - 5 nights

One departure available

August

€695

Per person

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4.8

Sunny weekend on Elba from Friday to Sunday

Italy: Tuscany

3 days - 2 nights

3 departures available

September - October

€325

€293

Per person

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4.8

Offshore and night navigation course on cabin cruisers

Italy: Tuscany

3 days - 2 nights

One departure available

October

€332

€282

Per person

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New

Discovering the Island of Elba

Italy: Tuscany

7 days - 6 nights

One departure available

July

€700

Per person

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New

Day trip to the island of Elba - Porto Azzurro

Italy: Tuscany

1 day - 0 nights

3 departures available

July - August

€80

Per person

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5.0

Sailing around the Island of Elba aboard a schooner

Italy: Tuscany

3 days - 2 nights

One departure available

July - August

€300

Per person

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New

Slow sailing in Portoferraio - daily trimaran trip

Italy: Tuscany

1 day - 0 nights

One departure available

August

€80

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

3844 reviews

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Island of Elba by Catamaran: 5 Days of Sea and Relaxation from Piombino

07/4/2026

Teresa P.

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IT

Thanks to Maurizio "Unforgettable 5-day experience, catamaran sailing is the best way to discover the Island of Elba: the large and comfortable spaces Total relaxation. An adventure absolutely recommended for those who love the sea.

Mini-cruise with WWF guide in the heart of the Tuscan Archipelago

07/2/2026

Bianca Matelda C.

-

IT

Beautiful days in the middle of the sea, freedom, discovery, full nature and new friends! The WWF guide Elisa and the skipper Nico were very good, nice, professional and prepared to manage the outings and make a group. These are days that I carry in my heart. I recommend bringing little stuff, just enough to protect yourself from the sun and feel good.. but above all to a lot of curiosity and team spirit!

Weekend on the island of Elba: among dolphins, enchanting bays and relaxation

07/2/2026

Laura N.

-

IT

We had a very pleasant and relaxing weekend. Salvatore is very knowledgeable and personable, and his boat is comfortable and very clean. Highly recommend!

Long live Elba and Capraia

07/1/2026

Marina M.

Beautiful experience. Filippo is a professional and experienced skipper. We sailed both under sail and by motor in complete safety, the skipper was available to explain the maneuvers, involving the crew members who wanted to do it in the management of the boat. Clean, comfortable, efficient, well-equipped boat. Very beautiful island of Capraia perfect for a three-day weekend.

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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 (445)Whole boat with skipper (315)Cooking service onboard (70)Family sailing cruises (60)Catamaran (35)WWF Sailing Cruises (30)Courses & regatta (25)Day trips (20)Sport & wellness (20)Gulet and sailing ship (5)

Other travel ideas

Sailboat (514)Whole boat with skipper (402)Cooking service onboard (117)Catamaran (87)All inclusive (53)Exotic destinations (28)Family sailing cruises (26)Courses & regatta (24)Day trips (21)Offshore (19)

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