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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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4.9

Super!

A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€280

Per person

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4.9

Super!

Midweek between Elba and Capraia

Italy: Tuscany

4 days - 4 nights

One departure available

September

€400

Per person

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5.0

Tuscany and Corsica: sailing sun adventure good food energy and well-being

Italy: Tuscany

3 days - 3 nights

4 departures available

August - September

Starting from

€350

Per person

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4.6

The Island of Elba, to make you live a special experience!

Italy: Tuscany

6 days - 5 nights

One departure available

August

€700

Per person

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4.8

Super!

Five days barefoot between Tuscany and Corsica

Italy: Tuscany

5 days - 4 nights

4 departures available

August - September

Starting from

€490

Per person

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4.8

Super!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

One departure available

September

€200

Per person

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4.9

Super!

Giglio Island - Festival of Grapes and Open Cellars

Italy: Tuscany

3 days - 3 nights

One departure available

September

€280

Per person

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4.8

Super!

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

Italy: Tuscany

2 days - 2 nights

5 departures available

September - October

Starting from

€230

Per person

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4.9

Super!

Squid Festival in Capraia

Italy: Tuscany

3 days - 3 nights

One departure available

October

€280

Per person

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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

3 departures available

September

€490

€466

Per person

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4.8

Super!

Vacation between Tuscany and Corsica on a magnificent 17m boat

Italy: Tuscany

6 days - 7 nights

One departure available

August - September

€900

Per person

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5.0

Super!

Weekend in the Tuscan Archipelago with PROFESSIONAL COOK SKIPPER

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€250

€238

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

3999 reviews

Long weekend among the queens of the archipelago - Elba and Capraia

08/13/2026

Gabriele B.

-

IT

Nice experience, Edoardo kind and helpful, to be done again.
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Weekend Elba or Capraia

08/11/2026

Ilaria Maria Z.

-

IT

I spent two really beautiful days. Wonderful places and great company! Sebastiano the skipper was great, in everything. Really congratulations to him.

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

08/11/2026

Anne-Laure Q.

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FR

Superb week between Italy and Corsica. We were able to meet 2 species of dolphins and spot a sea turtle.. The sailing experience was very pleasant and safe, only regret, a shame not to have been able to sail more. Thanks to Joëlle from WWF for the exciting courses!

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

08/11/2026

andrea p.

-

IT

hello exciting experience, in addition to being lucky with the weather, and for the company, I can only say positive words for the Biologist Sabrina who accompanied us in this adventure with passion and cordiality, Cesare, the skipper a person of heart as well as fun and experience, if I can afford I would recommend to have already on board at least the water to drink as if no guest arrives by car it becomes difficult to manage, Another small proposal concerns the cleaning of the boat, which as guests is also pleasant to do in company but I would recommend sanitation between cruises at least as far as pillows and mattresses are concerned

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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 (255)Whole boat with skipper (150)Cooking service onboard (35)Sport & wellness (30)Family sailing cruises (20)Catamaran (15)Day trips (15)Courses & regatta (10)WWF Sailing Cruises (10)

Other travel ideas

Sailboat (292)Whole boat with skipper (254)Cooking service onboard (83)Catamaran (67)All inclusive (44)Exotic destinations (22)Courses & regatta (18)Day trips (15)Offshore (14)Sport & wellness (13)

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