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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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4.8

Super!

Five days barefoot between Tuscany and Corsica

Italy: Tuscany

5 days - 4 nights

One departure available

September

€490

€440

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 15m 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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4.7

Voices of the Pelagos: artistic-scientific whale watching expedition with WWF guide

Italy: Tuscany

4 days - 4 nights

One departure available

October

Starting from

€453

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

4 departures available

September - October

Starting from

€230

Per person

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4.8

Super!

A taste of the magnificent Island of Elba

Italy: Tuscany

2 days - 2 nights

One departure available

September

€300

Per person

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5.0

Super!

Weekend on Elba on a 16-meter sports boat

Italy: Tuscany

2 days - 2 nights

One departure available

September

€400

Per person

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4.8

Super!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

One departure available

September

€200

Per person

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4.9

Super!

Two days in Elba without worries with a professional skipper

Italy: Tuscany

2 days - 2 nights

One departure available

October

€315

Per person

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4.8

Super!

Five days barefoot between Tuscany and Corsica

Italy: Tuscany

4 days - 4 nights

One departure available

September

€490

Per person

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4.8

Super!

Squid Festival: let's close the season on a 15m boat with a flourish! - 2 boats in company

Italy: Tuscany

3 days - 2 nights

2 departures available

October - November

€280

Per person

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5.0

Super!

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

3 departures available

October - November

€250

Per person

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4.8

Super!

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

Italy: Tuscany

7 days - 7 nights

One departure available

September

€850

Per person

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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.

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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

4130 reviews

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

09/17/2026

Emanuela D.

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IT

A really positive experience that I really feel like recommending to those who want to unplug and leave their ballast on dry land. Fantastic group and what about the captain? More than 30 years of experience at sea that translate into safety and reliability to which you can add sympathy and availability... The result? A beautiful holiday. I also add a note of merit to the cleanliness and organization of the catamaran ... in short, Rino, even for me you are from the BLUE STICKER! See you very soon!

Weekend Elba or Capraia

09/16/2026

Mauro G.

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IT

Fun boat in sailing. Too bad for the weather conditions of the previous days that made the sea not optimal. Still pleasant experience throughout. I recommend, for the optimal training of the guest crew, to plan the mood of the experience in advance. Thanks again to skipper Nicola who made us experience the thrill of upwind ⛵😊👍🏻

Week between the Tuscan Islands and Northern Corsica

09/16/2026

Rosanna B.

-

IT

Fantastic experience!! Splendid and very comfortable boat, wonderful itinerary!! Francesco is a very prepared, kind skipper, always present and attentive to any problem that may arise. He also knows the places on the itinerary very well and also provides very useful information on how to get around on land... I can only thank him!!
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Long weekend on Elba: 4 days of sun and sailing

09/16/2026

Arianna G.

-

IT

Four wonderful days, in which the wind and the sea were the setting for an experience that went far beyond the simple holiday. Paolo has been able to create a nice group, while respecting everyone's spaces and times. Always available, attentive to our needs and, above all... always proactive on aperitifs!! We were not looking for a sailing course, but a few days of sea, nature and freedom, and perhaps this is what I take home: the feeling that we too often live in a fast and constructed way, forgetting that sometimes the wind in our faces is enough, to raise our eyes to the sun or the moon and find some peace. Even if... you still haven't found what you are looking for. <3

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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

Other travel ideas

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