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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 78 opportunities to get on board a Sailboat adventure in Tuscany. A unique experience with a local skipper, starting at €350 a week.

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Approach to sailing: day on a boat with sailing lesson

Italy: Tuscany

1 day - 0 nights

58 departures available

July - October

Starting from

€77

Per person

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5.0

Two days on a sailing boat in Elba: zero stress!

Italy: Tuscany

3 days - 2 nights

4 departures available

July

Starting from

€400

€360

Per person

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4.9

Sailing in the Cetacean Sanctuary - Capraia and Corsica

Italy: Tuscany

7 days - 6 nights

5 departures available

July - August

Starting from

€580

Per person

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4.8

Sailing in the enchanting scenery of Elba, Giglio and Giannutri

Italy: Tuscany

7 days - 6 nights

One departure available

August

€870

Per person

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5.0

A week sailing to discover Capraia and North Corsica

Italy: Tuscany

7 days - 7 nights

One departure available

July - August

€820

Per person

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5.0

Weekend in the Tuscan Archipelago

Italy: Tuscany

3 days - 2 nights

2 departures available

August - September

€140

€126

Per person

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4.3

Magnificent weekend of sailing on the island of Elba

Italy: Tuscany

2 days - 2 nights

One departure available

July

€225

Per person

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5.0

Learn to sail in a week in the Tuscan Archipelago

Italy: Tuscany

6 days - 6 nights

One departure available

August

€600

Per person

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5.0

Talamone and Giglio Sailing Weekend with Geniale Vento, Mare, Libertà

Italy: Tuscany

3 days - 2 nights

One departure available

July

€395

Per person

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5.0

AperiBarca: afternoon sunset aperitif

Italy: Tuscany

1 day - 0 nights

One departure available

July

€35

Per person

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3.7

A wonderful weekend in the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

4 departures available

August - September

€240

Per person

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5.0

Sailing day at the Vada lighthouse

Italy: Tuscany

1 day - 0 nights

3 departures available

July - August

€100

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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 - Sailboat yacht sailing holidays & tours in Tuscany

3206 reviews

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Week between the Tuscan Islands and North Corsica

07/14/2025

Flavia G.

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Italy

Francesco is an experienced skipper, skilled in managing the unexpected and meeting the needs of the whole crew. The boat is comfortable and equipped with everything you need to spend a pleasant holiday.
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Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

07/14/2025

Alberto M.

-

Italy

Riccardo proved to be an excellent Skipper, a true professional, always ready to take advantage of any gust of wind to unfurl the sails. Great cook and great company. A boat experience with Riccardo is highly recommended.
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Whale watching cruise with WWF guide between Elba, Pianosa and the canyons of Corsica

07/14/2025

Simone O.

-

Italy

Good morning I'm Simone, what can I say, first of all I had wanted to have a different experience than usual and meet new people, and it happened, The one from the sailboat was a fantastic experience where thanks to Silvia, Paolo and Dario they were able to show us the cetaceans, because we were not able to see the whales as well. Silvia was a professional person in her work as a wwf, when it was time to explain or let us watch videos on cetaceans with her PC she was very clear and always chose the right time to give us a lesson not too long or too short, the right I would say and not every day. I would add that Silvia has always made herself available and interested if everything was fine in general or if we understood her about what she explained to us. WELL DONE SILVIA AND THANK YOU VERY MUCH. Paolo, our captain of the sailboat, was a clear person from the start, direct and above all hospitable to us. what about Paolo, who is a professional person, who immediately perceives that the sea is his whole life, and wants to pass on his knowledge and his passion as a sailor to others. GAZIE MILLE PAOLO Dario is the captain's helper, a young guy, helpful and with a great desire to do and learn, and one of the company. I conclude by thanking you and that I would have stayed another 2 or 3 days more. I'm recommending it to all my friends to have such experiences. Have a nice day and see you next time.
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Set Sail with Family: 5 Days of Comfort & Adventure Around Elba Island

07/14/2025

Giorgia Carla F.

-

Italy

Matteo was not only a skipper but also an extraordinary travel companion!! First of all, he is a TRUE SAILOR, rigorous when needed, prepared and prudent to the right point. But he is also very nice and company. The Skywalk is an exceptional, clean and organized boat. We didn't want to go ashore anymore and we will certainly be back on board soon. Yes, Matthew, get ready!!! We were three adults and three children about 9 years old in addition to the captain and his "deputy" and our children were thrilled!! 5 stars are also few. Thank you for everything captain

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