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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 109 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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5.0

Super!

A day of sun and swimming

Italy: Tuscany

1 day - 0 nights

One departure available

June

€70

Per person

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4.9

Super!

On holiday with Dad to discover Elba and Capraia

Italy: Tuscany

4 days - 4 nights

3 departures available

June

€400

Per person

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4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

2 departures available

September

Starting from

€441

€419

Per person

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5.0

Super!

Between Capraia and Northern Corsica: sailing, crystal clear sea and freedom

Italy: Tuscany

7 days - 6 nights

One departure available

July

€990

€891

Per person

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4.9

Super!

Midweek between Elba and Capraia

Italy: Tuscany

4 days - 4 nights

2 departures available

September

€400

Per person

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4.9

Super!

Sailing day in the Gulf of Follonica

Italy: Tuscany

1 day - 0 nights

One departure available

June

€100

Per person

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4.8

Super!

Sea, scents and colors on Elba

Italy: Tuscany

3 days - 3 nights

5 departures available

June - September

Starting from

€300

Per person

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4.8

Super!

Capraia and northern Corsica: sailing in the sea of cetaceans

Italy: Tuscany

7 days - 7 nights

One departure available

July - August

€600

Per person

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4.8

Super!

Five days barefoot between Tuscany and Corsica

Italy: Tuscany

5 days - 4 nights

3 departures available

September

€490

Per person

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4.9

Super!

Discovering the Island of Elba: 3 days of sea, wind and sun

Italy: Tuscany

3 days - 3 nights

One departure available

June

€450

Per person

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4.8

Super!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

5 departures available

June - September

Starting from

€200

Per person

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4.9

Super!

Leave everything for the Island of Elba

Italy: Tuscany

2 days - 2 nights

4 departures available

June - July

Starting from

€280

Per person

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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.

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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

3540 reviews

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Tuscan archipelago between nature and relaxation

05/26/2026

Francesco D.

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IT

Riccardo is a true professional, a reliable person and also an excellent travel companion. He was able to perfectly interpret our requests with availability and empathy, becoming in a few minutes a friend, an accomplice in adventures, a trusted person, as if we had always known each other ... Not just a skipper! Thanks to Riccardo and "[hidden]" for this wonderful experience!
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Weekend among the most beautiful coves of Elba

05/26/2026

Alessio B.

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IT

It is difficult to put into words the beauty of the three days spent on the [hidden] with Marco and Carmen. I was with my girlfriend and together with 4 other girls met on the morning of boarding we created a beautiful close-knit group with whom it was wonderful to share laughter and moments that will remain in my heart. I can only spend wonderful words about Marco and Carmen, they are two people who immediately make you feel at home and are really professional and prepared in the maritime world and in sailing in general. I recommend everyone to try an experience with them because I assure you you will not regret it, on the contrary. The [hidden] (name of the sailboat) is comfortable and does not let you miss anything, it took us to wonderful coves and made us visit postcard ravines on the island of Elba. At the time of the final goodbyes we were all excited. I am sure of one thing, we will not lose sight of each other because you are 'magical' and pure people. Alex
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Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

05/26/2026

Claudia M.

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IT

Beautiful weekend on Elba! The boat is spacious and very well maintained. Matteo's welcome was super! and the skipper Luca very nice, kind and helpful to explain how to collaborate in the various maneuvers on board. The company of the group was really pleasant! To be repeated soon
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A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

05/26/2026

Michele P.

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IT

Skipper available and attentive to the needs of each passenger, precise and organized, with valid experience of the sailing places. Large and well equipped boat. Recommended!

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