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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 110 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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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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4.7

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

Italy: Tuscany

4 days - 4 nights

One departure available

September

€567

€539

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!

Weekend of relaxation and fun to discover the Island of Elba

Italy: Tuscany

3 days - 2 nights

4 departures available

June - September

Starting from

€380

€342

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

7 departures available

June - July

Starting from

€490

€466

Per person

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4.8

Super!

Cruise course Pisa-Naples navigation

Italy: Tuscany

10 days - 10 nights

One departure available

June - July

€1,200

Per person

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5.0

Super!

Argentario, Giannutri and Giglio Island on wooden schooner

Italy: Tuscany

3 days - 2 nights

One departure available

June

€300

Per person

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4.9

Super!

Magical night on the Island of Elba

Italy: Tuscany

1 day - 1 night

One departure available

June

€145

Per person

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5.0

Super!

Long live Elba and Capraia

Italy: Tuscany

3 days - 3 nights

One departure available

June

€375

Per person

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4.8

Super!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

6 departures available

July - September

Starting from

€200

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

June

€380

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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Reviews - Sailboat yacht sailing holidays & tours in Tuscany

3542 reviews

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Weekend Elba o Capraia

05/26/2026

Sabrina S.

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IT

Fantastic holiday with the guidance of Francesco who involved us a lot in managing the destination and the boat, taught us how the sea can create bonds.
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Weekend among the most beautiful coves of Elba

05/26/2026

Samantha G.

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IT

We were literally welcomed by Marco and Carmen, it seemed to have known them for a lifetime. Evidently they attract beautiful people because the rest of the crew was also wonderful. Beautiful sailings (you can move as little as possible), but managed in full comfort. Finally, an excellent knowledge of the places that does not hurt and makes you enjoy unforgettable coves
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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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