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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 111 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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4.7

Youth cruise (18-23 years): whale watching with WWF between the Tuscan Archipelago and Northern Corsica

Italy: Tuscany

6 days - 7 nights

2 departures available

July - August

Starting from

€999

€949

Per person

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4.6

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

4 departures available

June - August

Starting from

€700

Per person

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4.9

Super!

Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

Italy: Tuscany

6 days - 6 nights

11 departures available

June - September

Starting from

€980

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

2 departures available

July - September

Starting from

€350

Per person

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4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

10 departures available

June - October

Starting from

€500

Per person

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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

4 departures available

June - September

€280

Per person

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5.0

Super!

Learn to sail in a week in the Tuscan Archipelago

Italy: Tuscany

6 days - 6 nights

4 departures available

August

Starting from

€849

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

€441

Per person

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5.0

Super!

Tuscan Archipelago: night and day sailing

Italy: Tuscany

4 days - 3 nights

One departure available

August

€320

€272

Per person

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4.8

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

8 departures available

June - August

Starting from

€395

€356

Per person

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4.9

Super!

Wind, sea and freedom: a week between Corsica and the Tuscan archipelago

Italy: Tuscany

7 days - 6 nights

8 departures available

August - September

Starting from

€650

Per person

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4.9

Super!

VelaTrek weekend on the Island of Elba All-inclusive - 2 boats

Italy: Tuscany

3 days - 2 nights

One departure available

September

€390

€351

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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