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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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4.9

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

12 departures available

May - October

Starting from

€500

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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4.9

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!

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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4.9

Super!

A taste of the magnificent Island of Elba

Italy: Tuscany

2 days - 2 nights

2 departures available

June

€350

Per person

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5.0

Wellness, sun, sea and adventure: a weekend full of sailing!

Italy: Tuscany

3 days - 2 nights

2 departures available

September

€230

Per person

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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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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

3533 reviews

Weekend among the most beautiful coves of Elba

05/18/2026

Stefania V.

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Italy

Marco and Carmen wonderful people. As if we had known each other forever. There was harmony and understanding on everything. We will definitely repeat!

Weekend among the most beautiful coves of Elba

05/17/2026

Giulia L.

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Italy

New experience for me and my partner, excellent company, beautiful places, well organized trip, Carmen and Marco nice and easy-going, they were able to put us all at ease, we will remain a beautiful memory!

May Day between Elba and Capraia

05/11/2026

Valeria C.

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Italy

The weather helped us enjoy a fantastic navigation also thanks to the experience of the skipper Enrico and the comfort of the boat. Mixed crew sea... It could have gone very badly or very well and it went very well!

May 1st long weekend between Elba and Capraia - 2 boats in company

05/6/2026

Massimo A.

-

Italy

Matteo is the most knowledgeable person on sailing I have ever met, and his boat has a comfort far superior to normal charters, having 18 meters in length. Perfect organization and reliability. The tour of Elba is easy but wonderful

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