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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 89 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!

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

5 departures available

September - November

€250

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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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

Tuscany and Corsica: sailing sun adventure good food energy and well-being

Italy: Tuscany

3 days - 3 nights

3 departures available

July - September

Starting from

€350

Per person

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4.8

Super!

Educational Sailing Cruise: from Cagliari to Marina di Pisa

Italy: Tuscany

7 days - 7 nights

One departure available

September

€750

Per person

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4.8

Super!

Midweek special on the island of Elba, 2 nights

Italy: Tuscany

3 days - 2 nights

2 departures available

September

€260

€234

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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4.7

Sailing day between the Apuan coast and the Gulf of Poets

Italy: Tuscany

1 day - 0 nights

3 departures available

July - August

Starting from

€90

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

2 departures available

September

€280

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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4.4

Magnificent weekend of approach to sailing on the island of Elba

Italy: Tuscany

2 days - 2 nights

One departure available

July

€250

Per person

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4.9

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

2 departures available

September

€390

€351

Per person

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Reviews - Sailboat yacht sailing holidays & tours in Tuscany

3624 reviews

Midweek getaway between Elba and Capraia

07/9/2026

Paola S.

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IT

Beautiful experience. Recommended. Good management of the unexpected.
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Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

07/8/2026

Fabio C.

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IT

Weekend on a sailing boat on the Island of Elba simply fantastic! Much of the credit goes to the skipper, an extremely professional, prepared and competent person, capable of transmitting safety and passion for the sea from the very first moment. In addition to his excellent sailing skills, he was always available, attentive to everyone's needs and good at creating a relaxed and pleasant atmosphere on board. Thanks to his knowledge of the island he took us to wonderful and uncrowded coves, making us experience places that we would hardly have discovered on our own. The boat was in perfect condition, well cared for and comfortable. It was a weekend of relaxation, fun and good company. An experience that I recommend without hesitation to anyone who wants to experience the sea in an authentic way. I would definitely do it again!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

07/7/2026

Davide C.

Fantastic experience thank you 🙏

Giglio or Elba the pearls of the Tuscan archipelago

07/7/2026

Benedetta S.

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IT

I gave the experience to my boyfriend, for us it was the very first time on a sailing boat and he exceeded all expectations! Simone and Milena made the experience incredible, making us feel immediately at ease. Simone is a great skipper and explained to us in detail how a sailboat works. This made the experience even more complete. We had the opportunity to see many beautiful coves and to enjoy good food in excellent company in an extremely serene environment. Really super recommended!!

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