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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 101 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

Whale watching cruise with WWF guide for children 14-17 on an 18-meter schooner

Italy: Tuscany

6 days - 6 nights

One departure available

July

Starting from

€1,052

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

4 departures available

June - September

Starting from

€950

Per person

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4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

3 departures available

August - September

Starting from

€1,041

Per person

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4.7

Whale watching cruise with WWF guide between Northern Corsica and the Tuscan Archipelago

Italy: Tuscany

6 days - 7 nights

One departure available

August

€1,157

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

6 departures available

June - September

Starting from

€490

€466

Per person

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4.6

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

35 departures available

January - December

Starting from

€300

€270

Per person

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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

One departure available

July - August

€999

Per person

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4.8

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

5 departures available

July - August

Starting from

€410

€369

Per person

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4.8

Super!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

Italy: Tuscany

6 days - 7 nights

6 departures available

July - September

Starting from

€900

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

10 departures available

July - October

Starting from

€230

Per person

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4.6

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

2 departures available

July - August

Starting from

€800

Per person

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4.8

Super!

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

Italy: Tuscany

2 days - 2 nights

9 departures available

July - October

Starting from

€230

Per person

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Reviews - Sailboat yacht sailing holidays & tours in Tuscany

3573 reviews

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

06/20/2026

Valentina P.

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IT

Our very first sailing experience with Luca, the skipper, was unforgettable. A week of pure relaxation, 24 hours a day at sea, nights at anchor in front of the coves and beautiful cliffs of the Island of Elba, fantastic sunsets sipping our aperitifs, the sunrise with the scent of coffee coming out of the mocha ... moments in which time stops and you finally find the true meaning of life. And what about our skipper Luca... A very kind person, helpful, affable and also discreet, always ready to fulfill any of our requests. I hope it will be the first of a long series! Fair winds to all!! Valentina and Federico

Three days on Elba for just four guests on board

06/20/2026

luca c.

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IT

Wonderful experience on Elba. The skipper Pier is very prepared and willing to pass on his experience in sailing. The boat is well maintained and the right space to enjoy a weekend at sea with friends. We highly recommend a weekend aboard the Kinky to those who want to experience the sea in peace, learn more about sailing and rely on a competent, passionate and attentive skipper.

A taste of the magnificent Island of Elba

06/17/2026

valentina t.

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IT

We with friends at the Top! The boat very clean and welcoming, Alberto always on the piece helpful and attentive.

Week-end all'Elba - Hostess a bordo

06/16/2026

Andrea P.

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IT

We spent a beautiful holiday beyond all expectations: the comfort and spaciousness of the boat, the beauty of the places, the kindness and skill of Giulia in the kitchen, the care and professionalism of Vittorio at the helm, together with the sympathy of the other day-trippers (and the wonderful weather!) allowed us to enjoy our first sail - around Elba - in a fantastic way, celebrating my wife's birthday in an exciting way on a holiday that we hoped would not end so soon. Five well-deserved 😀 stars

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