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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 93 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!

Tuscany and North Corsica on a sailing boat

Italy: Tuscany

7 days - 7 nights

One departure available

August

€1,060

Per person

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4.8

Super!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

One departure available

September

€200

Per person

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4.8

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

5 departures available

July - September

Starting from

€400

€360

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

One departure available

August

€849

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

5 departures available

August - October

€650

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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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

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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4.8

Super!

Sea, scents and colors on Elba

Italy: Tuscany

3 days - 3 nights

3 departures available

July - September

Starting from

€300

Per person

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4.8

Super!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

5 departures available

July - September

Starting from

€200

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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5.0

Super!

Weekend of Relaxation in the Argentario - Giglio - Uccellina

Italy: Tuscany

2 days - 2 nights

One departure available

July

€300

Per person

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Get onboard solo, with your family or your friends

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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

3588 reviews

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Midweek getaway between Elba and Capraia

06/26/2026

Stefano S.

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IT

Unforgettable holiday... I had already had an experience and even this time I was not disappointed... mentally I'm still in the boat 👏👏
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Long weekend between Elba and Capraia, from Thursday to Sunday

06/25/2026

Nicola A.

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IT

Really great experience. The boat is as it appears in the photos, no strange or unpleasant surprises. The places visited were lovely and the experience really great. Victor accompanied us on this trip, instead of Paolo, and he was a really great skipper, very helpful, company and very easy-going. Very very recommended

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

06/25/2026

silvia d.

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IT

A unique and unforgettable experience, one of those that remain in the heart I will definitely repeat it

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

06/24/2026

Giovanni G.

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IT

I would like to express my complete satisfaction with the experience. A special thanks goes to the biologist Elisa: an extremely prepared professional who was able to satisfy all our curiosity with precision and a wealth of details. I really appreciated his competence, professional rigor and his great kindness. I also thank the skipper Niko for the excellent welcome on board his beautiful boat. The navigation was excellent, supported by a constant presence and considerable experience. I was enthusiastic about the activity carried out and the excellent company of the sailing companions.

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