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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 110 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

5 departures available

June - September

Starting from

€950

€855

Per person

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4.9

Super!

Sailing holiday in the turquoise blue waters of Corsica

Italy: Tuscany

7 days - 7 nights

One departure available

August

€890

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

5 departures available

June - September

Starting from

€999

€949

Per person

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4.7

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

37 departures available

January - December

Starting from

€300

€270

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

9 departures available

June - September

Starting from

€490

€466

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

4 departures available

July - August

Starting from

€1,052

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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4.8

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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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

€999

Per person

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4.9

Super!

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

4 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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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

3553 reviews

2 June long weekend - Capraia and Cap Corse

06/5/2026

claudio p.

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IT

First experience on a sailing boat decidedly positive! Enrico has great experience and is an excellent captain (and cook!), helpful and pleasant company. Thanks to the wonderful weather and the right crew found on board, the long weekend to Corsica was perfect. The boat has all the necessary amenities, with bathrooms in each cabin and spaces suitable for relaxing in the waves. Till the next one!

June 2 long weekend between Capraia and Corsica - 2 boats

06/4/2026

Rebecca C.

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IT

It was a beautiful holiday, we sailed between Elba and Capraia and both Matteo and Alessio (the skippers of the two boats) were impeccable, really good and professional. On board I found a wonderful company that made these 4 days truly unforgettable! Super recommended experience
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Four days on a sailing boat

06/4/2026

fabio vittorio C.

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IT

Silvia and Andrea a winning skipper couple. too bad little wind, I would have enjoyed the sails a little more. but as we know you can't command the wind. very nice crew, Silvia very attentive to every detail. Andrea a sea dog. Do we want to talk about wines? I don't know about it but they really reach the heart. the passion that Andrea puts into the vineyard transpires. crowning the experience, visit to the suggestive Colonnade. A cuddle. I highly recommend this experience. I will definitely be back.

Long weekend of June 2 with WWF guide in the heart of the Tuscan Archipelago

06/4/2026

MARCO C.

-

IT

Excellent skipper. Kind and nice. Helpful and professional. Well maintained and functional boat.

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