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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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4.9

Super!

A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

Italy: Tuscany

2 days - 2 nights

3 departures available

June - September

€280

Per person

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4.9

Super!

Long weekend among the queens of the archipelago - Elba and Capraia

Italy: Tuscany

4 days - 3 nights

2 departures available

August

€510

€459

Per person

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4.6

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

4 departures available

June - August

Starting from

€700

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!

Tuscany and North Corsica on a sailing boat

Italy: Tuscany

7 days - 7 nights

2 departures available

August

Starting from

€1,060

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

10 departures available

June - October

Starting from

€500

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

€410

€369

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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4.7

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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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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4.9

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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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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