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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 35 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

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

Italy: Tuscany

3 days - 3 nights

2 departures available

September

€350

Per person

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4.8

Midweek on Elba, from Monday to Thursday

Italy: Tuscany

3 days - 3 nights

One departure available

September

€380

Per person

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4.1

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

30 departures available

January - December

Starting from

€300

€270

Per person

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4.7

Squid Regatta

Italy: Tuscany

2 days - 2 nights

One departure available

October

€180

Per person

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4.7

Week between the Tuscan Islands and Northern Corsica

Italy: Tuscany

7 days - 6 nights

3 departures available

September

€700

Per person

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4.8

Sunny weekend on Elba from Friday to Sunday

Italy: Tuscany

3 days - 2 nights

3 departures available

September - October

€325

€309

Per person

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New

Weekends immersed in the blue of the sea and the green of the island of Elba

Italy: Tuscany

3 days - 2 nights

3 departures available

September - October

€275

Per person

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5.0

Midweek Tuscan archipelago

Italy: Tuscany

4 days - 4 nights

2 departures available

September

€500

Per person

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New

Four days of relaxation midweek on the island of Elba with hostess

Italy: Tuscany

4 days - 3 nights

3 departures available

September

€424

Per person

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5.0

Between Capraia and Northern Corsica: sailing, crystal clear sea and freedom

Italy: Tuscany

7 days - 6 nights

One departure available

September

€990

Per person

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4.5

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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4.9

Four days exclusively on Elba between aperitifs and sailing

Italy: Tuscany

4 days - 3 nights

2 departures available

September

€317

Per person

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Reviews - Sailboat yacht sailing holidays & tours in Tuscany

3852 reviews

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

09/5/2026

Valentina R.

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IT

Very nice boat, excellent skipper and owner, delicious food. Costs a little too high given the decidedly downsized changes of course.
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The Island of Elba, to make you live a special experience!

09/4/2026

Gianluca D.

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IT

Very positive experience in a week in which the weather, due to the temperatures, did not help us much. Livio was always a center of gravity to which everyone on board referred, An extremely pleasant person and an excellent captain. Precise, prudent, fussy, aggregating and companion when it was time to relax. In addition to Livio, the real luck was to meet extremely pleasant and intelligent people who, despite not having a long experience of life on board like me, were able to live the holiday with the spirit necessary in this particular context. All this made the objective discomforts a minor thing and ignited my emotions making me live a week in which I never for once thought of anything other than what I was experiencing, for me it is a rare commodity ... The boat is to all intents and purposes Livio's second home so you have to tune in with this spirit and adapt to some lack of comfort compared to other more modern boats. Nothing that cannot be overcome with the right spirit... even the alcoholic one of the goliardic evenings that I will not forget ...
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Sailing week in the Tuscan Archipelago

09/4/2026

Beatrice M.

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CH

How many laughs, when well-being! We spent a week sailing around Elba in the company of Paolo. The boat is a gem and Paolo is an experienced skipper; He took care of everything leaving us the freedom to enjoy the experience. In addition to his professional skill he is also an interesting and nice person. We left in 4, and on the boat we met a third couple with whom we immediately integrated. And with 7 total people on the boat we found our harmony without ever feeling cramped. There are very precise rules that must be followed, ask Paolo as soon as you embark and if you follow them everything will be fine haha We spent a very special week made up of many baths in a beautiful sea, many peaceful roadsteads, many chats, lots of laughter and a record amount of beers! If you want to live a real experience and not just a holiday, it is the right boat for you :) p.s Paolo we will see you again soon!
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Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

09/2/2026

Giulio M.

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IT

Really great boat experience! A special thanks to Giacomo, our skipper, who despite his young age proved to be extremely professional, prepared and attentive at all times. A skill that is anything but obvious, which has allowed us to live the week in total tranquility and safety. The mood of the holiday is also beautiful: pleasant, relaxed and well balanced, with the right mix of fun, relaxation and conviviality. An experience that I absolutely recommend and that I would gladly do again!

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