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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 69 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 & Corsica Energy Program between food, sea, sun and adventure

Italy: Tuscany

6 days - 6 nights

3 departures available

July - August

Starting from

€950

Per person

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5.0

Super!

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

3 departures available

October - November

€250

Per person

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5.0

Wellness, sun, sea and adventure: a weekend full of sailing!

Italy: Tuscany

3 days - 2 nights

One departure available

September

€230

Per person

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4.9

Super!

Quattro giorni all'Elba - Hostess a bordo

Italy: Tuscany

4 days - 5 nights

2 departures available

August

Starting from

€750

Per person

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4.8

Super!

Sea, scents and colors on Elba

Italy: Tuscany

3 days - 3 nights

One departure available

September

€300

Per person

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5.0

New

Island of Elba on a sailing boat: coves, crystal clear sea and relaxation

Italy: Tuscany

7 days - 7 nights

2 departures available

July - August

Starting from

€835

€752

Per person

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4.7

Super!

Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

Italy: Tuscany

6 days - 6 nights

7 departures available

July - September

Starting from

€1,100

€935

Per person

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4.9

Super!

Midweek between Elba and Capraia

Italy: Tuscany

4 days - 4 nights

2 departures available

September

€400

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

7 departures available

September - October

Starting from

€230

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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4.9

Super!

Giglio Island - Festival of Grapes and Open Cellars

Italy: Tuscany

3 days - 3 nights

One departure available

September

€280

Per person

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4.8

Super!

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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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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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

3675 reviews

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Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

07/25/2026

Michele G.

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IT

Amazing holiday with a fantastic itinerary. A precise, prepared skipper who is very engaging in sailing manoeuvres. The boat is perfect.

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

07/24/2026

Eleonora F.

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IT

We couldn't have wished for a better skipper! Very professional but easy-going, prepared, always kind and available for any need. The boat is very well equipped and well organized. He made us experience the real thrill of sailing by explaining all the details of sailing. Highly recommended, we will definitely return to the sea with him! We saw beautiful places, a variety of coves and a super blue sea! THANK YOU EDO!

The Island of Elba, to make you live a special experience!

07/24/2026

Filippo C.

Livio is an attentive and scrupulous skipper, a connoisseur of Elba, but also a nice and jovial person with whom to spend quality time. Highly recommended as a first experience.

Midweek getaway between Elba and Capraia

07/24/2026

Manuela B.

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IT

Three different days, away from the daily routine. Lots of sun, lots of sea, new friends, the discovery of my spirit of adaptation ;-) and Marco very good and kind. See you next time!

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