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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 61 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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4.5

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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4.5

Holiday - School between the Tuscan Archipelago and North Corsica

Italy: Tuscany

7 days - 7 nights

2 departures available

August

€900

Per person

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5.0

Capraia and Elba Island - Sun, Sea and Fun!

Italy: Tuscany

4 days - 3 nights

4 departures available

September - October

Starting from

€400

Per person

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4.9

Between sunsets and aperitifs on a sailing boat

Italy: Tuscany

7 days - 6 nights

3 departures available

August - September

Starting from

€617

Per person

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5.0

New

Three days in Elba full comfort

Italy: Tuscany

3 days - 2 nights

2 departures available

August - 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

Starting from

€325

€293

Per person

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Excursion to observe the solar eclipse on a sailboat

Italy: Tuscany

1 day - 0 nights

One departure available

August

€187

Per person

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4.8

Offshore and night navigation course on cabin cruisers

Italy: Tuscany

3 days - 2 nights

One departure available

October

€332

€282

Per person

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5.0

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

Italy: Tuscany

2 days - 3 nights

One departure available

August

Starting from

€390

Per person

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5.0

Tuscany & Corsica Energy Program between food, sea, sun and adventure

Italy: Tuscany

6 days - 6 nights

One departure available

August

€1,200

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

4 departures available

September - October

Starting from

€275

€248

Per person

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80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

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

3740 reviews

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

08/7/2026

Carlotta T.

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IT

We spent unforgettable days. Great company, lots of aperitifs, beautiful landscapes and a special thanks goes to Livio who made us sail safely, involved in the management of the boat teaching us the tricks of the trade and pampered us with his delicacies!

Weekend on the island of Elba: among dolphins, enchanting bays and relaxation

08/6/2026

Daniela L.

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IT

Beautiful experience! A mini holiday full of unique landscapes, nature and new friendships. For most of the trips, the wind gave us the opportunity to use the sails. It takes a bit of adaptation to sharing spaces, but with a few tricks everything becomes manageable. A weekend to remember! Thank you Salvatore, you have passed on your passion for the sea and sailing.

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

08/5/2026

Elena C.

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IT

A wonderful experience, we collected beautiful memories thanks to Alberto who led us to truly magical places and gave us the first notions to understand the sailboat, also allowing us to try some maneuvers. The boat is very well organized, tidy and clean. A highly recommended experience!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

08/5/2026

Eliana M.

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IT

For me it was the first time on a sailing boat.... One of the best holidays of my life! A top captain who put everyone at ease, veterans and not. A group of unforgettable travel companions! You completely lose track of time, marked only by swimming in wonderful seas, lunches and toasts with lots of laughter! I doubt I can get used to the beach 😂 again

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