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Crewed yacht sailing holidays & tours in Tuscany

Get on board on a crewed sailing holiday in Tuscany for the most relaxed time ever.

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5.0

Super!

June 2nd long weekend in the Tuscan Archipelago with PROFESSIONAL CHEF SKIPPER

Italy: Tuscany

4 days - 4 nights

One departure available

May - June

€500

€475

Per person

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5.0

Super!

Weekend in the Tuscan Archipelago with PROFESSIONAL COOK SKIPPER

Italy: Tuscany

2 days - 2 nights

4 departures available

May - June

Starting from

€250

€238

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

16 departures available

April - October

Starting from

€350

Per person

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4.3

Premium

TUSCANY Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Tuscany

7 days - 7 nights

2 departures available

July - August

Starting from

€2,390

Per person - min 2 pax

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5.0

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

Italy: Tuscany

3 days - 2 nights

10 departures available

May - September

Starting from

€230

Per person

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5.0

Tuscany & Corsica Energy Program between food, sea, sun and adventure - cook on board

Italy: Tuscany

6 days - 6 nights

3 departures available

August

Starting from

€1,600

Per person

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

Italy: Tuscany

3 days - 2 nights

11 departures available

May - October

Starting from

€275

€248

Per person

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Seven days of sailing and sea between Elba, Capraia and North Corsica

Italy: Tuscany

7 days - 6 nights

7 departures available

July - September

Starting from

€795

€716

Per person

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

Italy: Tuscany

4 days - 3 nights

10 departures available

June - September

Starting from

€424

€382

Per person

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The world's largest marketplace for sailing holidays

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

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.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

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 - Crewed yacht sailing holidays & tours in Tuscany

206 reviews

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Magnificent week on catamaran between Corsica and Capraia with Hostess

09/23/2025

Angela T.

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Italy

Regenerating holiday, great company, great food, fantastic location, spacious and clean catamaran. The weather did not allow us to follow exactly the planned itinerary but it did not take anything away from the holiday, on the contrary it added walks in the beautiful and wild nature of Corsica as an alternative to just swimming in the sea that I would have expected If I close my eyes I am still there in the middle of the sea with its gentle lulling of us and the feeling of infinite freedom and serenity that the horizon transmits to me.
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Week-end all'Elba - Hostess a bordo

09/17/2025

Riccardo A.

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Italy

I had a very good time and Vittorio is very nice
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Magnificent week on catamaran between Corsica and Capraia with Hostess

09/15/2025

Gaia T.

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Italy

I give two stars respectively to hostess Manuela and travel companions. For the rest, the nervousness and unjustified anxiety of the commander led to a very unpleasant situation. A lot.
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Magnificent week on catamaran between Corsica and Capraia with Hostess

09/15/2025

Larisa N.

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Italy

Really pleasant holiday in Corsica, with lovely places, and great company and delicious food, however the experience was ruined by the very rude captain who on one occasion left part of the passengers on an island and picked them up after 30 minutes. He was evidently very stressed about the seasonal workload he should have avoided taking this group

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