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Yacht sailing holidays & skippered tours in Tuscany

Discover the magic of sailing holidays in Tuscany! Get onboard with a local skipper and live a unique adventure with your crew: learn to sail, explore incredible places, recharge your batteries and experience the local culture & gastronomy.

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4.9

Between sunsets and aperitifs on a sailing boat

Italy: Tuscany

7 days - 6 nights

3 departures available

July - September

Starting from

€583

Per person

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5.0

A tour of the Tuscan islands starting from Liguria

Italy: Tuscany

8 days - 7 nights

One departure available

August

€500

Per person

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Sailing around the Island of Elba

Italy: Tuscany

7 days - 7 nights

3 departures available

July - September

Starting from

€850

Per person

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5.0

Overwhelmed by an unusual destiny in the blue sea of Corsica

Italy: Tuscany

6 days - 7 nights

One departure available

August - September

€700

Per person

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5.0

Week in Corsica with wellness programme

Italy: Tuscany

6 days - 7 nights

One departure available

August

€1,559

Per person

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5.0

AperiBarca: afternoon sunset aperitif

Italy: Tuscany

1 day - 0 nights

One departure available

July

€35

Per person

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4.3

Four borders between Elba and Capraia

Italy: Tuscany

5 days - 5 nights

One departure available

July

€620

Per person

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5.0

A day of sun and swimming

Italy: Tuscany

1 day - 0 nights

2 departures available

July

Starting from

€35

Per person

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Daily sailing trip off the coast of beautiful Pisa

Italy: Tuscany

1 day - 0 nights

69 departures available

July - November

Starting from

€115

Per person

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4.3

Four borders between Elba and Capraia

Italy: Tuscany

4 days - 4 nights

One departure available

July

€498

Per person

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Approach to sailing - mini course

Italy: Tuscany

1 day - 0 nights

19 departures available

July - September

Starting from

€57

Per person

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5.0

Sailing trip in Tuscany

Italy: Tuscany

7 days - 7 nights

4 departures available

August - September

Starting from

€838

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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 - Yacht sailing holidays & skippered tours in Tuscany

3418 reviews

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Weekend only four guests - Elba Island

07/9/2025

Paola F.

-

Italy

Beautiful experience! Pierpaolo skipper super helpful both in the organization and in structuring the various stages to make us enjoy the sailboat to the fullest. To be redone!
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Weekend on Elba Island

07/8/2025

Giovanna B.

-

Italy

Wonderful sailing weekend! Excellent weather, full sails and pleasant company. Anthony is a very capable skipper and always active as well as having a winning sense of humor!! He always tried to satisfy every request, gave directions on the places seen and on boat life, He is very nice and .... last but not least.... A great chef! He has always cooked tasty and varied dishes, also taking care of the presentation !! And to think that you found yourself on board vegans, intolerant to fish and more!
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Week of sailing and sea between the Tuscan Archipelago and Corsica with Hostess

07/8/2025

sonia s.

-

Italy

-I spent a wonderful holiday with Paolo and Bianca. They are very kind, very nice, Bianca is a very good cook. They are very helpful . My first experience on a sailing boat was very pleasant. I saw beautiful places, coves that otherwise I could not have seen except by boat. I highly recommend a holiday with Paolo and Bianca
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Weekend of sailing and relaxation on Elba

07/8/2025

Andrea P.

-

Italy

Kudos to Jo.... prepared, helpful and friendly. Only two days but enough to unplug! Advised!

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Guides & tips


Italy

Tuscany, Sardinia, the Aeolian Islands and Liguria are just some of the most beautiful destinations for a sailing or catamaran holiday, let's discover them all!
Guide to Italy on a sailing boat

Tuscany

The island of Elba, Capraia, Il Giglio and Giannutri are just some of the best destinations for a sailing or catamaran vacation in Tuscany.
Guide to the Tuscany on a sailing boat

WWF Whale watching cruises

A close-to-nature sailing cruise that integrates unrepeatable emotions and new scientific knowledge, perfect for true lovers of the sea, ready to have fun, wonder and delve into the magical world of cetaceans.
Guide to the WWF Cruises

Catamaran vacations

An alternative to the sailboat, the catamaran is an ideal choice for those who do not want to give up comfort and convenience and for a first vacation at sea.
Guide to the catamaran vacations

Flotilla holiday

A perfect vacation for singles (and others) to experience sailing, meet new friends and multiply the fun.
Guide to the flotilla holidays

Singles and solo travellers

Set out alone and return enriched by an unparalleled baggage of freedom, new friendships and lasting bonds. It is on a sailboat that an adventure as a solo traveler turns into a unique sharing experience.
Guide to solo travellers sailing holidays

Sailing vacations for families

To leave with one's family and return home enriched by an unparalleled baggage of adventure, bonds and indelible memories.
What to know before you go sailing with your family?

Sailing with children

Have you ever wondered if there is a vacation that is both the best for children and parents? The answer is yes, and it is indeed on a sailboat!
uide to sailing vacations with children

Tuscany: the best travel ideas

Other travel ideas

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