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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.

125

experiences

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4.6

April 25 between the Tuscan islands and North Corsica.

Duration:

4 days - 4 nights

Italy:

Tuscany

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Riccardo

has booked

€350

Per person

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5.0

April 25th long weekend between Elba and Corsica

Duration:

4 days - 4 nights

Italy:

Tuscany

Give this experience a try!

€450

Per person

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4.8

LONG WEEKEND 25 April barefoot: 4 days between Capraia and the island of Elba

Duration:

4 days - 4 nights

Italy:

Tuscany

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+4 travellers

have booked

€349

Per person

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4.2

Ponte del 25 Aprile in navigazione con rotta per la Capraia.

Duration:

4 days - 4 nights

Italy:

Tuscany

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+4 travellers

have booked

€435

Per person

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5.0

Long weekend in Capraia and North Corsica

Duration:

4 days - 4 nights

Italy:

Tuscany

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+7 travellers

have booked

€375

Per person

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4.9

Long weekend of April 25 in Elba, Corsica and Capraia

Duration:

4 days - 4 nights

Italy:

Tuscany

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+7 travellers

have booked

€405

Per person

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5.0

Capraia and Corsica: 2 islands in 4 days!

Duration:

4 days - 3 nights

Italy:

Tuscany

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+2 travellers

have booked

€395

Per person

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5.0

Offshore cruise course in the Tuscan archipelago with PROFESSIONAL SKIPPER AND COOK 

Duration:

4 days - 4 nights

Italy:

Tuscany

Give this experience a try!

€475

€500

Per person

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4.6

April 25 long weekend: trekking and sailing at Capraia

Duration:

4 days - 4 nights

Italy:

Tuscany

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MARY

has booked

€510

Per person

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4.0

AUTONOMY Course

Duration:

4 days - 4 nights

Italy:

Tuscany

Give this experience a try!

€680

Per person

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5.0

25 April - 4 days of sailing between Elba and Capraia

Duration:

4 days - 3 nights

Italy:

Tuscany

Give this experience a try!

€300

Per person

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5.0

Mini Crociera Sail Academy

Duration:

4 days - 3 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€500

Per person

Why book a holiday with Sailsquare?

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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 - Yacht sailing holidays & skippered tours in Tuscany

3001 reviews

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Easter on the Island of Elba

04/22/2024

Antonios S.

-

Italy

Anche se il tempo non ha aiutato, è stata una bellissima esperienza
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Trekking and sailing weekend on the island of Elba

04/22/2024

Sara C.

-

Italy

Bellissima esperienza,grazie alla cordialità e professionalità di Marco e i compagni di avventura. Ho apprezzato molto anche la possibilità di fare trekking. Consigliatissimo!!
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Veleggiata verso il farò di Cecina con Aperitivo a bordo

04/11/2024

maurizio r.

-

Italy

Grazie per la bella domenica di relax in barca Maurizio e Giuliana
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A weekend of sailing between Capraia and the island of Elba

03/20/2024

davide C.

-

Italy

Enrico è un comandante che sa mettervi a proprio agio in un equilibrio di libertà e professionalità . Se vi piace oltre al vento il buon cibo siete sulla barca giusta ..

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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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