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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.

108

experiences

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4.8

May 1 BAREFOOT Bridge on a 17-meter boat

Duration:

3 days - 3 nights

Italy:

Tuscany

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+7 travellers

have booked

€300

Per person

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5.0

Weekend of May 1st in Capraia

Duration:

3 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€315

Per person

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4.3

May 1st on Elba - Stewardess on board -3 Cab./ 3 Bathrooms

Duration:

3 days - 3 nights

Italy:

Tuscany

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susanna s.

has booked

€399

Per person

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4.9

May Day Sailing Bridge in Capraia

Duration:

3 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€265

Per person

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4.5

Sailing on the Island of Elba

Duration:

3 days - 4 nights

Italy:

Tuscany

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Elettra

has booked

€350

Per person

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4.9

Trekking, E-bike & Sailing Experience, 1 May adventure on Elba.

Duration:

5 days - 5 nights

Italy:

Tuscany

Give this experience a try!

€618

€650

Per person

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4.6

May Day Long Bridge between Tuscany and Corsica

Duration:

5 days - 5 nights

Italy:

Tuscany

Give this experience a try!

€380

Per person

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5.0

May Day: I love you Capraia! Only for 4 guests

Duration:

5 days - 5 nights

Italy:

Tuscany

Give this experience a try!

€490

Per person

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4.8

Cruise in the Gulf of Baratti

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€216

€240

Per person

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5.0

May Day on Elba

Duration:

4 days - 4 nights

Italy:

Tuscany

Give this experience a try!

€365

Per person

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4.8

Ponte dal 1 Maggio al 5 Maggio su barca di 17 m

Duration:

3 days - 3 nights

Italy:

Tuscany

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+3 travellers

have booked

€340

Per person

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5.0

Weekend in Capraia, the island with timeless sunsets

Duration:

2 days - 2 nights

Italy:

Tuscany

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+12 travellers

have booked

Starting from

€225

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

3002 reviews

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A weekend of sailing between Capraia and the island of Elba

04/24/2024

Angelo C.

-

Italy

Bellissima esperienza, bella gente con uno skipper top!
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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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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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