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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.

98

experiences

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4.9

Sailing and trekking in Capraia

Duration:

2 days - 2 nights

Italy:

Tuscany

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+17 travellers

Have booked

€200

Per person

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4.9

Weekend on Elba between Sailing and Trekking

Duration:

2 days - 2 nights

Italy:

Tuscany

Be the first one to book!

Starting from

€280

Per person

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4.9

Trekking and sailing weekend on the island of Elba

Duration:

2 days - 2 nights

Italy:

Tuscany

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+3 travellers

Have booked

Starting from

€228

€240

Per person

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4.9

Trekking & Sailing Experience-Weekend lungo a Capraia, 2 barche

Duration:

3 days - 3 nights

Italy:

Tuscany

Be the first one to book!

Starting from

€295

€310

Per person

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4.9

Offshore and Night Navigation Course between Elba, Corsica and Capraia

Duration:

3 days - 3 nights

Italy:

Tuscany

Be the first one to book!

€290

Per person

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5.0

Trekking weekend on the Island of Elba

Duration:

2 days - 2 nights

Italy:

Tuscany

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+12 travellers

Have booked

Starting from

€228

€240

Per person

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4.9

A weekend of sailing between Capraia and the island of Elba

Duration:

2 days - 2 nights

Italy:

Tuscany

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+6 travellers

Have booked

€212

Per person

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4.9

Weekend on Elba between Sailing, E-bike and Tasting in a farmhouse

Duration:

2 days - 2 nights

Italy:

Tuscany

Be the first one to book!

€390

Per person

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4.9

E-bike & Sailing Experience with wine tasting on Elba - 2 boats

Duration:

2 days - 2 nights

Italy:

Tuscany

Be the first one to book!

€314

€330

Per person

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5.0

E-bike & Sailing Experience con degustazione vini all'Elba - 2 barche

Duration:

2 days - 2 nights

Italy:

Tuscany

Be the first one to book!

€314

€330

Per person

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4.6

Weekend a Capraia, trekking e natura

Duration:

2 days - 2 nights

Italy:

Tuscany

Be the first one to book!

Starting from

€180

Per person

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5.0

Educational Cruise

Duration:

3 days - 2 nights

Italy:

Tuscany

Be the first one to book!

€380

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

2997 reviews

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Weekend on the Island of Elba...Hostess on board

10/9/2023

Barbara B.

-

Italy

la professionalità e la compagnia di Vittorio e Giulia ci hanno regalato un week end bellissimo. Affidabili, super disponibili e divertenti Consigliatissimo!!!
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Elba... the scents, the sea and its colors!

10/9/2023

Lucia I.

-

Italy

Ivo molto bravo e professionale .beliissima esperienza
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Long weekend of sailing and trekking on the Island of Elba - 2 boats

10/6/2023

Roberta M.

-

Italy

Bellissima esperienza, bellissimo equipaggio, ma soprattutto ottimo Skipper!!! Marco mette a suo agio le persone, sempre disponibile e molto preparato. Mi ha permesso di affrontare serenamente la mia prima esperienza in barca a vela. Visitando nuovi posti grazie anche alla perfetta combinazione barca a vela + trekking (e ben organizzata, un ringraziamento anche Francesco "Checco" la nostra guida!) Grazie a tutto il meraviglioso gruppo che mi ha accompagnato in questa nuova avventura!!!
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Wine Experience with Sommelier on the Island of Elba

10/4/2023

Davide Q.

-

Italy

Una splendida esperienza, una crew affiatata e divertente che ha scoperto alcuni angoli suggestivi dell'Isola d'Elba e che ha potuto vivere una vera Wine-experience, tra visita in cantina, trekking in vigna, degustazioni e cena con abbinamenti. Il tutto guidato da esperti sommelier.

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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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