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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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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

4 departures available

June - September

Starting from

€793

€714

Per person

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4.9

Taste of the sea between the island of Capraia and Northern Corsica

Italy: Tuscany

7 days - 7 nights

3 departures available

July - August

Starting from

€700

Per person

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5.0

Super!

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

7 departures available

July - September

Starting from

€293

€264

Per person

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4.9

Super!

Midweek on Elba, from Monday to Thursday

Italy: Tuscany

3 days - 3 nights

One departure available

July

€395

€375

Per person

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4.9

Unforgettable Catamaran Cruise in Elba, Capraia and Corsica

Italy: Tuscany

7 days - 6 nights

8 departures available

June - August

Starting from

€1,148

€861

Per person

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4.8

Barefoot holiday: Weekend on Elba on a 17m boat

Italy: Tuscany

2 days - 2 nights

3 departures available

June - July

€330

Per person

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4.9

Super!

Long weekend on Elba: 4 days of sun and sailing

Italy: Tuscany

3 days - 3 nights

One departure available

September

€380

€342

Per person

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4.9

Super!

Sailing week in the Tuscan Archipelago

Italy: Tuscany

7 days - 6 nights

4 departures available

August - September

Starting from

€700

€665

Per person

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4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

5 departures available

July - September

Starting from

€1,041

€989

Per person

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5.0

Super!

Tour of Elba and Capraia on a Catamaran

Italy: Tuscany

7 days - 6 nights

4 departures available

July - August

Starting from

€1,100

Per person

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4.9

Super!

Weekend on Elba Island

Italy: Tuscany

3 days - 2 nights

One departure available

July

€290

Per person

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4.8

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

6 departures available

July - September

Starting from

€430

€409

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

3382 reviews

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Weekend a Capraia, trekking e natura

06/10/2025

Kristian G.

-

Italy

Esperienza positiva e skipper disponibile
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Weekend in the Tuscan Archipelago with PROFESSIONAL COOK SKIPPER

06/9/2025

Elisa P.

-

Italy

Riccardo è uno skipper professionale e attento, cucina divinamente. La barca è ordinata e pulita e la compagnia è stata perfetta!
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Midweek special on the island of Elba, 2 nights

06/9/2025

Emilio B.

-

Italy

Marco, valutazione da 1 a 10 gli do 11. Persona gentile, disponibilissimo, sempre pronto ad aprire le vele in tutte le condizioni. Barca non nuovissima, ma pulita ed ordinata. Mi è piaciuto molto e lo consiglio assolutamente a chi piace viaggiare in barca a vela.
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Weekend in the Wonderful Tuscan Archipelago

06/7/2025

Alessandro T.

Prima esperienza in barca a vela, è andata benissimo. Bello l’itinerario, barca splendida e in ottime condizioni, compagnia ottima. Un grazie speciale allo skipper Alberto per aver organizzato tutto alla perfezione.

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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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