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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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4.7

Mini-cruise with WWF guide in the heart of the Tuscan Archipelago

Italy: Tuscany

4 days - 4 nights

One departure available

September

€567

Per person

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4.7

Voices of the Pelagos: artistic-scientific whale watching expedition with WWF guide

Italy: Tuscany

4 days - 4 nights

One departure available

October

Starting from

€453

€430

Per person

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5.0

Midweek Tuscan archipelago

Italy: Tuscany

4 days - 4 nights

4 departures available

August - September

€500

Per person

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4.9

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

2 departures available

September

€390

€351

Per person

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5.0

Between Capraia and Northern Corsica: sailing, crystal clear sea and freedom

Italy: Tuscany

7 days - 6 nights

2 departures available

August - September

€990

Per person

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5.0

New

Educational cruise in the Tuscan archipelago and Cetacean sanctuary

Italy: Tuscany

7 days - 7 nights

One departure available

August

€865

Per person

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4.5

Educational Sailing Cruise: from Cagliari to Marina di Pisa

Italy: Tuscany

7 days - 7 nights

One departure available

September

€750

Per person

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4.9

Four days exclusively on Elba between aperitifs and sailing

Italy: Tuscany

4 days - 3 nights

2 departures available

September

€317

Per person

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4.5

Holiday - School between the Tuscan Archipelago and North Corsica

Italy: Tuscany

7 days - 7 nights

One departure available

August

€900

Per person

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5.0

Capraia and Elba Island - Sun, Sea and Fun!

Italy: Tuscany

4 days - 3 nights

4 departures available

September - October

Starting from

€400

Per person

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5.0

Sailing to discover the Tuscan Archipelago and Corsica

Italy: Tuscany

6 days - 7 nights

One departure available

August

€1,250

Per person

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4.9

Between sunsets and aperitifs on a sailing boat

Italy: Tuscany

7 days - 6 nights

3 departures available

August - September

Starting from

€617

Per person

Why book a holiday with Sailsquare?

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

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 more about the skipper and travellers who have already booked the holiday, to find out more about the

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

4015 reviews

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Sea, scents and colors on Elba

08/17/2026

Alberto B.

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IT

A beautiful experience, to be repeated. Thanks to Ivo, a very experienced skipper, available to teach those who want to learn the basics of sailing! Elba Island perfect for sailing, with its beautiful bays, plus Ivo adapted the route according to our preferences. Too bad for periods with little wind, but it is not to be taken into account.

The Wild Flotilla: dive into the wilderness of Tuscany & Corsica

08/17/2026

Margherita E.

-

IT

Fantastic week. Wonderful catamaran, group as well. Skipper kind, helpful, easy-going and always full of funny and interesting anecdotes. Beautiful places visited. A week was too short, I would have gladly done one more.

Sailing holiday in the turquoise blue waters of Corsica

08/17/2026

claudio d.

Beautiful week. Skipper Enrico and Simone very welcoming and helpful.... We also sailed as often as the wind permitted. Great cooks. I will be back in this boat........ thanks again

Week among the queens of the archipelago - Elba, Capraia and Corsica

08/17/2026

Andrea S.

-

IT

Truly incredible experience, everything perfect: boat, skipper and itinerary. We will definitely be back!

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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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