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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

Whale watching cruise with WWF guide for children 14-17 on an 18-meter schooner

Italy: Tuscany

6 days - 6 nights

One departure available

July

Starting from

€1,052

Per person

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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

€950

€855

Per person

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4.6

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

35 departures available

January - December

Starting from

€300

€270

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

3 departures available

August - September

Starting from

€1,041

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

6 departures available

June - September

Starting from

€490

€466

Per person

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4.7

Whale watching cruise with WWF guide between Northern Corsica and the Tuscan Archipelago

Italy: Tuscany

6 days - 7 nights

3 departures available

July - August

Starting from

€1,052

Per person

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4.7

Youth cruise (18-23 years): whale watching with WWF between the Tuscan Archipelago and Northern Corsica

Italy: Tuscany

6 days - 7 nights

One departure available

July - August

€999

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

10 departures available

July - October

Starting from

€230

Per person

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4.8

Super!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

Italy: Tuscany

6 days - 7 nights

6 departures available

July - September

Starting from

€900

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

9 departures available

July - October

Starting from

€230

Per person

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4.8

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

5 departures available

July - August

Starting from

€410

€369

Per person

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4.6

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

2 departures available

July - August

Starting from

€800

Per person

Why book a holiday with Sailsquare?

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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

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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

3806 reviews

A taste of the magnificent Island of Elba

06/17/2026

valentina t.

-

IT

We with friends at the Top! The boat very clean and welcoming, Alberto always on the piece helpful and attentive.

Week-end all'Elba - Hostess a bordo

06/16/2026

Andrea P.

-

IT

We spent a beautiful holiday beyond all expectations: the comfort and spaciousness of the boat, the beauty of the places, the kindness and skill of Giulia in the kitchen, the care and professionalism of Vittorio at the helm, together with the sympathy of the other day-trippers (and the wonderful weather!) allowed us to enjoy our first sail - around Elba - in a fantastic way, celebrating my wife's birthday in an exciting way on a holiday that we hoped would not end so soon. Five well-deserved 😀 stars
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A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

06/16/2026

Alessandro L.

-

IT

Enrico the skipper is a real sea dog and like all sea dogs he must be caressed by the way he furs. Nice experience..
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Giglio or Elba the pearls of the Tuscan archipelago

06/16/2026

Moira C.

-

IT

I spent 2 fantastic days, together with wonderful people, I couldn't ask for anything better. Cleanliness, kindness and safety assured! I have traveled a lot by sailboat and have always felt safe. I will definitely be back on the boat with Simone, an attentive, kind and polite skipper. Thank you!

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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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