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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!

The Squid Festival in Capraia

Italy: Tuscany

2 days - 2 nights

2 departures available

October - November

€320

Per person

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4.9

Super!

Long weekend among the queens of the archipelago - Elba and Capraia

Italy: Tuscany

4 days - 3 nights

16 departures available

May - September

Starting from

€430

€409

Per person

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4.9

Super!

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

Italy: Tuscany

7 days - 7 nights

9 departures available

July - September

Starting from

€700

Per person

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4.8

Squid Festival: let's close the season on a high note! - on board a 17mt boat

Italy: Tuscany

2 days - 2 nights

One departure available

October

€300

Per person

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4.9

Super!

The most important squid festival in the world - Capraia

Italy: Tuscany

3 days - 2 nights

One departure available

October - November

€310

Per person

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5.0

Super!

Squid Festival in Capraia!

Italy: Tuscany

2 days - 2 nights

One departure available

October

€290

€270

Per person

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4.8

Super!

The sea and sailing in autumn: two days on Elba

Italy: Tuscany

2 days - 2 nights

4 departures available

October - December

€190

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

12 departures available

June - September

Starting from

€793

€714

Per person

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4.9

Super!

Long weekend at the Capraia Squid Festival

Italy: Tuscany

3 days - 3 nights

One departure available

October - November

€350

Per person

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4.8

Offshore and Night Navigation Course between Elba, Corsica and Capraia

Italy: Tuscany

3 days - 3 nights

One departure available

November

€299

Per person

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4.7

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

59 departures available

January - December

Starting from

€200

€180

Per person

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5.0

Weekend in Tuscany between Argentario and Giglio Island

Italy: Tuscany

3 days - 2 nights

One departure available

October

€280

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

3736 reviews

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Weekend in Capraia, the island with timeless sunsets

10/14/2025

Gloria G.

-

Italy

Wonderful weekend. Super skipper! Very professional and helpful, he entertained us by telling us many curiosities about sailing and the places visited. The fantastic boat with ample space and equipped with everything you need! 100% recommended both the skipper and the destination!
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The sea and sailing in autumn: two days on Elba

10/13/2025

Roberto T.

-

Italy

Ivo is a professional skipper. We had a technical outing that was very formative for me and we had fun.
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Weekend Elba o Capraia

10/8/2025

Massimiliano L.

-

Italy

First time on a sailing boat, nice experience. Three stars because we could not follow the program due to the weather.
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Long weekend of whale watching with WWF guide on an 18-meter schooner

10/2/2025

Marco C.

-

Italy

Unforgettable experience aboard the Schooner Mahayana. An essential and shared life on board. Thanks to Captain Francesco, his crew and WWF guide Ilaria, a serene and pleasant atmosphere was established with all guests from the beginning. Browsing great places. Educational experience on the marine environment with a focus on cetaceans and environmental impact. As a first experience we particularly appreciated the pace of navigation, the life on board and the company.

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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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