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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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4.0

Weekend on the island of Elba aboard a 17-meter sports boat

Italy: Tuscany

2 days - 2 nights

One departure available

July

€400

Per person

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5.0

Tuscany & Corsica Energy Program between food, sea, sun and adventure - cook on board

Italy: Tuscany

6 days - 6 nights

One departure available

August

€1,600

Per person

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4.0

Midweek among the wonders of the island of Elba

Italy: Tuscany

4 days - 4 nights

2 departures available

June

€390

Per person

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5.0

Long live Elba and Capraia

Italy: Tuscany

3 days - 3 nights

One departure available

June

€375

Per person

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4.7

Sailing holiday with your children

Italy: Tuscany

7 days - 7 nights

One departure available

July

€970

Per person

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4.7

Cruise with WWF guide between Giglio, Giannutri and Montecristo

Italy: Tuscany

6 days - 7 nights

One departure available

August

€1,083

€1,029

Per person

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4.6

Week between the Tuscan Islands and Northern Corsica

Italy: Tuscany

7 days - 6 nights

8 departures available

June - September

Starting from

€650

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

One departure available

July

€990

€891

Per person

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Island of Elba on a sailing boat: coves, crystal clear sea and relaxation

Italy: Tuscany

7 days - 7 nights

2 departures available

July - August

€835

€752

Per person

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5.0

Week end Elbani

Italy: Tuscany

3 days - 2 nights

2 departures available

June

€310

Per person

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New

Educational cruise in the Tuscan archipelago and Cetacean sanctuary

Italy: Tuscany

7 days - 7 nights

One departure available

August

€865

€779

Per person

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4.7

Weekend on the Island of Elba

Italy: Tuscany

3 days - 2 nights

2 departures available

July

€350

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

3783 reviews

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Long weekend to discover the island of Capraia

06/3/2026

Eleonora C.

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IT

We had a great experience in [hidden]. The nice and caring skipper. The boat was perfect for sailing comfortably between coves and breathtaking views. We couldn't ask for anything better for our relaxation!

Long weekend of June 2 with WWF guide in the heart of the Tuscan Archipelago

06/3/2026

Eliana P.

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IT

Beautiful experience, fantastic skipper and guide, super travel companions, to be done again absolutely!

Weekend among the most beautiful coves of Elba

06/2/2026

Annalisa D.

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IT

It was a beautiful experience. Marco and Carmen guided us and accompanied us on a wonderful journey. The luck of meeting a group of beautiful people made everything much easier and even the small difficulties were overcome with ease. This time I think I can really say...... FAIR WINDS TO ALL!!!!
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Weekend among the most beautiful coves of Elba

06/2/2026

Gianmario B.

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IT

We spent the weekend with two professional, attentive and caring people towards guests. Carmen and Marco are people who enter into symbiosis right away, giving full availability to make you feel at ease and as if you have always known them. Boat in excellent condition, nothing is missing, you obviously need a spirit of adaptation not being in your bathroom at home. The relationship that is created during the experience with all the guests is also beautiful, in this experience we met wonderful people. We recommend everyone and Fair Winds

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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

Sailboat (550)Whole boat with skipper (375)Cooking service onboard (60)Family sailing cruises (60)WWF Sailing Cruises (35)Courses & regatta (30)Catamaran (25)Day trips (20)Sport & wellness (15)All inclusive (5)

Other travel ideas

Sailboat (604)Whole boat with skipper (469)Cooking service onboard (123)Catamaran (91)All inclusive (46)Family sailing cruises (30)Courses & regatta (30)Exotic destinations (26)Day trips (23)Offshore (20)

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