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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

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

Italy: Tuscany

6 days - 7 nights

2 departures available

July - August

€999

€949

Per person

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4.8

Long weekend on Elba: 4 days of sun and sailing

Italy: Tuscany

3 days - 3 nights

5 departures available

July - September

Starting from

€410

€369

Per person

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4.8

Special May - Weekend on Elba

Italy: Tuscany

3 days - 2 nights

One departure available

May

€220

€198

Per person

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4.9

Four days exclusively on Elba between aperitifs and sailing

Italy: Tuscany

4 days - 3 nights

11 departures available

April - September

Starting from

€233

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

3 departures available

August

Starting from

€1,600

Per person

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5.0

Sailing day between the Apuan coast and the Gulf of Poets

Italy: Tuscany

1 day - 0 nights

One departure available

June

€77

Per person

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4.7

Weekend Elba o Capraia

Italy: Tuscany

3 days - 2 nights

One departure available

May

€340

€306

Per person

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4.8

Week in the north of Corsica, via Capraia - in company

Italy: Tuscany

7 days - 6 nights

2 departures available

August

Starting from

€890

€801

Per person

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4.8

Long weekend between Elba and Capraia, from Thursday to Sunday

Italy: Tuscany

3 days - 3 nights

One departure available

June

€395

€356

Per person

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4.7

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

Italy: Tuscany

3 days - 3 nights

One departure available

May

€452

€429

Per person

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5.0

Tour of Elba and Capraia on a Catamaran

Italy: Tuscany

7 days - 6 nights

3 departures available

June - August

Starting from

€1,200

Per person

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Regatta on a sailing boat - 100 of Montecristo

Italy: Tuscany

3 days - 2 nights

One departure available

May

€535

Per person

Why book a holiday with Sailsquare?

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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

3750 reviews

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Offshore and night navigation course on cabin cruisers

04/13/2026

Marco B.

-

Italy

Sailing course... but also a holiday. Navigation to Giglio and back via Elba with departure at night. Despite the little wind that blew in those days, Paolo was able to convey notions and make the students practice, all with the utmost sympathy ... Be prepared to be made fun of, especially if you're an engineer.
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Easter on the Island of Elba

04/9/2026

Miriam C.

-

Italy

Very pleasant sailing experience. The boat was in good condition. Everything went according to expectations and the navigation was safe and relaxing. The only negative note concerns the owner, Enrico. During communications he was often grumpy, with a rather rigid attitude and not inclined to confrontation. This made the interaction less pleasant, especially at times when more availability and friendliness would have been useful. Overall, I recommend the experience for the quality of the boat and the service at sea, but I suggest the owner to improve the approach with customers to make everything really impeccable.
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Easter in Capraia and Corsica

04/9/2026

Monica L.

-

Italy

Weekend absolutely up to expectations. Marco is a trained skipper, with great experience, very helpful, kind and caring towards his crew. His boat is hospitable and excellently cared for by him. All positive!!
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Easter in Capraia and Corsica

04/8/2026

Giovanni G.

-

Italy

Unique and beautiful experience, from start to finish. Starting with the skipper: exceptional, inclusive and very experienced of the sea and the places visited, always constructive and aimed at making us live a positive experience; the places visited were beautiful, with exceptional views, small villages in the middle of nature, with trekking, walks and stops for local shopping; The company of the whole crew (and friendly boats) was fun and collaborative, aimed at creating an enjoyable group experience; The perfect boat, equipped with every comfort, including USB recharges for almost every bed just to give an example. An experience certainly to be repeated and that I recommend

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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 (370)Cooking service onboard (65)Family sailing cruises (65)WWF Sailing Cruises (45)Catamaran (40)Courses & regatta (30)Day trips (20)Sport & wellness (20)All inclusive (5)

Other travel ideas

Sailboat (623)Whole boat with skipper (461)Cooking service onboard (134)Catamaran (83)All inclusive (47)Courses & regatta (41)Exotic destinations (33)Family sailing cruises (31)Offshore (23)Day trips (23)

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