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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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4.8

Super!

Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

Italy: Tuscany

6 days - 6 nights

13 departures available

June - September

Starting from

€990

Per person

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4.8

Super!

A taste of the magnificent Island of Elba

Italy: Tuscany

2 days - 2 nights

4 departures available

October - November

€300

Per person

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4.9

Super!

Squid Festival in Capraia

Italy: Tuscany

3 days - 3 nights

One departure available

October - November

€280

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

One departure available

October

€230

Per person

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4.8

Super!

Elba, Tuscan archipelago or Corsica aboard a full opt catamaran.

Italy: Tuscany

7 days - 7 nights

15 departures available

June - September

Starting from

€754

Per person

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4.9

Super!

Sailing holiday in the turquoise blue waters of Corsica

Italy: Tuscany

7 days - 7 nights

13 departures available

June - September

Starting from

€641

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

16 departures available

June - October

Starting from

€778

€700

Per person

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4.8

Super!

Experience the sea in October!

Italy: Tuscany

2 days - 2 nights

One departure available

October

€200

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

One departure available

October

€230

Per person

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4.8

LET'S GO TO TOTANI - Festival in Capraia

Italy: Tuscany

3 days - 3 nights

One departure available

October - November

€375

Per person

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4.1

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

36 departures available

January - December

Starting from

€275

€248

Per person

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4.1

Corso di vela RYA Day Skipper Pratical sailing

Italy: Tuscany

4 days - 4 nights

9 departures available

October - December

€1,400

Per person

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Reviews - Yacht sailing holidays & skippered tours in Tuscany

4146 reviews

A taste of the magnificent Island of Elba

10/14/2026

Annachiara P.

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IT

It was a beautiful weekend!! Alberto is an experienced and prepared skipper who is totally dedicated to what he is passionate about. We really appreciated his willingness to meet us and, compatibly with weather conditions and times, to adapt the weekend to our needs: although we were licensed, we needed to regain confidence with going to sea (sailing!), without giving up relaxation. Alberto was a great teacher and we learned so much! He took us to beautiful places and we really enjoyed our time together (and the classical guitar under the stars added that extra touch :D). A special thanks to Claudia for her company and for the super aperitifs she prepared for us! The boat is beautiful, maintained with great care, order and cleanliness. They were two wonderful days. Thank you very much Alberto and Claudia!! We hope to repeat it soon!
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Experience the sea in October!

10/6/2026

Luigi V.

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IT

Super experienced and helpful skipper. He helped us learn the basics of sailing and life on a sailing boat. Great chef skills!

Sailing, sun and sea in the Tuscan Archipelago

10/3/2026

Luca P.

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IT

Overall the experience was positive: it was my first time on a sailing boat and I was left with a great desire to repeat a trip of this type, especially thanks to the good harmony that was created with the group. However, there were some organizational and management aspects that deserve room for improvement: Management and navigation: Claudio is a very nice person, but a more precise planning of the itinerary would have made the difference. By not booking ports in advance, last-minute searches often proved fruitless. In addition, we almost always sailed by motor instead of sailing (used only on two occasions), which is a bit of a shame for a holiday of this type. Movements on land: On the days at anchor near the ports there was little availability in the use of the tender to take us ashore; fortunately we were able to remedy this thanks to the support of a more experienced travel companion. Itinerary: Unfortunately we were unable to reach either Capraia or the Island of Giglio. The adverse weather certainly complicated things, but probably with a different management of the stops at least one of the two stages could have been reached. Boat: The boat itself was beautiful, but in my opinion not suitable for comfortably accommodating 8 people. Also worth mentioning is a small plumbing problem in one of the bathrooms (the backflow of water after draining). Overall an adventure that I would gladly do again, with the hope that these details can be taken as ideas for improvement.
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North Corsica & Tuscan Archipelago: we love to travel a lot

09/27/2026

Tudor M.

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IT

Super positive feedback for Marco! Beautiful experience.

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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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