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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 24 opportunities to get on board a Sailboat adventure in Tuscany. A unique experience with a local skipper, starting at €350 a week.

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5.0

Weekend in Tuscany between Argentario and Giglio Island

Italy: Tuscany

3 days - 2 nights

3 departures available

October - November

€280

Per person

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4.9

E-bike & Sailing Experience with wine tasting on Elba - 2 boats

Italy: Tuscany

3 days - 2 nights

One departure available

October

€250

€238

Per person

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4.7

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

11 departures available

June - August

Starting from

€660

Per person

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4.1

Totano's cup 2027 weekend of sailing and party on the island

Italy: Tuscany

3 days - 2 nights

One departure available

October

€350

Per person

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4.7

Four days on a sailing boat

Italy: Tuscany

4 days - 4 nights

One departure available

June

€625

Per person

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5.0

New

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

One departure available

October - November

€250

Per person

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5.0

Tuscany & Corsica Energy Program between food, sea, sun and adventure

Italy: Tuscany

6 days - 6 nights

6 departures available

July - August

Starting from

€801

Per person

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4.1

Corso di vela RYA Day Skipper Pratical sailing

Italy: Tuscany

4 days - 4 nights

10 departures available

October - December

€1,400

Per person

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4.1

Capraia & Corsica del Nord — 7 days of sailing in the blue

Italy: Tuscany

7 days - 6 nights

9 departures available

July - September

Starting from

€850

€723

Per person

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4.0

Three days at the Squid Festival in Capraia

Italy: Tuscany

3 days - 3 nights

One departure available

November

€560

Per person

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4.1

June 2nd long weekend towards Elba and Capraia between bays, sailing and freedom

Italy: Tuscany

5 days - 5 nights

One departure available

May - June

€540

€486

Per person

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5.0

Long live the legendary Squid Festival in Capraia!

Italy: Tuscany

3 days - 3 nights

One departure available

October - November

€290

Per person

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Reviews - Sailboat yacht sailing holidays & tours in Tuscany

3899 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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