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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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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

2 departures available

October - November

€250

Per person

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4.8

Offshore and night navigation course on cabin cruisers

Italy: Tuscany

3 days - 2 nights

One departure available

October

€332

€299

Per person

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4.1

Corso di vela RYA Day Skipper Pratical sailing

Italy: Tuscany

4 days - 4 nights

12 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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4.9

Weekend of relaxation and fun to discover the Island of Elba

Italy: Tuscany

3 days - 2 nights

One departure available

October

€250

Per person

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4.8

Squid Festival 2026

Italy: Tuscany

3 days - 2 nights

One departure available

October - November

€400

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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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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Reviews - Sailboat yacht sailing holidays & tours in Tuscany

3897 reviews

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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Five days barefoot between Tuscany and Corsica

09/26/2026

Cecilia M.

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IT

First time on a sailing boat and it was very pleasant :)

Wellness, sun, sea and adventure: a weekend full of sailing!

09/26/2026

Morena M.

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IT

A beautiful experience with Daniele and Maria Pia who made us feel pampered at all times, fantastic itinerary and great food. The [hidden] with its vintage atmosphere made us feel at home. A big thank you!

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