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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 87 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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4.8

Super!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

One departure available

September

€200

Per person

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4.8

Super!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

4 departures available

July - September

Starting from

€200

Per person

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4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

5 departures available

August - October

€650

Per person

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4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

2 departures available

September

€441

Per person

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4.8

Super!

Let's enjoy the wonders of the Tyrrhenian Sea - Elba, Capraia and Corsica

Italy: Tuscany

7 days - 6 nights

One departure available

August

€801

€761

Per person

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4.8

Super!

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

Italy: Tuscany

7 days - 6 nights

One departure available

August

€890

€801

Per person

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4.8

Super!

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

Italy: Tuscany

6 days - 6 nights

9 departures available

July - September

Starting from

€980

Per person

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4.8

Super!

Sea, scents and colors on Elba

Italy: Tuscany

3 days - 3 nights

2 departures available

August - September

Starting from

€300

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

2 departures available

July

€590

Per person

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New

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

Super!

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

5 departures available

September - November

€250

Per person

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5.0

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

Italy: Tuscany

3 days - 2 nights

2 departures available

September

€230

Per person

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Reviews - Sailboat yacht sailing holidays & tours in Tuscany

3608 reviews

Mini-cruise with WWF guide in the heart of the Tuscan Archipelago

07/2/2026

Bianca Matelda C.

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IT

Beautiful days in the middle of the sea, freedom, discovery, full nature and new friends! The WWF guide Elisa and the skipper Nico were very good, nice, professional and prepared to manage the outings and make a group. These are days that I carry in my heart. I recommend bringing little stuff, just enough to protect yourself from the sun and feel good.. but above all to a lot of curiosity and team spirit!

Weekend on the island of Elba: among dolphins, enchanting bays and relaxation

07/2/2026

Laura N.

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IT

We had a very pleasant and relaxing weekend. Salvatore is very knowledgeable and personable, and his boat is comfortable and very clean. Highly recommend!

Long live Elba and Capraia

07/1/2026

Marina M.

Beautiful experience. Filippo is a professional and experienced skipper. We sailed both under sail and by motor in complete safety, the skipper was available to explain the maneuvers, involving the crew members who wanted to do it in the management of the boat. Clean, comfortable, efficient, well-equipped boat. Very beautiful island of Capraia perfect for a three-day weekend.
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Weekend Elba or Capraia

07/1/2026

Chiara P.

My friend and I booked a sailing holiday taking advantage of the last two places available. Unfortunately, at the start we discovered that the number of participants was higher than what had been communicated to us, with a consequent reduction in the spaces on board, which on a sailboat are already quite limited. Also, no one had informed us that it was a bachelor party with a group of 9 men (more than those who were reported on the site and more than the number of people allowed to board) If we had known in advance, we would have definitely chosen another date or requested a refund, as it was not the kind of experience we were looking for. Nicola's willingness must be recognized, who tried in some way to manage the situation. However, throughout the holiday we had to adapt to the needs and schedule of the rest of the group, partially giving up on the experience we expected. Too bad, because with a more transparent communication from the organizing agency it would have gone differently. For the experience I still leave 4 stars, with the hope that in the future more attention will be paid to this type of situation.

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