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Sailboat yacht sailing holidays & tours in Tuscany

Discover more than 102 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!

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

Italy: Tuscany

5 days - 4 nights

5 departures available

June - July

Starting from

€490

Per person

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5.0

Super!

Tuscany and North Corsica on a sailing boat

Italy: Tuscany

7 days - 7 nights

One departure available

August

€1,060

Per person

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5.0

Super!

Learn to sail in a week in the Tuscan Archipelago

Italy: Tuscany

6 days - 6 nights

2 departures available

August

Starting from

€849

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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4.8

Super!

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

Italy: Tuscany

7 days - 7 nights

9 departures available

June - October

€650

Per person

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4.8

Super!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

2 departures available

July - September

Starting from

€200

Per person

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4.8

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

6 departures available

July - September

Starting from

€400

€360

Per person

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4.9

Super!

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

Italy: Tuscany

6 days - 6 nights

11 departures available

June - September

Starting from

€980

Per person

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4.9

Super!

On holiday with Dad to discover Elba and Capraia

Italy: Tuscany

4 days - 4 nights

One departure available

June

€400

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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4.9

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

2 departures available

July - August

Starting from

€410

€369

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

3571 reviews

A taste of the magnificent Island of Elba

06/17/2026

valentina t.

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IT

We with friends at the Top! The boat very clean and welcoming, Alberto always on the piece helpful and attentive.

Week-end all'Elba - Hostess a bordo

06/16/2026

Andrea P.

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IT

We spent a beautiful holiday beyond all expectations: the comfort and spaciousness of the boat, the beauty of the places, the kindness and skill of Giulia in the kitchen, the care and professionalism of Vittorio at the helm, together with the sympathy of the other day-trippers (and the wonderful weather!) allowed us to enjoy our first sail - around Elba - in a fantastic way, celebrating my wife's birthday in an exciting way on a holiday that we hoped would not end so soon. Five well-deserved 😀 stars
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A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

06/16/2026

Alessandro L.

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IT

Enrico the skipper is a real sea dog and like all sea dogs he must be caressed by the way he furs. Nice experience..
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Giglio or Elba the pearls of the Tuscan archipelago

06/16/2026

Moira C.

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IT

I spent 2 fantastic days, together with wonderful people, I couldn't ask for anything better. Cleanliness, kindness and safety assured! I have traveled a lot by sailboat and have always felt safe. I will definitely be back on the boat with Simone, an attentive, kind and polite skipper. Thank you!

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