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Sailboat yacht sailing holidays & tours in Italy

Discover more than 300 opportunities to get on board a Sailboat adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

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4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

8 departures available

July - September

Starting from

€700

Per person

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4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

11 departures available

July - October

Starting from

€590

Per person

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4.6

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

Starting from

€1,260

€1,070

Per person

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4.8

Super!

Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

Italy: Northern Sardinia

6 days - 7 nights

8 departures available

July - September

Starting from

€600

€570

Per person

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4.7

Midweek sailing trip in the Gulf of Naples

Italy: Naples & Amalfi Coast

3 days - 3 nights

One departure available

July

€390

Per person

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4.7

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

4 departures available

July - September

Starting from

€795

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

2 departures available

August - September

€1,150

€1,035

Per person

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5.0

Super!

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

August - October

Starting from

€690

Per person

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4.8

Super!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

Italy: Tuscany

6 days - 7 nights

6 departures available

July - September

Starting from

€900

Per person

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4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

2 departures available

August - September

Starting from

€1,041

Per person

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4.1

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

33 departures available

January - December

Starting from

€300

€270

Per person

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4.7

Whale watching cruise with WWF guide between Northern Corsica and the Tuscan Archipelago

Italy: Tuscany

6 days - 7 nights

2 departures available

July - August

Starting from

€1,052

Per person

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80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

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Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Sailboat yacht sailing holidays & tours in Italy

12937 reviews

All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

07/2/2026

Luigi C.

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IT

Good evening, the all-inclusive writing is misleading as it is not clear from the program that to go down to Positano and Capri there are other costs to be divided among the participants.

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.

-

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!
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Four days in the Pontine Islands, just a stone's throw from Rome

07/1/2026

Stefano A.

-

IT

We had a great time, we were lucky enough to have good weather (a bit warm), a group to have fun with and a skipper who, in addition to being a nice storyteller, solves one of the main critical issues: he cooks! A great

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