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Sailboat yacht sailing holidays & tours in Italy

Discover more than 164 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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5.0

Super!

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

7 departures available

September - October

Starting from

€275

€248

Per person

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4.9

Super!

Egadi paradise for sailing and snorkeling

Italy: Aegadian islands

7 days - 7 nights

2 departures available

September

€600

Per person

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5.0

Super!

Midweek relaxing in the Pontine Mountains

Italy: Pontine Islands

4 days - 3 nights

9 departures available

August - October

Starting from

€337

Per person

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4.8

Super!

Midweek special on the island of Elba, 2 nights

Italy: Tuscany

3 days - 2 nights

2 departures available

September - October

Starting from

€240

€228

Per person

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5.0

Super!

A week in the Aeolian Islands - 6 islands in seven days

Italy: Aeolian Islands

7 days - 7 nights

One departure available

September

€583

Per person

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4.8

Super!

ENJOY: in the blue painted blue of the Aeolian Islands

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

August - September

Starting from

€690

€529

Per person

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4.9

4 days in the Pontine Islands (sailing school)

Italy: Pontine Islands

4 days - 3 nights

One departure available

September

€270

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

Starting from

€441

€419

Per person

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4.8

Corsica and Tuscany in flotilla, boats of 16 and 17 meters.

Italy: Tuscany

6 days - 7 nights

One departure available

August

€900

Per person

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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

One departure available

August - September

€750

Per person

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4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

4 departures available

September - October

Starting from

€220

Per person

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4.8

Super!

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

One departure available

September

€360

€342

Per person

Why book a holiday with Sailsquare?

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The world's largest marketplace for sailing holidays

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

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.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

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

12097 reviews

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La Flottiglia Mediterranea: Capri, Ischia, Procida e le isole Pontine

08/21/2025

Andrea P.

-

Italy

An experience absolutely to be repeated. The organization of the trip was managed by LaFlottiglia with excellent success. It was the first group trip (I left alone) and despite the initial fear I found a magnificent group of both skippers and guys with whom I shared the experience. The established itinerary may undergo small variations due to bad weather but still very valid. If I have to find a flaw, it is due to the fact that we were not always cohesive in terms of distances to the other boats, this made it complicated to interact with the members of the other crews. For the rest, I have all had very pleasant experiences that I will definitely repeat.
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Weekend cruise from Trieste in Slovenia

08/20/2025

Nicola C.

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Italy

Beautiful experience, Flavio very good at organizing everything and making all the participants happy, (as well as cooking) Super recommended
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A full day on a sailing boat in the Gulf of ALASSIO

08/20/2025

Patrizia F.

-

Italy

It was a perfect day. Daniele was very kind, he is a really competent skipper and put all of us at ease at all times, making us feel "at home" on his boat. The boat is very comfortable and clean and it was beautiful both sailing and motoring. We had a wonderful day.
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Life Changing Experiences - Pontine Islands in mid-August

08/20/2025

Ginevra S.

-

Italy

It was a fantastic experience, after 4 days I still have melancholy of the sound of the sea and the stars. The [hidden]-sabi philosophy is what we were looking for on this holiday, let yourself be carried away and you will not regret it! Francesco was a super skipper, he introduced us to parts of Ponza and Palmarola that only a great expert of the archipelago knows. See you next adventure and thank you, Ginevra and Federico

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