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Sailboat yacht sailing holidays & tours in Italy

Discover more than 139 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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4.7

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

4 departures available

October

Starting from

€275

Per person

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4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

September - October

Starting from

€700

Per person

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4.7

Feast of Santa Candida in Ventotene

Italy: Pontine Islands

3 days - 3 nights

One departure available

September

€420

Per person

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5.0

Super!

Learn to sail in Liguria: First level sailing course

Italy: Liguria

2 days - 1 night

One departure available

October

€220

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

3 departures available

September

Starting from

€441

€419

Per person

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5.0

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

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

€690

Per person

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4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

September - October

Starting from

€750

€675

Per person

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4.9

Super!

Gulf of Poets

Italy: Liguria

3 days - 2 nights

One departure available

September

€280

Per person

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5.0

Super!

Long Weekend Santa Candida - Ventotene

Italy: Pontine Islands

5 days - 4 nights

One departure available

September

€550

Per person

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4.8

Super!

Week end in Costa Azzurra

Italy: Liguria

2 days - 2 nights

One departure available

August - September

€360

€324

Per person

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5.0

Super!

Weekend of the Pontine Islands to discover Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

2 departures available

September

€490

€441

Per person

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4.8

Super!

Five days barefoot between Tuscany and Corsica

Italy: Tuscany

5 days - 4 nights

4 departures available

August - September

Starting from

€490

Per person

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Reviews - Sailboat yacht sailing holidays & tours in Italy

13644 reviews

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Unforgettable adventure in the Aeolian Islands

08/27/2026

Daniele R.

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IT

An unfortunately very negative experience caused by a truly endless series of problems with the boat, such as: - boat refrigerator not working and replaced with one of the dimensions absolutely not suitable to accommodate 7 people, - faulty alternator that did not allow the battery to be recharged during motor navigation with substantial problems for all the electrical instrumentation on board -Gas cylinder finished after 2 days of navigation severely limiting us in the preparation of meals, which following recharging had already proved to be partially discharged and therefore not refilled from the last charter -Too superficial cleaning of the boat since the last charter Added to this is the lack of prior communication of the skipper change, with a person who did not speak Italian and which made general communication difficult while sailing with us, the skippers of the other boats and the port insiders, this lack of prior communication is really incomprehensible, was there a fear that people would cancel the experience? We got to get to most of the islands, but we didn't get to visit them as it should have been, because most of the time we spent in the ports fixing boat problems or waiting for technicians to do it. I think it would have been right for Gaetano to recognize and take responsibility for these inconveniences by reimbursing us at least part of the fee paid for this (non) holiday, instead he has always minimized every issue by demonstrating little intellectual honesty and little care of his customers. Unfortunately, a mention must also be made of Sailsquare, which, aware of the situation we were facing, left us at the mercy of the problems without offering us concrete and valid support. I leave only 3 stars to the destination because in fact we saw and enjoyed it very little, 1 star with our eyes closed for the skipper and the boat. Too bad.

Amazing Pontine Islands on a sailing boat

08/27/2026

Rita G.

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IT

We spent 3 wonderful and unforgettable days. Carlo is a very good skipper with a great deal of experience and a lot of passion for sailing.
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Magical Pontine: full sail to discover the archipelago

08/27/2026

Enrico V.

-

IT

I would say that the experience did not go badly but my expectations were a little higher. The crew was excellent company and a nice group was created that was able to manage all the various difficult situations in the best possible way.

Pontine and Flegree on a comfortable 15 meters: an adventure in the Mediterranean

08/27/2026

Giangiacomo G.

Beautiful experience! The skipper was always very helpful, prepared and nice. The boat was comfortable and adequate to accommodate the number of participants! The beautiful islands! I can't wait to set sail again! :)

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