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All inclusive yacht sailing holidays & tours in Italy

Discover more than 13 opportunities to get on board a All inclusive adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

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4.9

Super!

Traveling and dreaming in the Gulf of Poets - All Inclusive

Italy: Liguria

2 days - 1 night

2 departures available

September

€260

Per person

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4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

One departure available

September

€360

Per person

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5.0

Super!

A wonderful day.... on Lake Garda - ALL INCLUSIVE

Italy: Lake Garda

1 day - 0 nights

4 departures available

September - October

Starting from

€99

Per person

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5.0

Super!

Sailing, swimming and aperitif at sunset ... What else?

Italy: Lake Garda

1 day - 0 nights

One departure available

October

€69

Per person

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4.8

Super!

3 days - Sorrento, Capri, Positano, Amalfi - Luxury Sailing Yacht

Italy: Naples & Amalfi Coast

3 days - 2 nights

13 departures available

September - October

Starting from

€1,325

Per person

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4.8

Super!

Capri and Amalfi Coast by catamaran - ALL INCLUSIVE

Italy: Naples & Amalfi Coast

3 days - 2 nights

3 departures available

September - October

Starting from

€1,800

Per person

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5.0

Super!

Sailing, swimming and aperitif at sunset ... What else?

Italy: Lake Garda

1 day - 0 nights

6 departures available

September - October

Starting from

€69

Per person

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5.0

A day sailing in the fantastic Gulf of Trieste

Italy: Venice and the Gulf of Trieste

1 day - 0 nights

3 departures available

September - October

€99

Per person

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5.0

Weekend in Ogliastra, super Sardinia with skipper and hostess

Italy: Southern Sardinia

3 days - 2 nights

One departure available

September

€680

€612

Per person

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4.8

Let's sail in relaxation on Lake Garda - All Inclusive

Italy: Lake Garda

1 day - 0 nights

4 departures available

September

€150

Per person

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4.3

Premium

Capri Dream Premium - Catamaran cruise full board

Italy: Naples & Amalfi Coast

6 days - 7 nights

2 departures available

September - October

Starting from

€1,260

Per person - min 2 pax

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4.8

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

Italy: Naples & Amalfi Coast

6 days - 6 nights

One departure available

September

€1,385

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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 - All inclusive yacht sailing holidays & tours in Italy

546 reviews

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Gulf of Poets and Cinque Terre

09/3/2025

Valentina G.

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Italy

Giorgio and Francesca two excellent 'hosts': welcome, availability and kindness not for everyone. Serene seriousness at the helm of the boat and top aperitifs! P.s: we also saw dolphins!!!
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Sailing day between San Vito Lo Capo and Zingaro Nature Reserve

09/2/2025

Lorenzo B.

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Italy

Together with Jo and Andrea we did a beautiful day trip from San Vito Lo Capo to Scopello. Very pleasant weather on board, even if we were only one day, a great feeling was immediately created! The boat is great and well taken care of, and Jo and Andrea make you feel at home. The tour was also nice, and very relaxing. Highly recommended!!
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A wonderful day.... on Lake Garda - ALL INCLUSIVE

09/1/2025

Maria F.

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Italy

Very nice day with impeccable service, very nice atmosphere and great professionalism
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Sailing dreams in the Gulf of Poets and Cinque Terre

08/31/2025

Patrizia A.

-

Italy

Definitely recommended experience. Giorgio and Francesca very welcoming and kind, also experienced. They did everything to make us live a wonderful experience. Enchanting places.

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