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All inclusive yacht sailing holidays & tours in Italy

Discover more than 21 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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4.8

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

Italy: Naples & Amalfi Coast

6 days - 6 nights

2 departures available

July - August

Starting from

€1,150

Per person

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5.0

Super!

Weekend in Ogliastra, super Sardinia with skipper and hostess

Italy: Southern Sardinia

3 days - 2 nights

2 departures available

September

€690

€621

Per person

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4.4

Premium

CAPRI Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Naples & Amalfi Coast

6 days - 7 nights

16 departures available

June - October

Starting from

€1,320

€1,188

Per person - min 2 pax

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4.8

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

Italy: Lake Garda

1 day - 0 nights

34 departures available

June - October

€150

Per person

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5.0

From the sun to the moon - Afternoon All inclusive on Lake Garda

Italy: Lake Garda

1 day - 0 nights

5 departures available

June - August

Starting from

€135

Per person

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4.8

All-Inclusive Sailing: Capri, Positano, Amalfi

Italy: Naples & Amalfi Coast

3 days - 2 nights

7 departures available

July - September

Starting from

€790

€711

Per person

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4.9

Sailing in Tigullio: Half-Day Experience from Rapallo

Italy: Liguria

1 day - 0 nights

7 departures available

June - August

€91

Per person

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5.0

An all-inclusive day on a sailing boat

Italy: Liguria

1 day - 0 nights

9 departures available

June - August

€180

Per person

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4.9

Aperitif Trip to the Gulf of Tigullio - All inclusive!

Italy: Liguria

1 day - 0 nights

9 departures available

June - August

Starting from

€85

Per person

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4.9

Day at the Gulf of Tigullio on a Sailing Boat - All inclusive!

Italy: Liguria

1 day - 0 nights

9 departures available

June - August

Starting from

€150

Per person

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4.8

All Inclusive Tour: Capri, Amalfi, Cetara, e Sorrento

Italy: Naples & Amalfi Coast

5 days - 5 nights

2 departures available

August - September

€1,150

Per person

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2 days sailing between Palermo and Cefalù - All inclusive & flexible dates

Italy: Sicily

2 days - 1 night

12 departures available

June - September

Starting from

€215

€194

Per person

Why book a holiday with Sailsquare?

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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.

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

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

556 reviews

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Afternoon, aperitif and sunset on Verbano - Lake Maggiore

06/14/2026

Enrico C.

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IT

We had a wonderful day on board Stefano's sailboat, a very kind and helpful person. We visited the three major islands and even managed to swim. Finally, we had a pleasant aperitif at sunset in front of the Hermitage of Santa Caterina. It was a wonderful experience, which I recommend to anyone who wants to spend a relaxing day.
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CAPRI Paradise - Catamaran cruise with hostess FULL BOARD

05/17/2026

Cristina Anna R.

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IT

Beautiful experience! Unfortunately we could not do everything planned because of the sea but it was still a wonderful holiday! Skipper Gian Marco and cook Giacinto always available and kind! We chose the "superior" cabin and had a great time! Very cozy catamaran!

A day sailing in the fantastic Gulf of Trieste

11/11/2025

Armin F.

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IT

Everything worked out great, Paolo was super helpful!!!! Advice 100%

A day sailing in the fantastic Gulf of Trieste

10/20/2025

Monica C.

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IT

The skipper Paolo simply fabulous. The super cozy and high-performance boat. We had a beautiful, immersive experience and learned even a minimum basis of sailing concepts

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