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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

Super!

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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4.8

Super!

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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4.8

Super!

All-Inclusive Sailing: Capri, Positano, Amalfi

Italy: Naples & Amalfi Coast

3 days - 2 nights

7 departures available

July - September

€790

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

10 departures available

July - 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

32 departures available

July - 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

3 departures available

July - August

€149

Per person

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

Italy: Sicily

2 days - 1 night

8 departures available

July - September

Starting from

€215

€194

Per person

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4.9

Sailing in Tigullio: Half-Day Experience from Rapallo

Italy: Liguria

1 day - 0 nights

4 departures available

July - August

€91

Per person

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4.9

Aperitif Trip to the Gulf of Tigullio - All inclusive!

Italy: Liguria

1 day - 0 nights

8 departures available

July - 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

7 departures available

July - August

Starting from

€150

Per person

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Aperitif at sunset

Italy: Venice and the Gulf of Trieste

1 day - 0 nights

9 departures available

July

€110

Per person

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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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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

562 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.

An all-inclusive day on a sailing boat

06/29/2026

Rachele T.

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IT

Luigi and Federica are nice and welcoming and put you at ease. We took a tour near La Spezia, in order to take several baths. We had a lot of fun but also relaxed! Thank you!

A romantic and luxurious vacation in the Aeolian Islands

06/27/2026

Anna D.

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IT

Unforgettable days on board Zadar. The owners Ram and Ronit, in addition to being experienced sailors, are attentive and pleasant hosts. They welcomed us with great sympathy and made us feel at home immediately. The boat is very beautiful, comfortable and impeccably maintained. We built the itinerary together and they met all our desires. Top also the freedom to cook fresh fish bought directly from local fishermen: an authentic experience! We will gladly come back!

Afternoon, aperitif and sunset on Verbano - Lake Maggiore

06/22/2026

daniela m.

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IT

I gave this experience to my husband who had dreamed of steering a sailboat for years and was satisfied! Stefano was super kind and helpful in advising me in the best possible way when and how to book and the experience itself was very nice

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