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All inclusive yacht sailing holidays & tours in Italy

Discover more than 14 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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5.0

Super!

The awakening of the lake

Italy: Lake Garda

1 day - 0 nights

One departure available

June

€69

Per person

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5.0

Super!

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

Italy: Lake Garda

1 day - 0 nights

One departure available

June

€135

Per person

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5.0

Super!

Spring on Lake Garda

Italy: Lake Garda

1 day - 0 nights

One departure available

May

€99

Per person

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5.0

Super!

A wonderful day.... sul Garda - ALL INCLUSIVE

Italy: Lake Garda

1 day - 0 nights

One departure available

June

€119

Per person

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4.3

Premium

CAPRI Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Naples & Amalfi Coast

6 days - 7 nights

25 departures available

May - October

Starting from

€1,320

€1,188

Per person - min 2 pax

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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

€155

Per person

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4.8

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

Italy: Naples & Amalfi Coast

5 days - 5 nights

5 departures available

July - September

€1,150

Per person

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4.3

Premium

TUSCANY Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Tuscany

7 days - 7 nights

2 departures available

July - August

Starting from

€2,390

Per person - min 2 pax

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5.0

Weekend in Ogliastra, super Sardinia with skipper and hostess

Italy: Southern Sardinia

3 days - 2 nights

7 departures available

May - September

€690

€621

Per person

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4.8

All-Inclusive Sailing: Capri, Positano, Amalfi

Italy: Naples & Amalfi Coast

3 days - 2 nights

6 departures available

May - June

€790

€711

Per person

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Easter Mini Cruise to the Egadi Islands - Comfort & All Inclusive

Italy: Aegadian islands

2 days - 2 nights

One departure available

April

€470

Per person

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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

June - July

€1,150

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

554 reviews

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A day sailing in the fantastic Gulf of Trieste

11/11/2025

Armin F.

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Italy

Everything worked out great, Paolo was super helpful!!!! Advice 100%
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A day sailing in the fantastic Gulf of Trieste

10/20/2025

Monica C.

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Italy

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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A wonderful day.... sul Garda - ALL INCLUSIVE

09/30/2025

MARIA GRAZIA P.

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Italy

A wonderful sailing experience! 🚤⛵️ We spent Sunday in the company of nice people, with impeccable organization. Emanuele proved to be an exemplary professional: availability, kindness and attention to detail made us feel immediately at ease. Great food, stunning views and a relaxing atmosphere that made the experience truly unforgettable. Everything perfect: absolutely to try and recommend!
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Traveling and dreaming in the Gulf of Poets - All Inclusive

09/23/2025

Marta D.

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Italy

The boat is comfortable (especially the bed!!) and in excellent condition The service is all inclusive, so on the one hand it is practical on the other hand it is not certain that you will find what you would like They were very kind to buy gluten-free pasta for me who is celiac A shame not to sleep in the roadstead and the sea points were not always wow, but it is a nice experience that I would repeat!

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