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Yacht sailing holidays & skippered tours in Italy

Discover the beauty of Italy and treat yourself to a sailing holiday of relaxation, fun, and unique landscapes. Sail around the beautiful islands of Sicily and Sardinia, discover the Lipari, Pontine and Aegadian Islands by boat or anchor in the romantic bays of Tuscany or Cinque Terres.

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5.0

Super!

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

Italy: Aeolian Islands

7 days - 7 nights

18 departures available

May - October

Starting from

€689

Per person

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4.8

Super!

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

24 departures available

May - October

Starting from

€600

Per person

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5.0

Super!

In the Aeolian Islands with chef on board

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

July

€1,000

Per person

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3.0

7 islands in comfort and convenience

Italy: Aeolian Islands

6 days - 6 nights

One departure available

November

€600

Per person

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4.1

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

18 departures available

May - October

Starting from

€680

Per person

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4.9

Between seas and volcanoes, fall in love with the Aeolian Islands

Italy: Aeolian Islands

5 days - 4 nights

15 departures available

July - October

Starting from

€590

Per person

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4.6

Aeolian Islands: wellness, taste, fun with fabulous cook on board

Italy: Aeolian Islands

7 days - 7 nights

8 departures available

July - August

Starting from

€910

€865

Per person - min 2 pax

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5.0

Sea, sailing and relaxation in the beautiful Aeolian archipelago

Italy: Aeolian Islands

4 days - 4 nights

14 departures available

April - October

Starting from

€400

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

One departure available

November

€650

Per person

Why book a holiday with Sailsquare?

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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 - Yacht sailing holidays & skippered tours in Italy

2016 reviews

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We have known the Aeolian Islands for 20 years. - Live them with us.

10/20/2025

Marco F.

-

Italy

Pasquale is a profound lover and connoisseur of the Aeolian Islands. Beyond the experience at sea, it also suggests excursions and places to visit on land
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Aeolian Islands - Sea, Sun and Relax - big and new Catamaran Lagoon 42

09/29/2025

Stella H.

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France

Fantastic destination. Great sized catamaran. Food provided by our hostess was good. There are a few of issues that need highlighting: 1. The size of the boat and its starting point changed after I booked online. 2. I had asked if a single supplement applied to my booking as (at the point of booking) the boat/catamaran only had 4 berths. I was told there wasn’t a supplement. We were assigned a larger boat and I was allotted a single cabin - the same size as for the hostess/chef. 3. I did not receive a confirmation by email of what I had booked (so had no evidence of what I was to expect when I arrived). I was in a cabin suitable for a child and had to share a bathroom. There was no WiFi available. I had no exterior window. The fan in my room only worked by connecting 2 loose wires (like hotwiring a car!). The sockets in my room worked intermittently. 4. The skipper was extremely competent in his professional work. However, his English was not good enough to be listed as a second language. In addition, he could have been more regular about informing ALL the passengers at the same time about the itinerary for the day (which differed significantly in order from that on the website). Informing us whilst we were eating would have been the perfect time. 5. On the day of departure we were asked to meet 2 hours earlier than arranged but the cleaners had not finished their work and we left 2 hours behind schedule. This we were sitting around for 4 hours unnecessarily. Better communication might have avoided this. 6. The wording for the itinerary is not clear regarding the transfer from an airport. I feel it needs to be explicit that this isn’t included. 7. The skipper was in a hurry to return to port on the night before last and omitted a final swim stop. He left the boat before the others.
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Aeolian Islands - Sea, Sun and Relax - big and new Catamaran Lagoon 42

09/28/2025

Sara D.

-

Italy

Beyond expectations...
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Let's discover the Aeolian Islands together by sailing

09/28/2025

Alessandro N.

-

Italy

Very positive experiences, well organized and well managed. Amazing location

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Guides & tips


Italy

Tuscany, Sardinia, the Aeolian Islands and Liguria are just some of the most beautiful destinations for a sailing or catamaran holiday, let's discover them all!
Guide to Italy on a sailing boat

Tuscany

The island of Elba, Capraia, Il Giglio and Giannutri are just some of the best destinations for a sailing or catamaran vacation in Tuscany.
Guide to the Tuscany on a sailing boat

Aeolian Islands

Stromboli, Vulcano and Lipari are just some of the best destinations for a sailing or catamaran vacation in Sardinia.
Guide to the Aeolian Islands on a sailing boat

Sardinia

Costa Smeralda, Maddalena Archipelago and San Pietro Island are just some of the best destinations for a sailing or catamaran holiday in Sardinia.
Guide to the Sardinia on a sailing boat

Capri, Ischia and Procida

Enchanted landscapes and elegant haunts, thermal springs and seabeds full of surprises, simplicity and glamour: there is more than one reason to choose these timeless islands as a destination for a yachting holiday in stages.
Guide to Capri, Ischia and Procida on a sailing boat

Amalfi Coast

Positano, Amalfi and Cetara are just some of the best destinations for a sailing or catamaran holiday in the Gulf of Naples.
Guide to the Amalfi Coast on a sailing boat

WWF Whale watching cruises

A close-to-nature sailing cruise that integrates unrepeatable emotions and new scientific knowledge, perfect for true lovers of the sea, ready to have fun, wonder and delve into the magical world of cetaceans.
Guide to the WWF Cruises

Catamaran vacations

An alternative to the sailboat, the catamaran is an ideal choice for those who do not want to give up comfort and convenience and for a first vacation at sea.
Guide to the catamaran vacations

Flotilla holiday

A perfect vacation for singles (and others) to experience sailing, meet new friends and multiply the fun.
Guide to the flotilla holidays

Singles and solo travellers

Set out alone and return enriched by an unparalleled baggage of freedom, new friendships and lasting bonds. It is on a sailboat that an adventure as a solo traveler turns into a unique sharing experience.
Guide to solo travellers sailing holidays

Sailing vacations for families

To leave with one's family and return home enriched by an unparalleled baggage of adventure, bonds and indelible memories.
What to know before you go sailing with your family?

Sailing with children

Have you ever wondered if there is a vacation that is both the best for children and parents? The answer is yes, and it is indeed on a sailboat!
Guide to sailing vacations with children

Italy: the most beautiful places to sail

Tuscany (14)Aeolian Islands (9)Liguria (9)Pontine Islands (6)Lake Garda (6)Northern Sardinia (5)Naples & Amalfi Coast (4)Aegadian islands (3)Southern Sardinia (2)Sicily (1)

Italy: departures by month

december (6)january (1)march (1)april (7)may (25)june (35)july (29)august (22)september (23)october (9)

Other travel ideas

Sailboat (101)Whole boat with skipper (76)Cooking service onboard (41)Catamaran (41)Exotic destinations (36)All inclusive (34)Family sailing cruises (12)Day trips (8)Courses & regatta (5)Adventure (5)

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