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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

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

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

August - October

Starting from

€690

Per person

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4.8

Super!

A week in the Aeolian Islands - 6 islands in seven days

Italy: Aeolian Islands

6 days - 7 nights

3 departures available

August - September

Starting from

€583

Per person

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4.4

Unforgettable adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

11 departures available

August - November

Starting from

€540

€513

Per person

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4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

€700

Per person

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4.8

Super!

A week of sea, volcanoes and fun in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

August - September

Starting from

€750

€675

Per person

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5.0

Super!

Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

September

€950

Per person

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5.0

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

3 departures available

July - August

Starting from

€390

Per person

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5.0

Super!

Pure life in the Aeolian Islands: between volcanoes and crystal clear waters

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

July - August

Starting from

€690

€613

Per person

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4.8

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

7 departures available

August - October

Starting from

€750

€675

Per person

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5.0

Super!

Aeolian Islands with hostess/cook BOAT 16.5 mt exclusive x6 people

Italy: Aeolian Islands

6 days - 6 nights

One departure available

August

€999

Per person

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4.8

Discovering the Aeolian Islands Between Nature, Relaxation and Fun

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

August - September

Starting from

€795

€716

Per person

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4.8

Super!

Summer is made for the Aeolian Islands! Weekly cruise

Italy: Aeolian Islands

6 days - 7 nights

One departure available

August

€850

Per person

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Reviews - Yacht sailing holidays & skippered tours in Italy

2064 reviews

A week in the Aeolian Islands - 6 islands in seven days

07/23/2026

Deborah T.

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IT

Unforgettable holiday! We managed to tour all the islands included in the itinerary, discovering wonderful corners. Nicola was fantastic: he understood our tastes on the fly, guiding us to magical coves and uncrowded places, away from the chaos. Five well-deserved stars, highly recommended!

Authentic Aeolian Islands on a sailboat: between local flavors and crystal clear sea

07/22/2026

chiara a.

-

IT

I had contacted the skipper beforehand to warn him that I did not eat fish and he had told me that there were no problems. It was not made WhatApp group before and no one was asked for preferences on breakfast, food, alcohol etc etc. We found ourselves with a galley made without sharing with a charge of 320 of wine, spirits well hidden in the shopping at the supermarket and about 500 euros of fish. I have never been offered any alternative but an egg omelette (with 50 euros spent on eggs) and twice a participant friend of the skipper made me a sauce with great controversy because the skipper imposed himself as a cook denying us to be able to cook. When I represented my need, I was literally pilloried and forced to eat salad that others ate as a side dish after succulent fish dishes. Now I'm wondering if I could get a refund??!! I had already used your platform and I had found it well, this is the reason why I used it again. I represent that we did not have the skipper indicated but there was a switch with his father Andrea who imposed the presence of his partner for two days (I do not know if he contributed to the galley). criticized me continuously because I did not eat fish and in general everyone for everything and in particular those who did not drink as much as he did. The whole group had difficulty communicating with the latter and in the last few days the situation has worsened. If you want further details write to me

Aeolian Islands: sun, sport, music, good food... The rest is magic!

07/22/2026

Giulio A.

-

GB

Dario made us live a unique experience and an unforgettable holiday. The Aeolian Islands are a wonderful place, but surely sailing with a person with so much experience made the holiday even more unforgettable. Dario is a very prepared captain, very professional but also welcoming and helpful. His boat is spotless and is maintained with a very high standard of cleanliness throughout the holiday. Dario was able to adapt the navigation and choices according to our needs and characteristics, and this was greatly appreciated. In addition, among Dario's many qualities I would certainly include his culinary skills: his prawns and pasta are difficult to forget! Dario's big heart can also be seen in the way he takes children to heart and gives them unforgettable experiences. We will never forget this holiday. Thank you again for everything you have allowed us to experience!
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Sail to the Aeolian Islands with an experienced crew on a catamaran!

07/22/2026

Stella Z.

-

IT

A heartfelt thank you to Emanuele and Daniele for making this holiday in the Aeolian Islands truly unforgettable. The islands are wonderful, but they made the difference: always available, smiling and attentive to every detail. Emanuele, a trained and professional skipper, guided us in total safety through spectacular bays and coves, while Daniele, with his friendliness and availability, created a relaxed and welcoming atmosphere from the first day. The catamaran is spacious, extremely comfortable and impeccable in every respect: cleanliness and order have been a pleasant constant throughout the week. A positive note goes to the cuisine: aperitifs, lunches and dinners are always excellent, with a lot of care and attention. In addition to the breathtaking views of the Aeolian Islands, we will take with us the memory of a week lived between sea, relaxation, laughter and new friendships. An experience that we cannot fail to recommend!

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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 (79)Aeolian Islands (40)Northern Sardinia (33)Pontine Islands (26)Liguria (23)Aegadian islands (20)Southern Sardinia (17)Naples & Amalfi Coast (13)Sicily (12)Lake Garda (4)

Italy: departures by month

august (201)september (149)october (44)november (5)december (1)january (1)february (1)march (1)april (1)june (1)

Other travel ideas

Sailboat (411)Whole boat with skipper (334)Cooking service onboard (108)Catamaran (76)All inclusive (52)Exotic destinations (29)Courses & regatta (21)Family sailing cruises (20)Offshore (18)Day trips (18)

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