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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

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

Italy: Aeolian Islands

6 days - 7 nights

One departure available

September

€950

Per person

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4.9

Super!

Holidays on the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€716

Per person

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4.9

Super!

Giglio Island - Festival of Grapes and Open Cellars

Italy: Tuscany

3 days - 3 nights

One departure available

September

€280

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

5 departures available

September - October

Starting from

€230

Per person

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4.9

Super!

Three days of adventure in the Aeolian Islands

Italy: Aeolian Islands

3 days - 3 nights

One departure available

September

€400

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

One departure available

September

€1,150

Per person

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4.8

Super!

A taste of the magnificent Island of Elba

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€300

Per person

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4.9

Super!

Four days in the Aeolian Islands from Capo D'Orlando

Italy: Aeolian Islands

4 days - 4 nights

One departure available

September

€400

Per person

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4.8

Super!

Elba, Tuscan archipelago or Corsica aboard a full opt catamaran.

Italy: Tuscany

7 days - 7 nights

2 departures available

September

€850

Per person

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5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

5 departures available

September - October

Starting from

€370

Per person

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4.7

Voices of the Pelagos: artistic-scientific whale watching expedition with WWF guide

Italy: Tuscany

4 days - 4 nights

One departure available

October

€453

€430

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

3 departures available

September

Starting from

€490

€466

Per person

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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.

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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

14923 reviews

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North Sardinia and Corsica: blue seen from a sailboat

09/6/2026

Fabio B.

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NL

Almost twenty years of sailing holidays and I thought I had already seen so much beauty. This time even more so. Leonardo is not only a captain of great experience: he is a person of heart, attentive and helpful, who immediately makes you feel in good hands. And then there is Luigi, an impeccable sailor as well as surprising in the kitchen. The food was simply beyond all expectations: well-kept, tasty and never banal dishes. The Maddalena Archipelago and southern Corsica need no introduction: some of the most beautiful places in the Mediterranean to experience while sailing. In the end, however, not only the sea and the landscapes remain, but also the people with whom you shared them. And Leonardo and Luigi made this holiday very special. Thank you very much to you, see you next time.

Five days barefoot between Tuscany and Corsica

09/6/2026

Massimo M.

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IT

5 days and 4 nights sailing in the southern part of Elba anchoring in protected and quiet coves. Giacomo the skipper was perfect, prepared, polite and kind. Too bad we didn't go to Capraia but the last night in Porto Azzurro definitely gave a beautiful evening. Spacious, comfortable boat that sails well in little wind. RECOMMENDED

The Aeolian Islands aboard a fantastic Catamaran with Stewardess

09/6/2026

Natalia C.

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IT

Extraordinary week between crystal clear sea, relaxation and excellent food. The boat is cozy and perfect for life on board, but the real added value was the skipper Umberto. Sunny, overwhelming and with a contagious irony. He was able to create a super close-knit atmosphere between all of us from day one, making us immediately feel like a group of old friends. In addition to guaranteeing perfect navigation and in total safety, it was the soul of the holiday between laughter, aperitifs at sunset and unforgettable moments. We will definitely be back on board with him. Fundamental, and the perfect shoulder for Umberto was Monica. Not just a hostess. He is almost an engineer with a passion for the sea and good food. His kindness, his education and his never making a mistake in a dish or a word, were the perfect side dish. Highly recommended all: Monica, Umberto and the catamaran ♥️ I forgot Gigia: adorable!
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Four nights in the Pontine Islands - midweek

09/5/2026

Angela Chiara C.

-

IT

A more than positive experience. Antonio is an experienced skipper who led us through the beautiful bridges despite difficult days due to too much wind. He is also a very good cook, which is not a given. Above all, it is not obvious that the skipper cooks as well, and this is undoubtedly an added value since it leaves you even more time to enjoy the sea. The boat is all made of wood, old style and this is its beauty; certainly small improvements can be made but at the end of the season I think it is more than understandable; The spaces are sufficient and essential as they must be on a sailboat. We were also lucky enough to catch a tuna and meet a dolphin along the way, what else could we wish for? For all of us it went very well. Thank you for everything, Antonio!

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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 (36)Pontine Islands (18)Aeolian Islands (17)Liguria (15)Aegadian islands (10)Northern Sardinia (8)Naples & Amalfi Coast (7)Sicily (4)Southern Sardinia (4)Lake Garda (3)

Italy: departures by month

october (50)november (4)december (1)january (1)february (1)march (1)april (3)may (4)june (5)july (5)

Other travel ideas

Sailboat (185)Whole boat with skipper (159)Cooking service onboard (69)Catamaran (53)All inclusive (39)Exotic destinations (23)Courses & regatta (17)Offshore (13)Sport & wellness (10)Day trips (7)

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