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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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4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

3 departures available

August - September

Starting from

€1,041

Per person

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4.7

Whale watching cruise with WWF guide between Northern Corsica and the Tuscan Archipelago

Italy: Tuscany

6 days - 7 nights

One departure available

August

€1,157

Per person

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5.0

Super!

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

10 departures available

June - September

Starting from

€790

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

6 departures available

June - September

Starting from

€490

€466

Per person

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5.0

Super!

Weekend at the Pontine Islands between Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

One departure available

July

€350

Per person

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4.6

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

35 departures available

January - December

Starting from

€300

€270

Per person

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4.6

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

Italy: Northern Sardinia

6 days - 7 nights

8 departures available

July - October

Starting from

€650

€585

Per person

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4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

June - October

Starting from

€700

Per person

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4.7

Youth cruise (18-23 years): whale watching with WWF between the Tuscan Archipelago and Northern Corsica

Italy: Tuscany

6 days - 7 nights

One departure available

July - August

€999

Per person

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4.9

Super!

Trip with photographer to the Pontine - Life changing experiences

Italy: Pontine Islands

4 days - 3 nights

6 departures available

July - October

Starting from

€420

€399

Per person

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4.9

Super!

Gulf of Poets

Italy: Liguria

3 days - 2 nights

4 departures available

August - September

Starting from

€280

Per person

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4.7

Weekend of sea and colors between Ischia, Procida and Vivara

Italy: Naples & Amalfi Coast

2 days - 2 nights

5 departures available

September - October

Starting from

€275

€234

Per person

Why book a holiday with Sailsquare?

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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.

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

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

13941 reviews

Sail to the Aeolian Islands with an experienced crew on a catamaran!

06/21/2026

Barbara M.

-

IT

We spent a super holiday visiting all the Aeolian Islands, captain Emanuele and skipper Daniele despite their young age were very professional, they delighted us with excellent menus always based on fish and sashimi and what can I say.... Aperitifs, wine, beer and gin galore. The catamaran very comfortable, well maintained and always clean. We hope to be able to take another holiday with them again! Guys keep it up!! 😘
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We have known the Aeolian Islands for 20 years, live them with us!

06/21/2026

Anna M.

-

IT

A week in the Aeolian Islands that went far beyond a simple holiday. An authentic experience made of crystal clear sea, breathtaking sunsets, good food and special people. A heartfelt thank you to Pasquale, an exceptional skipper, always available, empathetic and able to put everyone at ease from the first moment. His sympathy and deep knowledge of the Aeolian Islands allowed us to experience the islands in the truest way, discovering enchanting bays, hidden corners and local traditions. Life on the boat made everything even more magical: sharing this adventure with people met on board, who in a few days became travel and laughter companions, was one of the most beautiful aspects of the experience. I return home with my heart full of memories, emotions and new friendships. A trip that I recommend to anyone at least once in their life and that, without a doubt, I will repeat. The Aeolian Islands seen from the sea have something special that remains inside. 💙

The wild south from Cagliari to CarloForte

06/21/2026

Danila G.

-

SM

My experience has not ended, but only begun! GianRoberto, a compound name, a lot of stuff already, is a skipper with whom it is easy to share life stories and first of all a competent and sensible navigation. Sardinia is the backdrop without problems, beautiful even where it does not seem, but which explodes with poignant beauty if discovered with the eyes of those who have been able to choose "a little of the best and a little more" for the available days. Thank you very much for Gian's exquisite hospitality and the management of the whole experience made even more comfortable by Skyfall, an elegant and refined boat.
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The wild south from Cagliari to CarloForte

06/21/2026

Dario V.

-

IT

.

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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 (107)Aeolian Islands (58)Northern Sardinia (45)Pontine Islands (40)Liguria (29)Aegadian islands (29)Naples & Amalfi Coast (16)Southern Sardinia (15)Sicily (12)Tremiti Islands (6)

Italy: departures by month

july (237)august (216)september (153)october (41)november (5)december (2)january (1)february (1)march (1)april (1)

Other travel ideas

Sailboat (566)Whole boat with skipper (435)Cooking service onboard (123)Catamaran (91)All inclusive (53)Family sailing cruises (31)Courses & regatta (27)Exotic destinations (26)Offshore (21)Day trips (21)

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