header cover
sailsquare logo

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.

cover image
avatar image

5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

5 departures available

September - October

Starting from

€337

Per person

cover image
avatar image

5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

7 departures available

September - October

Starting from

€337

Per person

cover image
avatar image

4.9

Super!

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

One departure available

September - October

€950

Per person

cover image
avatar image

4.8

Super!

Let's discover the Aeolian Islands together in Vela

Italy: Aeolian Islands

7 days - 7 nights

One departure available

October

€690

Per person

cover image
avatar image

5.0

Super!

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

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

October - November

€583

Per person

cover image
avatar image

5.0

Super!

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

Italy: Aeolian Islands

7 days - 7 nights

One departure available

September

€689

Per person

cover image
avatar image

4.7

Weekend a Capraia, trekking e natura

Italy: Tuscany

3 days - 2 nights

3 departures available

October

€200

Per person

cover image
avatar image

4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

One departure available

September

€441

Per person

cover image
avatar image

4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

4 departures available

September - October

Starting from

€220

Per person

cover image
avatar image

4.9

Super!

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

14 departures available

March - October

Starting from

€200

€180

Per person

cover image
avatar image

4.7

Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

One departure available

September - October

€850

Per person

cover image
avatar image

4.7

COUS COUS FEST: A Weekend of Sea, Sailing, Cous Cous and Music!

Italy: Sicily

4 days - 3 nights

2 departures available

September

Starting from

€390

€351

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 - Yacht sailing holidays & skippered tours in Italy

13591 reviews

avatar placeholder

Midweek relaxing in the Pontine Islands

09/13/2025

Alessandra S.

-

Italy

Despite the not exactly nice weather, it was a holiday to remember for the beauty of the coves, gentle even in the absence of sun, for the baths and SUP excursions, for the wonderful Pontine islands, seen from several perspectives from the sea and visited on foot when possible, rich in history and energy, for the spot-on company from all over Italy and...... especially for Mirko, the perfect skipper. Tireless, patient, helpful, proactive, reassuring and, to great surprise, an expert cook. Never on alert, it instills constant security in the crew. Congratulations to the organization, to us, who worked as a team, and to Mirko, our favorite skipper. 🥰
avatar image

The Egadi Islands as you've never seen them on a 16-meter boat

09/13/2025

Rosario P.

-

Italy

Unforgettable holiday
avatar image

4 days in the Pontine Islands (sailing school)

09/13/2025

Erica M.

-

Italy

great experience, our skipper Michele turned out to be very professional, attentive and extremely helpful. Although the weather was not the best, he did everything to make this holiday unforgettable. The boat is very well maintained, it is clean and tidy. Even my 13 year old daughter who was at her first experience came back very satisfied and happy. A big thank you also to our group with whom we shared 4 days superr!
avatar placeholder

4 days in the Pontine Islands (sailing school)

09/13/2025

Chiara C.

-

Italy

I have just spent four unforgettable days sailing between the Pontine Islands with skipper Michele, and I can only share an overwhelming enthusiasm for this experience! Although time was not always on our side, Michele demonstrated an uncommon competence and passion, guiding us with mastery through the wonders of this archipelago. His ability to handle the boat and find the best spots allowed us to enjoy every moment, even when the weather tried to throw a spanner in the works. The Pontine Islands are a true paradise: crystal clear waters, hidden coves and breathtaking landscapes that make you forget everything else. The boat was comfortable, well maintained and perfect for this adventure, with cozy spaces that made us feel at home. The company on board? Simply fantastic! Laughter, chats and shared moments that made the trip even more special. But the real highlight? Dolphin encounters! Not one, but several magical moments in which these beautiful animals accompanied us, swimming next to the boat for a time that seemed endless. It was exciting, an experience that I will carry in my heart forever. Michele is not only an experienced skipper, but also a person who knows how to convey love for the sea and for these islands. I highly recommend this trip to anyone who wants to experience the sea in an authentic way, between nature, relaxation and unforgettable moments. Thank you, Michele, for making these four days a daydream! Definitely!

Customer Support

nightLifeGeneralInfo

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

search

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

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

Italy: departures by month

Other travel ideas

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964