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.
110
experiences
5.0
Super!
Italy: Venice and the Gulf of Trieste
1 day - 1 night
One departure available
October
€280
Per person
4.7
Italy: Tuscany
4 days - 4 nights
One departure available
October
Starting from
€453
Per person
4.8
Super!
Italy: Tuscany
5 days - 4 nights
One departure available
September
€490
€440
Per person
4.7
Italy: Tuscany
3 days - 3 nights
One departure available
September
Starting from
€441
€419
Per person
4.8
Super!
Italy: Tuscany
2 days - 2 nights
2 departures available
September
€200
Per person
4.8
Super!
Italy: Tuscany
2 days - 2 nights
4 departures available
September - October
Starting from
€230
Per person
5.0
Super!
Italy: Tuscany
2 days - 2 nights
3 departures available
October - November
€250
Per person
5.0
Super!
Italy: Tuscany
2 days - 2 nights
One departure available
September
€400
Per person
4.9
Super!
Italy: Tuscany
3 days - 3 nights
One departure available
September
€280
Per person
4.9
Super!
Italy: Tuscany
2 days - 2 nights
One departure available
October
€315
Per person
4.8
Super!
Italy: Tuscany
4 days - 4 nights
One departure available
September
€490
Per person
4.8
Super!
Italy: Tuscany
3 days - 2 nights
2 departures available
October - November
€280
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
15035 reviews
The gems of the Amalfi Coast: Capri Light Blue, Positano Blue Sky, Amalfi Dreaming History
09/14/2026
Dali G.
-
FR
Catamaran cruise in Sardinia & Corsica with chef - full board (per cabin)
09/14/2026
Lendell S.
-
US
Long weekend on Elba: 4 days of sun and sailing
09/14/2026
Sara B.
A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia
09/14/2026
Lucrezia F.
-
IT
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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
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
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
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
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
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
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
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
A perfect vacation for singles (and others) to experience sailing, meet new friends and multiply the fun.
Guide to the flotilla holidays
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
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?
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
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