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.
416
experiences
4.7
Italy: Tuscany
6 days - 6 nights
5 departures available
June - September
Starting from
€999
€949
Per person
4.8
Super!
Italy: Tuscany
2 days - 2 nights
12 departures available
May - October
Starting from
€230
Per person
4.9
Super!
Italy: Aeolian Islands
7 days - 7 nights
7 departures available
June - October
Starting from
€650
Per person
5.0
Super!
Italy: Southern Sardinia
6 days - 7 nights
13 departures available
June - September
Starting from
€790
Per person
5.0
Super!
Italy: Pontine Islands
3 days - 2 nights
4 departures available
June - July
Starting from
€285
Per person
4.9
Super!
Italy: Liguria
2 days - 2 nights
3 departures available
July - September
Starting from
€390
Per person
4.7
Italy: Naples & Amalfi Coast
2 days - 2 nights
7 departures available
May - October
Starting from
€275
€234
Per person
4.9
Super!
Italy: Pontine Islands
4 days - 3 nights
8 departures available
June - October
Starting from
€420
€399
Per person
4.8
Super!
Italy: Tuscany
2 days - 2 nights
11 departures available
June - October
Starting from
€230
Per person
5.0
Super!
Italy: Pontine Islands
4 days - 3 nights
3 departures available
May - June
Starting from
€370
Per person
4.8
Super!
Italy: Aeolian Islands
6 days - 7 nights
7 departures available
June - September
Starting from
€583
€525
Per person
4.8
Super!
Italy: Tuscany
5 days - 4 nights
10 departures available
May - September
Starting from
€400
€380
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
13796 reviews
Weekend among the most beautiful coves of Elba
05/18/2026
Stefania V.
-
Italy
CAPRI Paradise - Catamaran cruise with hostess FULL BOARD
05/17/2026
Cristina Anna R.
-
Italy
Weekend among the most beautiful coves of Elba
05/17/2026
Giulia L.
-
Italy
Let's discover the Aeolian Islands together by sailing
05/17/2026
Tim D.
-
Germany
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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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