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.
391
experiences
391
experiences
5.0
Duration:
2 days - 1 night
Italy:
Venice and the Gulf of Trieste
12 travellers
€179
€199
Per person
Duration:
5 days - 4 nights
Italy:
Naples & Amalfi Coast
Give this experience a try!
€477
€530
Per person
4.5
Duration:
2 days - 2 nights
Italy:
Naples & Amalfi Coast
76 travellers
Starting from
€248
€275
Per person
Duration:
7 days - 7 nights
Italy:
Northern Sardinia
Give this experience a try!
€810
€900
Per person
4.9
Duration:
7 days - 6 nights
Italy:
Pontine Islands
5 travellers
Starting from
€675
€750
Per person
5.0
Super!
Duration:
6 days - 7 nights
Italy:
Tuscany
115 travellers
Starting from
€714
€793
Per person
Duration:
2 days - 1 night
Italy:
Tuscany
5 travellers
Starting from
€177
€197
Per person
4.7
Duration:
3 days - 2 nights
Italy:
Liguria
Give this experience a try!
€252
€280
Per person
5.0
Super!
Duration:
3 days - 2 nights
Italy:
Pontine Islands
Give this experience a try!
€441
€490
Per person
Duration:
7 days - 7 nights
Italy:
Aegadian islands
16 travellers
Starting from
€360
€400
Per person
4.9
Duration:
7 days - 7 nights
Italy:
Aegadian islands
6 travellers
Starting from
€621
€690
Per person
4.7
Duration:
6 days - 7 nights
Italy:
Aegadian islands
87 travellers
€1,332
€1,460
Per person
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Get onboard solo, with your family or your friends
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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
12220 reviews
Weekend catamaran in Portovenere and Cinque Terre
05/12/2025
Davide S.
-
Italy
Weekend in Capraia, the island with timeless sunsets
05/12/2025
Stefano F.
-
Italy
Stuffed anchovies: magical weekend from Genoa
05/12/2025
Maurizio S.
1 May long weekend sailing with RICCARDO PROFESSIONAL SKIPPER COOK
05/8/2025
Maria Pia D.
-
Italy
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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
Let's talk Sailsquare!
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