Yacht sailing holidays & skippered tours in the Gulf of Naples and Amalfi Coast
Whether it is for a weekend of good food, good sea and sweet life, or for a longer trip to discover the beauty of southern Italy, the Italy, sailing vacations in Ischia, Capri, Procida and the other pearls of the Gulf of Naples the other pearls of the Gulf of Naples know how to surprise everyone.
18
experiences
18
experiences
5.0
Italy: Naples & Amalfi Coast
7 days - 7 nights
14 departures available
July - October
Starting from
€795
Per person
5.0
Italy: Naples & Amalfi Coast
7 days - 7 nights
13 departures available
July - October
Starting from
€795
Per person
4.3
Premium
Italy: Naples & Amalfi Coast
6 days - 7 nights
6 departures available
August - October
Starting from
€1,260
Per person - min 2 pax
Italy: Naples & Amalfi Coast
7 days - 7 nights
One departure available
August
€1,500
Per person
Italy: Naples & Amalfi Coast
7 days - 7 nights
One departure available
August
€1,300
€1,170
Per person
4.6
Italy: Naples & Amalfi Coast
2 days - 2 nights
One departure available
September
€275
€248
Per person
Why book a holiday with Sailsquare?
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
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 the Gulf of Naples and Amalfi Coast
620 reviews
From the Pontine to the Amalfi Coast by sailboat
07/14/2025
Anna P.
-
Switzerland
Short sailing cruise in the Gulf of Naples
07/11/2025
Daniela D.
-
Italy
Capri LightBlue and Positano BluSKy
07/8/2025
Marianna D.
In the blue of Capri and the infinity of the Amalfi Coast
07/8/2025
Laura D.
-
Italy
Customer Support
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!
Call us at
+44 2035144220Read our
Contact & Support
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!
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
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
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
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
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!
uide to sailing vacations with children
Naples & Amalfi Coast: the best travel ideas
Let's talk Sailsquare!
Secure payments
© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964
