header cover
sailsquare logo

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.

cover image
avatar image

4.8

Super!

Capri LightBlue and Positano BluSKy

Italy: Naples & Amalfi Coast

3 days - 2 nights

7 departures available

July - October

Starting from

€294

Per person

cover image
avatar image

4.8

From the Pontine to the Amalfi Coast by sailboat

Italy: Naples & Amalfi Coast

8 days - 7 nights

5 departures available

July - September

Starting from

€660

Per person

cover image
avatar image

4.8

Super!

All Inclusive Tour: Capri, Amalfi, Cetara, and Sorrento

Italy: Naples & Amalfi Coast

5 days - 5 nights

2 departures available

June - August

Starting from

€1,115

€1,059

Per person

cover image
avatar image

4.6

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

One departure available

July

€320

Per person

cover image
avatar image

4.8

Super!

All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

Italy: Naples & Amalfi Coast

6 days - 6 nights

3 departures available

July - September

Starting from

€1,385

€1,316

Per person

cover image
avatar image

4.8

Super!

An unforgettable week between Capri, Positano, Amalfi, Ischia, Procida...

Italy: Naples & Amalfi Coast

7 days - 7 nights

3 departures available

August

€999

Per person

cover image
avatar image

4.8

Super!

All-Inclusive Sailing: Capri, Positano, Amalfi and Sorrento Coast

Italy: Naples & Amalfi Coast

3 days - 2 nights

3 departures available

June - July

€865

Per person

cover image
avatar image

4.6

Short sailing cruise in the Gulf of Naples

Italy: Naples & Amalfi Coast

3 days - 3 nights

One departure available

July

€350

€315

Per person

cover image
avatar image

4.7

Long weekend of whale watching with a WWF guide between the Amalfi Coast, Ischia and Capri

Italy: Naples & Amalfi Coast

3 days - 3 nights

4 departures available

June - September

Starting from

€452

€429

Per person

cover image
avatar image

4.8

7 days between Capri, Amalfi and Sorrento: dream sailing cruise

Italy: Naples & Amalfi Coast

7 days - 7 nights

2 departures available

August

€950

Per person

cover image
avatar image

4.8

Two hearts and a sailboat: discovering the Phlegrean Islands

Italy: Naples & Amalfi Coast

2 days - 2 nights

14 departures available

June - October

€312

Per person

cover image
avatar image

4.7

Whale watching cruise with WWF guide between the Amalfi Coast, Ischia and Capri

Italy: Naples & Amalfi Coast

5 days - 6 nights

One departure available

July

€1,009

€959

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 the Gulf of Naples and Amalfi Coast

600 reviews

avatar placeholder

In the blue of Capri and the infinity of the Amalfi Coast

06/10/2025

MARCO F.

-

Italy

Bellissima esperienza, barca perfetta, skipper Gennaro gentilissimo, destinazioni top.
avatar placeholder

Capri LightBlue and Positano BluSKy

06/10/2025

Simone D.

-

Canada

Eppena trascorsi due giorni stupendi in barca con Gennaro! Ci siamo trovati veramente bene, e ci ha pure accomandato per piccoli cambiamenti di percorso. Per ogni cosa lui è stato veramente a disposizione. La barca era veramente grande e ci ha fatto sentire un po’ casa per la comodità. Consiglierei a tutti questa esperienza perché ti fa vivere la costa di Napoli veramente in un modo straordinario. Grazie di tutto Gennaro!
avatar placeholder

2 June: Whale watching expedition with WWF guide between the Amalfi Coast, Ischia and Capri

06/9/2025

Hayley F.

-

United Kingdom

We had a super time on board the Audace. Skipper Rocco was great and Ludo the WWF guide full of enthusiasm and knowledge. Highly recommend.
avatar placeholder

April 25th: Whale watching expedition with WWF guide between the Amalfi Coast, Ischia and Capri

05/4/2025

Daniela M.

-

Italy

È il mio secondo viaggio con Le Vele del Panda e Sailsquare... e anche questa volta è stata un’esperienza semplicemente meravigliosa. Un grazie di cuore a Donatello C., la nostra guida: appassionato, preparatissimo e con un'allegria contagiosa. Un grande grazie anche al nostro Capitano, Rocco B., che ci ha accolti calorosamente a bordo della bella Audace, creando un’atmosfera amichevole e super rilassante. Infine, grazie per tutte le risate e i racconti anche a Francesca, Giulio, Isabel e Mauro: è stato un vero piacere condividere con voi queste giornate. Non vedo già l’ora di ripartire!

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


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

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

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

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

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!
uide to sailing vacations with children

Naples & Amalfi Coast: the best travel ideas

Other travel ideas

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

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