Homepage cover
logo

Log in

Sailboat yacht sailing holidays & tours in Naples & Amalfi Coast

Discover more than 15 opportunities to get on board a Sailboat adventure in Naples & Amalfi Coast. A unique experience with a local skipper, starting at €350 a week.

cover image
avatar image

4.7

Weekend of sea and colors between Ischia, Procida and Vivara

Italy: Naples & Amalfi Coast

2 days - 2 nights

6 departures available

June - October

Starting from

€275

€234

Per person

cover image
avatar image

4.8

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

Italy: Naples & Amalfi Coast

6 days - 6 nights

3 departures available

June - August

Starting from

€1,150

Per person

cover image
avatar image

4.8

Super!

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

Italy: Naples & Amalfi Coast

7 days - 7 nights

5 departures available

July - August

Starting from

€900

Per person

cover image
avatar image

4.8

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

Italy: Naples & Amalfi Coast

7 days - 7 nights

2 departures available

August

Starting from

€977

€879

Per person

cover image
avatar image

4.7

Midweek sailing trip in the Gulf of Naples

Italy: Naples & Amalfi Coast

3 days - 3 nights

2 departures available

June - July

Starting from

€390

€351

Per person

cover image
avatar image

4.7

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

Italy: Naples & Amalfi Coast

2 days - 2 nights

5 departures available

September - October

Starting from

€320

€272

Per person

cover image
avatar image

New

Capri Light Blue - Two boats in company!

Italy: Naples & Amalfi Coast

3 days - 2 nights

12 departures available

May - October

Starting from

€222

Per person

cover image
avatar image

4.8

The gems of the Amalfi Coast: Capri Light Blue, Positano Blue Sky, Amalfi Dreaming History

Italy: Naples & Amalfi Coast

4 days - 3 nights

2 departures available

August - September

Starting from

€333

€300

Per person

cover image
avatar image

4.8

Capri Light Blue - Two boats in company!

Italy: Naples & Amalfi Coast

3 days - 2 nights

5 departures available

May - October

Starting from

€242

€218

Per person

cover image
avatar image

4.8

All-Inclusive Sailing: Capri, Positano, Amalfi

Italy: Naples & Amalfi Coast

3 days - 2 nights

13 departures available

June - September

Starting from

€790

€711

Per person

cover image
avatar image

4.8

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

Italy: Naples & Amalfi Coast

5 days - 5 nights

2 departures available

August - September

€1,150

Per person

cover image
avatar image

4.0

Amalfi, Positano and Capri: what more could you ask for?

Italy: Naples & Amalfi Coast

5 days - 4 nights

One departure available

May - June

€500

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 - Sailboat yacht sailing holidays & tours in Naples & Amalfi Coast

650 reviews

avatar image

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

05/26/2026

Ludovica L.

-

IT

Weekend on the coast on a sailing boat?! Totally worth it! Beautiful experience!

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

05/26/2026

Mariaelena P.

-

IT

Wonderful experience, the first for me on a sailing boat. The boat is really very well kept, very clean, very pleasant crew, a nice group. Great credit must be given to the slipper, Gennaro, who was able to welcome and create an atmosphere of great collaboration and respect between everyone. Thank you Gennaro and the whole company.
avatar image

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

09/28/2025

Valerie D.

-

FR

Very nice experience, the boat is comfortable, the whole group was kind. Every day Ilaria made us aware of the life and environment of cetaceans, and their preservation. It was instructive. Rocco is a captain like no other! Very professional, you feel totally safe. Observation, anchoring in the port, swimming... A very good time out of time! Thank you to Rocco, Ilaria, and the other participants for this moment and their kindnesses.
avatar image

La Flottiglia Mediterranea: Capri, Ischia, Procida e le isole Pontine

09/23/2025

Ciro S.

-

IT

The flotilla holiday was an unforgettable experience, made special not only by the wonderful places we visited, but above all by the people who were part of it. Thanks to our skipper Gianfilippo, always attentive, competent and able to convey safety and serenity to the entire crew of the Duca del Sale. Together with him, thanks also go to Vladimiro and Antonello, skippers of Nora and Ludi respectively, the other two boats. A round of applause to Alessio and to the whole organization of the flotilla, who with professionalism and availability made everything smooth and pleasant. The itinerary, the activities and the management of every detail really made the difference. The team spirit that was created between the boats was also beautiful: we played, danced, ate and laughed together, turning every day into a precious memory. A unique atmosphere was established, made up of sharing, friendship and fun. An experience that I recommend to anyone who wants to experience the sea in an authentic, convivial and unforgettable way. Thank you all, we will see you again soon at sea. Fair winds!

Customer Support

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!

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!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

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