header cover

Yacht sailing holidays & skippered tours in the Gulf of Naples

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.



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

268 reviews

avatar image

Two hearts and a sailboat to discover the Flegrean Islands


Sara M.



Sergio è una persona eccezionale: sempre disponibile e un bravissimo skipper. Super consigliato!
avatar image

Last minute - Procida, Ischia and the Pontine on a 15m boat with an expert skipper





Una bellissima esperienza! Tour ben organizzato in tutti i dettagli grazie alla professionalità di Andrea, skipper esperto e proprietario della barca, che ci ha guidati nel tour delle Isole Pontine. Durante il viaggio abbiamo sempre veleggiato in sicurezza. Andrea sa fare gruppo e un paio di sere ci ha preparato un ottimo piatto di pasta. Per chi è in cerca di una bella vacanza in barca a vela consiglio vivamente di provarne una con Andrea, io lo farò sicuramente.
avatar image

Last minute - Procida, Ischia and the Pontine on a 15m boat with an expert skipper


Angelo Salvatore B.



Organizzazione semplice ed efficiente. Imbarcazione funzionale sotto ogni punto di vista. Lo skipper Andrea competente e disponibile alle nostre esigenze è stato un valore aggiunto per l'ottima riuscita della nostra vacanza.
avatar image

Last minute - Procida, Ischia and the Pontine on a 15m boat with an expert skipper


Maria A.



È stata la mia prima esperienza in barca a vela e mi sono trovata benissimo. Il gruppo è stato davvero fantastico, tutte persone gentili e disponibili. Lo skipper Andrea è molto preparato, ci ha fatto viaggiare in modo sicuro nonostante le condizioni sfavorevoli di meteo. È simpatico e soprattutto un ottimo chef. La consiglio vivamente come vacanza, io la rifarò sicuramente.

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!

7 reasons to choose the Gulf of Naples, Capri and Ischia for your next sailing holiday

  • Experience the thrill of navigating with Vesuvius in view, and constantly feel its powerful presence during your boating vacation from Ischia to Capri.
  • Discover why Ischia is known as the green island. It's not only because of its lush vegetation, but also because of the tuff of Monte Epome, the island's typical precious stone, which geologists believe owes its particular color to its long contact with crystal clear sea water.
  • The movida di Capri, which has made Via Tragara famous throughout the world among VIPs and celebrities.
  • Swim in the crystal-clear waters of Campania and explore some hidden gems like Capri's Grotta Azzurra.
  • Pass by the legendary Faraglioni of Capri and take your place in the roadstead among the boats and yachts of famous people. Be careful to show off your best costume, you may be photographed!
  • Breakfasts with delicious Ischian croissants, lunches on the boat with freshly caught fish, luxurious dinners with typical products in the most beautiful restaurants in the area, and night parties in VIP venues (to be carried out strictly by boat). All this and much more will enliven your sailing cruise in the Gulf of Naples
  • A perfect destination for a weekend of sun and sea, as well as for a week of sailing to the north (Ventotene, Ponza, etc) or to the south, in the beautiful Amalfitan Coast

The best places to visit during your vacation in the Gulf of Naples

Sailing along the Gulf of Naples

From Naples to Sorrento, the shadow of Vesuvius is a presence with a strong emotional impact as you sail along the shores of this wide gulf. Change perspective and discover one of Italy's most beautiful cities from the sea: Castel dell'Ovo, Herculaneum, Torre Annunziata, from which you can take a shore excursion to the mythical Pompeii, where time literally stood still thousands of years ago. Continuing to sail towards Sorrento, you find yourself framed between the hollow figure of Vesuvius and the high walls of the Monti Lattari. This is the most beautiful part of the Gulf of Naples to discover by sailing, admiring the coast of Vico Equense, Meta di Sorrento, Massa Lubrense, Punta Campanella.

Sailing on Capri as a VIP

A small island that has earned a great place in the hearts of luxury lovers around the world. Greeting you on your arrival on the island are the legendary faraglioni of Capri, even more impressive and majestic when seen from the deck of your boat. You can't help but go ashore and explore this Italian jewel: from typical boutiques for leatherwork, to sampling the world's finest limoncello, and ending with a stroll along its steep cliffs overlooking the sea, Capri offers every traveler something unique. Not to be missed is a trip to the Grotta Azzurra, where an underwater cavity tinges the water and walls of this magical place with an electric blue hue.

Holidays in Ischia on a sailing boat, to discover it from the sea

Another jewel of the Gulf of Naples, the Green Island offers emotions both on land and at sea. Unlike Capri, which is a volcanic island, its thermal waters are rich in minerals and attract people from all over the world for their beneficial properties. But the wonders are also under the sea: to the east, off Cartaromana beach, you will find Roman remains for a "dip in history". Enjoy the best restaurants of Ischia with a view of the Aragonese Castle and stroll through the streets and alleyways full of romance of this island.

Everything you need to know to make your dream of sailing the Gulf of Naples come true

  • A sailing vacation between Ischia, Capri, the Sorrentine Peninsula and the entire Gulf of Naples is wonderful all year round. The climate is pleasant even in low season, but from May to September you can enjoy the sea at its best. However, if you want to have the islands in the area almost entirely to yourself, the best choice is to take a sailing cruise between September and October
  • To try the sailing experience in Ischia, Capri and the Gulf of Naples you can either go with friends or join a group of new people you meet on board, or even a flotilla of boats sailing together. In any case, the best way to enjoy this area is by sailing, as evidenced by the many luxury boats that crowd the shores of Capri and the rest of the Gulf. And if you want to feel really VIP, choose to embark on a sailboat all inclusive in Capri.
  • To get to Ischia, Procida and Capri, the most convenient way is to take a train or plane to Naples. Many sailing cruises leave directly from its port, for others you'll have to take the fast, scenic hydrofoils to the islands. As always, transportation can be expensive if you decide to travel in high season, so it's advisable to book well in advance.
  • The budget for a skippered sailing vacation in the Gulf of Naples varies greatly depending on the number of days and level of comfort, but is always affordable. The price starts at 200€ for a weekend, and less than 700€ for a week that includes other beauties in the surroundings.

The best sailing travel itineraries to Capri, Ischia, Gulf of Naples and beyond

Whether it's for a long weekend or an entire week, you'll easily find the sailing vacation in the Naples area that's right for you with Sailsquare:

  • Long weekend around the Gulf of Naples: embark directly on your sailboat or catamaran in Procida, after a short trip by hydrofoil or ferry from Naples or Pozzuoli. Lift anchor in the direction of Capri, and arrive just in time to enjoy a aperitif at sunset on deck and the nightlife on land. Before setting sail for Ischia the next day, you can't miss a dip in the blue at the Grotta Azzurra. End the weekend circumnavigating Ischia and Procida, filling your eyes with the beauty of these coastlines.
  • Week of relaxation in and around Naples: after dancing and partying in the clubs of Capri, explore Ischia and Procida at a more leisurely pace: treat yourself to a day at the thermal baths at Negombo on the former, and a long walk to Corricella on the latter, with dinner based on local produce. At this point, together with your local skipper, depending on weather conditions and your desires, you will be free to continue the week north, heading towards the Pontine Archipelago, or south, discovering from the sea the wonder of the Amalfitan Coast that the world envies us.

Other travel ideas

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaAmerican ExpressApple pay

© 2023 Sailsquare Srl SB • All rights reserved - VAT IT07860990964