Yacht sailing holidays & skippered tours in the Gulf of Naples

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.

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Reviews - Yacht sailing holidays & skippered tours in the Gulf of Naples

257 reviews
20 / 10
Matilde P.

Matilde P.

review about Short break in Ischia and Procida July 2022

8 / 10
My first sailing holiday and I can only think that it will be only the first of many!!! Nicola reliable and experienced led us safely between Ischia and Procida facing with great professionalism even a decidedly "adventurous" storm ...
Anna I.

Anna I.

review about Sailing & Fun from Naples to Rome: Ischia, Procida, Ventotene and Ponza August 2021

10 / 10
A week of real sailing holiday, made of bays, coves and beautiful places. XXX is an experienced and helpful skipper who knows how to stay by sea. It transmits absolute safety, passion for the wind, knowledge of the places and love for the environment. His boat is perfect for sailing and also more than comfortable for life on board. Too bad to have happened with some people of the crew not willing to life on board, who did not have even a little curiosity for what it is to live sailing and with little respect. Very nice week anyway!!
Sara V.

Sara V.

review about Procida, Capri, Amalfi August 2021

10 / 10
Exceptional sailing experience with skipper Alessandro extremely kind, empathetic and helpful. Wonderful sunset at anchor in front of the Faraglioni of Capri and beautiful stop on the island of Procida. Recommended holiday!
Andrea M.

Andrea M.

review about Course of Navigation between the islands of the Gulf of Naples August 2020

10 / 10
Vincenzo, a real sea wolf with a rough character. In addition to being a well of experience in navigation, it transmits very well the skills that are needed in the management of a boat. It was an experience I would do again right away. Course not recommended for those who only think of sunbathing on a boat!
Roberta M.

Roberta M.

review about Flegrean Islands July 2020

8 / 10
We had a very good time! For me and my friends it was the first sailing experience and with the 2 days with Nicola, our expectations were met. Nicola is helpful, unobtrusive, polite and patient. We will definitely have other experiences in the future.
Andrea C.

Andrea C.

review about "5 days sailing between the Flegree and Pontine - relaxation and fun GUARANTEED !!! August 2019

10 / 10
Fantastic experience to repeat absolutely. The boat is wonderful, spacious and well maintained despite the age; Carlo, his captain, proved to be an expert in every situation, nice and accommodating to the needs of the whole crew. We visited lovely places having fun in full harmony. The only drawback of the holiday, unfortunately, was the wind but ..... we will definitely do it again next time. Thanks Carlo!
Pascal V.

Pascal V.

review about Sailing around Ischia September 2019

10 / 10
Thank you Irene for this beautiful day. This gave us the idea to start with Sailsquare. Your boat is nickel clean and with you we are in total safety. Beats
Flavio S.

Flavio S.

review about One week in Flottiglia Costiera Amalfitana and Cilentana maximum comfort August 2019

10 / 10
Stefano is a skipper capable of transforming a normal holiday into an experience full of surprises and in total safety. The knowledge of the sea, the sympathy and professionalism have allowed us to fully appreciate the wonders that surrounded us. Also always patient in explaining all aspects of sailing on a sailboat. Thanks Stephen!
Valentina T.

Valentina T.

review about Sailing between Procida, Ischia and the Gulf of Naples July 2019

6 / 10
Davide is a man of the ocean rather than of the sea, full of attention and prudence towards the boat and the crew. It governs the sail of the owner who appoints him in almost total autonomy. It moves more with an eye to the sea than to docking, also because it is new to the area. Delegation totally in the kitchen - except coffee, coffee killer and dishwashing. His is an offer more for those looking for relaxation than nautical training or suggestions on what to do / see / eat. Before leaving, I would recommend to read up independently on options/activities/restaurants available, agree well on the tour and clearly divide the tasks on board. Good wind!
Annamaria G.

Annamaria G.

review about Flotilla of three boats, See Naples and then ... Sea June 2019

10 / 10
Good morning the holiday was gorgeous, wonderful and fantastic. Perfectly organized... top marks... what to say... we will repeat as soon as possible. Thank you all Good wind Anonymous
Lorenzo S.

Lorenzo S.

review about Amalfi coast, islands of Capri, Ischia and Procida! September 2018

10 / 10
Wonderful week with wonderful places and sea. Luca was a great skipper with whom I got to know notions and with whom I had the opportunity to collaborate. Super positive experience!!
Roberto T.

Roberto T.

review about Procida, Ischia and Ventotene: Along the WE among the most beautiful islands of the gulf August 2018

10 / 10
It was our first experience on the boat, I must say it was a WONDERFUL trip. Umberto the skipper, was much more than a captain, he welcomed us in his boat making us stay at home. He even caught a tuna which he deliciously served us at dinner with the paccheri directly on the boat. In addition to being an experienced captain, Umberto is an excellent connoisseur of the places. This experience has taught us a lot and we hope, to be able to undertake as soon as possible another similar holiday., because Umberto has made us live unforgettable moments. Roberto and Lorj Thanks Umberto
Marina C.

Marina C.

review about Fire at the Castle - The great festival of Ischia on a sailing boat July 2018

10 / 10
My first sailing experience exceeded all my expectations. Pierluigi and Nicoletta manage, with their passion and professionalism, to make you spend an unforgettable trip on board their boat. A perfect mix suitable for everyone, good food, relaxation, fun, sun, sea, music...
GIORGIA F.

GIORGIA F.

review about But it's enough to work, take a vacation! July 2018

10 / 10
My sailing experience (the first of my life) was great! Fabio is a skipper prepared and able to handle any situation, able to transmit to others his great passion for the sea and for sailing. The 4 days we spent between the Pontine Islands and the Gulf of Naples were a lot of fun, I recommend everyone a trip with captain Fabio!! :)
Claudia N.

Claudia N.

review about May 1 Bridge: 4 boats in flotilla! April 2018

8 / 10
Absolute 360 degree security! When he cooks he is an excellent cook, but to improve the organization of lunches and dinners according to the itinerary and the days
Chiara G.

Chiara G.

review about May 1 Bridge: 4 boats in flotilla! April 2018

10 / 10
For those who come from a daily reality made of precise schemes and schedules, life on the boat may seem a contradiction: there are no pre-established programs because the only existing rules are dictated by the sea and the wind. But this is precisely the beauty: you are immediately catapulted into another dimension, where you learn to let yourself be carried away by emotions, to live every moment, you return to laugh and savor the little things .. the meaning is rediscovered! And this is Umberto. Welcoming and sensitive, available to understand and satisfy the needs of the group, he gave us unique moments, full of lightheartedness and smiles, leaving in each of us that feeling of lightness typical of children that as adults we tend to forget .. In a short time he managed to turn perfect strangers into a real family! His boat was our home: elegant and with attention to detail, functional and comfortable. Therefore.. thanks Umbo! If the ground sickness sooner or later will go away, this holiday does not, it remains cu'mme!!
Stefania M.

Stefania M.

review about May 1, 4 boats in flotilla April 2018

10 / 10
First experience with sailsquare, first I always left with skipper that I already knew ... and I fell very well. I put 5* to Andrea, I would say that you do not need words, just that!
Different Sailing .

Different Sailing .

review about Last summer flotilla between Procida, Ischia and Capri September 2017

10 / 10
Ettore is an excellent skipper, good and precise with a great sailing experience. Do not be fooled by age, he shows much less years and has an extremely youthful spirit, always available and ready to participate in aperitifs and parties ;) He always likes to teach you something about sailing or sailing. Definitely Recommended, Great Hector, in Presto :)
Luca S.

Luca S.

review about Navigating south October 2017

10 / 10
Beautiful boat, Marco is very nice and an excellent sailing instructor
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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.

Gulf of Naples: best travel ideas

Other travel ideas