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Gulf of Naples + Pontine Islands

Gulf of Naples

Naples is the vibrant southern Italian city known across the sea for its alluring tattered edges. Home to the ancient city of Pompeii and indulgent cuisine, it’s the culprit for dried pasta and yes, the birthplace of pizza. This major port city is the jumping off point to the Sorrentine Peninsula and the Campanian Archipelago including the seductive island of Capri, Procida, Ischia, Ventotene, and Ponza. Headed west you can sail to the intoxicatingly wonderful Phlegraean Islands: Ischia, Procida, Vivara, and Nisida. The islands sit centered off the Sorrentine Peninsula between the two gulfs and extends to the Pontine Islands.

Homer’s epic poem, the Odyssey, depicts a voyage that sails through here and several of the islands are mentioned in recognizable detail although the names have changed. Local residents don’t doubt the existence of the fabled sirens who lured greek sailors onto the rocks even if they have never heard them sing. Life at sea is the backbone of their society and its dangers are respected just as the merits are celebrated by local residents and visitors alike, as a sailor you arrive to welcome understanding of what it means to journey on the sea.


Aug 28th — Sep 4th 2021

7 days, 6 nights


Gulf of Naples + Pontine Islands


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Sitting just six nautical miles from Procida is the renowned island of Ischia and the largest of the Phlegraean Islands. Volcanic origins left Ischia with an imposing mountain peak and its famed natural thermal baths that flow along the ocean's edge. Even when the island is busy in the summer months it is a quiet retreat compared to Naples, sailing by you see its lush greenery and brightly colored flowers from afar. Groves of vineyards and olive trees grow on terraced farmland along the steep edges. Home to four safe marinas and some less well protected anchorages, including many secluded coves only accessible by boat-- the distinctive features of this island do not disappoint. 

Baia di Sorgento

Baia di Sorgento, located along the southern coast of the island is a rocky and steep cove home to a small restaurant and a natural thermal baths. Steaming hot freshwater flows from the island into the cove and when it hits the salty ocean water, it creates a natural thermal bath in the rocky water along the beach


From the watchtowers of Ischia’s castle, fifteen nautical miles away Capri appears in the heat of the summer haze. The island sits off the coast of the Sorrentine Peninsula and is perhaps the most famous island in the Mediterannean. Sheer cliffs rise from the ocean dramatically for hundreds of meters on most of Capri’s shoreline.


The Town of Amalfi sits in a dramatic valley cut into a steep coastline that is famous for its combination of rugged terrain and beautiful architecture. The cliffs that dwarf the cathedral in town only serve to make it’s grandiose steps and Italian gothic facade more impressive.


The population currently is 300 yearly residents, and the population jumps to about 700 Italians during the summer months. During peak season, the harbors are full with transient sailors passing by during their Pontine Islands itinerary. Stepping off your boat and onto the island is like going back in time, where children swim in the ancient grottos lined with Roman-era carved steps that lead into the sea, while grandparents enjoy conversations in the island’s town square with the stresses of modern life nowhere to be seen.


The eastern face is known for its steep limestone cliffs that drop dramatically into the emerald sea below. When making the approach to Ponza sailing west from Ventotene, the first thing you’ll notice is the island’s jagged cliffs that become illuminated upon closer reach. The anchorages are lined by chalk-colored white and beige cliffs with its eroding edges drop into the sea, while lush plants line the layered landscape above. It’s popular among sailors and the anchorage is busy during the summer months with boats of all sizes lining the coast, from megayachts to dinghys. Swimming off the boat looking up at the dramatic rocks above is a highlight of anyone’s life. It smells fresh, pure air and when swimming, you can see octopus and other local fish along the sandy seafloor. 


Palmarola is a small island located eight nautical miles from Ponza and an easy day sail from the main port. The island is characterized by its sheer beauty and the dramatic size of the sheer cliffs along the eastern coast.


Dayyan Armstrong

Dayyan Armstrong

Creative Director & Founder

Dayyan Armstrong founded the Sailing Collective out of a passion for connecting people with the world through adventure and sailing. Having been raised with values based on multi-cultural awareness and the importance of global culture, Dayyan combined his enthusiasm for sailing and exploration to create an integrated sailing vacation organization open to adventures, explorers, and sailors alike. With a background in music performance, social theory, and a graduate degree in economics from the New School for Social Research, Dayyan is always excited to participate in discourse in topics of theory, art, adventure, and exploration.  Outside sailing and exploration, Dayyan is passionate about cured meats, design, Maine, social theory, Cook’s Illustrated, a good museum, photography, Harper’s Magazine, and various types of cooking over fire or coals.

Amy Yi

Amy Yi


Amy Yi believes that food is community. For her, the power of food is most deeply demonstrated in the bonds it can forge; the social, environmental and economic implications it can illuminate; and the experiences it can bring to life for those who come together to break bread. Born and raised in Los Angeles, Amy was initially drawn to the competitive pace of New York City as an advertising associate for magazines such as Glamour and Fortune but soon realized that what she craved was a much more visceral connection to her work and an opportunity to nourish and delight others through food. With the pioneering spirit of the west coast coursing through her, she skipped culinary school, instead opting to jump right onto the line. What followed was a remarkable journey through stages at Mugaritz and Noma, influential experiences at esteemed restaurants such as Degustation and Jean Georges, Executive sous chef at Upland, and most recently, culinary director at West-Borne. Grounded in her California-Korean heritage with a serious case of wanderlust, Amy’s culinary inspiration and worldview draws from family traditions infused with a passion for cultural diversity. Amy strives to bring an everyday rapture to what you crave, how you care for your community, and why a collective impact matters.

General Information


Sailing Collective will provision your journey with local foods and produce.  Cooking Aboard: Your Sailing Collective chef/crew is incredibly talented and can handle the group's needs with ease. We are all about participation and learning, so if you'd like to help, just ask and we'll get you involved! Collective groups may choose to dine out more times than scheduled if the group or individuals choose.

Included in provisioning package: 

  • 7 Breakfasts

  • 6 Lunches

  • 3 Dinners

  • Light Snacks

  • Water

  • Coffee & Tea

Dietary Restrictions: We can accommodate as long as we know in advance! It is important to notify us of any dietary restrictions ahead of time and include full details in the Guest Form that you will fill out prior to the start of the trip.


We recommend planning on having at least $300 – $600 in spending money depending on spending habits. You will be responsible for paying for:

  • All expenses on shore including meals and drinks

  • Flights and transportation to and from the marina location

  • Onboard Alcohol


Please ensure your passport is valid for the period of travel and for six months after you return. Your passport name must match the name on the flight ticket otherwise you may not be able to travel and insurance may be invalid. It is the responsibility of each individual to ensure relevant visas are obtained where necessary. The Sailing Collective cannot be held responsible for refusal of entry or travel due to lack of visas. If you are in any doubt please contact your Embassy for full details.


Tipping your captain and crew is welcomed. If you are satisfied with your service, the industry standard for yacht charters ranges from 10-20% of the cost of the charter. Gratuity is split evenly between the crew and can be paid via cash, check, Venmo, or PayPal. Please contact your Sailing Collective Journey Coordinator if you have any questions.


Collapsible bags in place of large rigid suitcases are advised for ease of transport on and off the boat. Loading and unloading from the dingy can be a wet activity, a pair of shoes such as flip-flops that you can get wet if we are landing on a beach.

During days on the water, you’ll want to be wearing light and comfortable clothing.  As the vast majority of your time will be spent outside, prepare for elements - bring a light raincoat just in case, a hat to shield yourself from the sun, and a warm layer.  Throughout the week we may dine out at a nice restaurant, so bring an outfit looks nice and suits your style. Loading and unloading from the dingy on beaches can be a wet activity, a pair of shoes that you can get wet is recommended.

We also encourage that people bring ecologically appropriate products into ocean environments. You can read more about those recommendations on the Sailing Collective Journal here: Packing for a Healthy Ocean

  • Passport

  • Camera or sketchpad - a dry bag or waterproof case for your phone and camera is highly recommended

  • A hat - something with a little sun protection

  • Sunglasses

  • Sunscreen - preferably reef safe

  • A light raincoat/wind jacket

  • Boat shoes or non-slip shoes such as sneakers or tennis shoes

  • Shoes you don’t mind getting wet such as flip-flops

  • Any special dietary foods

  • Water bottle

  • Toiletries

  • Beach towel, Turkish towel, or Sarong (1 bath towel is provided with linens)

  • A handful of bathing suits

  • Printouts or notes of important info such as meeting details and travel documents


Naples Trip Details


Embarking: Meeting time is after 7 p.m. at Marina Di Stabia. Upon arrival, look for the boat flying a Sailing Collective flag or ask a charter rep to point you towards the Sailing Collective boat. If you arrive earlier in the day, you can store your luggage at the marina and explore the area. If you plan on arriving after 7 p.m., please let us know as soon as possible so we can make accommodations!

Disembarking: The journey will end on the last day of the charter at 9 a.m.


The closest airport to Castellammare di Stabia is the Naples International Airport (NAP). 

Castellammare di Stabia is about a 30-minute taxi ride from the airport. Taxis are readily available at the airport, but please be in touch if you would like for us to arrange a transfer for you in advance. Private transfers can be arranged from the airport to the marina for approx. EUR 80 for up to 4 passengers.


Naples Italy Hotels

  • Grand Hotel Vesuvio:

    The Grande Dame of Naples’ hotels has a long and illustrious history, a magnificent setting overlooking the Castel dell’Ovo and a traditional, discreetly luxurious atmosphere.

  • Hotel Piazza Bellini:

    This city centre hotel offers contemporary design in the context of a venerable old palazzo with good facilities and service for its three-star rating. The location is ideal for anyone who wants to experience the vibrant, beating heart of Naples' centro storico, and prices are very reasonable.


    Old world charm meets luxurious facilities and great views. The interiors ooze Italian elegance and grandeur - marble floors, chandeliers, and tasteful decoration. The gorgeous roof terrace and restaurant has splendid views of the bay. A quintessential Napolese spot.


    Eclectically contemporary B&B. Slick white rooms decorated with modern art and styled in neutral tones. Smart bathrooms with large jacuzzi baths. Ideally situated in the heart of the historic city. Excellent views and indulgent breakfasts. A stylish yet affordable choice.

Casttellammare di Stabia Hotels

  • Hotel Miramare Stabia:

    A 5-minute walk from Castellammare Di Stabia train station, this sleek, contemporary hotel beside a Gulf of Naples beach is 7 km from the Amphitheatre of Pompeii.

  • Hotel Stabia:

    A minute's walk from the beach, this 19th-century art nouveau-style hotel is a 3-minute stroll from Castellammare Di Stabia train station and 8 km from the ancient ruins of Pompeii.

Amalfi Coast Hotels

  • Le Sirenuse, Positano, Amalfi Coast: 

    Stylish and immaculate, in the centre of this chic and vertiginous resort. An exceptionally romantic candle-lit dining room, a shady pool terrace and small but beautifully presented spa make it particularly popular with honeymooners, well-heeled European couples, touring Americans and occasional celebrities.

  • Hotel Santa Caterina, Amalfi, Amalfi Coast:

    A mix of familial warmth, glamour and professionalism makes Hotel Santa Caterina stand out from the competition. Now run by the fourth generation of the family that opened it as a hotel in 1904, it’s the sort of homely yet sophisticated place that you long to return to (repeat bookings amount to nearly 40 percent).

  • Hotel Villa Cimbrone: 

    Ravello, Amalfi Coast  - Occupying one of the most romantic spots in the world, Villa Cimbrone comprises beautiful gardens, open to the public during the day, and rooms full of antiques, paintings and frescoes. This is a hotspot for anyone wanting to enjoy the special magic of Ravello.


The climate of Italy is ideally suited for sailing, with hot, dry summers and mild, wet winters. Winds are generally north-westerly averaging 8 to 12 knots (8 – 14 mph) with the windiest period being July and August. During the cruising season of April to October, the skies are blue and the weather warm, with water temperatures averaging 80 F 

Italy Travel Protocal

U.S. travelers entering Italy must show a completed vaccination certificate or a negative molecular or antigen swab Covid test taken 48 hours prior to entry. Travelers are also required to complete the digital PLF (https://app.euplf.eu) prior to entering the country.

Please review local travel requirements prior to departure. A helpful resource is can be found here.

The Sailing Collective will arrange for re-entry tests for sailors returning to the U.S. directly following the journey.


Our meals aboard are VERY important to us and we take great pride in the unique culinary innovation that takes place. Provisions are sourced locally and every meal while living aboard is a journey of its own.


Bali 4.3

Bali 4.3

The BALI 4.3 is characterized by having a single area for the cockpit and the saloon with a 30 m² open space on a single level, entirely free of bulkheads, and accessed by a huge glass door which is entirely retractable on electric struts. With that, the saloon becomes a terrace with a sea view in a flash.

Gulf of Naples



Aug 28th — Sep 4th 2021



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