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15563

  • May 29th – June 5th, 2027
  • 8 Days | 7 Nights

Overview

Join our Amalfi Coast flotilla for an unforgettable sailing experience that combines breathtaking scenery, cultural discovery, and a welcoming community at sea. Navigate the stunning waters of the Amalfi Coast and Sorrentine Peninsula, with stops at iconic gems like Capri, Procida, and Positano. You’ll explore charming coastal towns, swim in crystal-clear bays, and savor authentic Italian cuisine — all at a relaxed Mediterranean pace. Whether you’re a seasoned sailor or just discovering the joy of sailing, you’ll enjoy the perfect blend of freedom and support, guided by our expert team. Space is limited to just three catamarans — reserve your spot today!

The Amalfi coast, south of Naples, is one of the most scenic and popular sailing areas of Italy. Like all our flotillas, this one is a mixture of fun sailing camaraderie, intriguing culture and history combined with mouthwatering local gastronomy. Visit with us the historic ruins of Pompei and Herculaneum, sail to Procida and swim in thermal waters of Ischia, anchor at Capri, wander the streets of Amalfi, Positano and Salerno and enjoy a delicious meal at an agrotourism family farm. This flotilla has become one of our most popular trips and, because of some of the small ports we visit, we have to limit to three catamarans. All our cats come with generator and air conditioning for the occasional warm nights.

FLOTILLA LEADERS

Our flotilla is led by experienced, ASA-certified flotilla leaders who bring deep local knowledge and a passion for creating exceptional sailing experiences. You’ll enjoy the camaraderie of traveling with a group. Each evening, there are optional group dinners ashore, but you’re welcome to explore on your own or dine onboard under the stars. We offer a flexible, friendly format with expert support — whether you’re skippering yourself or simply relaxing as a guest.

Jean De Keyser & Mila Cueva

Jean De Keyser and “Admiral” Mila have been organizing and guiding flotillas for over 15 years. They know the best itineraries, anchorages and places to visit. Capt. Jean is an ASA instructor teaching 101, 103, 104, 105, 118 and 114 certifications. He has a USCG Master license 200T with towing and sailing endorsement. “Admiral” Mila is a USCG 50T certified Captain.

Sample Itinerary

We recommend arriving in Naples on Thursday, giving yourself time to ease out of travel mode, shake off any jet lag, and truly settle into the rhythm of la dolce vita before the adventure begins. On Friday, don’t miss our optional land excursion—a perfect introduction to the region. Step back in time as you explore the fascinating ruins of Herculaneum and Pompeii, followed by a relaxed lunch at a charming local vineyard, complete with wine pairings that showcase the flavors of southern Italy. It’s the ideal way to immerse yourself in the culture, history, and cuisine before we set sail.

Day 1
ARRIVAL
SATURDAY MAY 29, 2027

We’ll gather around noon at the marina in Castellammare to handle paperwork with the charter companies, while some of our crew take care of provisioning for the week. Once the boats are checked out and orientations over, we’ll board and get settled, and later relax over a pizza dinner and night at the marina.

 
Day 2
PROCIDA
SUNDAY MAY 30, 2027

Early morning we will leave the marina and start heading to our first destination, Procida.  The island will captivate you with its charming fishermen’s villages and pastel-colored houses. We will spend the night at Marina di Procida.  The 20 NM sail will give you a perfect introduction to the beauty of the region.  We will enjoy a relaxing stroll in the town, possibly a nice swim on the beach and later a dinner onshore at one of the many local restaurants.

Day 3
ISCHIA
MONDAY MAY 31, 2027

We will sail from Procida to nearby Ischia (13NM), known for its beaches, medieval villages, crystal-clear sea, and thermal springs. The largest island in the Gulf of Naples displays all its beauty surrounded by nature and the sea. Historic buildings complete the island’s rich tourist heritage. We can anchor below the Aragonese Castle and visit the ancient villages with narrow streets full of shops and restaurants.  We make docking reservations at the Port of Sant’Angelo. Dinner at one of the many great restaurants and if you are not afraid of a walk uphill, we definitely encourage you to go to the town of Sant’Angelo and discover the place away from the touristic hassle.

Day 4
CAPRI
TUESDAY JUNE 1, 2027

After a relaxing stop at Baia di Sorgeto, where you can soak in naturally heated thermal seawater (35–37°C), we’ll set sail for approximately 19 nautical miles toward one of Italy’s most iconic destinations—Capri.

Set in the heart of the Gulf of Naples, Capri is renowned for its dramatic beauty, with the striking Faraglioni rock formations and its lively, elegant atmosphere centered around the famous piazzetta.

We’ll anchor for the night on the southern side of the island in the beautiful bay of Marina Piccola. From here, you can take a water taxi to the Sirens’ Beach, and then continue up to Capri town by bus or taxi, both easily accessible from the small square at the top of the steps leading from the beach.

Day 5
AMALFI
WEDNESDAY JUNE 2, 2027

From Capri, our next destination is Amalfi, 17NM away. The Amalfi Coast opens with a first inlet of extraordinary beauty: the Baia di Leranto, a nature reserve. Continuing navigation, one encounters the three islets of Lì Galli, located opposite Positano. Homer described these islets as the place where Ulysses was tempted by the Sirens. Once in Amalfi and safely docked, let’s go explore the narrow streets and monuments, following the main road that starts from the central square and connects all the places of interest, like the Cathedral of Amalfi, the Paradise Cloister and Sant’Andrea’s fountain. The beaches offer unique scenery, clear deep blue waters surrounded by rocks and trees overlooking the sea. Dinner on shore, of course, with Limoncello for after dinner drinks.

Day 6
POSITANO
THURSDAY JUNE 3, 2027

After a short sail, we arrive in Positano, where we’ll pick up a mooring buoy just off the village, offering a front-row view of its colorful cliffside charm. The buoy typically includes water taxi service, making it easy to go ashore and explore.

In the late afternoon, we’ll head out together for a special visit to a local lemon farm, where you’ll discover the secrets behind traditional limoncello and mozzarella making—followed, of course, by a tasting of their delicious products. Afterward, you’ll have time to wander through Positano at your own pace.

With its vibrant energy and stunning setting, Positano always delivers an unforgettable atmosphere.

Day 7
SORRENTO
FRIDAY JUNE 4, 2027

Sailing between Positano and Castellammare offers the opportunity to explore breathtaking coastal gems.  The most famous is definitely the town of Sorrento.  

Sorrento’s location is truly unrivaled. Perched atop a 50-meter rocky cliff, the town offers breathtaking views of the entire Gulf of Naples, with Capri, the island jewels, and the iconic silhouette of Vesuvius all in sight. A visit to the Villa Comunale from the heart of Sorrento is essential for taking in this panoramic beauty. Don’t miss Piazza Tasso and Corso Italia, the town’s bustling hubs filled with charm and history. The Costa delle Sirene is equally famous for its crystal-clear waters, teeming with marine life and perfect for diving enthusiasts. 

We will arrive at Marina di Stabia by 5:00 pm

Day 8
FAREWELL
SATURDAY JUNE 5, 2027

Disembark and say goodbye. Yachts must be vacated by 09:00 am, but the memories, new friendships, and unforgettable experiences will stay with you long after you have left.

*Itineraries are subject to change due to weather or other circumstances beyond our control.

AVAILABLE BOATS
  • Bali, Fountaine Pajot, and LagoonYou’ll be sailing aboard premium catamarans only, including models from Bali, Fountaine Pajot, and Lagoon. Each catamaran with four cabins and four private heads, offering exceptional comfort and privacy for couples or solo travelers. Whether you're relaxing on the spacious foredeck, dining alfresco in a picturesque marina, or swimming from the boat in a secluded bay, these yachts are designed to deliver the perfect balance of comfort and adventure. Throughout the week, we’ll be docking in marinas, mooring at buoys, and anchoring — giving you a well-rounded sailing experience.

PHOTOS

Testimonials

This was my first sailing trip and I had no idea what to expect, but it was the experience of a lifetime! Jean and Mila lead our crew and made the trip flow seamlessly by taking care of every detail. They are knowledgeable, experienced and passionate about what they do! The Med was beautiful and each day, Jean and Mila arranged for us to experience new islands, foods, people, and activities. I would absolutely recommend sailing with them and I cannot wait to return!

Alyssa V.

Loved it. Inclusive, welcoming, great training, fun.

Chris B.

What an incredible Amalfi trip! This marks our second experience with Med Sailing Adventures, and we had an absolute blast. My husband and I are on a journey to become certified sailors, and our first experience with Capt. Belem in 2024 was fantastic as we successfully completed our 103 and 104 certification exams. This time, we had the pleasure of experiencing a catamaran for the first time, and it was absolute luxury! Our boatmates made the experience even more enjoyable by exploring exotic islands with both new and old friends. Capt. Belem, once again, made the practical sailing lessons fun and easy, preparing us for passing our 114 exam. I will cherish our unforgettable experiences in Italy on the Amalfi coast forever. Many thanks to Mila and Jean for their planning and execution of a successful expedition.

Cheryl & Chris

Marina of Departure

Our flotilla departs from Marina di Stabia, Castellammare di Stabia, just south of Naples, and takes you on a curated route through charming coastal towns, pristine bays, and legendary islands like Capri, Procida, Positano, and Amalfi. This region offers a perfect mix of lively ports, peaceful anchorages, and breathtaking scenery — ideal for sailors and non-sailors alike.

Included

Your fully equipped catamaran with linen, towels, dingy and outboard; a dedicated flotilla leader, welcome briefing, support throughout the week, route planning assistance, and a detailed flotilla itinerary

Not included

Airfare & airport transfers.

Onboard expenses such as provisioning (food and drinks), fuel, and mooring or marina fees are typically managed through a shared onboard kitty and split evenly among the crew of each boat. With space limited to just 3 to 4 catamarans, we recommend securing your spot early for this unforgettable sailing experience.

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