Italy · 29 May - 5 June 2027

Italy Flotilla - Amalfi Coast

Sail through the picturesque waters visiting hidden gems like Procida, Capri and Positano.

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Overview

Join our Amalfi Coast flotilla for an unforgettable sailing adventure that blends stunning landscapes, cultural immersion, and camaraderie. Sail through the picturesque waters of the Amalfi Coast and the Sorrentine Peninsula, visiting hidden gems like Procida, Capri, and Positano, while enjoying the freedom of life at sea. You’ll explore historic towns, savor local cuisine, and have time for swimming, or simply relaxing. Whether you’re an experienced sailor or new to sailing, this flotilla offers the perfect balance of structure and flexibility, with expert guidance along the way. We will limit this flotilla to 3 catamarans, secure your spot soon!

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.

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SATURDAY

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.. 

Procida

SUNDAY

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.

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MONDAY

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.

Capri

TUESDAY

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.

Amalfi

WEDNESDAY

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… 

Positano

THURSDAY

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.

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FRIDAY

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

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SATURDAY

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.

Hosts

Capt. Jean and

Capt. Jean and "Admiral" Mila

Capt. Jean and 'Admiral' Mila have been organizing sailing flotillas with the American Sailing Association since 2009, introducing both sailors and non-sailors to captivating destinations in the Mediterranean and other destinations such as Seychelles, Brazil, Thailand, BVI and the Bahamas. With their deep knowledge of the sailing waters, they take participants to hidden gems not typically known to tourists. Safety is their top priority, ensuring that every participant returns home with unforgettable memories and a sense of adventure.

Jean, a native of Belgium, holds a USCG 100T Master License and teaches ASA 101, 103, 104, 114, 105, and 118 in both Florida and the Mediterranean.

Mila, originally from Peru, is the Admiral of the flotilla and the mastermind behind the organization. As a US Coast Guard captain with a six-pack license, she commands the respect of her crew while maintaining a dynamic leadership style that keeps everything running smoothly.

Together, they operate Whitecaps Sailing, an American Sailing-certified school based in Southwest Florida.

Catamaran

Catamaran

Double Cabin - Private Head

FROM$2,950.00/pp

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Enhance Your Journey

Catamaran Endorsement - ASA 114

Catamaran Endorsement - ASA 114

Obtain your Catamaran Endorsement while Sailing the Amalfi Coast

FROM$595.00/pp

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Reviews

CherylandChris

What an Incredible Amalfi trip! This marks our second experience with Med Sailing Adventures, and we had an absolute blast! Will cherish our unforgettable experiences in Italy on the Amalfi Coast forever!

Cheryl & Chris - Florida
SandyHarriet

We love the flotillas organized by Med Sailing Adventures! Mila and Jean are wonderful hosts and they create great trips at interesting locations. They foster an air of camaraderie. We've made great friends from the trips and we have kept in contact with them. We've been to Croatia, BVI and the Amalfi Coast with them. Very well organized, focused on creating very enjoyable experiences and always keeping everyone's safety in the top of their minds. The captains they choose are all very experienced and safe sailors. You'll have a great time!

Harriet & Sandy - Connecticut

Dates

May 2027
  1. Mon
  2. Tue
  3. Wed
  4. Thu
  5. Fri
  6. Sat
  7. Sun

Catamaran

29 May - 05 June 2027

FROM$2,950.00/pp

BOOK NOW
Italy Flotilla - Amalfi Coast

Italy · 29 May - 5 June 2027 · 7 nights

FROM$2,950.00/pp

BOOK NOW