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Amalfi Coast, Italy

A Guided Flotilla

hosted by Whitecaps Sailing
  • June 07 - 14, 2025
  • 8 Days | 7 Nights

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.

FLOTILLA LEADERS

Don Doggett

Don Doggett is the owner of Sea Safaris Sailing School based in Milwaukee. He is an experienced
sailor and a licensed USCG 100-ton Master Captain. Over 20 years ago, he began his sailing journey on
Lake Michigan and has since been active in the Great Lakes sailing scene. He is also involved in teaching ASA (American Sailing Association) courses for sailors of all skill levels. Don is known for his patient and dedicated teaching style, with a focus on liveaboard cruising courses on Lake Michigan, Lake Superior, Southern Florida, and the Caribbean. In addition to Sea Safaris, Don is also an evaluator for ASA instructor certifications and teaches U.S. Coast Guard (USCG) Merchant Mariner courses.

Sofia Deambrosi

Sofia Deambrosi is a skilled sailor from Uruguay with significant experience in both the Mediterranean
and Caribbean regions. She has become known for her expertise in long-distance sailing and yacht deliveries. Notably, Sofia gained international recognition when she became the first person from Uruguay to row across any ocean. As the skipper of The Bristol Gulls, an all-female team, she successfully completed the Talisker Whisky Atlantic Challenge, rowing 3,000 miles from Spain to Antigua in 2021.

SAMPLE ITINERARY

Day 1
EMBARKATION

We’ll gather around noon at the Marina Castellammare di Stabia 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 the orientations over, we’ll set sail for the stunning island of Procida, a hidden gem far from mass tourism.

Procida will captivate you with its charming fishermen’s villages and pastel-colored houses. Our destination is Marina Corricella, where we’ll spend the night. The 20NM sail will give you a perfect introduction to the beauty of the region, and we’ll enjoy a relaxing evening with dinner onshore at one of the local restaurants.

Day 2
PROCIDA / ISCHIA

We will sail from Procida to nearby Ischia, 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. Roman remains and historic buildings complete the island’s rich tourist heritage. We can anchor below the Aragonese Castle and visit the ancient village of Ischia Ponte and Ischia Porto with its narrow streets full of shops and restaurants. Another place of special interest is the strategically located Torrione di Forio.

Finally, you cannot leave Ischia without visiting the characteristic Borgo di Sant’Angelo, with its colorful houses, outdoor tables and souvenir shops. There are many beautiful beaches, but don’t miss a swim at Cartaromana beach or at Baia di Sorgeto, where you can take a thermal bath in sea water (35/37°C).

We make docking reservations at the Port of Sant’Angelo. Dinner at one of the many great restaurants.

Day 3
CAPRI

Today, we sail about 19NM to one of Italy’s most iconic places, Capri! Capri is a unique island in the heart of the Gulf of Naples. The Faraglioni and the Blue Cave are symbols of its beauty, as is the characteristic piazzetta that attracts thousands of visitors all year round.

The island has a busy port on the northern side, Marina Grande but it is very expensive. Therefore we will go to the the southern side of the island, in the bay of Marina Piccola, where we will anchor for the night. From Marina Piccola you can take the water taxi down to the Sirens’ beach and then go to Capri by bus or taxi, which you will find right at the top of the steps leading from the beach to a small square.

Day 4
AMALFI

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 5
POSITANO

Wednesday always seems like the flotilla hump day. Only two days left after this, but we still have some awesome places to visit, and today it is Positano does not have a harbor but it is possible to anchor in the bay and take one of the buoys provided by the local mooring concession holders, just in front of the village. The price varies according to the time of stay and usually also includes a taxi boat service for those who wish to go ashore in comfort without using their boat’s tender.

Mid-afternoon, we leave for the Bay of Nerano, where we have dinner planned at
Ristorante Il Cantuccio. The restaurant will pick us up from the boats at the buoys.

This is a fun place and ambiance is guaranteed!

Day 6
SORRENTO

Sailing between Amalfi and Sorrento offers the opportunity to explore breathtaking coastal gems, including the Bay of Neranto and Punta Campanella, a protected marine area that stretches 40 km, connecting Massa Lubrense and Positano (be mindful of the reserve’s restrictions).

A stop at Puolo Beach is a must, where the remnants of ancient Roman villas still stand, offering a glimpse into history. As we sail, you’ll spot the striking Vervece Rock, located just off the coast of Massa Lubrense. Beneath this rock lies a statue of the Madonnina, where each September a deeply moving ceremony is held.

Punta Campanella is the perfect place to refresh both body and spirit, offering an array of activities from trekking and diving to climbing for the more adventurous. This hidden treasure of Campania is a true paradise for nature lovers.

Since the port of Sorrento is too small for an overnight stay, we’ll anchor nearby and enjoy the evening either onshore or aboard, with dinner under the stars.

Day 7
SORRENTO / CASTELLMMARE DI STABIA

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. Sorrento’s culinary treasures are another highlight—signature dishes like gnocchi or spaghetti alla sorrentina, and stuffed cuttlefish alla sorrentina are beloved worldwide. Pair them with local specialties such as walnuts, Gragnano pasta, regional wines, and of course, the famous limoncello.

As our flotilla journey comes to an end, we’ll return to base. You’re welcome to spend the final night aboard or opt for a hotel stay. However, the yachts must be vacated by 09:00 on Saturday.

Please Note. This itinerary is meant to serve as an example, however, it is important to note that the actual itinerary is subject to change due to weather conditions or circumstances beyond our control.

PHOTOS
Testimonials
My wife and I loved the bareboat charter flotillas organized by Med Sea 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’ve kept in contact with them. We’ve been to Croatia, the British Virgin Islands and the Amalfi Coast of Italy with them. I’ve been on over a dozen week-long bareboat charters and these are definitely some of the best ones I’ve experienced. They are very well organized, they are focused on creating very enjoyable experiences and they always keep everyone’s safety in the top of their minds. The captains they choose are all very experienced and very safe sailors. Also, the accommodations were very good, and most, if not all the boats that were chartered were relatively new. You’ll have a great time, enjoy!
Samuel & Harriet - Shelton, Connecticut

Great option for sailors and sailor wannabes who do not own a boat, to join Jean and Mila for an amazing family style vacation exploring well organized tours of sea side towns, beaches, caves, historic sites and great food and friends! My only wish is that they would adopt me as a son, and take me along every time!

Joe Coirazza - Quebec, Canada
My husband and I have joined 3 flotillas and have found that Captain Jean’s experience as a sailor and his knowledge of the cruising waters along with “Admiral” Mila’s knack for finding the finest restaurants and interesting places to visit on shore makes Med Sailing Adventures a fantastic, one-of-a-kind vacation! We look forward to many more trips with them.
Dave & Dody - Hood River, Oregon

I have had the pleasure of sailing with Med Sailing Adventures twice in Croatia and in Greece! Both times have been an incredible experience. Both Mila and Jean have the unique skill of bringing people of all ages and experience level together to create an amazing experience no matter where you are in the world. They encouraged me to learn to sail and even get certified to make this a life long sport. There’s nothing quite like it and I feel very safe and secure with Med Sailing Adventures trips knowing I will have the time of my life.

Prestley - Apalachicola, Florida

Details

Marina of Departure: Castellammare di Stabia
Closest Airport: Naples
Currency: Euro
Credit Cards Accepted: Visa and MasterCard

Boats

  • Monohulls $2,295/person
  • Catamaran $2,395/person

Prices are based on double occupancy. To book, a 50% deposit is required. Balance due 60 days before departure.

Not included

Airline tickets, airport transfer, hotel before and after sailing trip, meals ashore.

Shared Costs

Provisioning, refueling, and docking fees are shared among the crew on each boat.

CONTACT US

Please complete the form below if you have questions or would like to make a reservation.

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