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Mediterranean Flotilla ~ Italy's Amalfi Coast

a guided flotilla hosted by Whitecaps Sailing
  • 7 Days & 6 Nights
  • May 25 - Jun 01, 2024

This will be an amazing sailing experience along the most popular coastline of Italy. Discover the top attractions, like Sorento, Amalfi, Capri, Pompei.

Enjoy the world-famous Italian cuisine and wines and learn about the amazing Italian culture and history while sailing the azure blue Mediterranean waters.

We will be sailing catamarans and monohulls and we will be offering the possibility for students to earn ASA sailing certifications during this flotilla.

Amalfi promises to be one of the most sought after destinations in Italy in 2024 and early booking is a must.

Flotilla Leaders

Capt. Jean and “Admiral” Mila have been organizing sailing flotillas with American Sailing since 2009 and have introduced many sailors and non-sailors to fascinating destinations in the Mediterranean and Seychelles. They know the sailing waters and show participants places that many tourists do not know. They put a very heavy emphasis on safety while ensuring that all participants go home with fun and unforgettable vacation memories.

Jean, a native of Belgium, lives with Mila, his Peruvian-born wife, in Florida. He holds a USCG 100T Master’s license and is qualified to teach ASA 101, 103, 104, 105, 114, and 118. Together they run Whitecaps Sailing, an ASA sailing school in Punta Gorda, Florida.


After a lazy morning, “Admiral” Mila will lead the provisioning party and raid the local market and grocery stores.

Once our check-in of the yachts and chart orientations are done, we should be able to drop the lines and leave the marina around 17:00 and sail to the island of Procida, where we will have dinner on shore and spend the night.

Procida will amaze you with its scenic beauty. It is an island away from mass tourism, characterized by its fishermen’s villages with pastel-colored houses, we plan to spend the night at Marina Corricella.


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 will visit to the Aragonese Castle, its 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 Ischia. Dinner at one of the many great restaurants.


Today, we sail 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.

After touring the island by sea, you can take the chairlift up Monte Solaro, walk along the Pizzolungo path through the Natural Arch, visit the Gardens of Augustus with Via Krupp below, the Charterhouse of San Giacomo, look out over the Tragara Belvedere and visit the Roman remains of the Villa di Tiberio.

The island has a busy port on the northern side, Marina Grande but, for those who like the coves, the southern side of the island, in the bay of Marina Piccola, towards the Faraglioni is the place to moor. From Marina Piccola you can take the tender down to the Sirens’ beach and then go to Capri by bus, which you will find right at the top of the steps leading from the beach to a small square.

We will try to get docking arrangements in advance at Marina Grande, from where we can go in search of dinner in one of the local trattorias.


Next stop… Positano. 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.

Maybe have dinner on board tonight and make it a flotilla potluck party?

Before we leave on Wednesday, let’s have breakfast at the bar Pasticceria La Zagara, one of the most famous and fragrant terraces in all Positano. The magnificent vertical town on the Amalfi coast, with its steep staircases and winding paths, has been a vacation resort since Roman times.

For those who want to walk a bit we recommend walking along the Sentiero degli Dei with a breathtaking panorama that includes the Amalfi Coast and Capri. Positano also has beautiful beaches such as Spiaggia Grande, Fiumicello, Fornillo, La Porta or San Pietro Laurito.


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 Amalfi.

The Amalfi Coast opens with a first inlet of extraordinary beauty: the Baia di Ieranto, 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.


Sailing between Amalfi and Sorrento offers the possibility of visiting beautiful coastal areas such as the Bay of Ieranto and Punta Campanella, a marine protected area that joins the municipalities of Massa Lubrense and Positano for 40 km (pay attention to the restrictions of the reserve).

Puolo Beach, where the ruins of some Roman villas still can be seen, is worth a stop. We then come in sight of the Vervece rock, which stands opposite the Massa Lubrense beach. A statue of a Madonnina has been placed in the depths under the rock and every year, in September, a very evocative ceremony takes place there.

Punta Campanella is ideal for rejuvenating the body and spirit. This gem of Campania is perfect for numerous activities, from trekking to diving to climbing for the more adventurous.

Docking for the night in Sorento and dinner on shore.


Sorrento occupies an extremely advantageous position. Situated on a 50- meter rocky spur, it offers a unique vantage point from where to observe the entire Gulf, including Naples, Capri and the unmistakable profile of Vesuvius. Starting from the center of Sorrento, a visit to the Villa Comunale is a must!

Piazza Tasso and Corso Italia are among the town’s most important urban destinations.
Crystal-clear waters and outcropping rocks provide an ideal habitat for many sea creatures and are a true delight for divers. Another strong point of the Costa delle Sirene is the rich culinary tradition that has produced recipes known everywhere, such as gnocchi or spaghetti alla sorrentina or stuffed cuttlefish alla sorrentina. Walnuts, wine, limoncello, and the traditional Gragnano pasta are some of the area’s specialities.

This is the last day of the flotilla and to the base return we must…

You can elect to stay on board for the night or book a hotel but, by 09:00 on Saturday we must vacate the yachts.

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


Jean’s sailing and organizational skills are of the highest quality! Everyone took turns at the helm while Jean kept an eye out for trouble. We had a wonderful experience cruising with Jean and Mila. We would sail anywhere in the world with them!

Kevin and Delana
Oklahoma City, OK

After listening to Jean’s presentation about sailing in Croatia at Strictly Sail Chicago, I was sold! My instincts did not fail me. The trip to Croatia was so fantastic that we signed up for the flotilla in Spain a few years later. With their vast experience and knowledge of Mediterranean sailing, Jean and Mila lead groups of both novice and skilled sailors to explore beautiful islands and enjoy the culture and gastronomy that each destination offers. We are looking forward to many more trips with Med Sailing Adventures!

Hood River, OR

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. Thank you Jean and Mila!

Apalachicola, FL

We just finished a week sailing with Jean and Mila! They were absolutely wonderful and took us to some amazing places in Croatia and Montenegro! I highly recommend sailing with them. We had some great laughs and created some incredible lifelong memories. Bravo Jean and Mila…

Robin and Tom
Jackson, TN

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