Tuscany , Mediterranean hosted by Whitecaps Sailing June 24th - July 1st 2023 starting from $2,095

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Jean & Mila De Keyser
Tuscany, for many years, has been some of the most popular tourist attractions of Italy but is still relatively undiscovered by North American sailors. Here is a unique opportunity to combine a vacation in Italy with a sailing trip to explore the magical beauty of the Tyrrhenian Sea where you will sail to the islands of Elba and Capraia.Visit Napoleon Bonaparte’s house in Portoferraio on Elba, the charm exuding small ports of Capraia, Porto Azzurro, Marciana Marina and anchor in a scenic cove for a refreshing swim. At the end of an exhilarating day of sailing, reward yourself with a delicious dose of Tuscan cuisine and wines.

Flotilla Leader

Jean “John” and Mila De Keyser have been organizing sailing flotillas for over a decade and have introduced many sailors and non-sailors to fascinating destinations. They know the sailing waters and show participants places that many tourists do not know. They put a heavy emphasis on safety while ensuring that participants go home with fun and unforgettable memories.

Jean a native of Belgium, is a U.S. Coast Guard licensed Captain and Master 100T as well as a sailing instructor certified by the American Sailing Association. He teaches 101, 103, 104, 105 114 & 118 in Florida and in the Mediterranean.

Mila, born and raised in Peru, is for all intents and purposes the Admiral of the flotilla, master organizer, first mate and the proverbial strong woman behind her husband.

Together, they run Whitecaps Sailing, an ASA certified sailing school in Florida and offer charter brokerage services.


Departure is from Scarlino Marina in the bay of Follonica, about 140 miles from Rome and 105 miles from Florence.
Currency: Euro
Monohulls (Oceanis, Sun Odyssey). Catamarans (Bali)

Prices are based on double occupancy starting at $2095 per person, includes flotilla fee, charter fee, tourist tax, outboard. Airfare, airport transfers, hotels before and after the cruise, and dinners on shore are not included. Provisioning, docking and mooring fees, and final refueling are shared by means of a common kitty on each boat. The cost per person is about $250.00 and final accounting is done for each boat at the end of the week.

ASA 103, 104 & 114 instruction and certification available. One dedicated yacht with an ASA instructor will follow, students will enjoy the flotilla experience while training. Minimum 2 students, maximum 6. Contact us for pricing.


  • 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!

    Prestley N. – 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 I. – Jackson, TN

  • We went with Jean and Mila to Croatia on our first “Flotilla” several years ago. It was a superbly orchestrated event. The sailing was outstanding and the ports were spectacular. The trip gave some independence but was “group” enough for the novice Cruiser too! Jean was great “tour guide’ for the trip. We returned with Jean and Mila to Mallorca with the whole family, this trip too was outstanding! The culture, the food, The sailing!

    Kevin S. – 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!

    Dody L. – Hood River, OR