Overview
Tuscany... The name evokes images of rolling vineyards, Renaissance art, medieval villages, and the irresistible charm of La Dolce Vita. Yet beyond its celebrated countryside lies another side of Tuscany that few travelers experience—a stunning coastline and the breathtaking islands of the Tuscan Archipelago. Join us as we set sail from Follonica to discover the crystal-clear waters, picturesque harbors, and timeless beauty of Elba and Capraia. Explore charming island ports including Porto Azzurro, Portoferraio, Marciana Marina, and Capraia, each offering a unique blend of history, culture, and authentic Italian island life. Walk in the footsteps of Napoleon Bonaparte on Elba, swim in beautiful secluded coves, savor the flavors of Tuscan gastronomy, and experience the relaxed rhythm of Mediterranean sailing. This adventure combines the best of Italy’s history, cuisine, natural beauty, and the camaraderie of sailing with fellow travelers. Sailing Tuscany is more than a sailing trip—it is an invitation to discover a hidden side of one of Italy’s most beloved regions, where history, island beauty, and the magic of the Mediterranean come together.
Itinerary
Your Sailing Tuscany adventure begins in Scarlino, the gateway to the stunning Tuscan Archipelago. We recommend arriving on Thursday to allow time to relax, adjust to the time difference, and enjoy a welcome dinner at Il Veliero, a wonderful local restaurant where you can meet your fellow sailors over delicious food and wine. On Saturday, after gathering at Hotel La Darsena, we prepare our yachts and set sail toward the island of Elba, beginning our journey through some of Italy’s most beautiful coastal waters. Over the week, we explore the islands of Elba and Capraia, visiting charming ports, swimming in crystal-clear waters, discovering historic villages, enjoying local gastronomy, and embracing the relaxed rhythm of Mediterranean sailing. From Napoleon’s legacy on Elba to the wild beauty of Capraia, Sailing Tuscany offers the perfect blend of sailing, culture, history, and authentic Italian island life.
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SATURDAY
We meet in the late morning at Hotel La Darsena in Scarlino before heading to the marina for lunch and provisioning. In the afternoon, we check in aboard our yachts and prepare for the week ahead.
Around 17:00, we set sail toward the island of Elba and the charming waterfront village of Porto Azzurro, where we will spend our first night. Enjoy dinner at one of our favorite seaside restaurants, followed by a stroll and, of course, a stop at Sub Zero for an unforgettable gelato.
SUNDAY
Embracing the Italian philosophy of Dolce Far Niente, we enjoy a leisurely sail to Portoferraio, with time for a refreshing swim and lunch on board along the way.
Explore this charming historic town, discover its colorful waterfront, and follow in the footsteps of Napoleon Bonaparte, who spent his exile here. In the evening, enjoy dinner at one of the many excellent local ristorantes or trattorias.
MONDAY
We leave the scenic harbor of Portoferraio and set sail on a 24 NM crossing to the beautiful island of Capraia, part of the Tuscan Archipelago National Park.
Arriving in this charming fishing village, take a walk up to the old fortress overlooking the harbor and enjoy the island’s unique atmosphere. In the evening, celebrate the day’s adventure with dinner and a bottle of local wine at one of Capraia’s welcoming restaurants.
TUESDAY
After a relaxing night, we sail along the coast of Capraia and anchor at Cala del Moreto for a swim in its beautiful waters. Discover the island’s fascinating geological formations and enjoy views toward distant Corsica before sailing back to Elba.
We arrive at Marciana Marina, a charming seaside village on the western coast of Elba, where we will spend the night and enjoy dinner at one of the local restaurants.
WEDNESDAY
Today we leave the coast and head into the mountains above Marciana. A short transfer brings us to this charming medieval village, where we will enjoy a refreshment before walking to the unique cable car that takes us to the summit of Monte Capanne.
At 1,019 meters (3,343 feet), Monte Capanne offers spectacular views across Elba and the surrounding islands. Bring a sweater or light jacket—the mountain air can be cool, but the breathtaking scenery is well worth the ride.
THURSDAY
Time to head back to the mainland. We cross from Marciana Marina to Punta Ala at the entrance of the Bay of Follonica, about 25NM. Dinner on shore.
FRIDAY
Sadly, our final day has arrived. We make the most of our last hours on the water with a leisurely sail through the Bay of Follonica as we return toward our base in Scarlino.
If the wind is light, we will enjoy one last swim from the boats or relax at a nearby beach before returning to the marina and saying farewell to a memorable week of sailing.
SATURDAY
After breakfast, we say goodbye to our yachts by 09:00 and take with us the stories, friendships, and moments that made this sailing adventure special.
The islands of Elba and Capraia may be behind us, but the beauty of Tuscany, the friendships forged along the way, and the spirit of the sea will remain long after we step ashore.
Hosts
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.
Gallery
Reviews
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
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
