Sail with us through the beautiful Tuscan Archipelago, where the relaxed rhythm of Mediterranean sailing meets the charm, history, and flavors of Italy. This flotilla is as much about the people you meet as the places you discover—sharing sails, meals, laughter, and adventures with a wonderful group of fellow travelers and sailors, and often returning home with friendships that last long after the week is over. With experienced flotilla leaders, daily guidance, and the comfort of having a group around you, there is safety in numbers while still giving you the freedom to enjoy the trip at your own pace. From the timeless beauty of Elba and the wild character of Capraia to crystal-clear waters, charming island villages, and authentic Italian hospitality, this is Tuscany from a completely different perspective.
Join us for a week of sailing through the beautiful Tuscan Archipelago, exploring the islands of Elba and Capraia. Enjoy crystal-clear waters, charming Italian villages, fascinating history, great food and wine, and the freedom to experience Tuscany from the water.
You’ll sail aboard a cruising catamaran or monohull, with comfortable private cabins. Whether you are an experienced sailor or simply love being on the water, you can participate as much or as little as you wish.
The beauty of a flotilla is having the freedom of an independent sailing vacation with the reassurance of an experienced team and other boats around you. With daily skippers’ meetings, weather guidance and group communication, there is safety in numbers—and plenty of opportunities to share sails, meals, laughter and adventures with fellow sailors. Many of our guests come as strangers and leave as friends.
Included: flotilla fee, use of the yacht, linen and towels, dinghy and outboard, and final cleaning.
Not included: airfare, hotels and airport transfers.
The crew of each yacht shares equally the cost of provisions for meals aboard, fuel at the end of the week, and mooring and docking fees.
Capt. Jean and Mila have been organizing sailing flotillas with the American Sailing Association since 2009, leading sailors and non-sailors through some of the Mediterranean’s most beautiful and fascinating destinations. Capt. Jean is a U.S. Coast Guard Master 100T and ASA-certified sailing instructor with extensive experience aboard both private and charter yachts, while Mila holds a U.S. Coast Guard Captain’s license and serves as the flotilla’s “Admiral,” overseeing the organization, logistics, and guest experience. Together, they bring decades of sailing, chartering, teaching, and flotilla experience to every trip, with safety, camaraderie, and fun at the heart of their leadership.
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.
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.
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.
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.
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.
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.
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.
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.
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.
What an Incredible trip! This marks our second experience with Med Sailing Adventures, and we had an absolute blast! Will cherish our unforgettable experiences in Italy forever!
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!
