Tuscany, Italy, Mediterranean hosted by Sea Safaris Sailing School
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Jean & Mila De Keyser
Tuscany has, for many years, been one 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 coves for a refreshing swim. At the end of an enjoyable day of sailing, reward yourself with a delicious dose of Tuscan cuisine and wines.

Tuscany Flotilla Leader

Capt. Jean and “Admiral” Mila used to own the charter company and sailing school, Yachting Vacations, in Punta Gorda, Florida. Jean is an ASA sailing instructor (201, 203, 204, 214, 218 and 205) and holds a USCG Master 100T with sailing and towing endorsement. He has extensive sailing experience in the Gulf of Mexico and the Mediterranean as well as in offshore sailing. Jean and Mila have been leading ASA flotillas in Croatia for the past 10 years and in Spain, Italy, Montenegro and other destinations.

Tuscany Flotilla Details

Our itinerary will be to sail from Scarlino to Porto Azzurro on the island of Elba, where Napoleon Bonaparte was briefly exiled. We will spend the first night there. From Porto Azzurro, we will sail to the north coast of Elba to Portoferraio and visit the house of Napoleon and the old city. The next day we head towards the island of Capraia, where we will overnight in its beautiful little port, walk up to the old fortress that dominates the harbor and have dinner at a local restaurant. After a restful night, we will sail along the coast of Capraia and anchor for a swim at its southernmost point in the Cala del Moreto, then cross back to Elba and sail to Marciana marina. The following day, weather permitting, we will go by bus to the old village of Marciana and take the cable lift from there to Monte Capanne for an impressive panoramic view of the island. After spending the night at Marciana marina we will be sailing back on the mainland and spend the night at Castiglione della Pescaia, a lovely old fishing village with excellent marina and restaurants. Friday we return to Scarlino with some more good sailing in the Bay of Follonica and some last refreshing swimming on the way back.

We strongly encourage you to add some Italian tourism to this trip either before or after the flotilla. Tuscany is worth staying a few days. Visit Florence, Sienna, Pisa and some hidden gems like Pittigliano in the mountains. Of course, nobody should forget a stop-over in Rome with its hundreds of historic attractions.

Airports: Rome (3 hours away by car) , Pisa (1 hr 20 min) , Florence (2hr 10 min)
Flotilla Departure: Marina di Scarlino, near Follonica.
Currency: EUROS

Our yachts will include Jeanneau’s, Beneteau’s and Bavaria’s.
The flotilla cost per person will be $1,750.00 based on double occupancy.
Each yacht has a purse or kitty to cover docking or mooring fees, provisioning and final refueling.

  • Included: use of the yacht, flotilla fee, flotilla souvenir, welcome party.
  • Not included: airline tickets, excursions, on shore dining.

Need more convincing that this is an amazing flotilla? Read the recap of our 2019 Tuscany flotilla >>

  • Dody & Dave
    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.

    Dody & Dave

  • I thought the trip was an experience of a lifetime with opportunities to see new geography and to get to know nice and interesting folks. There were balanced occasions to sail and crew, all the while learning from experienced mariners. The luxurious boats that Med Sailing Adventures chartered were first class with more bells and whistles than one could image. Jean was very astute about the local culture and history. Of course, there were great pastries, pizzas, stuffed squashed blossoms, and wine ashore. Not to forget the water – it was crystal clear!

    Richard D.