Experiencing Greece on an American Sailing Flotilla

Flotilla: A group or fleet of boats that embark on a shared sailing adventure or voyage. Each vessel operates independently with its own crew, along with a lead boat and flotilla leader who knows the local area well. A flotilla provides opportunities for camaraderie, shared experiences, and the chance to learn from one another. Flotilla organizers often offer support and guidance, assisting with navigation, provisioning, and arranging social activities ashore.

By definition, a flotilla is sailing in a group, but in its essence, it is a social event—a group of boats traveling together from anchorage to anchorage. In Corfu, Greece, this flotilla is accented by stops for swimming in the warm waters of the Ionian Sea, visits to small villages with restaurants that highlight the owner’s prized tomatoes, and seaside historical sites that speak to the rich culture and history of the region.

Yes, a flotilla is about sailing. The sails went up, the boat heeled over, and the chart plotter helped us navigate, but the ocean and our diverse backgrounds bound us forever together.

The Menu 

The Greek alphabet is cruel to Americans. We can’t decipher the simple sounds, and the problematic spellings are confusing. Flavors, on the other hand, are universal. Fried cheese, fish roe pate, octopus, Greek salads, the language of food is both spoken and unspoken.

Captain Dimitris of Fairwinds Sailing Greece, introduced us to a bread salad similar to the Italian Panzanella. It is crusty to start and structured in such a way that when the olive oil seeps into its crevices it resists becoming soggy but instead becomes a receptacle of flavors. Feta cheese has never delivered its flavors as it did in the cockpit of our sailboat. Hummus is creamier when you are sailing in Greece. Savory, salty, sweet, and sour all take on new personalities. Our Jeanneau Sun Odyssey 45 and its spacious cockpit doubled as the dining room of a Michelin-starred restaurant. Our captain delivered dishes like he had studied in a famed culinary school. 

He waived off our praise, “It’s all about ingredients, the tomato, the cheese, the GREEK olive oil, and the oregano.” The crew on the boat all dismissed his humility as he smiled at us while keeping an eye on the wind.

With names like Saganaki (fried cheese), Spanakopita (Greek phylo spinach pastry) and Loukoumades (fried dough balls with honey) the dishes were inspiring to adventurous eaters. As Captain Dimitris explained our sailing itinerary, he received more questions about his ingredients and their cultural significance than his sail trim technique. The sailors took notes on how to make Fava beans with capers and caramelized onions. We jotted the instructions that would make us as talented as our skipper.

How could three ingredients coupled together with Greek olive oil be so good?  Again, Captain Dimitris gave us a simple smile as if he was hiding some special ingredient down in the galley.

The Tourists

When you visit a new town while on vacation, you will surely see obvious signposts that direct you to the tshatshkes that you inevitably fill your carry-on with. But behind every main street populated with tourist traps are the local streets filled with small shops and Tavernas. On this flotilla, we followed a curious cat to a small shop with some handmade leather goods and discovered a bakery on another. Bougainvillea overgrows the windows of quaint shops, and ancient architecture seems to be posing for pictures.

On our first night in Corfu Town, I considered jumping the fire, but I did not have enough liquid courage. An older Greek gentleman tried to coerce me to leap over three piles of burning wood. I wonder why they were burning the wood or why so many people were watching in this dimly lit narrow walkway. The fire illuminated the small alley, and the old buildings’ details glowed in the flames’ hue. I didn’t jump, but on night one in Corfu, on a tiny street behind Corfu Town’s action,  I sensed that this region of Greece was all about fun. Smile as you leap over the fire. Dance when you make it across unscathed, even if no music is playing. 

If there is a simple lesson you get from a flotilla and the travelers you meet on this type of sailing adventure, it is a sense of curiosity. As we congregate on our boats, drinking Greek wine late into the evening, each sailor explains the sights they discovered. Few of them failed to venture into the outskirts of these anchorages. Sailors inevitably want to keep exploring, even on land. By the end of the flotilla, we all would have leaped at the chance to find a few piles of burning wood to jump over.

The Journey

The journey begins in Corfu Town, a blend of Venetian, French, and British influences that grace its architecture and culture. Explore the Venetian fortress, stroll through narrow alleys lined with charming shops, and dine on fresh seafood at the waterfront. American Sailing’s Fairwinds Sailing Greece is headquartered here at Mandraki Marina, so your flotilla begins and ends in this enchanting town. As you set sail, the bustling town fades into the distance, replaced by the deep blue of the Ionian Sea.

Our flotilla ventured south from Corfu to the enchanting bay of Syvota, where lush greenery meets crystal-clear waters. Nestled along the coastline, Syvota is a hidden gem that offers a peaceful escape. We dropped anchor in a quiet cove and swam in some of the clearest water we had ever seen. This first stop on the Greece flotilla was our first experience with rafting our boats together. We went from an individual boat to four vessels of happy sailors. In an instant, we were all friends, and soon we explored the other vessels and shared stories while basking in the sun.

On our next stop, Captain Bampakos suggested one of his favorite restaurants, and they treated us like royalty. The fish was fresh at Taka Taka and the atmosphere was intoxicating. Paxos makes you want to make this quaint village your new hometown. The colorful homes that dot the green hillsides rush down to colorful fishing boats that line the dock. The afternoon sun is chilled by a breeze descending the main channel and delivers a refreshing wind onto our laps as we sample the local wine with massive mezze platters to satisfy our midday lunch needs.

If there was a town that resembled a tourist mecca, it is Parga. Its vibrant palette of colors—turquoise waters, terracotta roofs, and emerald hills is a feast for your senses because they pair well with the aromas coming from the waterfront restaurants. After we dropped anchor, we explored the labyrinthine streets leading to the medieval castle overlooking the town. Dinner along the waterfront and late-night dancing at a local bar had the entire group planning its next sailing adventure together.

One of the great moments in any flotilla is the day before the experience ends. The phrase, “If you know, you know,” applies here. You get to the marina, perform challenging Mediterranean mooring on a tight dock, and then are greeted with a real restroom with showers that have so much water pressure, a toilet with plenty of space, and a place to wash a week’s worth of clothing. Maybe not everybody gets this excited about a marina but our flotilla and every flotilla I have ever been on reacted with joy. 

Mpenitses is a small town on the Island of Corfu at the base of bright green hills. Captain Bampakos called ahead to make sure the prized tomatoes of a local restaurant owner were on the menu. They were. The tomatoes had the texture of a slightly ripe vegetable with the sweetness of ripe dark fruit and a hint of acidity. The entire group of flotilla participants dotted the outdoor seating area of this small but popular restaurant. Our final meal together lasted late into the night and culminated in line dancing on the dock and an out-of-key sing-along.

We all became friends forever.

A Flotilla in Greece 

A Greece flotilla that begins in Corfu differs from what you would expect if you find yourself mesmerized by the Greece on social media. The Ionian Sea is not the Aegean, which is good. The memories made, the sights discovered, and the beauty of the Ionian Sea are unique because of that difference. Greece’s Ionian islands offer a tapestry of landscapes, cultures, and experiences that enrich your soul and rejuvenate your spirit. From the vibrant Corfu Town to the tranquil bays of Syvota, the elegance of Gaios, the vividness of Parga, and the serenity of Mpenitses, this sailing odyssey is your own Greek epic that influencers on social media will not replicate. 

In Greece, the sea is both a path and a destination, leading you to discover the harmonious blend of nature, history, and hospitality that make sailing these waters an unforgettable experience. Captain Dimitris Bampakos of American Sailing School Fairwinds Sailing Greece, fills your imagination with tales about the region’s history and satisfies your cravings with his culinary talents. 

When you arrive back in Corfu, you immediately wish you had a few more days to soak in the smiles of the Greek people and the space to fit in more Greek food and wine.