Last month, 13 crews and roughly 55 sailors handed our passports to the gate agents and boarded flights to Greece for the start of the 2026 club flotilla.
Eventually, the armada joined up at Marina Gouvia in Corfu for boat boarding late in the afternoon. After briefings with the dock crew and provisioning runs to the local supermarket, everyone relaxed in their cockpits for the night and got some rest before the first sail of the trip. (with the exception of those that took part in the Ouzo tasting aboard one of the boats)
Marina Gouvia sits on the northern end of Corfu, while our float plan had us spending most of the week south of the island. That meant a decent 25-mile sail to Sivota on mainland Greece for Day 1. We left the marina with a nice 12-knot breeze on our sterns, but it quickly disappeared and shifted to the bow just a mile or two outside the harbor. Unfortunately, that would become a trend for the rest of the week.
Nonetheless, we took our time heading south, motor sailing until we reached Karvouno Beach in Sivota, where we had prearranged a private dock for the fleet.
Our arrival was a bit confusing because we couldn’t see the dock anywhere, but we were positive we were in the right spot. Then the dockmaster, Nicos, appeared and explained that the dock was invisible and to just follow him in his dinghy. What followed was an epic raft-up of 13 boats just 75 yards off the beach. We settled in, enjoyed happy hour onboard, and eventually made our way ashore by dinghy for dinner.
The next morning, boats peeled away from the raft-up one by one for what was supposed to be a pleasant 12-mile downwind sail to Lakka on the stunning island of Paxos. Instead, we rounded the corner and were greeted with 15+ knots from the south, making for a great upwind beat into Lakka and what would turn out to be the best sail of the trip.
Lakka is the most popular bay on Paxos, so we came prepared to be close to our neighbors and put our newly learned shoreline anchoring skills to work. Using an anchor off the bow and a long line tied to shore allows far more boats to fit in an anchorage while eliminating swing.
As the first boats entered the bay, we picked our spots and deployed this new style of mooring. Just when you thought there was absolutely no room for another boat, five more would arrive and somehow squeeze in. Then it happened again. And again. The process continued right up until sunset.
The waters in Lakka were a brilliant turquoise and made for an amazing day of swimming, paddle boarding, kayaking, and exploring the town and its restaurants. Later in the week, many crews said the meal they had in Lakka was the best of the trip.
The following day, the fleet headed a few miles farther south to enjoy the beauty of Antipaxos for lunch before turning back north for the overnight stop in Mongonisi on the southern tip of Paxos. Leaving Lakka, we again found ourselves sailing upwind, which was almost exactly opposite of the prevailing wind direction. Conditions ranged from 2 knots to more than 20 knots over the course of the nine-mile trip to Voutoumi Beach on Antipaxos.
Voutoumi is home to some of the clearest water in the world, and despite arriving in 15+ plus knots of breeze with a bit of swell, we can confirm the water absolutely lived up to the hype. The fleet soaked it all in. Some hiked to the restaurant perched above the cliffs overlooking the anchorage, while others enjoyed the water before everyone made the short trip to Mongonisi for the night.
Mongonisi is a smaller bay with a town quay and room for a dozen or so boats in the inner harbor. The Harbor Sailboats navy rolled in at the exact same time as what felt like every other charter boat in Greece. A handful of boats secured good spots inside the harbor while the rest took overflow positions in the outer bay.
Holding wasn’t great, and the lead boat was dealing with a poorly timed mechanical issue, so it took a few attempts to get everyone secured using either shorelines or traditional anchoring techniques. Some boats heard the increase in VHF chatter and detected the slightly elevated adrenaline in our voices, so they elected to continue a mile north to Gaios.
In the end, everyone was safely secured with good holding, and we headed ashore for dinner in this small harbor town. Once again, the food was excellent, and with the minor chaos behind us, Mongonisi turned out to be a great overnight stop.
The next day called for a short one-mile move to Gaios, where we would med-moor along the town quay. Gaios is the main harbor of Paxos, and spots along the quay are highly sought-after real estate, so we planned for a 10:00 a.m. arrival.
We enjoyed the daily entertainment of watching boats depart with crossed anchors and tangled lines before it was our turn. The fleet absolutely nailed this new to us style of docking, and we spent the rest of the day exploring Paxos from the interior.
E-bikes, cars, scooters, and ATVs were rented as crews spread out across the island. One flotilla member posted a photo of themselves standing on an arch more than 100 feet above the water, which immediately inspired everyone else to make the hike in search of their own core memory photo. Those with a fear of heights definitely had sweaty palms and shaky legs, but most would agree the view was worth it.
The end of the week was approaching quickly, but we had one more incredible anchorage still to enjoy, the Blue Lagoon near Sivota.
By this point the wind had completely checked out, so a pridefully hoisted mainsail and a reliable diesel engine carried us 10 miles north toward Sivota. This stop had a Plan B in case space was limited or strong northwesterlies developed. Fortunately, the first boats to arrive found the best little cove in the area open, planted the flag, and began filling it in.
With two unrelated boats already occupying the middle of the cove, we still managed to raft and shoreline eight boats inside while the rest anchored just outside.
Naturally, as the last boat approached, the wind that had been absent all day suddenly arrived at 12+ knots from the northwest and kicked up a bit of chop and swell. Unfortunately, it was far too late for Plan B. It was a little sporty for the boats outside the cove for a couple of hours, but the wind eventually eased and everyone enjoyed one of the most beautiful anchorages of the trip.
Shortly before sunset, a local boat with a sign reading “Cocktails and More” rafted up alongside us and jump-started happy hour aboard one of the larger catamarans. After a fun pop-up party, everyone returned to their individual boats for dinner aboard on the final night at anchor.
The next morning, we had nowhere to be except back at the marina by 5:00 p.m., so we took our time exploring the Blue Lagoon, participated in a yoga session on the same catamaran that hosted happy hour, and eventually made our way more than 20 miles north back to Marina Gouvia.
Once again, there was no wind to be found, so we proudly hoisted the mainsail while letting the engine move us along at five knots. We enjoyed the last of our provisions and took our time making the final passage back to the dock.
Back at the marina, we ended the trip exactly the way we started it, relaxing in the cockpit and sharing whatever food and drinks remained.
The next morning, the 13 crews and 55 sailors went their separate ways, but everyone seemed to share the same thought: This was an incredible sailing vacation, and we can’t wait to come back.
2027 Flotilla? Stay tuned around the start of the new year when we announce plans and share the details on how you can join!