Greece is a special and wonderful place for us. We love the people, food, history, architecture, and especially the gorgeous islands! Given this, we decided to take a Grecian holiday on a sailboat for two weeks. Before sailing, we began with a few nights in Alexandroupolis (also Alexandroupoli) and then sailed from the Kavala harbor to the islands of Samothraki (also Samothrace), Limnos (also Lemnos), Agios Efstratios, and Lesvos (also Lesbos). Afterwards we enjoyed Athens for a few days of basking in the beautiful Acropolis. There was drama and adventure amongst gorgeous islands in the Aegean Sea!
Prologue (before sailing): Our first few days in Alexandroupoli (Αλεξανδρούπολη) were delightful in the cute seaside town. The prominent Alexandroupolis Lighthouse is one of the tallest in Greece. It was built to help ships navigate between Türkiye’s Bosporus through the Dardanelles Strait and into the Mediterranean. We enjoyed exploring, walking the promenade, eating at local cafes, and the sweet cats.
Sailing Day 1: The sailing departure location adjusted (originally Alexandroupoli) to Kavala (Καβάλα). So we took a bus (with the most helpful staff and driver) to meet up with the beautiful catamaran (Magdalena), Italian Captain (Fulvio), and crew from the USA (Giannis & Jordan). Our 14 day sailing adventure begins!
After dropping off our bags, we wandered through Kavala enjoying the stunning Kamares (“Arches”) aqueduct which likely has Roman origins though the current structure was constructed by the Ottomans. We walked up to the Kavala Fortress that overlooks the sea port and beautiful water (and the very reason Kavala is called the Blue City). Kavala is along the Via Egnatia, the ancient road from Rome to Istanbul (formerly Constantinople) built by the Romans in 2 BCE.





Sailing Days 2-3: Our first sail of the trip was from Kavala to the gorgeous island of Samothrace (Σαμοθράκη)! The crew didn’t have sailing experience, so Bob taught them some sailing basics along the way (he’s an amazing teacher!). We explored the island for a couple of days in while docked at Kamariotissa (Καμαριώτισσα). Our first afternoon, Bob, Fulvio, Jordan, and I (Giannis stayed on the boat) visited Samothraki village/Chora (Σαμοθράκη) where we saw the Church of the Assumption of Mary including the reliquary containing the skulls of the five neo-martyrs from the Massacre of Samothrace. We also found a sweet kitten that was both lazy and feisty, walked through the streets by the Castle of Chora, and enjoyed the view from the beautiful Cafe “Tower” (Καφε “Ο Πύργος”).





The next morning, Bob and I rented a car for the day so that all five of us could adventure along the north side of the island to the Fonia Gorge (Φαράγγι του Φονιά). We hiked to and swam in multiple pools with waterfalls! On our way back, we stopped in Therma for a final swim at the Cascadas “Paradise” (Βάθρες “Παράδεισος”). Sadly, we were too late from our hike to visit the beautiful Sanctuary of the Great Gods (Ιερό των Μεγάλων Θεών), the original location of the glorious Nike of Samothrace in the Louvre! Next time!




Sailing Days 4-9: We motor-sailed on to the island of Lemnos (Λήμνος) where we anchored in Mirina (Μύρινα) harbor. It was a stressful sail because the Captain didn’t want to plan moves in advance (extremely helpful for teaching and minimizing mistakes) and yelled at the crew a lot (an issue in sailing, more here and here―though I fully acknowledge that sometimes dire situations need yelling and sometimes you have to speak loudly to be heard). Once anchored and ashore, we enjoyed walking in town with with Jordan and Giannis, hiking up to the castle, and saw a gorgeous sunset across the sea behind Mount Athos (Άγιο Όρος).




The following morning, Giannis left the boat. It was a hard and tough situation, due to poor communication (the aforementioned yelling, uncommunicated expectations about crew duties, playing favorites, and additional last-minute guests during the second week for a very full boat). Bob and I were able to enjoy a final morning coffee with him before he left. The small silver lining was that he headed to visit family in Greece for the rest of his vacation.
Later that day the now four of us left from western Lemnos, sailed around the south of the island, and found the loveliest cove. Bob and I enjoyed swimming to shore, walked around, and even took a little hike for a beautiful sunset showcasing the catamaran and Mount Athos once more! The wind picked up and we had an easy sail back to Mirina (Μύρινα) where we picked up two couples from Italy for our second week on the boat. We enjoyed hiking to the Castle of Myrina again with one of the Italian couples and visited more of the restaurants and shops.






Sailing Days 10-11: We sailed on to the tiny but lovely island of Agios Efstratios (Άγιος Ευστράτιος)! We docked there and found the sweetest kitty that really wanted Bob’s dinner (he resisted) at the delicious restaurant Artemōnas (ΑΡΤΕΜΩΝΑΣ). The next day we walked around town, discovered a gorgeous mural, enjoyed a hike, and took beautiful photos at the Church of the Holy Five Martyrs.








Sailing Days 12-14: From Agios Efstratios, we sailed on to the island of Lesbos (Λέσβος). We first stopped on the north side at Mithymna (Μήθυμνα) where we enjoyed a quiet visit. The next day, we sailed a bit and on our way, we stopped at a swimming hole and discovered pretty rock formations. We then sailed to the town of Sigri (Σίγρι). It was very windy from the north so we anchored in the south cove.
After anchoring we took a little siesta… when Bob noticed that we were dragging our anchor and were rapidly were getting closer to the boat behind us. In an instant, Fulvio got the engine started and Jordan pulled anchor, but our anchor caught the chain of the boat behind us (which we saw when our anchor stopped just out of the water with the other boat’s chain on one side―and also because the other boat was now following us closely as we motored forward to pick up our chain and anchor). We were unable to separate the two using a line from inside the boat. Given this, the only solution we could think of was to have Bob get in the water (if at all possible NOT recommended, though everything turns out okay). Fulvio captained and had the helm, Jordan worked the windlass, and I shouted (yes, yelled) orders at everyone. Fulvio did an amazing job of keeping the boat in a single spot, Jordan perfectly dropped the anchor on my command, and Bob assisted with all of this from the water without getting caught in anything. We ultimately were able to drop our anchor quickly enough that the chain came off. WHEW!!! It was very tense and dramatic! We then re-anchored and got situated.
After an actual siesta, we headed ashore where we enjoyed walking by the Sigri windmill (now a private home), our visit to the Molyvos Castle, and Captain Fulvio (also our chef) bought squid and made delicious calamari! The next morning, we visited the Natural History Museum of the Lesvos Petrified Forest (Μουσείο Φυσικής Ιστορίας Απολιθωμένου Δάσους Λέσβου). The island has one of the most intact petrified ecosystems in the world formed from a volcanic eruption 20 million years ago. There are fully preserved standing tree trunks, roots, leaves, and amber!









Our final stop was Plomari (Πλωμάρι) where we had a dramatic docking. We had never done stern-to docking (also Mediterranean or “Med” mooring) where a boat is anchored in front, and then backed in to a dock and didn’t know that was the plan. It ultimately worked but there was confusion and yelling. After this, Bob and I skipped dinner at the boat as it had been a long second week including translation challenges (please don’t speak about people using their names and then don’t translate or bring them into the conversation, especially when you know they don’t speak that language) and the aforementioned super full catamaran (9 people by this point in 4 cabins+2 crew cabins).
Epilogue (after sailing): All said, however, we had a successful trip, many fun memories, and we truly do love Greece. We learned that we do know a ton about sailing (gaining perspective from a more seasoned captain), we are capable (figuring things out when challenges arise), and that we can help those interested in sailing learn (teaching the crew the basics and methods).
From Plomari, Jordan joined Bob and I on a bus to Mytilene/Mitilini (Μυτιλήνη) where we enjoyed visiting and seeing the gorgeous views from the Castle of Mytilene (Κάστρο Μυτιλήνης). Jordan departed after our castle visit and Bob and I stayed and enjoyed Mytilene for two nights. Before leaving, the hotel owner in Mytilene offered us another night for free because we were such great guests. We were unable to stay due to our travel plans, but how sweet is that?!? We then took our flight to Athens (Αθήνα) feeling very cool (rock star vibes!).




Athens was as fun and glorious as we remembered (previous post here: #28 Athens and Ancient Greece). This time, we saw the Panathenaic Stadium (Παναθηναϊκό Στάδιο), revisited the Gate of Athena Archegetis (Πύλη Αρχηγέτιδος Αθηνάς), and the Tower of the Winds (Ωρολόγιο Ανδρονίκου Κυρρήστου).
We also visited the Acropolis Museum (Μουσείο Ακρόπολης) for the first time and enjoyed the full LEGO Acropolis, preserved history, and beautiful reconstructions. We revisited Little Kook which had a princess romantic theme (they fully commit to their decorations)! Our final stop was another stunning Areopagus Hill (Λόφος Αρείου Πάγου) sunset which is always both busy and beautiful. Athens is a wonderful little big city and I so love the history, cats, and stones (i.e. architecture and structures)!










Thanks for making it to the end! Your reward is a Greek island video walk with me enjoying the fuzzy locals… they help make the best cheeses!
