Watch Sailing & Boating Adventures Around the World – Page 2 of 6
Explore sailing, boating, and water sports through our curated video archive. From epic sea voyages to serene diving escapes, discover unforgettable adventures from top YouTube creators. Start your journey. Dream big. Sail far.
Showing 25-48 of 138 results
Sailing the Peloponnese | Methoni Fortress, Pylos & Life at Anchor 🇬🇷
Ep. 210 ~ After leaving Kalamata, we sail down the western side of the Peloponnese to the beautiful anchorage of Foinikounta before continuing on to one of the most impressive historical sites we've visited in Greece. We explore the incredible Methoni Fortress, a massive Venetian stronghold su...
Sailing Greece: Sparta, Mystras & the Stunning Castle of Koroni 🇬🇷
Ep. 209 ~ In this episode of Sailing Okaliptus, we take a break from chasing weather windows and explore some of the most fascinating historical sites in the Peloponnese, Greece. After arriving in Kalamata Marina aboard our catamaran, we rent a car and head inland to discover the incredible Byzanti...
TRAPPED Between Two Storm Systems in Greece 🇬🇷⛈️ | Sailing the Peloponnese
Ep. 208 ~ We leave the medieval town of Monemvasia and sail south around the first and second fingers of the Peloponnese, Greece… straight toward two storm systems about to collide right where we are. 😳 After rounding the legendary Cape Malea, dealing with sudden gusts, uncomfortable swell and nons...
Peloponnese Sailing | Monemvasia, Wildfire Planes & Tight Harbor Maneuvers 🇬🇷
Ep. 207 ~ After finally escaping Milos, we change sail plans and return to mainland Greece and sail to the Peloponnese. We are thoroughly entertained by a few dolphins and arrive to one of the most incredible places we’ve visited in Greece... the medieval fortress town of Monemvasia. This sail had...
We Survived 11 Days of Meltemi Winds in Milos, Greece… Then Sailed Into a Military Firing Zone 🇬🇷
Ep. 206 ~ After surviving 11 straight days of powerful Meltemi winds while anchored in beautiful Milos, Greece, we finally decide to leave the Cyclades and sail back across the Aegean to Monemvasia. What started as a peaceful Greek island sailing adventure quickly turned into stress-filled anchorin...
We Got Through the Storm… Then Dragged Anchor 😳 | Sailing Greece (Poros)
Ep. 205 ~ We sailed from the Ionian Sea through the Corinth Canal and into the Saronic Gulf, heading toward Poros with no real plan—just going with what felt right. After anchoring near Poros, a strong southerly storm rolled through with gusts over 30 knots. We were fully prepared, stayed alert, an...
We Sailed the Corinth Canal ⛵️ While People Bungee Jumped Above Us 😳
Ep. 204 ~ We sailed our catamaran through the famous Corinth Canal… and somehow ended up passing directly under bungee jumpers mid-air 😳 In this episode, we leave the Ionian Sea and cross the Gulf of Corinth, passing under the impressive Rio–Antirrio Bridge before transiting one of the most iconic...
Ionian Sailing 🇬🇷 Lefkada to Ithaca | Regatta + Unexpected Raft-Up
Ep. 203 ~ We sail the stunning Ionian Islands of Greece, departing Lefkada and heading south to Ithaca—home of Odysseus and one of the most beautiful sailing destinations in the Mediterranean. What starts as a peaceful anchorage in Desimi Bay quickly turns into an adventure, with shifting winds, an ...
Lefkada Floating Bridge Guide | Sailing the Ionian + New Crew Member 🐶
Ep. 202 ~ Thinking about sailing in the Ionian Islands? If you’re planning a charter in Greece, the Lefkada floating bridge is something you’ll likely have to navigate—and timing, positioning and awareness are everything. In this episode, we walk you through our real-life Lefkada bridge crossing ex...
Is Meteora Worth the Trip? 🇬🇷 | 24 Hour Travel Guide
Ep. 200 ~ Is Meteora worth the trip? In this video, we spend 24 hours exploring one of the most unique places in Greece—home to ancient monasteries perched on towering rock pillars that feel completely unreal. We visit all six active monasteries, including Great Meteoron Monastery and Holy Trinity ...
We Didn’t Expect THESE in the Ionian 🇬🇷 | Life in a Greek Winter Marina
Ep. 199 ~ After a winter of land travel through Central Europe, we’re back aboard our catamaran in Preveza, Greece getting ready for another sailing season in the Mediterranean. But life in a winter marina isn’t just boat work… In this episode, we experience Greek Carnival festivities, celebrate S...
4 Days In Budapest 🇭🇺 The least expensive city in our Europe travels (Part 1)
Ep. 197 ~ In this episode of our Central Europe winter travels, we arrive in beautiful Budapest and spend our first day exploring some of the city’s most iconic landmarks. Starting near the magnificent Hungarian Parliament Building, we wander along the Danube, climb up Gellért Hill for incredible p...
👉 4 Days in Prague 🇨🇿 | Prague Castle, St. Vitus Cathedral & Dancing House (3–4)
Ep. 196 ~ Winter may take us off our sailboat, but it doesn’t stop the adventure. In Days 3 and 4 of our time in Prague, we explore some of the city’s most iconic landmarks — from the hilltop views at Prague Castle to the stunning Gothic architecture inside St. Vitus Cathedral. We also visit the mo...
Too Stoned for Cold War history in High School… Berlin in My 50s Changed Everything 🇩🇪 Travel Vlog
Ep. 194 ~ This winter, we stepped off our sailboat and onto solid ground to explore Berlin, Germany — a city layered with history, resilience and stories that still feel shockingly recent. From the Berlin Wall and Cold War escape tunnels to WWII memorials, Checkpoint Charlie and the neighborhoods w...
Germany Travel Vlog 🇩🇪 | Bamberg & Leipzig | UNESCO Old Towns & Hidden History
Ep. 193 ~ In this episode, we trade our sailboat for solid ground and explore Germany through slow travel, visiting the historic cities of Bamberg and Leipzig. From Bamberg’s perfectly preserved UNESCO-listed Old Town and medieval streets to Leipzig’s powerful monuments and layered history, this jou...
Germany Travel Vlog 🇩🇪 | Munich, Dachau Concentration Camp, the Nuremberg Trials & Zeppelinfeld
Ep. 191 ~ In this episode, we step away from life aboard our sailboat in the Mediterranean and travel deep into Germany’s history. After spending time in Munich, we visit Dachau Concentration Camp, the first Nazi concentration camp, and confront one of the most sobering chapters of World War II. Ou...
Germany Travel Vlog 🇩🇪 | Inside Munich’s Most Powerful Palace | Royal Scandals, Mad Kings & Mystery
Ep. 190 ~ Step inside Munich’s most powerful palace as we explore the Munich Residenz, home of Bavaria’s ruling family for over 700 years. In this episode, we trade life aboard our catamaran for land travel through Europe and uncover the royal scandals, mad kings, hidden rooms, and dark mysteries be...
Austria Travel Vlog 🇦🇹 | We “Sailed” Into Hallstatt | Austria’s Most Instagrammed Town
Ep. 189 ~ Living aboard a sailboat in the Mediterranean usually means salty air, anchorages and open water—but this time, we did something different. We left our catamaran behind and traveled inland to explore Hallstatt, Austria, one of the most Instagrammed villages in the world. In this episode, ...
Austria Travel Vlog 🇦🇹 | Exploring Vienna in Winter
Ep. 187 ~ After months of sailing the Mediterranean, we left our sailboat Okaliptus safely in the marina and headed inland for a winter adventure—starting in Vienna, Austria. In this episode, we explore Vienna’s imperial past and cozy winter charm: wandering Stephansplatz, visiting St. Stephen’s Ca...
Christmas in Greece With Our Winter Family…and Our Emotional Farewell to Zoë 💔🇬🇷
Ep. 186 ~ Join us for a magical Christmas season in Greece as we explore charming winter towns, celebrate with our incredible marina family, and navigate the emotional farewell to our beloved Zoë. From the historic streets of Ioannina and the snowy beauty of Metsovo to the seaside charm of Parga and...
Our Winter Marina in Greece: Life Afloat Over the Legendary Battle of Actium
Ep. 185 ~ Join us in Preveza, Greece, where we're spending our second winter aboard — literally floating above the ancient Battle of Actium. Our winter marina sits right in the Ambracian Gulf, the same waters where Octavian, Cleopatra, and Mark Antony once clashed in one of history’s most defin...
34-Hour Adriatic Crossing: Sailing Montenegro to Greece in Massive Swell
Ep. 184 ~ We spent 34 hours sailing from Montenegro to Greece, surfing massive Adriatic swells, the entire way southbound. The passage itself was beautiful — glowing sunsets, calm skies, and steady rolling seas that kept us surfing hour after hour. With night watches, AIS monitoring, and cargo ships...
From Herceg Novi to Kotor to Tivat: Sailing Montenegro’s Dramatic Coastline
Ep. 183 ~ We were finally ready to sail out of Montenegro’s stunning Bay of Kotor… but the weather had other plans. Again. In this episode, we explore the beautiful seaside town of Herceg Novi, wander its ancient fortress walls, and chase shelter from another incoming storm. From eerie fog-covered f...