Tallinn Estonia, Medieval Old Town Looks Like a Fairytale… Until Russia!

632 views · 33 likes · 13 comments · Oct 2, 2026 · 33:39 · Long
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Tallinn, Estonia old town looked like a medieval fairytale… until we started noticing what was hiding in plain sight. Red rooftops, medieval walls, cobblestone streets, church spires and some of the best views we’ve seen in the Baltic. But the deeper we walked into Tallinn Old Town, the more the story changed. We found a massive Soviet-built complex on the waterfront, a Russian Orthodox cathedral whose location carried a message of power, and a memorial to Estonian government leaders who were executed or died in Soviet prisons and labor camps. Today, inside those same government walls, Estonia runs an independent country. Along the way, we climbed 258 medieval steps inside St. Olaf’s Church, squeezed through one of the tightest stairways we’ve ever tackled, found a tiny chapel that once became a telephone booth, and visited a pharmacy operating since at least 1422, where old remedies included burnt bees, hedgehog, earthworm oil and even human fat. We also explored Tallinn’s ghost stories, Short Leg Gate, Toompea, the House of the Blackheads, Town Hall Square, Alexander Nevsky Cathedral and the Russian Embassy, where today’s tensions made the city’s history feel a lot less distant. We came ashore expecting a beautiful medieval Old Town. We left understanding why Tallinn is about much more than the fairytale you see in the pictures. If you’re visiting Tallinn, Estonia on a Baltic cruise, wondering what you can do independently from the Tallinn cruise port, or just curious about the darker story behind one of Europe’s most beautiful medieval cities, come along with us. ❤️ SUPPORT HUBBARD’S JOURNEY We are not paid by the cruise lines or destinations we feature. We travel, film, and share these experiences independently so we can give you our real opinions and honest experiences. If our videos have helped you plan smarter, avoid surprises, or simply enjoy the journey with us, your support helps us keep traveling, filming, and sharing it all with you. 👇 Become a Hubbard’s Journey Member https://www.youtube.com/@HubbardsJourney/join 👇 Buy Us a Coffee — or a Drink! https://buymeacoffee.com/hubbardsjourney Chapters 0:00 — Tallinn’s Fairytale Has Another Side 0:43 — We Almost Got Hit by a Train 1:14 — The Soviet Giant Tallinn Never Tore Down 2:24 — Fat Margaret & a Tragedy at Sea 4:59 — Once the Tallest Building in the World? 7:21 — 258 Medieval Steps… How Bad Could It Be? 16:25 — This Tiny Chapel Became a Telephone Booth 17:06 — Money, Power & the House of the Blackheads 18:07 — Our “Quick” Food Stop Took OVER AN HOUR 20:37 — The Café That Survived Changing Empires 21:23 — What We Found Outside the Russian Embassy 23:20 — The Medieval Pharmacy That Sold WHAT?! 24:47 — Tallinn’s Ghost Monks 25:33 — The Gate That Split Tallinn in Two 26:52 — Why the Russian Empire Built This Cathedral HERE 28:39 — Tallinn’s Most Famous Seagull? 29:10 — 66 Names Outside Estonia’s Government 29:51 — Why Estonia Felt Different to Us 30:39 — Inside Tallinn’s Medieval Walls 🛍️ SHOP OUR FAVORITES ✅ Hubbard’s Journey Amazon Storefront https://amzn.to/3NOggCA ✅ Cruise Essentials — Pack Like a Pro https://amzn.to/4hs473P As an Amazon Associate, we may earn from qualifying purchases at no extra cost to you. WATCH MORE HUBBARD’S JOURNEY 🎬 View All Hubbard’s Journey Playlists: https://www.youtube.com/@HubbardsJourney/playlists 📱 FOLLOW & JOIN US Facebook Page: https://www.facebook.com/HubbardsJourney Facebook Group — Hubbard’s Journey Crew: https://www.facebook.com/groups/hubbardsjourneycrew 👍 HELP THE CHANNEL GROW If you enjoyed the video, a quick Like, Comment, Thanks, or Subscribe really helps support the channel. Thank you for coming along on our journey. All the best, Michael & Andrea #HubbardsJourney

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