Eclectic Estonia: Coastal Cliffs to Prison Quarry

Our private tours skillfully walk the line between rich historical depth and an engaging, fun narrative style – led by a knowledgeable and passionate native Estonian guide who knows this country inside out. We weave honest personal anecdotes into our grand narratives, connecting Estonia's picturesque and versatile sights with centuries of triumphs and tragedies, present-day realities, and future aspirations. Real stories, real history, no fluff. We respect your time.

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Estonia might be a tiny country, yet it hides a long, layered, and often hidden history, waiting to be explored. This tour is an excellent example of the many historical contrasts you can find relatively close together here — in fact, this route gives us glimpses of most of the foreign invasions and their corresponding fortifications in Estonia. From the medieval crusades, through centuries of oppression under foreign nobility, to grand imperial ambitions and stark Soviet occupation. Fortunately, it won't feel too oppressive, as the day will be spent driving around the countryside, with multiple stops and walks in picturesque parks and on dramatic coastal cliffs towering above the Baltic Sea.

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• We'll start the day with an underground visit to the remnants of an audacious imperial defense plan that was never finished due to the revolution, the royal massacre and the crumbling of the empire in Russia.

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• At various points today, we'll pull over on the towering coastal cliffs to gaze over the deceivingly calm-looking Baltic Sea. In the otherwise rather flat Baltics, this is the closest you can get to a dramatic vertical scenery.

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• A lovely little walk will take us into the Keila-Joa Manor park with views of what's considered Estonia's most romantic waterfall and the neogothic castle itself perched above it. 

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• Onwards in Paldiski, we would have entered a town that did not exist, at least on the Soviet-era maps, for it became one of only three nuclear submarine training complexes in the entire Soviet Union.  Paldiski hides many secrets, some lost without a trace, while others can still be glimpsed. We'll show you what is still left!

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• We'll explore what's left of the mighty 14th-century Padise Monastery — at turns a monastic retreat, military stronghold, and noble estate. Its stone walls have stood since almost the beginning of written history in this land.

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• To finish the day, we'll visit the surreal landscape of the former Rummu prison quarry, reclaimed by nature and elements for half a century, and now rediscovered again as an odd alternative adventure playground.​​

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​The usual tour route will specifically show and tell you about all the following sights:

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• Remnants of Peter the Great's coastal military fortifications from the heyday of the Russian Empire

• North Estonia's limestone coastal cliffs & the Baltic Sea​

• The picturesque Keila-Joa Manor park, Keila-Joa Castle & the romantic Keila-Joa waterfall

• Paldiski, the former top-secret Soviet military town

• 14th-century Padise Monastery

• The sunken Rummu prison quarry

If there’s a place you’re curious about that's not listed, just let us know. We’ll do our best to weave it into your tour and our story. Book your own journey along Estonia's north coast and through its diverse history, and let's turn your visit into a personal and meaningful experience, full of stories and emotions that you'll actually remember!

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​​​​Photo credits: Thank you to Kaupo Kalda; Rasmus Jurkatam; Rene Altrov; Aleksandr Snitovskii; Sam Mcallister; Kadi-Liis Koppel; Thomas Lotter; Mark Harisson; Jorden Tually; Vivian Velle; VisitTallinn.ee