The Iron Curtain Archipelago

Arrive in Tallinn. Morning briefing and kit check, then ride west along the coast to Haapsalu — a town that was itself a restricted Soviet zone. The railway station at Haapsalu was built with an extended platform to accommodate Stalin's armoured train during state visits; the platform is still there, longer than anything the town could currently need. Night in Haapsalu.

Early ferry from Rohuküla to Heltermaa. Hiiumaa was a restricted zone throughout the Soviet period — the island housed radar installations and served as a buffer for the naval approaches to Tallinn. Entry required Interior Ministry approval. Ride the western coast on narrow asphalt and packed gravel, with almost no traffic. The landscape has not recovered a sense of being visited. Night in Kõrgessaare.

Circumnavigate Hiiumaa. The Tahkuna peninsula in the north — a lighthouse and German WWII defensive positions facing the sea. The Ristna lighthouse on the westernmost point of Estonia. Pine forest tracks through the island interior where Soviet military installations were built away from the coast and away from satellite visibility. Night in Kärdla.

Cross from Hiiumaa to Saaremaa via the Sõru–Triigi ferry. Saaremaa was the most militarised of the Estonian islands — home to a strategic air base, coastal missile batteries, and radar arrays that monitored NATO shipping in the Baltic. Ride south through the forest interior to Kuressaare. The bishop's castle, one of the best-preserved in the Baltic, was used as a Soviet military headquarters for most of the occupation. Night in Kuressaare.

The Tehumardi night battle, September 1944: Red Army forces landed on Saaremaa's southern coast in darkness and encountered German defenders in close-quarters fighting. A monument marks the site. Coastal gravel tracks east to the Stebel battery — concrete Soviet gun emplacements facing the sea, built in the 1950s to defend against NATO surface incursions. The emplacements stand open in the grass, the guns removed, the infrastructure intact. Night in Kuressaare.

South to the Sõrve Peninsula — a narrow strip of land 35 km long that was the last part of Estonia held by German forces. The Wehrmacht held the peninsula until November 1944 to cover the evacuation of Army Group North. Soviet-era radar and missile facilities in the pine forests inland from the main road — some accessible on forest tracks, most unmarked. The peninsula tip, where the sea is visible on three sides. Night in Kuressaare.

Morning ferry back to the mainland. Ride north to Tallinn. Final debrief at the old port — the same harbour through which Soviet military equipment arrived to garrison the islands. The restricted zone began at the water. It ended there too.