Most visits to Estonia include time in Tallinn with a side trip to Tartu or the western islands. These are all good ideas but there is a lot more to see of Estonia’s busy history and wooded eastern expanses. A hire car is essential to be able to travel readily although the distances are not great.

Cold War Islands

Saaremaa is Estonia’s largest island, and was a major Soviet Cold War defensive site with restricted entry during the Soviet occupation. The Sorve Peninsular has a series of sites from the Cold War and it’s an easy day trip south of Kuressaare.

Taking a counterclockwise route round the peninsular, you pass first through the site and memorial of the Battle of Tehumardi, where in October 1944 advancing Soviets – largely consisting of recently conscripted Estonians – encountered a German blocking position. A confused night battle led to the German withdrawal south until they evacuated for East Prussia and further defeat. Today it’s a partly reforested area running down to the sea, with a Soviet memorial and military cemetery.

Driving further south will take you to the abandoned missile base at Maantee (https://maps.app.goo.gl/3pLnvfLQwdzjBK7h6) with its dingy abandoned Soviet administrative blocks.

There are random observation posts dotted around the coastline, where many a Soviet conscript spent a freezing and pointless night looking for incursions.

The southern tip of the Sorve peninsular has a good local Cold War museum (https://www.visitestonia.com/en/sorve-museum) that houses wartime and occupation artefacts as well as random military items recovered locally.

Northwest of the Sorve museum along the coast road is the Stebeli Battery (https://maps.app.goo.gl/qJWEohHVpQzDiHsA6), named for the Russian commander who commanded it during the German October 1941 invasion. There’s a memorial and a multi-level command bunker (enter at your own risk), but the twin artillery pieces have long since been removed.

Kuressaare is an excellent base from which to cover the island. It’s superbly preserved 17th-century castle, dominating the small town harbor, is worth a visit and set in a large park. There is a set of modern “spa hotels” just south of town that offer clean rooms and solid breakfasts – I stayed at the Meri which worked out great. There is a good choice of pubs and restaurants within walking distance along Tallinna road.

Road Tripping Estonia

Unless you are heading in and out of a city in rush hour, or on the main Tallinn-Riga/Narva highways, Estonian roads are largely quiet – more so if you cut across the country. Driving east from Kuresaare, you can stop at Viljandi for its castle ruin overlooking the local lake, and a history that largely consisted of being in the center of various conflicts from the 17th century onwards. Kohvik Fellin (Tasuja pst 1, Viljandi) is a good lunch stop.

From there it’s a short drive to Tartu, Estonia’s second city, main university town and home of the Estonian independence movement. It’s a good stopover and worth a visit in it’s own right, more details here https://www.aerotrekka.com/tartu-time/.

From Tartu, you can drive along Lake Peipsi, which takes up much of Estonia’s eastern border with Russia. Lake Peipsi is a popular summer destination but can be appreciated for it’s desolation in the winter.

You can drive up along its northern side until you reach the border village of Vasknarva, which overlooks the Narva River and has a small castle ruin. After that, head through the forest to Johvi and join the road to Narva. Stalinist-era architecture enthusiasts should consider a pause at the planned 1950s city of Sillamae, built on the site of a popular 19th century seaside resort (Tchaikovsky visited) and then industrially repurposed for oil shale and uranium processing.

Castles Galore

Estonia has had the experience of being located in a region contested by German Balts, Poles, Swedes and Russians, as reflected in the number of fortifications covering various strategic points. The otherwise drab post-Soviet border town of Narva – pulverized in the 1944 battles and functionally rebuilt – offers Narva Castle, a huge and well-preserved largely 15th/16th-century castle that gives you a view of the corresponding Ivangorod fort on the opposite side of the River Narva, as well as the auto queue into Russia. The castle has a well-laid out tour guide, and after taking in the large courtyard and grounds (look for the statue of Lenin, pointing East, located in a maintenance yard), you can go up the main Herman Tower for views into Russia.

From Ivangorod, St Petersburg is a 160-kilometer straight shot, but you should take your visitor dollar impact elsewhere.

From Narva Castle, take the footpath north under the road bridge and walk along the riverside walk, made up from bastions built by the Swedes to (ultimately unsuccessfully) protect from Russian invasion.

From there, you get a good view of Ivangorod across the river. On the road back to Tallinn, Rakvere is a good stopover, with its own 13th-century castle.

Logistics

As ever, I recommend a Bradt Travel Guide whenever available – they do a great job covering smaller countries, especially when you want to see more than the main attraction. Kuressaare is a good base from which to explore Saaremaa and similarly Tartu for the east.

Traveling to Estonia’s western islands by car requires ferry tickets – it’s worth booking ahead online at https://www.praamid.ee/en/homepage/ once you have your arrival time at the ferry dock worked out.