Best of Estonia

Your chauffeur meets you at Tallinn airport (TLL) and drives you through the cobbled streets to the Hotel Telegraaf inside the medieval walls. After you settle in, your guide-historian joins you for a walk through the Old Town: a climb inside a defensive wall tower, then a look inside a merchant guild hall, with the stories of the Hanseatic League told where they actually happened. The rooftops and spires spread out over the best-preserved medieval capital in northern Europe before the day gives way to a Michelin welcome dinner. The night afterward is your own.

After breakfast inside the walls, your guide-historian opens the modern chapter of Estonia's story with a walking introduction to e-Estonia, on how one of the world's most advanced digital societies handles voting, banking and identity online, told as you go rather than inside a briefing room built for trade delegations. From there you walk together to the Telliskivi creative quarter, a former rail yard now filled with studios, galleries and design shops, where you have time to browse at your own pace and stop for coffee. The afternoon turns to the recent past: the KGB museum on the top floor of the Viru hotel, the once-secret floor from which the Soviet security service watched its guests. You return to the Old Town in the early evening and the rest of the night is free to dine where you choose.

You leave Tallinn before dawn with your guide-historian and chauffeur, heading east into Lahemaa National Park along the northern coast. You reach the Viru raised bog as the first light lifts: strapped onto wide bog-shoes that spread your weight over the soft ground, you walk the bog while the mist still sits on the pools and the cranes call. After the walk your chauffeur carries you on to Vihula Manor, a restored 16th-century estate inside the park, where breakfast is waiting and the afternoon is yours to wander the grounds and the watermill spa. At dusk your guide-historian leads the initiation into the Estonian smoke sauna, a ritual on the UNESCO Intangible Heritage list, in a blackened log bathhouse on the estate. A manor dinner closes the evening.

After breakfast at Vihula Manor you leave with your guide-historian and chauffeur, driving west as the landscape opens toward the flat shore of the Väinameri. At Virtsu you board the ferry to Kuivastu on Muhu, with the low islands passing on either side of the crossing. Your chauffeur drives across Muhu with a stop at Koguva, a village of thatched stone farmhouses, then over the causeway onto Saaremaa. By late afternoon you reach Kuressaare and check in at Arensburg, a boutique hotel with a spa in the old town, a short walk from the castle. Dinner is in Kuressaare.

After breakfast in Kuressaare your chauffeur drives you inland across Saaremaa, the largest of Estonia's islands. Your first stop with your guide-historian is the Kaali meteorite crater, a near-perfect water-filled bowl punched into the land thousands of years ago and long wrapped in local legend. From there you return to Kuressaare and its moated bishop's castle, the best-preserved medieval fortress in the region, where you have time to walk the ramparts and look around at your own pace. The afternoon eases into the hotel spa, a tradition the island is known for, and the evening is yours in the old town for a second night in Kuressaare.

Your last morning begins in Kuressaare with no particular rush. Take breakfast at your own pace, then a final walk round the castle moat or a last turn in the spa before you pack. When you are ready, your chauffeur drives you over the causeway and across Muhu to Kuivastu for the ferry back to Virtsu, with a last look at the islands from the water. From there it is a steady drive across the country to Tallinn, where your chauffeur drops you at the airport (TLL) in good time for your afternoon flight. Your guide-historian sees you off, closing a journey that ran from the medieval wall to the western islands.