Sleep in luxury at The Three Sisters (from $306), Estonia’s only member of the Relais & Châteaux group. Built across three neighboring 14th-century merchant houses on Tallinn’s medieval main drag, Pikk (Long) Street, this hotel still boasts reminders of its centuries-long history, from the wooden crane once used to lift supplies to the upper floors to the original ceiling frescoes, unearthed beneath 14 layers of paint and wallpaper during the 2003 restoration. The 23 rooms are decidedly modern, each done up in a unique style: some with Nordic-inspired, blond-wood furnishings, others with curtain-draped canopy beds and freestanding bathtubs. Relax by the lobby’s wood-burning fireplace or in the cobblestone courtyard garden, and end the day in the cellar Beluga Bar, where czarist-era indulgences like caviar, cigars, and crisp, cold Russian vodka are on offer.
Enjoy the view of Tallinn’s historic Old Town at the Hotel Telegraaf (from $201). Dating back to 1878, this elegant building became the city’s post office and telegraph center upon the 1918 founding of the independent Republic of Estonia. The 86 refined rooms boast high ceilings, subtle Art Deco and historical touches (antique phones), and tiled soaking tubs perfect for relaxing tired limbs after a day traversing the city. Try dinner at the on-site French-Russian fusion restaurant Tchaikovsky, where chef de cuisine Vladislav Djatšuk, a finalist in the gastronomic Olympics known as the Bocuse d’Or, crafts intricate dishes like roasted-pigeon fillet and cabbage rolls of pigeon confit with parsnip and pomegranate sauce ($34).
Kick back in the cozy, 37-room Merchants House Hotel (from $104), built in the shell of neighboring 14th- and 16th-century buildings on a narrow cobblestone street just off of the town square. With chalky limestone walls, crackling antique fireplaces, twisty passageways and beamed ceilings, the space feels straight out of Shakespeare or Chaucer, but the amenities are decidedly contemporary: sleekly simple furnishings, exposed brick walls, and spacious bathrooms with basin sinks and claw-foot tubs. Relax with a steam in the on-site sauna or a treatment at the hotel spa, such as hot-chocolate or warm-honey massages (from $83) and Dead Sea salt exfoliation therapy ($87). Then cool off with a cocktail (from $6) served in a hand-molded ice glass at the lobby Ice Bar.