Venturing out into the Old Town, your first port of call should be a staple of the Tallinn wine-bar scene – Gloria Wine Cellar. This place carries about it an air of prestige, fitting for what is considered a local institution. The restaurant upstairs echoes days gone by, and the wine-cellar downstairs takes you on a journey to a time long-forgotten. Sit by the fireplace or find refuge in one of the many grottos; Gloria’s wine cellar evokes a feeling of good times celebrated about a century ago, with a wine selection to match.
Head on out to Rataskaevu street just beyond the fairytale-like Town Hall Square – it’s a blink-and-you’ll-miss-it kind of a spot, but Osteria del Gallo Nero certainly lives up to its Italian name. It’s a small bar, serving wine and simple food in a very Italian atmosphere. There’s usually italopop blasting on the stereo system and the selection of fine Italian snacks ranges from your standard prosciutto, all the way up to more exquisite cheeses and marinated vegetables. The tiny room is usually heated up to a temperature that matches hot summer nights in Tuscany, as the owners wish to make their customers feel at home… their home, to be more precise.
From Rataskaevu, it’s only a grapeseed’s throw to get to Lai street, where one can continue the international adventure in discovering viticulture. Just around the corner you’ll find a simple but clever place with a name that carries the most appropriate of all questions – Wine Not? Young wine enthusiast Carlos takes immense pride in showcasing the best his home country has to offer to the world. It may come as a surprise to some, but Portuguese wine is not only limited to just vinho verde, there’s much more to offer. Carlos will not shy away from giving you a lengthy (but very interesting!) lecture on the finer aspects of Portuguese wine. And thanks to a brilliant invention called Coravin, all bottles can be tapped to sample without ruining the quality of the wine.
Taking it even more international by a notch means that you have to walk a few hundred yards further down Lai street to get to Pan y Vino, managed by a Peruvian named Tony. Attracting both tourists and locals, you may walk in on any random weeknight and find yourself surrounded by a lively bunch of people who do not have to worry about having to wake up for that 9am work shift the next morning.