When you hop off the plane in Moscow, there are plenty of sites that are probably first and foremost on your mind … with or without a guidebook in hand.

When you finally get a glimpse of the Red Square and St. Basil’s Cathedral, or take in the uber-Sovietness that is the Kremlin and the KGB Museum, you’ll practically feel the chill of the Cold War traveling up your spine.

But the beauty of exploring a new city is uncovering its local essence, so here are just a few to get you started …

Forget about wine tasting, Moscow locals know that it’s still all about vodka, baby.

Petrov Vodkin is an upscale-yet-affordable Russian restaurant that offers more than 60 types of vodka. You can even order your bottle of vodka frozen into a block of ice—keeps it chilled to that perfect temperature. The restaurant was named after a vodka connoisseur (not the Russian painter by the same name), and his collection of more than 300 vodkas is on display, plus “guest” vodkas from Asia and Europe.

Don’t forget to chase your drinks with some Russian home-style cooking, like “country fish soup,” roast lamb and, er, something that translates into Red Bull Fetish: “Primordial bull tecticles [sic] fried with leek onion and carrots, undressed in white wine & cream sauce, aromatically confused inside the puff paste nest, full of vital force for real men and inquisitive women.” Mmm, sounds….uniquely Russian? +7 495-923-53-56, www.vodkin.ru (in English)

And though Russia has long been known for its vodka, that isn’t to say wine should be avoided completely. Russia has something of a wine industry, with most grapes growing in the southern region. But instead of jetting off to the Black Sea coast, a burgeoning wine bar scene in Moscow means you can stay right in the city for a tasting. It can be a pricey venture, but locals have been flocking to the wine bar Vinosyr which opened last year. Located deep underground, the red-walled room boasts a long bar where jet setters choose from the surprisingly extensive menu of both affordable and expensive wines. +7 495-739-1045

Sampling street food is a great way to experience local flavor … and blinis are truly Russian treats. So how about a blini stand? Teremok Pancake Stalls is a Russian chain that serves up crepe-style blinis. The blinis are made right in front of you with either savory or sweet stuffing—try the herring or the caviar, or if you’re a traditionalist, stick with chocolate filling or a healthy applesauce. You can’t miss the bright orange stands that are scattered throughout the city. https://teremok.ru (in Russian)

This one isn’t quite off the brochure, but it’s sure worth a mention. Head to the Ritz-Carlton, Moscow and splurge on something called the Tsar’s Breakfast … you’ll surely get your protein fix on a $700 meal includes a truffle omelet with Kobe beef, foie gras, a hearty serving of Beluga caviar and a bottle of Crystal champagne. After all, this is the glory of post-Communism. Ritz-Carlton Moscow

If you’re brave enough to travel to Russia in the winter, why not make the best of it and try ice skating? As you can imagine from watching the Olympics (or the weather!), ice skating is practically a national pastime.

For this, it’s worth a visit to the somewhat on-the-brochure Gorky Park. In the summertime, the park is something of a fairground, complete with a Ferris wheel. As Russian carnivals go, it’s one of the least depressing ones.

But rather than shutting down during the frigid winters, Moscovites make the best of it with ice skating. Rent a pair of skates and join the locals as they glide along to blaring music and disco lights, or venture off onto the pathways to avoid the crowds.

You’ve heard of the Bolshoi Ballet, which has long dominated the Russian dance and opera scene. But you may not be familiar with something called the Helikon Opera, founded in 1900. Located in what was once an 18th century home, this intimate theater houses renowned opera, ballet and orchestral performances. You’ll find an interesting mix of classical favorites (coming up are Carmen and La Traviata) along with rarer works and even some experimental theater. www.helikon.ru (in English)

Once the summer residence of an 18th century Russian aristocrat, Kuskovo Estate and Palace Museum is now often referred to as the “Russian Versailles.” The neoclassic estate is located about 10 miles east of Moscow, which is accessible by taking the subway and a bus. Sitting before a man-made pond, the sprawling pink Kuskovo Palace is a massive wooden structure marked by white columns and a rolling horseshoe-shaped staircase. Several cottages on the grounds represent other types of European architecture (i.e. an Italian villa and a Dutch cottage), and you can visit a ceramic museum which features an impressive collection of works. The estate is surrounded by a French-style gardens (hence the Versailles comparison), notable for its manicured grounds and elegant statues. www.kuskovo.ru (in Russian)

Located in the southeastern Taganka region of Moscow, the Novospassky Monastery is said to be the oldest monastery in Moscow. It’s believed to have been built as a fortress in the 1100s, under the reign of Prince Yury Dolgoruky, the founder of Moscow. It was reconstructed in the 1600s, and it has served as Bolsheviks concentration camp, an orphanage, and a clinic for alcoholics. Nowadays, it’s a peaceful site where you can soak in traditional Russian architecture and lounge about on the banks of a small pond.

Lastly, you may have heard of this one, but remember that the Trans-Siberian Express can take you far, far off the Moscow brochure. The train travels three major routes: the “official” Trans-Siberian route to Vladivostok, the Trans-Mongolian route to Beijing, and the Trans-Manchurian route to Beijing. One-way fares start at about $320, and trust us, it’s worth every penny to brag that you traveled on the longest railway in the world, partied with traveling Russians, and took a break from riding by wandering into the depths of Siberia. www.waytorussia.net

By Sarika Chawla and Celestine Albert for PeterGreenberg.com

Don’t forget to check out another helpful trip planning page for discovering Moscow.

For more cities, check out our “Off the Brochure” series.