If you’re on a budget, try Cheburechnaya (multiple locations), a cool Soviet-era throwback. The main dish is, of course, chebureki (a deep fried pastry with meat or cheese filling) but the cafe also offers a range of other Russian classics. If you have some extra money to spend, try Cafe Pushkin (Tverskoy bulvar 26A – metro Pushkinskaya, Tverskaya). Although it’s called a cafe, Cafe Pushkin is really more of a luxury restaurant. The restaurant has been decorated to look a noble per-Revolution estate house and the food is so good it might well have been prepared by someone’s ultra-talented servant. Classic Russian food and, of course, vodka is served.

Red Square is classic Moscow at any time, but it’s best at night. With the GUM department store, Saint Basil’s Cathedral, and the Kremlin walls lit up late at night, you’ll skip the giant crowds that appear during the day and get a perfect memory. Trust me: you + Red Square at 4 AM = magic.

​Known lovingly as “Soviet Disneyland”, VDNKh (short for Exhibition of Achievements of the People’s Economy in Russian) is a sprawling testament to the achievements of the USSR’s states, and now a curious mix of slowly decaying Soviet buildings and shiny new office spaces. It began in 1939 as a dedication to the achievements of the collectivization attempts and morphed into an ongoing Soviet-style World Fair. Today you can still ride a rickety, open-air Ferris Wheel and get a full view of the park and Moscow itself for just about $10.

You can’t get much closer to a sky-high view of Red Square O2 without scaling the Kremlin walls (Ritz Carleton, Tverskaya 3 – metro Okhotny Ryad). Keep an eye out for the rich and famous – most visiting celebrities make time for at least one drink on the rooftop bar. The bar is open year round, but really only worth a visit in the warmer months when the terrace is open.

​Like the popular song said “Moscow never sleeps” – and it’s true! Stay up all night (or at least until the metro opens at 5:30 AM) at one of Moscow’s many all-night clubs. If you want a classic, techno-thumping Moscow experience, try Propaganda (Bolshoi Zlatoustinsky pereulok – metro Kitai-Gorod;) or Che (Nikolskaya 10/2 – metro Lubyanka;). If you like live music, head to Krizis Zhanra (ulitsa Pokrovka 16/16, bldg 1 – metro Chistye Prudy), always filled to the brim with young locals and expats alike.

Located on the third floor of the GUM department store on Red Square, Stolovaya no 57 is a Soviet- style stolovaya (cafeteria) where you can sample different Russian dishes for prices decidedly lower than the rest of GUM. Make sure to grab a table by the window to get a great view of Red Square and the Kremlin walls.

For an ‘everyman’ experience, Kruzhka (Locations throughout the city) can’t be beat. Easily identified by the orange sign outside the entrance, Kruzhka (Russian for ‘mug’) is well-loved among students and football hooligans – often one and the same. The bars are always dark but much improved after the smoking ban enacted in 2014. For cheap beer and greasy appetizers, Kruzhka is hard to beat.

Located south of Moscow’s center, Tsaritsyno Estate (ulitsa Yunosti, 2 – metro Tsaritsyno) is known for its time as the almost-home of Catherine the Great. (Almost-home because a first estate was built that she didn’t like. The second version was almost done when she died.) Muscovites love Tsaritsyno, especially after recent renovations, and there’s nothing better than strolling the bucolic grounds with an ice cream cone.