Round Robin Bar
Allegedly, Kentucky Senator Henry Clay established the official recipe for the mint julep on the site of the Willard in the early 1800s, and the stately Round Robin Bar still proudly serves it today -- Maker's Mark bourbon, mint, sugar, and branch water for $15. Upstairs, the Scotch bar serves from the menu of over 130 Scotches -- one of the most extensive selections in the city.
The Oak Bar
Overlooking Grand Army Plaza on the southeast corner of Central Park, the Oak Bar -- which first opened in 1907 for men only -- is almost as iconic as its parent hotel. Stick to the classics, and sip slow: that sidecar cocktail will cost you $19.
Alibi is located in the "drunk tank" of the former Charles Street Prison, where those arrested for public intoxication were kept overnight -- a unique place to relive a little Boston history (hopefully on better terms). Thick brick walls with cell doors and windows, original stone floors from the jail, mugshots of celebrities like Sinatra, Morrison, and Nolte hanging on the walls, and jail-themed cocktails like "the doing thyme," "the walk of shame," and "Gordon Gekko," are unsubtle reminders of the bar's theme. But leather couches, dark wood tables, and candelight make the experience much pleasanter today than it was for its former visitors.
With its butterfly-covered ceiling, stuffed peacock in the corner, and plush banquettes, this 1930s Vietnam-inspired bar is one of the best places in Hollywood to share a drink with a starlet in hiding. Beyond the celebrity factor, the Chateau's comfortable bar is a wonderful place to enjoy the fantastic food. The "damn good burger," we can assure you, lives up to the name.
King Cole Bar
Even if you can't afford to stay at the St. Regis, it's worth stopping in the King Cole Bar for a nip. According to legend, it was the first place in the country to serve a Bloody Mary, here called the Red Snapper. The signature cocktail can be had for a mere $18, while other cocktail prices inch into the $20 range. The bar also serves small plates like a half-dozen oysters ($20) and a sliced steak sandwich ($34). Behind the bar is the famous Maxfield Parrish mural. (Why are the courtiers in the painting laughing? Supposedly because the king has just passed gas.) Grab a seat in the small, dark woody bar if you can.
The Last Hurrah
The Last Hurrah delivers a taste of historical Boston -- literally and figuratively. Located inside one of the country's oldest hotels, the bar has a classy, old-time atmosphere -- leather-cushioned chairs; wood paneling; men in sports coats -- and here you can sample the hotel's famous Boston cream pie, invented at the hotel in the mid-19th century. Or better yet, you can order the Boston cream pie martini from the bar's extensive martini menu. Other drinks, like the Dickens Punch (Charles Dickens read A Christmas Carol for the first time on American soil here), also relate to the hotel's history, and the whiskey menu is one of the most impressive in Boston.
Top of the Mark
Come for a drink, stay for the view. The Mark Hopkins' famous bar is, as the name suggests, on the top floor of the historic hotel. That places it 19 stories up, in a landmark building that sits at the apex of Nob Hill, one of the highest points in San Francisco. All that elevation adds up to one of the best views in a city renowned for its views, as you can see to the left. And unlike at the top of Coit Tower or Twin Peaks, at the Top of the Mark you're protected from the wind and totally free to imbibe.
The dark-wood-paneled Oak Bar, located in the historic Fairmont Copley Plaza (founded in 1912) is evocative of a Bristish Officer's Club in East Asia -- coffered ceilings, mirrors, marble. It feels like the kind of place where dashing men in suits casually make deals over martinis and oysters while eyeing a blonde in the corner. But the venue knows who it's catering to -- a more mature crowd who can splurge on one of the most extensive martini menus in the city.