Alibi at The Liberty Hotel, Boston (pictured above)

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,  mug shots of celebrities like Frank Sinatra, Jim Morrison and Nick 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 candlelight make the experience much pleasanter today than it was for its former visitors.

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: Those tasty cocktails aren't cheap.

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 its name.

Top of the Mark at the Intercontinental Mark Hopkins San Francisco

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; it's a pretty sweet spot.

Round Robin Bar at The Willard Intercontinental, Washington, D.C. [mhc1] 

Allegedly, Kentucky Sen. Henry Clay established the official recipe for the mint julep — Maker's Mark bourbon, mint, sugar and branch water — on the site of the Willard in the early 1800s. Upstairs, the Scotch bar serves from a menu of more than 130 Scotches — one of the most-extensive selections in the city.

The dark wood-paneled Oak Bar is located in the historic Fairmont Copley Plaza (founded in 1912) and is evocative of a British Officers' 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 that can splurge on one of the most-extensive martini menus in the city.

You can’t return a bad vacation. That’s why Oyster.com, “The Hotel Tell-All,” and partner of The Travel Channel, comprehensively visits, photographs, reviews and rates each hotel we feature. Basically, we uncover the truth, before it’s “uh-oh” time.