Sazerac at the Sazerac Bar in the Roosevelt Hotel
The Sazerac is the Official Cocktail of the City of New Orleans, so you should start your crawl at the bar that bears its name. Situated in the Roosevelt Hotel, which stretches the entire block between Baronne Street and University Place, the Sazerac Bar was a favorite watering hole of former senator Huey P. Long in the 1930s. Not much has changed since then—you'll find the same elegant polished dark wood and cozy-yet-ritzy atmosphere that made the place famous. The ritual of this classic drink is worth observing: your bartender will rinse a glass with Herbsaint and then pour in the perfect propotion of Sazerac Rye, simple syrup, and Peychaud's bitters, garnished with a perfectly-trimmed lemon swath. Though almost any bar in town will serve a Sazerac, you'll be doing yourself a service by visiting its spiritual home to receive a drink made with careful attention, good rye, and respect for tradition.
Sazerac Bar in the Roosevelt Hotel: 123 Baronne Street, New Orleans, LA 70112 (map) 504-648-1200; therooseveltneworleans.com/dining/the-sazerac-bar.html
Ramos Gin Fizz at Cure
If there is any cocktail in the world that requires love and attention, it's the Ramos Gin Fizz, and you can trust the professionals at Cure to take the time and effort to deliver a drink that'll live up to the hype. Cure has hit nationwide Best Cocktail Bar lists since opening in 2009, well over a hundred years since Henry C. Ramos first introduced the drink that bears his name. Back in Mr. Ramos' time he used to employ a line of dozens of drink-makers to keep shaking up his fizzes. Now at Cure each bartender is willing to take the (significant) time to shake this classic to to its fullest potential—first, there's a full minute without ice to emulsify the egg white and cream, and then another minute with ice to finish it off and bring down the temperature. At Cure, the combination of Tanqueray gin, egg white, lemon juice, simple syrup, cream, sparkling water, and a few drops of orange flower water turns into something greater than the sum of its parts.
Vieux Carré at the Carousel Bar in the Hotel Monteleone
For over sixty years the slowly-revolving Carousel Bar in the Hotel Monteleone on Royal Street has entranced visitors. The bar itself, fashioned as an ornate Merry-Go-Round, stays still as its patrons enjoy a quarter-hour-long tour of the room. The Vieux Carré was invented here in 1938, and named for the French Quarter, or "Old Square." The cocktail features Sazerac Rye, cognac, Benedictine, sweet vermouth, and both Peychaud's and Angostura bitters; the staff at the Carousel Bar knows how to hold back the Benedictine just enough to keep it from over-sweetening the drink and making it a cloying mess. The view out onto Royal Street from the recently revamped lounge area can't be beat, and you never know who you'll find sitting next to you on your journey.
Milk Punch at Perestroika at Pravda
Brandy Milk Punch is typically a brunch cocktail, but this rich drink is by no means limited to morning hours. Perestroika at Pravda is an up-and-coming cocktail dealer on lower Decatur Street. In the process of shifting the space from the vodka and absinthe bar they inherited to the rum-focused establishment they intend to be, they still have time to focus on the classics. Their version of the Brandy Milk Punch splits the difference with the Bourbon Milk Punch by going half and half on the main liquors (they use equal parts Fighting Cock Bourbon and Landy Cognac.) Demerara syrup adds extra richness, and freshly-grated nutmeg gives the drink a lively aroma.
Pimm's Cup at Napoleon House
The perfect balm for the serious Louisiana summer heat can be found in the Pimm's Cup, a relatively low-alcohol highball that has become a part of New Orleans tradition—particularly at Napoleon House, which is situated in a building that's over two centuries old. The Napoleon House Pimm's Cup—best enjoyed in their open-air courtyard—is simple and hangover-soothing, made with Pimm's No. 1, lemonade, 7-Up, and a cucumber garnish.