Book lovers with room on their itinerary for destination drinking may want to raise a glass to their favorite scribes at these legendary watering holes. Books and booze continue to be a classic combination, as demonstrated by some of history’s greatest writers and their barhopping habits. F. Scott Fitzgerald, Dylan Thomas and Ernest Hemmingway definitely weren’t strangers at their local pubs. At these literature-themed hotels, wine and the written word go hand in hand.
The Friends of the Library Association (now a division of the American Library Association) designated this French Quarter hotel a literary landmark, and it’s easy to see why. Authors who’ve visited the hotel’s famous spinning Carousel Bar or booked a stay include Anne Rice, William Faulkner, Stephen Ambrose, Truman Capote and John Grisham. The hotel makes an appearance in several written works, including Tennessee Williams’s play, The Rose Tattoo, Eudora Welty’s short story, The Purple Hat, and Ernest Hemingway’s short story, The Night Before Battle. Keep an eye out for the five literary suites named after famous writers.
Age of Innocence author and Pulitzer Prize winner Edith Wharton designed The Mount in 1902, in keeping with the architectural principles outlined in her book, The Decoration of Houses. Though the estate has gone through many incarnations following Wharton’s self-imposed exile to France in 1911 (including a stint as a girls’ school and a theater), it still seems to embody her spirit and is open for tours. Don’t miss the ghost tour offered at night—it touches on Wharton’s infamous supernatural experiences chronicled in her writing. After a stroll through the mansion and lovely, landscaped grounds, stop by the Terrace Café for light sandwiches, wines and beer from local Big Elm Brewing from May until October
One block away from the stately New York Public Library, The Library Hotel stays true to theme. It offers 60 bookshelf-stuffed rooms devoted to subjects from astronomy to ancient literature. Inspired by the Dewey Decimal System, floors are dedicated to the 10 major classifications of knowledge, including art, literature, philosophy and language. With more than 6,000 books scattered throughout the rooms and common spaces, there are plenty of nooks for reading. Don’t miss the complimentary wine and cheese reception held daily from 5–8 pm in the Reading Room. It includes a selection of Prosecco, red and white wines and imported cheese to peruse while you get your literary fill.
Virtually unchanged for decades, the Red Key Tavern is a neighborhood institution and served as a backdrop in Dan Wakefield’s novel, Going All the Way. The cash-only bar has a throwback vibe that would inspire any budding author. The jukebox is stocked with rare 45s. You won’t find any newfangled cocktails here, just a solid lineup of 32 beer choices, a smattering of wine and a full bar.
Although the bar has undergone a few changes since it was a hangout of Ernest Hemingway (the bar was then called Russell’s), Sloppy Joe’s is a legend in the Florida Keys. In the years following Prohibition, the bar attracted Lost Generation scribes including Hemingway and a motley crew of creative types like author John Dos Passos and artists Waldo Pierce and Henry Strater. Each summer, the bar holds a Hemingway lookalike contest, and crowds come year-round to scope the writer’s pictures, memorabilia and to enjoy live music.
For a bonus sip, check out Captain Tony’s Saloon halfway down the block, a storied bar that has long-claimed to be “The First and Original Sloppy Joe’s.” The endless tug-of-war between the two bars over where Hemingway frequented has become a part of Key West lore, but most locals agree that “The Bard” probably had his fair share to drink at both.
Whether you come to study your date or simply get lost in one of the many volumes that line the walls, this intimate Fillmore District hangout creates an ambient yet cerebral atmosphere. In addition to more than 30 wines by the glass, wine-based cocktails and saké flights, there are “study snacks” like potato skins and BLT bites. Don’t feel like reading? Take in an offbeat flick projected on the bar’s brick walls or stop by on a weekend, when deejays spin heady R&B and funk tunes.
Framed photos of Jack Kerouac and Allen Ginsberg adorn the walls of this eclectic bar. Established in 1948, it became the stop of choice for Beat Generation writers in San Francisco. Grab a beer or a mixed drink—the Swinging Beat combines organic vodka, Cointreau, pomegranate liqueur and fresh lime juice—and take in this literary landmark. Vesuvio is conveniently located across the street from the classic indie book shop/publishing house City Lights Bookstore, founded by poet Lawrence Ferlinghetti and professor Peter D. Martin.
This West Village tavern is most famous for being a Dylan Thomas hangout, whose portrait adorns a wall. Sadly, the Tavern was also the last stop of the poet’s final bender in 1953. The story goes that Thomas collapsed after consuming 18 shots of whiskey, and later died at St. Vincent’s Hospital. Other famous authors that purportedly enjoyed a pint at the Tavern include Hunter S. Thompson, Norman Mailer and Jack Kerouac. Today, the crowd is a mix of tourists and undergrads, but true poetry fans will want to make the pilgrimage.
Inspired by Oscar Wilde’s love of good drinks, this former hardware store is now a shrine to the witty Irish writer. His sayings, famously including “love and gluttony justify everything” adorn the restaurant’s walls, and a modern portrait of Wilde hangs above a working fireplace. In addition to creating a plush Irish pub feel, there are stained-glass touches and a library nook perfect for an evening read. There’s also an extensive brew selection, including flights and cocktails.