Louie's Afterdeck (& Upper Deck)
A wooden deck with a bar that juts out over the Atlantic, this one is all about the beautiful setting. Sunset proper happens on the other side of the island but watching the evening fall over the ocean, with the clouds illuminated with brilliant oranges and pinks, is just as spectacular. Designed as a sort of waiting lounge for upscale restaurant Louie's Backyard, the deck works just as well for a peaceful drink or two at dusk, as you listen to the waves lap against the beach below. And if you're hungry but don't feel like dinner at the restaurant, the more casual Upper Deck located upstairs (among the tops of the trees) offers smaller plates and an excellent wine selection.
• +1 305 294 1061, louiesbackyard.com. Afterdeck open daily 11.30am-1am, Upperdeck open Tue-Sat 5pm-10pm
Orchid Bar
One of the smaller bars you're likely to come across, this eight-seater craft cocktail spot delivers in a big way on quality drinks and a stylish setting. Located poolside in the beautifully revamped 1950s-style motel The Orchid Key Inn, the Orchid Bar offers fresh and seasonally inspired cocktails with syrups and cordials that are made on premises. It's a perfect grown-up spot to observe cocktail hour.
• +1 305296 9915, orchidkeyinn.com/orchid-bar.html. Open Sun-Thurs 1pm-11pm, Fri-Sat 1pm-midnight
The Chart Room
Tucked inside the sprawling luxury resort of The Pier House, the snug Chart Room has stood on the same spot since the 1960s – in fact, the hotel was built around it as specified in the original contract. A dive hidden in the middle of a fancy hotel, this is a funky little wooden cave with photos of famous guests pinned to the walls: Tennessee Williams, Truman Capote, Jimmy Buffett – and offering free popcorn, hot dogs and peanuts, with the discarded peanut shells carpeting the floor.
• +1 305 296 4600, pierhouse.com/Dining/chart_room.asp
The Gardens Hotel/d'vine Wine Gallery
A sprawling former private estate has been converted to a 16-room luxury hotel, and the main house features the d'vine Wine Bar, with over 35 wines on offer, and multiple options of tastings. Enjoying a glass in the secluded grounds, surrounded by palm trees, flowering bushes and hanging orchids, is idyllic. Jazz combos play on Sunday afternoons when the pool bar is open to non-guests. The no-kids policy is just one part of why this is a highly civilised spot to get a quiet drink.
• +1 305 294 2661, gardenshotel.com. D'vine Wine Gallery open Wed-Sun 5pm-10pm, Pool Bar open Sun 5pm-8pm
The Porch
Somewhat improbably located in the middle of the touristy end of Duval Street, where the bars are loud and geared to frat boys and cruise-ship passengers, The Porch is tucked away from the main drag and partially obscured by a large garden. The clientele are cool, friendly locals who are there to relax, so you could find yourself sitting next to an architect, a stand-up paddle board instructor or a bartender (this is a big off-duty bartender hangout). With an impressive rotating selection of craft beers and wines, The Porch is a chill haven at this end of town.
• +1 305 517 6358, theporchkw.com. Mon-Sat 10am-2am, Sun midday-2am
Bagatelle
Downstairs at this restaurant/bar is a solid fine-dining restaurant, but it's when you pass through the lounge and ascend a hard-to-find (just ask) staircase that you find a hidden gem: an outdoor deck, nestled atop a lush canopy of palm trees. The martini bar within the restaurant is front loaded with stirred cocktails such as The Mexican (Don Julio Silver, fresh lime and agave – perfect on a balmy night) and the astro-tastic Buzz Aldrin (a vodka and Tang martini). This is a late-night, service-industry party spot, with DJs on deck at the weekends.
• +1 305 296 6609, bagatellekeywest.com. Open daily 9am-midnight
Don's Place
This down-and-dirty bar caters to both serious late-night drinkers as well as early risers: Don's Place only closes briefly between 4am and 7am (opening at a restrained noon on Sundays). Situated a few blocks off the main strip, it's all about beer and shots here. There's always a game of pool to be had, and there's a dilapidated outdoor "tiki bar", as well as a convenient drive-through liquor store in the same building – Don's really has all your partying needs covered. It's far from fancy but, of course, its very lack of pretension is its principal charm.
• +1 305 296 8837, donsplacekeywest.com. Open Mon-Sat 7am-4am, Sun midday-4am
Hogfish Bar and Grill
Stock Island is the considerably more ramshackle neighbouring key just north of Key West and it's there, among trailer parks and dusty boatyards, that you'll find this waterfront seafood shack. Overlooking the fishing docks of Safe Harbour, the open bar and grill serves fresh seafood – you can literally watch the boats carrying your meal to the dock across the way. Beers served in metal pails filled with ice are the drink of choice here, and peeled pink shrimp caught that morning and Baja fish tacos are the standout dishes. Great for a lazy afternoon of drinking and snacking.
• +1 305 293 4041, hogfishbar.com. Open Mon-Sat 11am-midnight, Sun 9am-midnight
Point 5 Lounge
Situated on the second floor of a Victorian house (atop the restaurant 915), the vibe at this lounge is decidedly mid-Atlantic cool crossed with sub-tropical island laidback vibes, and the soundtrack is chill-out mixes peppered with groovy DJs on weekend nights. The proprietor is a former club-owning Brit and this is one of the more urbane, even trendy, spots on the island. The menu consists of savoury nibbles – the Vietnamese chicken rolls are excellent but there are also several good vegetarian options, as well as a smart assortment of thin, brick-oven pizzas. A Eurocentric beer and wine list is nicely complemented by a strong cocktail list: the gin and tonic with house-made tonic is a standout.
• +1 305 296 0669, 915duval.com/point5-lounge. Open Mon-Thurs 5pm-midnight, Fri-Sat 6pm-2am, Sun 6pm-midnight
2 Cents
The casual atmosphere at this outdoor restaurant/bar belies the seriousness of the cuisine and the cocktails. Chef Chris Otten cut his culinary teeth in Portland, Oregon, and brings that local and seasonal aesthetic to Floridian ingredients, with his own eclectic sensibility and light touch. With an exemplary gin selection, a large collection of bitters and an array of champagne cocktails, this is one of the best places for a proper cocktail in Key West. Sunday evenings are taco nights, with a buzzy atmosphere fuelled in part by verdita shots – a tequila shot with añejo, chased by an invigorating blend of mint, coriander, jalapeno and pineapple.
• + 1 305 414 8626, 2centskw.com. Open Mon-Sat 6pm-11pm
Jason Rowan is the author of the drinks blog emburycocktails.com
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