Swanky & Snazzy
The Roost
A relaxed wine and cocktail bar focused on charcuterie, caviar, and small plates.
508 Flemming Street
(305) 294-2600
General horseplay
Cocktail-forward bar with inventive drinks up front and live music out back.
423 Caroline Street
(305) 741-7599
Point Five
An intimate wine and cocktail lounge offering small bites and a quietly sophisticated late-evening atmosphere.
915 Duval Street
(305) 296-0669
Dive Bar Charm
The Chart Room
Strong cocktails, no frills, and a classic old Key West vibe.
1 Duval Street
(305) 296-4600
www.pierhouse.com/dining/chart-room-bar
Willy T's
High-energy live music, nonstop people-watching, and walls full of dollar bills.
525 Duval Street
(305) 294-7674
Bobby's Monkey Bar
All-welcome, locally loved bar with karaoke nightly, shenanigans always — cash only, ATM on site.
900 Simonton Street
(305) 294-2655
Bobby's Monkey Bar Facebook Page
Hank's
Off-Duval favorite known for live music and a true local crowd.
409 Caroline Street
(305) 509-7758
Tiki Bar at Sunset Pier
Tiki bar at the end of Duval offering waterfront drinks, live music, and stunning sunset views.
0 Duval Street
(305) 296-7701
Coffee and Plant Buzzes
Kava Key
A relaxed kava lounge offering alcohol-free options including house-brewed kava, THC beverages, elixir teas, and coffee. The atmosphere is laid-back and social, with a subtle nautical, pirate-ship theme that feels more below deck on a galleon than over-the-top. A large screen highlights sports, while plenty of armchairs and sofas make it easy to settle in and stay awhile. With speedy Wi-Fi and outlets throughout, it’s also a comfortable spot to get some work done.
420 Flemming Street
Kava Culture
A social, beach-vibe kava lounge offering alcohol-free drinks including traditional kava, botanical elixirs, THC beverages, and coffee. The atmosphere is relaxed and open, with an easygoing, community feel that encourages conversation and lingering. It’s a popular spot to unwind, meet locals, or spend a casual afternoon or evening in a setting that feels effortlessly Key West.
901 Flemming Street
(305) 440-3076
Old Havana Cigar Company
Classic cigar lounge with a relaxed patio and a strong selection, including Cuban-seed cigars grown in Nicaragua. This is a perfect spot to step out back and enjoy a quiet oasis in the heart of downtown, or to select a few cigars to enjoy throughout your trip and possibly for back home.
606 Duval Street
Wine Lover's Spots
Grand Vin
Wine-focused shop on Duval offering seating for on premise enjoyment in a relaxed, grown-up atmosphere. (try the frozen rose with sangria on top.)
1107 Duval Street
(305) 296-1020
Viv Wine Bar
French bistro–style small plates, charcuterie, and cheeses paired with a thoughtful wine selection.
300 Petronia Street
(305) 741-7268
Uva
A neighborhood wine shop on Simonton Street offering a thoughtfully curated selection of bottles.
916 Simonton Street
(305) 296-5455