Duval Street does not care what day it is.
The Duval Crawl, deep-sea fishing charter, Hemingway's old haunts, sunset sail, conch fritters, rum bars, no shoes after 3pm. The Caribbean-lite bachelor weekender.
brunch crawl • 3-4 hours
Walk the 'Duval Crawl' from Atlantic to Gulf hitting every bar along the way.
snorkeling • 3 hours
Catamaran trip to the reef with snorkeling, unlimited drinks included.
fishing • 4-8 hours
Offshore or flats fishing for tarpon, mahi, and yellowtail.
boat cruise • 1.5 hours
Guided jet ski tour through the backcountry mangroves.
bar • unhinged • $
Hemingway's old haunt — live music and strong drinks since 1933.
club • unhinged • $$
Multi-level Duval complex with DJs, live music, and a dance floor.
Dress code: Upscale nightlife attire, no athletic wear
dive bar • balanced • $
Iconic dive bar off Duval with live music and zero pretense since 1890.
dive bar • balanced • $
The original Sloppy Joe's location — bras on the ceiling, history on the walls.
wine bar • chill • $$
Craft beer and wine bar with rooftop overlooking Duval Street.
bar • unhinged • $
Duval Street sing-along bar with live performers and crowd participation.
bar • chill • $$$
Waterfront bar at Mallory Square with the best sunset views on the island.
bar • balanced • $
Open-air bar with live music, cheap beer, and a classic Key West vibe.
beer garden • balanced • $$
Craft brewery in the birthplace of Pan Am Airways — great courtyard.
Tapas / Latin • $$$ • Best for: group-dinner
Creative tapas and cocktails — perfect for group sharing.
Caribbean / Brunch • $$ • Best for: brunch
Open-air brunch with roosters roaming — banana bread French toast is legendary.
Seafood / Fine Dining • $$$$ • Best for: dinner
Ferry-access-only restaurant on a private island — bucket-list dinner.
Seafood / Casual • $ • Best for: lunch
Cash-only fish sandwich shack — quintessential Key West casual.
Seafood • $$ • Best for: lunch
Fresh-catch market with outdoor seating and cold beer.
New American / Tapas • $$$ • Best for: group-dinner
Upscale tapas on Duval with porch seating and creative plates.
Cuban • $ • Best for: lunch
Authentic Cuban food at local prices — the ropa vieja is perfect.
Dessert • $$$ • Best for: late-night
Intimate dessert-only restaurant with provocative names — group favorite.
resort • Max 4 guests
Harbor-front resort with rooftop pool and Cero Bodega bar.
resort • Max 4 guests
Jimmy Buffett's resort with pool bar and marina right on the Gulf.
airbnb • Max 12 guests
Historic Old Town home with pool and walking distance to Duval.
boutique-hotel • Max 4 guests
Marina hotel on Stock Island with great restaurant and pool.
resort • Max 4 guests
Beachfront resort at the Southernmost Point with tiki bar.
Bottle service, beach clubs, and bad decisions until 5am.
Emerald water, charter boats, and Harbor Walk bar crawls.
Ybor City goes harder than you expect.
Miami's beach without Miami's attitude.
Offshore charters, a pedal boat, Palafox bars
Private pontoons, sail-and-snorkel, steakhouse nights
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