Duval Street does not care what day it is.
Key West is a tropical party island where Duval Street runs from the Atlantic to the Gulf and every bar along the way is packed. The vibe is laid-back and unapologetically boozy — sunset celebrations at Mallory Square, open-air bars everywhere, and a strong 'no judgement' energy that makes it perfect for party weekends.
brunch crawl • 3-4 hours
Walk the 'Duval Crawl' from Atlantic to Gulf hitting every bar along the way.
boat cruise • 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.
food tour • 1.5 hours
Nightly sunset festival with street performers, artists, and food.
food tour • 1 hour
Tour Hemingway's home with 60+ polydactyl cats.
food tour • 2-4 hours
Rent scooters to explore the whole island at your own pace.
food tour • 1.5 hours
Walking ghost tour of America's most haunted island.
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 — bachelorette 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.
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