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Things To Do

Corner Sandwich Shop

1514 Bertha Street, Key West, FL 33040

Coffee stop at Corner Sandwich Shop – Cuban coffee + chorizo, egg & cheese sandwich = perfection.

Angelina's Pizzeria

208 Duval Street, Key West, FL 33040

Late-night pizza at Angelina’s Pizzeria – The best slice in Key West!

Blue Heaven

729 Thomas Street, Key West, FL 33040

A true Key West classic — famous for Lobster Benedict, live music, roaming chickens, and island vibes.

Rick's Bar

202-208 Duval Street, Key West, FL 33040

Get the Double O Seven (007). Trust me!

FishMonster & IslandJane Charters

700 Front Street, Key West, FL 33040

Fish Monster has a party boat that can fit up to 50 people and is only like $79/Person.

The Key West Nature Preserve

1799-1691 Atlantic Boulevard, Key West, FL 33040

Awesome Private Beach to hang out at you can walk like a mile off shore as the water is so shallow. You can also fish right from shore!

Sloppy Joe's Bar

201 Duval Street, Key West, FL 33040

Most Famous Bar in Key West. Live Music

Mallory Square

Key West, FL 33040

Don’t miss sunset — street performers, local artists, and one of the best views in the Keys.

Fort Zachary Taylor

Angela Street, Key West, FL 33040

Beautiful beach, crystal-clear water, and the best sunset spot if you want something quieter.

Hogfish Bar & Grill

6810 Front Street, Stock Island, FL 33040

Local favorite — incredible hogfish sandwich and a laid-back marina atmosphere.

Southernmost Point of the Continental U.S.A.

1400 Whitehead Street, Key West, FL 33040

Iconic photo op — yes it’s touristy, but you have to do it at least once.

El Siboney Restaurant (Downtown)

900 Catherine Street, Key West, FL 33040

Authentic Cuban food at great prices — casual, delicious, and loved by locals.

Key West Fishing Charters

1 Duval Street, Key West, FL 33040

Half-day or full-day trips available — reef fishing, deep sea fishing, and unforgettable memories.

Lazy Dog Adventures

5114 Overseas Highway, Key West, FL 33040

Kayaking and Paddleboarding

Chart Room Cocktail Lounge

1 Duval Street, Key West, FL 33040

📍 Chart Room Cocktail Lounge — Key West’s legendary hidden bar Nestled inside the Pier House Resort on Duval Street, this cozy nautical bar is a slice of old-Key West history — dim lighting, walls covered in memorabilia, and drinks with character. It’s known for classic cocktails, complimentary popcorn, peanuts & hot dogs with your drink, and a lived-in island vibe locals and regulars love. The place has connections to music and culture legends and feels like a true Key West discovery worth stopping by on your trip

Fury Key West Watersports

631 Greene Street, Key West, FL 33040

Sunset Pier

0 Duval Street, Key West, FL 33040

Best spot to catch the sunset and have a drink!

SunShine Scooters, Inc.

1910 North Roosevelt Boulevard, Key West, FL 33040

Rams Head Southernmost

804 Whitehead Street, Key West, FL 33040

Great Breakfast or Brunch spot!

Conch Republic Seafood Company

631 Greene Street, Key West, FL 33040
For all the days along the way
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