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Exploring Key West is one of the great pleasures of time spent on the island, especially when you move beyond the obvious. I’m drawn to its history, architecture, and cultural landmarks that reward a slower pace, just as much as the quieter corners, scenic walks, and places that blend naturally into daily island life.
It doesn’t have to be about famous names or rigid must-see lists. What matters is authenticity and a genuine connection to place. The points of interest on this page reflect that balance, from well-known landmarks to understated spots that offer a more complete understanding of Key West beyond the postcard view.

Set within the state park, this beach offers clearer water and a more natural setting than most others on the island. Rock formations and tree cover make it a favorite for snorkeling and lingering into sunset.
Best for: snorkeling, natural scenery, sunset views
601 Howard England Way, Key West, FL 33040
Key West’s longest stretch of shoreline, Smathers Beach is open, breezy, and easygoing. It’s a good choice for swimming, sunbathing, or a casual walk along the water, with plenty of space to spread out and a lively daytime feel.
Best for: swimming, space to spread out, daytime beach time
2601 S Roosevelt Blvd, Key West, FL 33040
More local in feel, Higgs Beach blends shoreline access with shaded areas, walking paths, and nearby cafés. It’s less about crowds and more about settling in for a relaxed afternoon by the water.
Best for: relaxed afternoons, nearby food, local vibe
1000 Atlantic Blvd, Key West, FL 33040
A small, low-key beach just off the western edge of Old Town, Simonton Beach is an easy stop for a quick swim or a laid-back break from walking Duval. Its proximity to Loggerheads Beach Bar keeps food and drinks close by.
Best for: casual stops, drinks nearby, low crowds
800 Simonton Street, Key West, FL 33040
Small and centrally located, South Beach is more of a pause than a destination. It’s ideal for cooling off briefly while exploring Old Town or watching the waves roll in near the southern edge of Duval Street.
Best for: quick dips, central location, short stops
1405 Duval Street, Key West, FL 33040

Stretching from the Gulf to the Atlantic, Duval Street is the island’s main artery—lined with shops, bars, restaurants, and landmarks. It’s lively at nearly all hours and offers a constantly shifting mix of people, music, and movement.
Best for: people-watching, nightlife, first-time visitors
Duval Street, Key West, FL 33040
https://www.fla-keys.com/duvalstreet/
Famous for its nightly sunset celebration, Mallory Square comes alive in the early evening with performers, vendors, and crowds gathering along the waterfront. It’s less about quiet views and more about shared energy as the day winds down.
Best for: sunset atmosphere, street performers, evening crowds
400 Wall Street, Key West, FL 33040
https://www.mallorysquare.com
A working marina turned social hub, the Historic Seaport blends waterfront dining, bars, and boardwalk strolls with views of boats coming and going. It’s an easy place to linger, especially in the late afternoon and early evening.
Best for: harbor views, dining, relaxed waterfront walks
201 William Street, Key West, FL 33040
https://www.keywesthistoricseaport.org
Marks the symbolic southernmost tip of the continental United States and is one of Key West’s most recognizable landmarks. The brightly painted buoy sits just steps from the water and serves as a classic snapshot moment rather than a place to linger, best visited with a bit of patience for crowds.
Best for: first-time visitors, quick photo stops, and early-morning walks before tour traffic builds.
Whitehead Street & South Street, Key West, FL 33040
A favorite among locals for early mornings and unhurried walks, White Street Pier offers wide-open ocean views and a quieter side of the island. It’s especially peaceful at sunrise, when the water is calm and the island feels like it’s just waking up.
Best for: sunrise walks, casual fishing, peaceful ocean views, and a laid-back local vibe
1801 White Street, Key West, FL 33040
Rooted in Key West’s Bahamian heritage, Bahama Village offers a more residential and culturally rich feel. Colorful homes, local restaurants, and community landmarks give this area a strong sense of place away from the busiest blocks.
Best for: local culture, dining, quieter neighborhood exploring
Bahama Village, Key West, FL 33040
https://www.bahamavillagekw.com
An expansive green space along the harbor with walking paths, shaded lawns, and sweeping water views. Truman Waterfront Park is an easy place to stretch your legs, catch a breeze, or watch boats move in and out of port. Don't miss the farmer's market on Thursday afternoons.
Best for: relaxed walks, waterfront picnics, a playground, and the weekly local farmers market.
21 E Quay Road, Key West, FL 33040
Some links on this site are affiliate links, which means I may receive a small commission at no extra cost to my guests. This is standard in the industry and never influences my recommendations — I only share experiences I genuinely trust to deliver a premium experience.
KEy West, Florida
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