Where to Go in Key West: The 4 Best Beaches, Restaurants, and More

Where to Go in Key West: Key West is an island city in the Florida Keys known for its great weather, beautiful beaches, good food, and historic sites. The island has historically been a favorite of many U.S. dignitaries and artists, and was once home to a long list of historical figures, including Harry Truman, Ernest Hemingway, and Tennessee Williams. Today, the island continues to be a popular vacation spot, attracting over 5 million visitors per year, particularly in the winter months, when snowbirds and vacationers from the north flock to the island.

If you are planning a vacation to Key West, it is important to plan out your stay and determine what you want to see and where you want to go, in order to get the most out of your vacation. The island city encompasses only 5.6 square miles, but packs a lot of activities and sights into a small space. Without planning an itinerary, it can be easy to be overwhelmed with the variety of choices. Here is a list of the best places to go on your vacation to Key West.

Where to Go in Key West


Where to go in Key West: The Best Beaches on the Island
Where to go in Key West: The Best Beaches on the Island

It is no secret that Key West’s primary attraction for most vacationers is its beaches. The island is renowned for its white-sand tropical beaches, which are perfect for swimming, snorkeling, fishing, and more. The best beach for you in Key West will vary depending on what you want to do. There are quiet beaches that are perfect for relaxing and swimming in the shallow waters, and more active beaches, where jetskiing and parasailing are popular activities. Here are the best beaches on the island and a short summary of what to expect at each:

Smathers Beach

The most popular beach on Key West, Smathers Beach is a long, calm beach, with serene turquoise waters that are perfect for swimming. The beach maintains an active atmosphere, with jetskis, kayaks, and snorkel equipment available for rent. Despite this, the beach is also great for relaxing and sunbathing, and it has no entrance fee, which makes it very convenient, although that also means it can get crowded. 

Overall, Smathers Beach is a perfect beach for families, with plenty of activities for everyone to engage in. 

Simonton Beach

Located in downtown Key West, ​​Simonton Beach is one of the quieter, more laid-back and less crowded beaches on the island. Popular with locals, Simonton Beach is very small and somewhat secluded, with clear waters that are perfect for swimming. Just off the beach, you’ll find the Lagerhead Beach Bar, a popular establishment where you can grab a beer and a bite to eat, and then enjoy it right on the beach.

Fort Zachary Taylor Beach

Located in the historic Fort Zachary Taylor State Park, Fort Zachary Taylor Beach is one of the island’s best beaches. Featuring wide, natural beaches with beautiful green-tinted waters and abundant plant and animal life, Fort Zachary Taylor Beach is perfect for nature lovers. 

The beach is one of the best snorkeling beaches in the area, with coral located just off shore, and plenty of schools of fish, turtles, and dolphins frequently visiting the area.

South Beach 

A small but beautiful beach located on Key West’s southern coast, South Beach is very popular with the locals, and is said to have been the favorite beach of playwright Tennessee Williams. The beach is great for swimming and sunbathing, but has no public restrooms, so is not ideal for a daytrip or travelers with young children. If you are staying in the area, however, South Beach is a perfect spot to relax in the sun and go for a dip.

Historical Sites

Ernest Hemingway House

Where to go in Key West: The Hemingway House
Where to go in Key West: The Hemingway House

Located at 907 Whitehead Street, just across from the Key West Lighthouse on the western end of the island, the Ernest Hemingway House was the residence of the writer and his family throughout the 1930s. The house was where Hemingway completed some of his most famous works, including The Green Hills of Africa and The Snows of Kilimanjaro. The house is also famous for the ​​polydactyl cats that live on the property; descendants of cats that Hemingway had owned. Today the house is a popular tourist destination, attracting thousands of visitors for tours of the property.

The Little White House

Located in Key West’s Old Town neighborhood, the Little White House was the winter residence of President Harry S Truman, and had previously been inhabited by President William Howard Taft and inventor Thomas Edison. Truman conducted meetings and other official business from the Little White House throughout the late 1940s and early 1950s, and later presidents, including Eisenhower and Kennedy used the house as an occasional winter retreat.

Old Town

Key West’s Old Town district, located on the eastern side of the island is the site of the earliest neighborhoods in Key West. Famous sites in Old Town include Mallory Square, which is Key West’s historic waterfront plaza; Duval Street, home of some of the oldest houses on the island as well as some of the best bars and restaurants; and Fort Zachary Taylor, a Civil War era fort, which today sees frequent Civil War battle reenactments.

The Southernmost Point in the United States

Where to go in Key West: The Southernmost Point
Where to go in Key West: The Southernmost Point

One of Key West’s famous attractions is a buoy marking the southernmost point of the United States. Located on the southeastern end of the island, the buoy was first erected in 1983, and says “Southernmost Point Continental U.S.A” and “90 Miles to Cuba,” although the actual distance is closer to 95 miles.


Where to go in Key West: Key West's Restaurants are Famous for their Key Lime Pie
Where to go in Key West: Key West’s Restaurants are Famous for their Key Lime Pie

Key West is famous for its fresh seafood, Caribbean and southern-US influenced cuisine, and its key lime pie. Some of the most popular restaurants on the island include:

Santiago’s Bodega

An excellent Spanish restaurant named for the main character in Hemmingway’s The Old Man and the Sea, Santiago’s Bodega is famous for its tapas-style dining, which features small plates meant to be shared. The fresh seafood, authentic Spanish dishes, and excellent sangria make Santiago’s Bodega one of the best restaurants in Key West.

Garbo’s Grill

Located in downtown Key West, Garbo’s Grill is a Caribbean and American-style restaurant well known throughout the island for its excellent seafood, tacos, and burgers. Founded in 2009, the restaurant quickly became a favorite among locals and visitors alike, and have maintained its reputation for excellence for over a decade.

Seaside Cafe at the Mansion

A Key West favorite for over 10 years, Seaside Cafe at the Mansion is famous for putting unique spins on class cuisine from around the world. The family-friendly restaurant is famous for its lobster pizza, lobster biscuits, key lime honey mustard sauce, truffle fries, and more. Located just steps away from the beach, the atmosphere at Seaside Cafe is excellent.

See Also:

5 Best Secret Caribbean Islands for your Next Vacation

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