The Best Things to Do During a Key West Day Trip

Found at the southernmost point of Florida, Key West is a unique island city packed with personality. From cultural landmarks to vibrant bars and restaurants, this tropical town offers more than can be experienced in a single day—but that won’t stop us from trying. Located just under two hours from Islamorada, Key West is a great choice for a fun-filled day trip from Cheeca.

Ernest Hemingway Home and Museum

First stop: The Ernest Hemingway Home and Museum on Whitehead Street. As the former residence of legendary author Ernest Hemingway, this historic property is a must-see for book worms and cat lovers. Take a tour of the house, check out the bookstore and gift shop, and don’t forget to say hello to the 40-plus feline residents.

Location: 907 Whitehead Street, Key West, FL 33040

Key West Lighthouse

Located across the street from the Hemingway House, the Key West Lighthouse (the first in Key West) offers another storied piece of local history. Visitors are welcome to explore the Lighthouse Tower and Keeper’s Quarters; notably, the first Keeper was a woman, which was considered a rarity in the 19th century.

Location: 938 Whitehead Street, Key West, FL 33040

Blue Heaven

In the afternoon, head to Blue Heaven, a beloved neighborhood spot that specializes in Caribbean cuisine, seafood, and vegetarian dishes—a little something for everyone. We recommend dining al fresco (as long as you don’t mind the occasional rooster) and you’d be remiss not to order at least one slice of the key lime pie. 

Location: 729 Thomas Street, Key West, FL 33040

Key West Butterfly and Nature Conservatory

The family-friendly Key West Butterfly and Nature Conservatory is truly a delight for visitors of all ages. Featuring 50 to 60 butterfly species from around the world, this awe-inspiring conservatory features glass-enclosed habitats, a robust Learning Center, a gallery with original artworks, and a gift shop full of keepsakes.

Location: 1316 Duval Street, Key West, FL 33040

Duval Street

End your day in Key West with a stroll down Duval Street, which runs from the Gulf of Mexico to the Atlantic Ocean. Shop for unique souvenirs at the locally-owned boutiques, grab a refreshing drink at your choice of eclectic bars, or simply relax at one of the beaches off this bustling commercial street.   

Location: Duval Street, Key West, FL

Plan unforgettable day trip to Key West when you stay at Cheeca in Islamorada.