Key West is definitely worth the trip, even during the pandemic – and about a 3-hour non-stop flight from Chicago O'Hare International Airport on United Airlines. Here's a dandy dozen Key West Musts, in no particular order:
History of Diving Museum
Look for diving items from more than 30 countries and the museum has the world's largest collection of armored suits, diving helmets and other diving accessories.
Ernest Hemmingway Home
The legacy of Ernest Hemingway in Key West dates to the 1930s and his house is a major tourist attraction. The grand Southern exterior of the house protects his eclectic collection of furniture, art and other accessories while the grounds act as a haven for wildlife, plants, and countless cats.
Old Town Literary Walking Tour
Visit the homes and haunts of writers tied to Key West, such as Tennessee Williams, Robert Frost, and Shel Silverstein.
Sunset at Mallory Square
Geographically, this is the southernmost end of the United States and always a perfect spot to watch the sunset, with plenty of nearby cocktail options. Mallory Square also has performers, artists and numerous food vendors.
Drag Shows
Two must-see spots for sass: Aqua and 801 Bourbon Bar, both located on Duval Street and about a 3-minute walk between them. Aqua has nightly performances, as does 801, which also has Drag Bingo every Sunday night. Bring your $1s or $5s, the dancers walk around and, because of the pandemic, now use a fish net to capture tips.
The Southernmost House
This boutique hotel is also a museum, built in 1897 and has hosted over 20 presidents and dignitaries. And no two rooms look the same.
Pose at Mile Marker 0
US Highway 1 is a 2,369-mile-long interstate that connects almost every city on the East Coast. Mile Marker 0 is a photo-must.
Pose at the Southernmost Point in the Continental USA
Everyone gets a selfie at this colorful concrete buoy that marks the southernmost point in the continental U.S.
Duval Street
Always a fun stop as Duval Street is filled with restaurants, bars, souvenir shops, clothing boutiques, and more.
Kermit's Key West Lime Shoppe
No Key West visit is complete without a slice (or two) of this local favorite, and Kermit's has been offering key lime treats for more than 20 years.
Breakfast at Blue Heaven
What formerly was a boxing ring where Hemingway refereed, Blue Heaven is known for its brunch and super-sized meringue. Yes, key lime pie for breakfast is acceptable – and encouraged – at Blue Heaven.
Sunset Cruise
Another must, especially if you need a new profile photo for social media. Try the Commotion on the Ocean Sunset Sail from Fury Water Adventures, featuring live music, appetizers, and plenty of drinks. Or the Champagne Sunset Sail on the Schooner America 2.0 from Classic Harbor Line, with drinks, snacks, and a friendly, professional crew.