Changes in Latitude, Changes in Attitude: A Long Weekend in Key West


We’re nearly two months into the school year, which means we’re all in need of a break from chaotic mornings, packed afternoons, and non-stop weekends. Why not jet off to Key West for a long weekend of R&R? With a 55-minute direct flight from Orlando Sanford International Airport, you can fit in a morning at the office, grab your kids from school (if they’re invited!), and arrive in the land of the Conch Republic in time for happy hour. 

Below, we offer up some of our favorite spots to stay, eat, and play in Key West.

Where to Stay

The Marker Key West Harbor Resort is a great option for families. Located on the Key West Historic Seaport and just three blocks from Duval Street, you’re perfectly situated to fully enjoy the five-square-mile island. Thanks to spacious rooms, three saltwater swimming pools, and plenty of options for water sports, you may be tempted to stick around the hotel all weekend long!

If you’re lucky enough to squeeze in some one-on-one time with your partner, book a stay at the Eden House Resort. The rooms are small, but thanks to the lush landscaping, tiki bar, and pool, you’ll spend most of your time outside anyways. Be sure to enjoy brunch or dinner on-site at Azur Restaurant.

Where to Eat in Key West

During any trip to Key West, breakfast at Blue Heaven (pictured above) is a must. From veggie eggs Benedict to pineapple pancakes, you can’t make a bad choice when it comes time to order. Get there early and add your name to the waitlist before walking across the street to sip on a Bloody Mary.

For lunch and dinner, you’ll want to partake in both fresh seafood and authentic Cuban food. Be sure to plan a meal at the Half Shell Raw Bar. It’s our top pick for a fried grouper sandwich, conch fritters, and a cold rum drink. 

Don’t miss a mandatory stop at Sloppy Joe’s, another Key West institution. If you need a break from seafood, order The Original Sloppy Joe Sandwich: delicious ground beef in a sweet rich tomato sauce with onions, peppers, and spices. Their homemade key lime pie is the best of the best. End your visit with a stop at their retail store — the perfect place to grab some souvenirs!

For your next meal, jump in line at The Lobster Shack for a Key West lobster roll or shrimp roll. We promise the wait is worth it. 

Locals swear by the authentic Cuban food at 5 Brothers Grocery and Sandwich Shop — so it must be good, right? Order a high-test cortadito and pressed sandwiches on Cuban bread. Or stop in at one of three locations of Cuban Coffee Queen for sandwiches, salads, and smoothies.

Finish a day of fun with homemade ice cream at Flamingo Crossing. Order a scoop of Cuban coffee, lavender, or passion fruit. It’s so good, you might need more than one trip! Note that it’s cash only.

Where to Play

If you need a break from the sand and surf, visit the Hemingway House, Key West Aquarium, or Key West Shipwreck Treasure Museum. You can also take a walking tour of the historic cemetery.

As the sun goes down, head to Green Parrot, where the locals go to enjoy live music. A quick history lesson: This spot first opened in 1890 as a grocery store for Cuban and Bahamian immigrants. Next, have some fun at Mallory Square. You’ll run into jugglers, magicians, musicians, tarot card readers, and more. For a night of peace and quiet, sit on the pier at Fort Zachary Taylor Historic State Park and take in a beautiful sunset. 

A version of this article originally appeared in the Summer 2021 issue of Edible Orlando.