Weekend In Key West
Are you dreaming of a weekend in Key West? This tropical paradise has everything you need for a relaxing (and fun) getaway. There are plenty of beautiful beaches, fun bars/restaurants, and activities, making it perfect for any trip type. If you are spending a weekend in Key West, here is a sample itinerary to help plan your trip!
Weekend In Key West
Day 1
Breakfast @ Sarabeth's
Sarabeth's is the perfect way to kick off your weekend in Key West. Be sure to try the eggs Benedict, lobster roll sliders, or avocado toast.
Visit the Hemingway Home
If you're a literature buff, going to Hemingway House is a must. The home belonged to Ernest Hemingway, who lived and wrote there during his life. Now, the property is a museum giving visitors a glimpse into Hemingway's life and work, with tours that take visitors through the house and gardens.
Climb The Key West Lighthouse
Climb to the top of the historic lighthouse and experience beautiful views of the island. You can also explore the museum, which tells the story of the lighthouse keepers and their families.
Go To The Southernmost Point
The Southernmost Point is one of Key West's most iconic landmarks. It's a quick walk from Duval Street and is marked by a large concrete buoy that serves as a marker for the southernmost point in the continental United States.
Lunch @ Garbo's Grill
Grab a bite to eat at Garbo's Grill, a food truck that serves up some of the best fish tacos and burgers in town.
Walk Around Duval Street
Duval Street is lined with historic buildings that date back to the 1800s - many of which have been restored and repurposed as boutiques, art galleries, and cafes. It is also home to the Ernest Hemingway Home and Museum and the Southernmost Point buoy.
Watch the sunset @ Mallory Square
Every evening, tourists (and locals) head to Mallory Square to see what is arguably one of the most beautiful sunsets in the world. Mallory Square also has a nightly Sunset Celebration with live music, street performers, and local artisans.
Dinner @ Louie's Backyard
Louie's Backyard is the perfect spot to end your day. It's a beautiful restaurant that offers stunning ocean views, a romantic ambiance, and great seafood.
Dessert @ Better Than Sex Dessert Bar
End the first night of your weekend in Key West at Better Than Sex Dessert Bar. The menu is mostly focused on indulgent desserts: Cookie Nookie Pie and the Kinky Key Lime are some popular ones. The vibe is dark and moody, so it's perfect to follow dinner at Louie's. They also offer wine, cocktails, and beer.
Day 2
Breakfast @ Blue Haven
Blue Haven is one of Key West's most popular restaurants - and for good reason. They don't take reservations for breakfast, so plan accordingly. Be sure to try the Lobster “BLT” Benny and the pancakes. Also, if you find yourself coming back - their Key Lime pie is so good.
Lay Out @ Smathers Beach
After breakfast, head over to Smathers Beach for some relaxation in the sun. Smathers is one of Key West's most popular beaches. If you're looking to be more active, rent paddle boards or kayaks.
Lunch @ Sloppy Joe's Bar
For lunch, grab a bite to eat at Sloppy Joe's Bar. It's a local favorite that's been serving up delicious sandwiches, seafood, and drinks since the 1930s.
Sunset Catamaran Cruise
Keep the relaxation going and head on a sunset catamaran cruise. You'll get to see stunning views of the sunset over the water while sipping a cocktail. It doesn't get much better than that.
Dinner @ Santiago’s Bodega
Santiago's is a tapas restaurant with a laid back feel, outdoor seating, and a lively bar. They're known for their shrimp and grits, crispy duck confit, and bacon wrapped dates. Be sure to save room for dessert - their homemade key lime pie is a must.
Bar Hop On Duval Street
A weekend in Key West would not be complete without experiencing Duval Street. It is the heart of Key West and is a fun spot to continue the evening. There are plenty of bars to choose from. Each has their own unique vibe and drinks, and all walking distance from each other. The Green Parrot is one of the most famous bars, known for its live music and laid back vibe (though it's technically not ON Duval Street). Rick's Bar, Sloppy Joe's, and Small Bar are classics too.
The Quick List
Day 1
Breakfast @ Sarabeth's
Hemingway Home
Key West Lighthouse
Southernmost Point
Actual Southernmost Point
Lunch @ Garbo's Grill
Walk Around Duval Street
Watch the sunset @ Mallory Square
Dinner @ Louie's Backyard
Dessert @ Better Than Sex Dessert Bar
Day 2
Breakfast @ Blue Haven
Lay out at Smathers Beach
Lunch @ Sloppy Joe's Bar
Sunset Catamaran Cruise
Dinner @ Santiago’s Bodega
Bar hop on Duval Street
Looking for more?
*If you're looking for more, be sure to check out the Key West travel guide post
*Check out the Key West travel guide which includes where to stay, how to get around, 30+ things to do, and 40+ places to eat/drink
*This post is not affiliated with any of the mentioned establishments.