The Best Weekend Itinerary for Key West

Ernest Hemingway may be Key West’s most well-known former resident, but plenty of famous faces have sailed, drank, and partied their way through the popular Florida island getaway. Jimmy Buffet, Judy Blume, and Ralph Lauren have all spent time basking in the mix of adventurous artsiness and beachside pleasures here. The island is approximately four square miles, so it’s small enough to tackle on a quick weekend jaunt, especially for those looking for a break from the cold winter up north. With that in mind, we rounded up the best itinerary for a weekend in Key West.

Friday: Arrive and Check-In

Sunset Key Cottages, Key West/Oyster

While Miami may be the most popular airport destination for a trip to Key West, keep in mind you’ll need to drive over three hours after you land. If you can afford to fly directly into Key West (the extra mileage will likely add $50 or more to your ticket), you may save yourself some road wear and gas money. 

Once in town, check into your hotel. The island offers many properties with white-sand views and ultra-plush rooms. The Casa Marina Resort (part of the Waldorf Astoria chain) features in-room espresso machines and a swimmable beach. The Sunset Key Cottages caters to the upscale traveler with luxurious, beach-chic cottages and high-end amenities, including a lovely pool, a gorgeous (though somewhat rocky) beach with palm trees and clear, calm waters, and a pleasant spa. However, note that it’s set on a small residential island off Key West and only accessible by boat.

Stroll Through the Seaport

Ocean Key Resort, Key West/Oyster

Key West’s historic seaport is a great introduction to the destination since it has a lot of what visitors want to see plus access to stellar sunsets. Several local watering holes start happy hour at 4 p.m., so hopefully you’re prepared to get your drink on. Hungry travelers who want to get started on a Key West seafood binge should head over to the Half Shell Raw Bar, which shucks 200 oysters, on average, every happy hour. For anyone inspired to have a cookout on the beach, Half Shell also owns its own fish market. Conch Republic Seafood Company offers 80 brands of rum and claims to have the largest bar between Miami and Cuba. Regardless of what you’re drinking, the restaurant’s four, 160-gallon saltwater tanks filled with local marine life make for some seriously impressive decor.

You can also scope out one of the numerous fishing day trips that leave from the port. Clearly Unique Charters rents glass-bottom kayaks and the Key West Eco Tours meanders through coral gardens. Sailers can also choose to take a trip on the svelte Echo Catamaran or historic, 90-year-old Hindu wooden schooner.

Celebrate the Sunset

Key West/Oyster

Commemorate the end of a fun day with drinks along the water. Grab a pastel stool on Sunset Pier (located at Ocean Key Resort) and soak in a horizon filled with tangerine and lavender hues. Another popular watching spot is the Galleon Tiki Bar at the Galleon Resort and Marina. Plenty of nearby bars have excellent happy hour specials, so as long as you can see the sunset, be sure to celebrate. After a long day of travel you’ll probably want to rest up for the big day ahead.

Saturday: Get a Cuban Breakfast

Cayobo/Flickr

Since Cuba is only 90 miles away, go ahead and salute our southern neighbors with a pressed breakfast sandwich. Cuban Coffee Queen (also located near the seaport) serves the Key Wester (eggs, American cheese, and chorizo) for $7 and a Cuban breakfast burrito (eggs, cheese, rice, and beans) for $8.50. Many tourists say the best local food is also the cheapest -- find out for yourself, then wash it down with the Queen’s roasted java.

Sail Away

steve lyon/Flickr

If you’ve planned ahead, you can board one of the numerous charter trips from the seaport. Much of the game fishing is -- by law -- catch and release. However, grouper, mahi-mahi, and snapper can be eaten. Many of the expeditions include fishing gear, or you can rent it at places such as The Angling Company or Key West Bait & Tackle. Those who don’t have a hankering to hook a fish can choose from sailing trips that include dolphin watching and snorkeling. Luxury excursions serve up the sunset with Champagne. Some boats even take tourists out to Dry Tortugas National Park, home to one of America’s largest coastal forts. If you can fit in a trip to Dry Tortugas during the weekend, it will likely be worth the extra organizing.

Stroll Duval Street

Duval Street, Key West/Oyster

Depending on your perspective, Key West’s Duval Street is party central and top-notch people-watching territory or an extremely long tourist trap. If you’re in Key West, you definitely need to stop by and see the array of crafty boutiques, brash bars, and mom-and-pop fresh seafood restaurants. Taking a stroll is a nice way to unwind from a half-day boat ride. While there are plenty of tourists who go on a “Duval Crawl,” the street is also safe and family-friendly. You can easily browse the shop windows and get a slice of Key lime pie or a couple of scoops of ice cream. The clothing store options can be either kitschy or artisanal.Indigo boutique has bohemian-inspired swimsuits and handmade jewelry. The Green Pineapple sells affordable  eco-chic choices, including Rich Hippie fragrances and animal print home decor. For eats, DJ’s Clam Shack has one of the best lobster rolls in town ($18) and Mangoes is known for its friendly service and Caribbean-influenced comfort food.

Go on a Self-Guided Art Tour

Mark Mitchell/Flickr

Key West’s art galleries boast a collection much more impressive than you would expect to see on an island at the tail end of Florida. Many of these outposts are located on the streets just beyond Duval, making for an easy detour during a shopping tour. Gallery on Greene showcases the work of several Pulitzer Prize-winning photographers and cartoonists as well as Cuban and Key West painters. Curator Nance Frank has worked with museums in Switzerland, Chile, New York, and Cuba, and developed a collection that also includes pieces by one-time local residents Tennessee Williams and Annie Dillard. Frank also takes groups to Cuba for private art tours. Alan Maltz, the official wildlife and fine art photographer for Florida, keeps his fine art pieces in an eponymous gallery. In addition to nature prints, he also sells images of the Everglades and coastline on note cards and lithographs. The Key West Art Center celebrates local artists who work in numerous disciplines and also organizes the Key West Craft Show in January and Old Island Days Art Festival in February. If you want to view some of Key West’s best art, be sure to keep an eye on the clock, as many of the galleries close at 5 or 6 p.m. Tip: You may want to call ahead to check on closing time.

Enjoy a Night Out on the Town

Duval Street, Key West/Oyster

If you’re only in Key West for the weekend, Saturday is your big night to go out, and there are plenty of bars to enjoy. Sloppy Joe’s opened its doors on the day alcohol prohibition ended -- December 5, 1933 -- and has been grooving ever since. Yes, Ernest Hemingway drank there and the bar is now home to an annual look-alike contest every July during the Hemingway Days festival. It also has live bands -- blues, country, rock -- every night. The Bull and Whistle Bar has three floors that each have a different theme, including the Garden of Eden -- a rooftop watering hole that's clothing optional. Feeling a little more introverted? The Green Parrot Bar is a dive located a block off the main drag, and is popular with locals and tourists looking for a low-key place to tie one on and listen to classic soul and rock on the jukebox. If you’ve planned wisely, your hotel is within walking (or stumbling) distance.

Sunday: Have Breakfast in Heaven

Sam Howzit/Flickr

If you want a memorable morning, Blue Heaven has al fresco dining under the trees and a selection of silly artwork. The Blue Heaven Benedict gives the traditional dish a local twist with lime hollandaise sauce. The lobster and grits are a hearty mix of upscale and down-home.

Soak in the Key West Culture

Mandy/Flickr

After a night of debauchery, pop your synapses back into action with a little Key West culture. First stop: The Ernest Hemingway Home, an 1851 Spanish Colonial-style structure where the writer finished “A Farewell to Arms” and “To Have and Have Not” and lived with his wife Pauline. The Hemingways’ European art collection still decorates the house. Feline fans will appreciate the six-toed cats that roam the grounds -- descendants of the one that lived with the Hemingway family. 

The San Carlos Institute was the location where Jose Marti launched the expatriate movement to free Cuba from Spanish colonial rule. Cuba’s government still owns the stately house with scrolled details and ornate ironwork. 

In the early 1900s, the Key West fishing industry nearly drove turtles to extinction. The Key West Turtle Museum explains how the species was brought back from the brink and also hosts lectures about other local conservation efforts. 

Relax on the Beach

Beach at the Sunset Key Cottages, Key West/Oyster

Hanging out on the beach is a great way to unwind from a busy weekend in Key West. Tennessee Williams would swim at South Beach at the end of White Street almost every morning when he lived on the island. Visitors who want to do more than swim can head over to Smathers Beach, where Sunset Watersports sells a pass ($89) that allows you to use their kayaks, paddleboards, and windsurfing boards for one price all day. If you want to mix a bit of history with swimming, the encampment located at Fort Zachary Taylor Historic State Park dates back to the Civil War.

Depart

Leaving from the Miami airport? Be sure to give yourself plenty of time for the return drive. Visitors taking a taxi to Key West International Airport can grab one last mojito at the Conch Republic Seafood Company or Willie T's. 

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