As the southernmost point in the United States, Key West has always been a top tourist destination. An easy three-and-a-half hour drive from Miami, it’s peppered with pastel hued Victorian style houses and has a distinctly Caribbean vibe. Park your car for the weekend; Key West is 4.5 miles long and one mile wide so it’s easily walkable–and that’s a good thing, because Open Bottle laws don’t apply here. If you load up on shopping from many of the cute boutiques on Duvall Street, rent a bike from your hotel or any of the street vendors to explore this little slice of island heaven.

One weekend in Key West and I nearly caught “Keys Disease”– that sudden urge that’s lured many a famous person to relocate to the area and call it home. But there’s more to Key West than beaches, boutiques and boats; there’s a lot of history here, and African American history is deeply embedded in the fabric of this island’s splendor, making this staycation a real winner for Black travelers.

Want to get away for the weekend? Here’s what you can do with just 48 hours in Key West


Two Hours Before Sunset: Mallory Square Sunset Celebration

Arrive in Miami early, have a leisurely lunch (hotel check-ins aren’t until 3 or 4 pm) then hit the road for the scenic drive to Key West via the Overseas Highway. I’m big on collecting hotel points, and while there are plenty of boutique hotels in the area, I opted for the Hyatt Resort Key West, strategically located on a small beach, overlooking the Gulf of Mexico.

After check in, exit on Front Street and pop in the shops while making your way to the island’s most famous sunset celebration. A tradition since the 1960s, each night, locals and tourists alike line the boardwalk to frolic with the magicians, food and liquor vendors, psychics, and artists before watching the sun slowly set over the Gulf of Mexico. I chase sunsets, and I was captivated by the glowing pink and orange hues of the sky. Tip: bring your best camera because cell phones can’t adequately adjust to capture the hues while shooting into the sun.

9:30: Dinner on Duval

There are so many choices ranging from tequila bars and street food vendors, to high end dining, just take your pick. But in my opinion, dinner at Nine One Five is, a must. Set in a charming conch-styled house with a glorious porch, this two-time James Beard Award nominee has a sophisticated menu with unsophisticated prices. The Asian Continental menu has something for every palate; I had the Lobster Ravioli flavored in a simple light tomato broth. Book a table on the porch for people watching while sipping wine chosen from their extensive wine list.


10:00 a.m: Take it to the Beach

Key West is hot and humid, so it’s best to hit the beaches early. You have to choose your beaches wisely as many, like the Hyatt’s, are rocky and not well equipped for sunbathing and swimming. Higgs Beach, though, is a winner in more ways than one. Firstly, it’s a real beach. It’s swimmable, and you can rent 2 chairs and an umbrella all day for $20.00.

Higgs Beach is also home to the African Cemetery, which is located directly on the beach, adjacent to where you’ll be chilling, so walk over there for a piece of history fit for a movie. In 1860, 3 illegal slave ships–the Wildfire, the William and the Bogota–were intercepted by the U.S. Navy and diverted to Key West. Over 500 Africans were rescued from the Wildfire, 513 rescued from the William, and 407 were rescued from the Bogota. The Key West community was so appalled at the treatment of the “cargo” (read Africans) that the residents pulled together to provide food, medical treatment and shelter for the rescued, who would have otherwise been sold into slavery. Despite this, 294 died and were buried in Key West in unmarked graves.  The cemetery is now on the National Register of Historic Places.

2pm: Hemingway House

A leisurely walk from Higgs Beach, The Hemingway Home is where Ernest Hemingway lived with his second wife Michelle Pfeiffer from 1931-1939 and wrote seventy percent of his novels. Still furnished with many of the Hemingways’ original items, this is, not surprisingly, Key West’s top tourist attraction. Currently home to 52 cats, (half of them six toed), which are direct descendants of the cats that famously lived here with Hemingway and his wife. It also houses Key West’s first in-ground pool, built by his then-wife while Hemingway was on assignment (with his mistress) covering the Spanish Civil War. A tour costs $13.00, money well spent for a lively tour guide who will drop fun filled facts and anecdotes about the hard living Pulitzer and Nobel Prize winning author. After the tour, visit Hemingway’s study where he wrote daily from 8am until 2pm, which sits exactly as he left it before running off with his mistress, turned third wife.

4pm: Harry S. Truman Little White House

First built as a naval headquarters during the Spanish American War, this Key West house, now a museum, became legendary in 1946 when President Harry S. Truman started “wintering” here for health reasons. Truman spent 11 vacations and 175 working days here, where he implemented several important executive orders. In 1948, Truman merged the Department of War and the Navy, and on this porch, Truman gave his infamous speech enacting his fifth Civil Rights Executive Order, mandating contractors hire minorities. Since then, several presidents have stayed here, including John F. Kennedy, who visited the house before the Bay of Pigs invasion and again following the Cuban Missile Crisis. Presidents Jimmy Carter and Bill Clinton have also vacationed here while in office.

9pm: Lobster Fest

Visit A&B Lobster House for dinner al fresco. Overlooking the marina, this spacious restaurant is reminiscent of an old world speakeasy, and has a killer menu for fish and meat lovers alike. After dinner, grab a seat at the bar, listen to live music and have a cigar before heading in for the night.


10am Henrietta Marie Slave Ship Exhibition

Sunday morning, pop into the Mel Fischer Museum, a maritime museum that highlights treasures from its namesake’s expeditions and other historical shipwrecks. I paid $15.00 and headed straight upstairs to the Henrietta Marie exhibition, which contains artifacts from the British Slave ship that sunk off the Florida coast. I was moved to tears as I perused the authentic receipts for clothing purchased for slaves, the currency (iron bars) used to pay for enslaved people (12 bars for a male, 9 for a female), and personal accounts of the treatment of enslaved Africans, referred to as cargo. The exhibit, entitled “A Slave Ship Speaks,” really highlights the fact that we were thought of by some as 3/5th human, and also highlights accounts of those who vehemently opposed this treatment of enslaved people while lobbying for their freedom.

Noon: Don’t forget the Key Lime Pie!

When you’re in Key West, even if you’re not a dessert eater, you can’t leave the island without indulging in the island’s namesake dessert: Key Lime pie. We headed to Bagatelle, winner of Open Table’s 2016 Diner’s Choice Award for what was truly a culinary experience. Set in a two-story conch-style house with an affordable yet delicious menu, grab a table upstairs on the balcony overlooking the street where you’ll feel like you’re in New Orleans. The lobster mac and cheese was a winner, as were the fish tacos, but hands down, the dessert stole the show! One bite of this pie, and I was instantly transported to food heaven. Not too tart, not too sweet, the light pie is perched gloriously atop a graham cracker crust, and topped off with a meringue cooked to perfection. It was hands down the best dessert I have had…ever! To say I would make the trip to Key West again just for this pie is seriously not an exaggeration.

Actually, I so loved Key West, I would indeed make the trip all over again. And in my 48 hours in the city, I do believe I came down with early onset “Keys Disease.”


Lisa Bonner is an Entertainment Lawyer and travel aficionado on a path of creative transformation. Follow her on Twitter @lisabonner.