The southernmost point of the United States is found at Key West’s famous red, yellow and black anchored concrete buoy just steps from the ocean. It’s 150 miles from Miami and 90 miles from Cuba, but worlds apart from traditional island life.
Most of the Florida Keys are known for outdoor activities; and while Key West offers such pastimes, many visitors are drawn to Duval Street, the city’s vibrant walkable strip filled with restaurants, galleries, boutiques and a mix of conchs (locals), street performers, tourists and more.
STAY
This luxury full-service resort overlooks the Gulf of Mexico and is adjacent to Mallory Square, home of Key West’s famous daily Sunset Celebration. Watch boats coast by from your balcony. Featured image credit: Ocean Key Resort & Spa.
B&BS can be ideal for travelers on a budget. Just a short walk from Duval Street, this 3-story Victorian is located in the William Russell House (circa 1898) and listed on the National Historic Register.
Also consider…
PLAY
Hop on Fury’s fast-power catamaran for a fun double dip: snorkeling and sunset booze cruise. Spend two incredible hours snorkeling North America’s only living coral reef; then toast to your sunset-kissed day in paradise with wine, champagne or beer.
This brick landing, and home to cruise ships, hosts a nightly sunset celebration. As the sky illuminates with orange hues, watch colorful characters perform ─ musicians, card readers, artists and famed Dominique LeFort and his troupe of trained house cats that brave tightropes and flaming hoops.
Shopping
Between sunset cruises and umbrella cocktails, find time to shop at retail gems like 7 Artists & Friends Gallery (nearly 100% local art), Kino’s (handmade sandals), Peppers of Key West (aka the best hot sauce store in the world) and more.
Fort Zachary Taylor Historic State Park
Florida’s southernmost state park ─ designated a National Historic Landmark in 1973 ─ is a popular destination for both history and recreation. Take a 30-minute guided tour or wander on your own using the informative placards. Walk or bike the short nature trail before soaking up the sun at Fort Zachary Taylor Beach.
Ernest Hemingway House & Museum
While living here (1931-1942), Hemingway wrote approximately seventy percent of his life’s work. Today, photographs help tell his tale. Cat fanatics will especially find the writer’s former limestone house to be the cat’s meow with about 50 roaming polydactyl (six-toed) cats. Hemingway was given a white six-toed cat by a ship captain and some of the cats who live on the grounds today are descendants of that original cat, Snow White.
Located about 70 miles west of Key West, this remote,100-square mile park is comprised of seven small islands and is only accessible by boat or seaplane. Surrounded picturesque blue waters and coral reefs, this is an excellent place for snorkeling, diving and swimming.
Harry S. Truman Little White House Museum
Since 1890, this site (which is still actively used for political engagements) has served as a government building with visits from dignitaries and presidents, including John F. Kennedy, Jimmy Carter, Bill Clinton and Harry Truman, who used the space as his winter home and, thus, dubbed the Little White House.
Key West Lighthouse & Keeper’s Quarters Museum
For the best view of island, climb 88 steps to the top of this 1847 lighthouse. The female keeper lived in the adjacent home which is now filled with photographs, lighthouse artifacts and other memorabilia.
EAT
Breakfast
Right on Duval, dine at Banana Café for crepe and Benedict choices. Or pop into Pepe’s Cafe, the eldest eating house in the Florida Keys (established in 1909), for build your own pancakes or NY strip (yup, you order steak during the a.m. hours). You’ll love “breakfast with the roosters” at Blue Heaven with yummy, homemade menu options like a pink shrimp omelet and towering key lime pie.
Lunch
Sunset Pier has phenomenal pier seating with loud entertainment. Find prime Duval patio seating at Fogarty’s to eat up huge portions and world famous Flying Monkey Saloon frozen drinks!
Dinner
Turtle Kraals, located at Key West Bight Marina in the city’s renovated Historic Seaport district, offers a diverse menu influenced by the nearby Caribbean islands, including an assortment of fish selections such as the Key West Ceviche made of diver-caught hogfish, avocado, sour orange, jalapeño, cherry tomato and basil. Aside from live music, this fun restaurant hosts live turtle races on three nights of the week!
Dessert
Those with a sweet tooth will find plenty to satisfy, especially since key lime pie is on nearly every menu. Find sweet and tart pies made fresh daily at Key Lime Pie Co.; pop into Kermit’s for a slice of frozen chocolate-covered key lime pie, toffee and more; or sip the best key lime martini you’ll ever have at Virgilio’s. Snack on sticky pastries at Old Town Bakery, cool off with Boardwalk Frozen Custard or indulge with a gourmet dessert date night at Better Than Sex.
DRINK
Pub Crawl
Drink up Key West by going with the flow… of beverages. There are several crawl options, such as the Duval Bar Crawl, or a DIY crawl to spots of your choice. Don’t miss:
- Half Shell Raw Bar: Overlooking the docks, feast on a raw bar happy hour, chew on conch fritters and gulp down an oyster shooter of hot pepper vodka, horseradish and (oh my) an oyster.
- Hogs Breath Saloon: This open air watering hole has web cameras so you can show off to your loved ones back home as you sip playfully named drinks like Havana Hog Punch, a blend of fruit juices and Bacardi Rum.
- Captain Tony’s Saloon: Visit the oldest bar in Florida to see walls lined with business cards, money and bras. Challenge: Stand backwards under the sign to toss a penny into the fish mouth.
- The Smokin’ Tuna: As the namesake encourages, eat up the smokin’ tuna dip, a smoky, spicy, creamy blend served with tortilla chips. You’ll enjoy talented musicians as you nosh, especially if you visit during the Key West Songwriters Festival, the largest festival of its kind with chart-topping artists such as Kenny Chesney.
- Kelly’s Caribbean Grille & Brewery: This southernmost brewery was opened by Kelly McGillis, aka the actress who played the love interest of Tom Cruise in Top Gun. Order coconut crusted yellowtail snapper and pair with one of three on-tap brews: Havana Red Ale, Key West Golden Ale and Southern Chipper Wheat.
- The Waterfront Brewery: With views of the fishing boats, order the fresh catch (served with key lime dipping sauce). The view is better than the beer but opt for the Crazy Lady, blonde ale brewed with local honey; but skip the Key Lime Witness beer and just get a slice of pie.
- Bone Island Brewing: This humble tap room has earned praise at the Florida Brewers Guild Festival. Sample their selections with a beer flight.
- Key West Winery: While tastings are offered, it’s more of a wine shop than traditional winery. With tons of wines infused with exotic flavors, you have a hard purchasing decision to make.
- Key West Distilling: Pop in to learn about their premium locally-made rums, whiskey and vodka.
KNOW BEFORE YOU GO
Getting there
The island has a small airport ─ Key West International Airport (EYW). However, because flights are limited, many prefer flying into Miami International Airport (MIA) and driving the gorgeous 110-mile trek on US 1 with crystal clear water on both sides of the road. Or fly into Fort Myers and take the Key West Express, a high-speed catamaran ferry. You can also stop in Key West for a few hours via a cruise ship, but honestly, a few hours just won’t be enough time to enjoy this destination.
Transportation
Historic Old Town is walkable, however transportation is needed to explore the rest of the island. Some rent cars but most opt for moped or bicycle rentals or use taxis when needed. Parking in Old Town is tricky so best to leave your car at your hotel or inn and travel by pedicab or foot.
When to go
Key West is fun year-round! Book accommodations early if visiting during winter and early spring or during Fantasy Fest (October).
Nancy DeVault is the managing editor of Date Night Guide and a contributor to publications such as Babble, AmeriDisability Services Magazine and Orlando Magazine. She enjoys outdoor adventures with her husband and toddler.