A beautiful Key West sunset over Mallory Square. Photo © Ed Schipul, licensed Creative Commons Attribution.

A beautiful Key West sunset over Mallory Square. Photo © Ed Schipul, licensed Creative Commons Attribution.

Luxury, history, and revelry combine on this whimsical island, a popular place for romantic getaways. Whether you fly or drive here, you and your sweetheart will surely have a memorable weekend in Key West. Here are a few suggestions for making the most of your time while visiting the Southernmost City.


When planning your romantic getaway, book a room at one of Key West’s unique hotels, such as Eden House or the Marquesa Hotel, both of which offer deluxe accommodations and relaxing pool areas. For a stunning ocean view and access to a private beach, you might prefer a waterfront location like Southernmost on the Beach. No matter where you decide to stay, though, reservations are highly recommended, especially on weekends during the high season.

After checking into your hotel and freshening up, take a stroll to Mallory Square, where artists, musicians, acrobats, and tourists converge daily to pay homage to Key West’s gorgeous sunsets. To avoid the crowds, head to The Westin Key West Resort & Marina, where you can watch the sunset while sipping cocktails on the Sunset Deck.

Once the sun goes down, head inland for an early dinner, perhaps at Michaels Restaurant or Café Solé, two of Key West’s most intimate eateries. Afterward you can stroll along the quiet residential roads and make your way to Duval Street, a popular thoroughfare that’s rife with lively, late-night bars—plus curious shops and art galleries, some of which feature enticing window displays.

For a sensual nightcap, stop by Better Than Sex on Simonton, a bordello-style lounge and restaurant that focuses exclusively on wine, beer, coffee, and decadent desserts. Often hosting live jazz, this romantic, dimly lighted gem is usually open until midnight.


Start the day with breakfast at the Banana Cafe, a popular French-style eatery that specializes in delectable crepes. Afterward rent a pair of bicycles from Eaton Bikes on Margaret Street (or have them delivered to you) and tour Key West at your own pace. Be sure to ride up Whitehead Street, where you can visit such tranquil places as the Audubon House & Tropical Gardens and the Ernest Hemingway Home and Museum, both of which offer quiet spots to relax and gaze at the lush foliage. If you have time, stop by the Key West Lighthouse, which lies opposite the Hemingway Home, and climb the spiral staircase for an incredible view of the verdant city below.

Pedal over to Duval Street and stroll through The Key West Butterfly & Nature Conservatory, which features a glass-enclosed habitat filled with colorful birds and butterflies. Roughly 10 blocks away lies Nancy Forrester’s Secret Garden, yet another peaceful spot to relish nature. For lunch, head to the Schooner Wharf Bar, where you can enjoy fresh seafood on a breezy upper deck overlooking the yachts and sailboats in the adjacent Historic Seaport.

Following lunch, you can either continue your biking tour through Key West or head to Key West Eco Tours or Lazy Dog, both of which offer guided kayaking trips. Sharing a two-person kayak, you and your sweetheart can wind along mangrove creeks and get an up-close look at tropical fish, aquatic birds, and other marine wonders.

For another memorable adventure, spend the evening on a sunset cruise. Among those available, Sunset Watersports Key West offers a tropical buffet and a variety of libations during the excursion. Couples will especially enjoy watching the sunset together and dancing on the lighted dance floor.

After the cruise, head back to your hotel for some much-deserved relaxation. Of course, if you’re not yet ready to call it a night, you’ll find no shortage of distractions along Duval Street, from late-night dancing at the Aqua Nightclub to clothing-optional shenanigans at the rooftop Garden of Eden.


If you have yet to return your bicycles to Eaton Bikes, a pickup can be arranged in the morning. After checking out of the hotel, stroll to Martin’s Key West, a stylish German fusion restaurant on Duval, for brunch. Specialties include grilled bratwurst, seafood crepes, and eggs Benedict with lobster medallions. Following brunch, take a taxi or drive to Fort Zachary Taylor Historic State Park, where you can take some time to swim in the warm waters, snorkel amid colorful coral and parrotfish, and enjoy the best beach in town before heading back home.

Excerpted from the Second Edition of Moon Florida Keys.

Travel map of Key West, Florida

Key West