Romantic Things To Do in Key West

Key West is a tropical paradise ideally suited to kindling romance in history buffs, nature lovers and literary devotees.

Mallory Square Sunset Celebration

Watching a beautiful sunset together is a time-honored tradition for many couples. One of the best places to watch the event is Mallory Square. Although it is a busy spot each afternoon, Mallory Square has breathtaking views especially as the sun starts to set. The Sunset Celebration begins two hours before sundown as a variety of performers gather to create a street festival that is uniquely Key West. Soak up the celebratory atmosphere while watching street performers and enjoying a variety of treats. Grab a drink to toast the spectacular sunset with your loved one.

Bike Around Old Town

The quaint side streets and their aromatic, colorful gardens are best explored by bike. The leisurely pace of a beach cruiser enables you to see and experience more of the island’s distinctive character. Pedal down streets lined with shade trees, white picket fences and pastel-colored cottages with gingerbread trim that evoke romantic storybook images.

Picnic at Fort Zachary State Park

A romantic Key West daytime activity is to grab a bathing suit and picnic basket to enjoy a lovely afternoon at this popular, well-maintained beach. Along with the Civil War-era fort, the 54-acre national historic landmark is home to several nature trails and a stunning coral reef just offshore. Relax on the warm, sandy beach or explore the beautiful habitat together.

Visit the Sails to Rails Museum

Embark on a journey through Key West’s maritime past at the captivating Sails to Rails Museum. Discover the remarkable transition from sailboats to steamships and railways that shaped the island’s history. Explore meticulously preserved artifacts and interactive exhibits, including the opportunity to lift a real silver bar and delve into maritime tales. Immerse yourself in the sights and sounds of Key West’s rich heritage with a Fort Jefferson diorama, offering a glimpse into the island’s strategic importance.

Tour Ernest Hemingway’s House

Hemingway was a romantic at heart; a lover so to speak. It should be no surprise that his former residence and gardens is a romantic, quiet oasis in the middle of Key West. Inside the estate walls, see the beautiful house and wander through the fragrant tropical garden. It was here that Hemingway wrote the nonfiction work “The Green Hills of Africa” and the novel “To Have and Have Not.” A popular site for weddings and other romantic events, the gardens are some of the most beautiful green spaces of their kind on the island.

Enjoy a Sunset Sailing Cruise

Head offshore on a romantic voyage for a spectacular waterborne view of an iconic Key West sunset. Snuggle up to that special someone as the sun dips below the horizon and creates a kaleidoscope of vibrant colors. Depending upon the cruise, you can enjoy wine, Champagne and a variety of snacks and hors d’oeuvres. In addition to a catamaran, you can choose to sail on a tall-mast schooner or other vessels that harken back to the romantic age of wooden ships and sea travel.

Visit the Truman Little White House

In addition to the historic former Commandant’s Quarters built in 1890, the grounds include a one-acre botanical garden featuring trees and tropical foliage. See houseplants normally grown indoors in colder climates achieve oversized dimensions in Key West’s frost-free weather. Used by numerous presidents as a vacation retreat, the home was the setting for several important events in American history. With its tree-canopied, manicured grounds, the national historic site is a popular spot for romantic Key West weddings.

Dine at El Meson De Pepe

Located in Old Town near Mallory Square, El Meson de Pepe has been preparing authentic Cuban dishes for more than 30 years. With a passion that started in Cuba, this family-owned eatery now thrives as a staple of the city’s culinary scene. Its menu, décor and atmosphere reflect and preserve the island’s Cuban Conch heritage.

Visit the Key West Butterfly and Nature Conservatory

Along with soothing music and flowing fountains, these enchanting gardens are filled with birds and fish as well as turtles and more than 80 species of butterflies. Surrounded by the beautiful flora and fauna in this incredible habitat, you can take amazing close-up photos of these colorful insects.

Tour the Audubon House and Tropical Gardens

Strolling hand-in-hand, you can explore the lush tropical gardens and the home of Captain John Geiger who hosted John James Audubon. The former residence of the affluent, mid-19th century master wrecker brings history to life. Adorned with elegant period furnishings, the residence also features works by the famed ornithologist who stayed here in the 1830s.

The colorful sunsets, sandy beaches and warm breezes beckon couples looking for a romantic time together in a tropical setting. Removed from the stress of the mainland, Key West is a paradise retreat with numerous romantic things to do across the island. It is the perfect spot for date night, a weekend getaway or a romantic honeymoon.