The Best Things To Do In Key West For Couples

Key West, Florida

Key West has enchanted visitors for decades, capturing the hearts of legendary figures like Ernest Hemingway, who famously declared it “the best place I’ve ever been any time, anywhere.” Today, Key West continues to charm with its swaying palm trees, crystal-clear waters, vibrant nightlife, and storied history, including tales of pirates, shipwrecks and treasure hunting. Its historic charm is evident in quaint “conch-style” homes, saloons adorned with decades of memorabilia, and the timeless allure of the azure sea.

Key West offers couples a romantic tropical getaway where they can soak up its unique ambience, delight in vibrant culinary experiences (paired with spirited libations!), and create unforgettable memories of relaxed tropical days and nights. Here, we highlight the best things couples can do and see in Key West, from historic sights and beautiful beaches to top-notch restaurants and bars.

Harry S. Truman Little White House

Famous as where Truman spent 175 days of his presidency, The historic Harry S. Truman Little White House is a must-see when visiting Key West. Restored to its 1949 appearance, the house showcases preserved rooms where the Trumans lived, worked, and relaxed during their time in Key West. Open every day, visitors can explore the house through tours included in the admission fee, gaining deeper insights into Truman’s presidency.

Smathers Beach

Smathers Beach - Key West, Florida

The largest public beach in Key West, Smathers Beach offers an idyllic, tropical atmosphere with its palm-lined shores and all the essentials for a perfect beach day, including food trucks, rentable chairs and umbrellas, and activities such as catamarans, paddleboards, and jet skis. Public bathrooms are also available. While there is no fee to visit, it’s best to avoid the Spring Break season when it becomes a lively party spot.

Key West Lighthouse & Keeper’s Quarters

Key West Light House - Key West, Florida

The Key West Lighthouse offers some of the finest views in the area for those willing to climb its 88 steps. At the top, visitors can enjoy a bird’s-eye view of one of Key West’s famous sunsets from the observation platform during sunset experiences, which include snacks and a bottle of wine or Prosecco. If you’re short on time, a quick ascent for a few Instagram shots is worthwhile.

Fort Zachary Taylor Historic State Park

Fort Taylor- Key West, Florida

Fort Taylor, a national historic monument and state park, houses the world’s most extensive collection of Civil War armaments. You can learn about the fort’s involvement in the Civil and Spanish-American Wars by taking a guided tour or exploring independently. The park also boasts one of Key West’s best beaches, making it a versatile stop for history enthusiasts and nature lovers alike. Activities include birdwatching, snorkelling, and relaxing on the sand.

Related article: The Ultimate Travel Guide to Florida for Couples

The Ernest Hemingway Home & Museum

The Ernest Hemingway Home & Museum - Key West, Florida

The Hemingway House is one of Key West’s most visited attractions, once home to the celebrated American author for over a decade. Visitors can explore the well-preserved rooms and tour the lush gardens. The home is filled with Hemingway memorabilia, including photos, books, and furniture, providing a glimpse into his life in South Florida. Local residents lead guided tours with a quirky charm akin to Hemingway himself.

Dry Tortugas National Park

Fort Jefferson Dry Tortugas National Park- Key West, Florida

Dry Tortugas National Park, primarily composed of open water, is home to incredible marine life and bird species. Visitors can camp, dive, snorkel, and swim in this remote park, one of the least-visited in the country. Highlights include Fort Jefferson, built after the War of 1812, and the Windjammer wreck site, where experienced divers can explore the remains of an early 20th-century iron-hulled ship.

Duval Street

Duval Street- Key West, Florida

No visit to Key West is complete without a stroll down the iconic Duval Street, the vibrant artery of the island stretching from the Gulf of Mexico to the Atlantic Ocean. This bustling thoroughfare includes various attractions, including eclectic shops, art galleries, and renowned eateries that cater to every palate. Daytime offers historic sites like the Ernest Hemingway Home and Museum, while evenings bring a lively nightlife scene with famous bars featuring live music and local brews. Duval Street has something for everyone, embodying the spirit and charm of Key West.

The expansive Key West First Legal Rum Distillery offers free tours that delve into the local rum-making process, tastings, and snacks such as rum cakes. A popular feature is the free mojito-making class, inspired by the owner’s experiences in Havana. Tours are open to all, including children, making it a pleasant stop for a break with a local twist.

Key West Butterfly & Nature Conservatory

Blue butterfly at Key West Butterfly Nature Conservatory

The Key West Butterfly & Nature Conservatory is home to over 50 species of butterflies and 20 species of exotic birds. Visitors can learn about butterfly anatomy, physiology, life cycles, feeding, and migratory patterns and watch flamingos up close. The highlight is the learning centre, where live caterpillars feed on their host plants. This quick activity offers a refreshing break from the beach.

Snorkel Over Living Coral

The Florida Keys feature North America’s only living coral reef, making Key West an excellent destination for underwater exploration. Key West is renowned for its top snorkelling and diving spots with clear waters, vibrant reefs, and accessible shipwrecks. Rock Key, located seven miles southeast of Key West, offers the chance to encounter moray eels, grouper, and remnants of shipwrecks.

Enjoy Various Water Activities

Beyond exploring North America’s only living coral reef with a snorkelling or diving tour, couples can enjoy a new water adventure every day. Rent kayaks or paddleboards to navigate the mangroves and coastal waters for a serene and scenic experience. Take a guided jet ski tour around Key West for an exhilarating adventure.

Southernmost Point

Southernmost Point Key West

A prime photo opportunity in Key West, Southernmost Point is the southernmost point of the continental United States, marked by a giant buoy statue. It is a popular spot for Instagram-worthy photos, so visiting early or late in the day is recommended to avoid crowds. Catching a dramatic sunset here can make the experience even better.

Mel Fisher Maritime Museum

The Mel Fisher Maritime Museum might be small but is a treasure trove of distinctive historical artifacts. Housed within a 1910 building initially serving as a Navy storehouse, it showcases relics retrieved from four notable ships: the Nuestra Señora de Atocha and the Santa Margarita, lost during a devastating 1622 hurricane; The St. John’s Wreck, which carried conquistadors in the mid-16th century; and the Henrietta Marie, an English slave ship wrecked near Key West. This museum provides a captivating glimpse into Key West’s rich maritime history.

Red Barn Theatre

The Red Barn Theatre was built as a carriage house in 1829 and has been a theatre for many years. It hosts a variety of performances, including plays, musicals, live music, and family shows. Notable figures such as Tennessee Williams and Jimmy Buffet have graced the theatre, making it a cherished local spot that adds a dose of culture to Key West.

Captain’s Corner Dive Center: Vandenberg Wreck Dive

Meet at the dock for an underwater adventure at the Vandenberg shipwreck, the world’s second-largest artificial reef. This former WWII missile tracking ship is a top dive site, offering plenty of sea life to discover. Even seasoned divers benefit from hiring a private guide to explore the vessel safely and find the best spots for marine life sightings.

Key West Food Tours

Enjoy the gourmet delights Key West offers with Smith’s Key West Food Tours. Smith provides a variety of tours, including a tasting and cultural tour showcasing the island’s Cuban and Caribbean flavours, a seafood experience, a bar crawl, and even a food tour dedicated to Hemingway.

Best Nightlife in Key West

Nightlife in Key West is a vibrant mix of eclectic bars, live music, and unique experiences, making it the perfect destination for nocturnal adventurers. From the bustling energy of Duval Street to the laid-back charm of waterfront bars, there’s something for everyone. Whether you’re looking to dance the night away, enjoy a sunset celebration, or explore the island’s haunted history, Key West has it all. Here are a few venues to put on your itinerary:

The Green Parrot

One of the oldest bars in Key West, The Green Parrot is the place to mix and mingle with locals. The bar is well-known for its local music and stellar drinks, but don’t come hungry – it only serves snacks.

The Bull and Whistle

Enjoy even more of Key West’s divine weather by sipping a cocktail or cold beer at The Bull and Whistle, an open-air bar on Duval Street. The bar offers table seating facing its small stage for local acts, a large bar to belly up to, and plenty of pool tables so you can challenge your travel companions to a game.


Key West has a vibrant drag scene, and there’s no better place to experience it than at Aquaplex. The nightclub puts on shows every Monday and Tuesday at 9 p.m. and every Wednesday to Sunday at 7 p.m. and 9 p.m., giving you plenty of opportunities to see your favourite act.

Mallory Square Sunset Celebration

Mallory Square Sunset Celebration - Key West, Florida

Head on down to Mallory Square for the nightly sunset celebration! You can catch street performers, grab some delicious food, and join a lively crowd to watch the sun dip below the horizon. Since the early 19th century, Key West’s stunning sunsets have been documented, with naturalist John Audubon writing about their beauty. It’s said that playwright Tennessee Williams initiated the first sunset celebration by applauding the sun as it set. Today, Mallory Square remains the go-to spot for these nightly festivities, where locals and visitors salute the sunset amidst performers and vendors, creating a vibrant community atmosphere.

Best Restaurants


For a romantic dinner, Latitudes on Sunset Key offers a secluded experience accessible only by a brief boat ride. The menu, featuring locally sourced ingredients, changes regularly and features dishes like grilled lobster tail and Wagyu beef.

Glazed Donuts

Glazed has transformed from a local secret to a must-visit in Key West. Known for its artisanal approach, it offers unique treats like Key lime pie doughnuts and peach-blessed dissents, paired perfectly with a whole coffee bar experience.

Blue Heaven

Blue Heaven’s laid-back vibe and live music create an atmosphere akin to a backyard gathering. Their eclectic menu blends Caribbean spices with Keys flavours, offering seafood, jerk seasoning, and hearty dishes like filet mignon and pork tenderloin. Save room for their famous “Mile-High” Key lime pie.

Cuban Coffee Queen

With three locations in town, Cuban Coffee Queen serves more than just great coffee. Enjoy classic Cuban dishes like pressed Cuban bread with guava and cream cheese, perfect for a morning bite in the sun-drenched streets of Key West.

El Siboney

Despite its unassuming appearance, El Siboney surprises with authentic Cuban flavours. Favourites include whole fried fish, garlic chicken, and Cuban staples like ropa vieja and picadillo, all served casually with pitchers of homemade sangria.

Little Pearl

Little Pearl blends a chic wine bar with a seafood eatery, offering a tasting menu highlighting their culinary creativity. Dishes like Japanese baby back ribs with Daikon slaw showcase their innovative approach amidst Key West’s nautical surroundings.

Café Marquesa

Located off Duval Street, Café Marquesa offers an intimate dining experience in a lush garden. Their menu features elevated classics like shrimp and grits with andouille sausage and crispy pork osso bucco, ensuring a memorable dining experience.

A&B Lobster House

Since 1947, A&B Lobster House has been a fine dining staple in Key West. With marina views from its wraparound balcony, the restaurant offers decadent dishes like Caribbean lobster thermidor, grouper Oscar, and strip steak au poivre, paired with classic cocktails and an impressive wine list.

Getting to Key West

You have two main options for reaching Key West: car or air. Direct flights to Key West International Airport (EYW) are available from various cities nationwide, including Chicago, Dallas, New York City, Boston, Charlotte, and Atlanta.

Alternatively, driving from Miami to Key West offers a unique experience. Visitors can rent a car in Miami and travel along the US 1, the Overseas Highway. This scenic route spans 106 miles and includes 42 bridges, providing stunning views throughout the journey.

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