A Southernmost Honeymoon
Key West, Florida
Story by Kathleen Mansfield
Photography by Ocean Key Resort & Spa, The Gates Hotel Key West
At the very end of U.S. Route 1, on the southernmost tip of the continental United States, an intriguing island city awaits newlyweds embarking on their new adventure together. Key West, Florida, fondly known as the Conch Republic by locals, offers its visitors warm temperatures year-round, delicious cuisine inspired by local culture, and perfect activities for couples that entertain as much as they educate. Honeymooners may choose to stay on the quiet northeast end of the island, away from the bustle of downtown, or right in the thick of things near Mallory Square; either way, they will find relaxing accommodations and convenient transportation to their next tour, meal, or mojito.
Located near the entry point of Key West, The Gates Hotel Key West offers a casual, no-frills outdoor retreat for the new Mr. and Mrs. Its recently renovated guestrooms are thoughtfully decorated with cool earth tones and driftwood-inspired contemporary furnishings. Poolside rooms include a private terrace for morning coffee or a nightcap from Rum Row, the hotel’s outdoor bar with a creative Prohibition theme.
Rum Row serves poolside refreshments daily in the form of signature cocktails, local craft beers, and a private selection of rum from Key West First Legal Rum Distillery, a partner of The Gates Hotel. Rum Row also serves appetizing food from the Blind Pig, a food truck permanently parked between The Gates and its sister hotel 24 North. Guests at The Gates are welcome to enjoy the amenities of 24 North such as its trendy indoor bar, refreshing pool with private cabanas, outdoor games, and poolside restaurant the Toasted Coconut. Both hotel pools feature plenty of lounge seating and private cabanas.
Cigar lovers enjoy the humidor at The Gates Hotel filled with Rodriguez hand-rolled cigars, made in partnership between the hotel and Rodriguez Cigars to commemorate the legacy of cigars in Key West.
Between The Gates Hotel and 24 North, a romantic grassy lawn called Sunset Green hosts live music and special events such as destination weddings. In its downtime, Sunset Green is the scene of children playing games on the grass and couples enjoying the peaceful atmosphere with books in hand.
Honeymooners can step outside the entrance of The Gates and explore the northeast end of the island with a walk along the waterfront or with a leisurely pedal on one of the hotel’s blue cruisers. For a more adventurous tour, newlyweds can take a five-minute bike ride to Lazy Dog Adventures and enjoy a quiet kayak or paddleboard tour of the mangrove jungles of Key West, observing native birds, sting rays, Cassiopeia jellyfish, and even manatees. The Gates Hotel and 24 North provide easy access to downtown Key West via the complimentary Old Town Shuttle Service, which runs daily.
Key West is a highly walkable and bicycle-friendly island, and hotel shuttles make getting downtown from the other side of Key West a quick trip. However, the city’s public transportation is essential for tourists to fully appreciate all it has to offer. Locals praise Key West’s Duval Bus Loop, a free bus system established to alleviate the hassle of congested narrow streets and limited parking options. The air-conditioned bus loops around downtown’s most popular attractions with frequent stops from six a.m. to midnight daily.
A short walk from any stop on the Duval Street Loop, the diverse flavors of Key West abound. Turtle Kraals Restaurant and Tower Bar, located on the waterfront of the Historic Seaport and Bight, is one of the oldest restaurants on the island and the official viewing location of the local Cleveland Browns Backers Club. Award-winning ceviche highlights the Bahamian and Caribbean inspired menu and turtle races entertain the dinner crowd every weeknight.
Lucy’s Retired Surfers Bar and Restaurant, which recently moved to a new location just a couple blocks from Mallory Square, is a surf-themed restaurant with a colorful atmosphere, a delicious menu of coastal fusion, and a selection of specialty cocktails and local craft beer. Visitors make merry with live music and a Wipeout margarita or Shark Attack in the heart of downtown Key West.
Key West First Legal Rum Distillery is a small batch private distillery that makes just 17 gallons of rum at a time; each bottle is filled and labeled by hand. Rum from Key West First Legal Rum Distillery is unique in that it is distilled with demerara cane sugar, which is a very pure form of cane sugar reputed to have the best flavor. The distillery also salt-cures its barrels during aging by rolling them into the Gulf of Mexico to soak in salt water. Visitors can enjoy rum at the bar in the distillery gift shop or buy a souvenir to remember their romantic getaway. They can also see the distillery in person through a free tour or mojito-making class. Key West First Legal Rum Distillery celebrates those early rumrunners who helped create Key West and made rum into the popular spirit it is today.
Other bars and restaurants downtown share their own piece of Key West history. Sloppy Joe’s Bar was the 1930s watering hole of adventurous author Ernest Hemingway, who wrote such works as The Old Man and the Sea and Farewell to Arms. The home he built when he lived in Key West is now a historic site with one of the most informative tours a visitor will experience in Key West. Throughout the well-maintained Hemingway home and gorgeous gardens, visitors can see pieces of furniture and art from the Hemingway family, Hemingway’s writing studio, one of the first in-ground swimming pools on the island, and Hemingway cats, properly known as polydactyl for their extra toes. The dozens of cats have free range of the property and are descendants of Hemingway’s cat Snow White.
A few blocks down from the Hemingway Home sits the Southernmost Point Buoy, a large painted monument and popular tourist photo op marking the southernmost point of the U.S. 90 miles north of Cuba. Nearby is the Butterfly Conservatory, a romantic indoor garden that flourishes with hundreds of butterflies and birds year-round. From these attractions, newlyweds can visit Fort Zachary Taylor for a tour or snorkel, explore any number of museums, or shop one of the local art galleries to find a painting to take home. They can learn about native animals at the Key West Aquarium in Mallory Square, or stroll through colorful residential streets in downtown and marvel at historic Key West architecture and the natural beauty of orchids, Banyan trees, and other tropical flora. They can also sit down with Danny DiFabio of Rodriguez Cigars and appreciate the flavors of a fresh hand-rolled cigar and espresso while learning about the history of his family business since it began in the 1940s in Cuba.
After a full day of new experiences, honeymooners will surely enjoy a rest at Ocean Key Resort & Spa, the island’s sophisticated resort getaway nestled between Key West Harbor and Mallory Square. Ocean Key Resort & Spa is an oceanfront haven within walking distance of everything downtown and with onsite amenities that would make any married couple swoon.
Ocean Key’s 100 deluxe guest rooms embody the energy and warmth of Key West, and its prestigious spa SpaTerre provides luxurious massages, facials, and other spa treatments of the highest quality, including relaxing outdoor treatments that take place on a shaded private balcony. LIQUID pool-bar-lounge is another refreshing amenity of the resort with a sun-filled view of Mallory Square and the oceanfront. Ocean Key Boutique in the lobby has it all for a newlywed couple – home goods, island-inspired clothing, jewelry, and skincare, as well as souvenirs for family back home.
Ocean Key’s Hot Tin Roof is an award-winning restaurant with a calming atmosphere and divine menu of “Conch fusion” dishes with Florida and Caribbean influences. Its quiet ambiance perfectly mimes that of the resort with an “island style” elegance and breathtaking views of Sunset Key. Honeymooners will enjoy a romantic dinner on the restaurant terrace as the sun sets while live music plays at the outdoor bar below.
After dinner, guests often visit the colorful Sunset Pier, a lively extension of the bar that was completely rebuilt in 2018 after being destroyed by Hurricane Irma. The pier is a popular site for destination weddings and other private events, but also a common stop for visitors seeking a daytime drink on the water.
Both The Gates Hotel and Ocean Key Resort & Spa offer top-notch concierge services that can assist with booking additional tours or water activities for newlyweds, such as a jet ski tour, sunset cruise, or snorkeling adventure. There is certainly no shortage of relaxing or exciting activities in the Conch Republic for a couple celebrating their love.
