Top Places to Pop The Question in the Florida Keys



There is something about warm sunsets, sandy beaches and swaying palm trees that stoke the flames of romance. Perhaps that is why so many great love stories begin in the Keys. If it’s time to sweep her or him off their feet with a stunning proposal, here are a few ideas for making it a most memorable moment — both tried-and-true and unexpected and new.


Key West

Key West is proposal central. Between beaches, sunset celebrations and historic tall-ship cruises, the hardest part of finding the right place to propose is simply deciding amongst the multitudinous possibilities.

Most popular: A perennial favorite involves dinner at Latitudes restaurant on Sunset Key. Take a short ferry ride from the waterfront near Mallory Square to the glitzy resort island. Dine on fine island cuisine under the stars, then take a moonlight stroll on the beach. You can figure out what to do next…

Adventurous: Rise to the occasion by proposing on top of the Key West Lighthouse. It will take a moment to catch your breath after climbing the 88 stairs to the top, and once you do the view from the tallest point in Key West will take it away again. Of course you need to prepare to lose it for a third time, too, when she says “yes.”

Historic: Fort Zachary Taylor evokes the sensation of a trip back in time, to the days of swashbuckling buccaneers and knights saving damsels in distress. Okay, maybe it’s not quite that old, but the Civil War-era fort is an impressive piece of architecture, complete with romantic brick parapets to stroll along while taking in expansive views of the ocean. It’s also good for a playful game of hide-and-seek among the cannons and old hallways.

Tender: Stroll through an exotic orchid pavilion, under a romantic brick archway being reclaimed by giant strangler fig tree and contemplate for a moment in a magical butterfly garden. The walk through the Key West Garden Club grounds at West Martello Tower is awash in exotic plants from around the world, all housed in the ruins of a Civil War fort. When you get near the end, look for the small, secluded gazebo overlooking the ocean. What an excellent place for a rest and to create a most special moment.


Big Pine & Lower Keys

Nature brims forth in the Lower Keys. Peaceful Key deer graze while warm waters gently lap pristine beaches. Here, time slows down, as days gently blend together with hues of happiness and relaxation — a perfect cornerstone of memories on which to build the rest of your lives together.

Most popular: The ultra-exquisite Little Palm Island serves up complete relaxation. Here there are no phones or televisions, just crystal-blue waters, pristine beaches and lots of luxury. It’s where presidents and movie stars come to escape, and where many a happy couple have become been engaged. The staff here are accustomed to helping prepare the moment, whether that entails setting up candles in the shape of a giant heart on the beach, delivering a shell with a very special ring inside or helping you execute whatever other clever notions cross your mind.

Adventurous: Love doesn’t have to be expensive. Launch a kayak or canoe from Sugarloaf Lodge and paddle just a short ways into the mangrove channels. As they get narrower and narrower, the current propels you through the maze of nature, before landing you in peaceful lagoons where herons wade and ospreys fish. Perhaps it’s best to tie a string to the ring, though, to ensure it doesn’t accidentally escape into the water.

Artful: The world-famous beaches Bahia Honda State Park make a great backdrop for a proposal, but for a truly photo-genius moment take a stroll to the old railroad bridge. The nearly century-old structure rises above the south end of the park in picturesque abandonment, a silent monument to the balance of man and nature.



As the heart of the Keys, Marathon by nature makes romance come alive. Between fishing, scuba diving and beaches, both of you will find plenty of adventure before and after the big moment.

Playful: Sombrero Beach is one of the Keys most coveted and versatile oceanside expanses. With interesting snorkeling, plenty of sand, clean restrooms and covered picnic tables, it’s a chill place to spend the day or evening, and one of the only beaches in the Keys to allow alcohol. Pour a cup of wine (glass is not allowed on the beach) and challenge her to a sand drawing competition. Make sure to include the question, as part of your artful work.

Adventurous: Charter a boat to the Sombrero Lighthouse. The striking 142-foot-tall structure was completed in 1858, and since has helped keep countless ships from certain doom against the shoal. Today the shoal isn’t feared, but rather cherished as a first-rate snorkeling and diving destination. Or come at night, when the stars and our Milky Way Galaxy shine enthrallingly brightly, thanks to the lack of nearby city lights.

Historic: The Seven Mile Bridge with the nearby tiny and enticing Pigeon Key is probably the most photographed aerial scenic in the Keys. That’s because the island invokes such curious emotions, wondering what it would be like to live on that cozy retreat surrounded by colorful reefs and waters. Life was a little difficult there in the early 1900s, when it was home to workers constructing the Overseas Railway. But today, the 5-acre paradise makes for an intriguing afternoon of exploration among historic shacks and tropical foliage. There are also several secluded stretches of waterfront, perfect for a romantic stroll… and question. The walking bridge is closed until 2017, but the ferry from Knight’s Key adds another layer of enchantment.



Islamorada is home to a good number of upscale and comfortable resorts, all of which are well-versed in helping set the stage for and executing the perfect proposal setting. Miles of beaches and fine food only add to the dreamy possibilities. Here are a few ideas, but don’t forget to ask the concierge about their signature romantic traditions.

Most popular: With its colorful Caribbean-style architecture and hearty atmosphere, Morada Bay Beach Café sets the stage for a classic romantic evening straight out of a movie. Dine al fresco by candlelight with your toes in the sand. Yes, in the sand. They don’t have beach-front tables here, but actually tables on the beach. Dance to some live music, whisper sweet nothings in each other’s ears, take a walk along the water and wash off those tears of joy with a moonlight swim.

Sports: If you and your love share a fondness for fishing, then a proposal to remember can happen right on the charter boat. Share in the exhilaration of pulling in Mahi and wahoo, then set a different kind of lure. Tie the ring to your hook and ask her to please help you with your bait. The captain should also be more than happy to make sure the stage is properly set.

Family Surprise: During low tide a sandbar becomes exposed a little ways in front of the Postcard Inn. People boat out to it, and the scene can be a bit of a party. If you plan to have friends and family surprise her or him for the big question, then this is a perfect place to hide them. Take a little romantic kayak, and end up on a picturesque sandbar amongst all of your loved ones.


Key Largo

Key Largo is so romantic they wrote a song about it. “Key Largo, Montego, baby why don’t we go…” Okay, so Kokomo isn’t a real place, but Key Largo really is one of the best places to “get there fast and then take it slow.” And as for creative spots to propose, the sky is the limit — or rather the sky, the land and the water.

Classic: After a fanciful beach dinner at Breezer’s Bar and Grille, stroll down the sand at the Marriott Resort. A small waterfront tiki with a hammock awaits. Pelicans bob on the water, cormorants majestically dry their wings, and as the sun begins to set magic is truly in the air. Or if you’re both a bit more adventurous, have lunch and then swim out to the floating dock, just 50 feet or so past the tiki.

Movie Buff: In the ‘50s, Katherine Hepburn and Humphrey Bogart created a romantic spark onscreen with the African Queen. Now that nostalgic vessel lives in Key Largo, where couples can hop aboard to kindle their own flames on this intimate, old-time steam boat. For an extra bit of romance, don a fedora and say something like, “We’ll always have Paris.”

Playful: They Keys are known for their lost and found treasure galleons. Make a treasure hunt of your own. Create clues for your soon-to-be fiancée to follow, that lead to the ring. Try a message in a bottle or burying the ring in the sand. Or for a little more challenge, hide it in a treasure chest underwater, perhaps near the iconic Christ of the Abyss statue or the Spanish canons at John Pennekamp State Park.