An Unforgettable Romantic Weekend Getaway in Key West, FL

by | May 27, 2022 | Destinations, Family Adventures, Romantic Retreats, South East, USA

(This article may or may not contain affiliate links. What does that mean?)


It’s hard to think about emails and deadlines when the fronds of a palm tree are hypnotically dancing before you in the arms of the wind.

Which is why, for our wedding anniversary this year, my wife and I decided to completely disconnect. To do this, we organized a romantic weekend getaway to a destination renowned for its fresh fruit, ocean views, sandy beaches, and spectacular sunsets: the tropical island paradise that is Key West, Florida. 



Key West Pin #1


Why Key West?

Also known as the Conch Republic, Key West sits at the southern tip of the Florida Keys and is the southernmost city in the contiguous United States. Although it measures only about four miles across, Old Town Key West manages to pack in 41 must-see bars, 150 boutique hotels, 400 homespun restaurants, and what feels like 1,000 free-range chickens. Nowadays, it’s a popular romantic vacation getaway for those looking to soak up the sun, eat delicious seafood, and enjoy some quality time with your better half.


Saturday: Things To Do On Duval Street 

Southernmost Point of the Continental U.S.

The best place to begin your romantic journey is at the southernmost tip of world-famous Duval Street which is at the buoy marking the Southernmost Point of the Continental U.S. (Okay, so technically the southernmost point is a little to the south; but this buoy is still super cute!)


Fun Fact! It’s at this spot that you’ll only be about 90 miles north of Cuba. 


Southernmost Point of the Continental U.S. and Key West

This buoy is the perfect spot to commemorate the start of your romantic vacation over a glass of bubbly or tropical cocktail. Image by Paul Brennan via Pixabay.


Key West Butterfly and Nature Conservatory

After taking an album’s worth of selfies, we decided it was time to get motoring. Leaving the oceanview behind, we forged our way inland to our first stop: the Key West Butterfly and Nature Conservatory. This enormous terrarium is home to hundreds of winged creatures. In addition to all the butterflies, there are parrots, parakeets, and even flamingos flitting through this botanical Garden of Eden. We were even lucky enough to catch some of these pink swans as they refreshed themselves under the miniature cascades that dot the conservatory; an auspicious start to our romantic holiday, if I do say so myself. 

But don’t take my word for it: This video gives you a taste of what you can expect when you visit the conservatory. 



We were feeling pretty peckish by this point, so we popped into the Banana Cafe for a light breakfast of coffee and savory crepes. 

My wife ordered the “La Veggie & Avocado,” whereas I leapt for the “La Mahi Piccata.” Both were delicious and filled us up just enough to last until lunchtime.


Key West Lighthouse

Pushing back our plates and unbuckling our belts, my wife and I figured it was time to work off our breakfast bellies with some serious hiking, ergo time to pay a visit to the Key West Lighthouse. Huffing and puffing, we braved the dizzying spiral staircase (88 steps in all) to reach the top of this 73-foot beacon and were rewarded with breathtaking views of Key West usually reserved for seagulls. 


The Key West Lighthouse is located in Key West, Florida

As it’s one of the tallest structures on the island, we were able to see all of Key West and the surrounding shoals from up there. Image by Paul Brennan via Pixabay.


Don’t Miss! 9 Perfect California Lighthouses For Kids


Bahama Village Key West

After reaching terra firma once more, we were encouraged by a garrulous staff member to take a detour and check out a local oddity a few minutes’ walk away: Bahamas Village

We did so and spent a pleasant half-hour wandering among the Bahamian-themed gift shops and booths selling every possible variety of Panama hat in existence. Both having purchased one, my wife and I sauntered across the street and into the former residence of one of America’s great authors, the Ernest Hemingway Home and Museum


Ernest Hemingway House

Skipping the tour, we chose to wander the grounds ourselves, peeking into nooks and crannies and playing with the cats that call this historic building home. 


Fun Fact! Take a careful squint at these cats’ paws and you’ll notice many of them have six or more toes. Hemingway loved these polydactyl felines and the 50 or so cats currently on the premises descend from his original one, Snow White. In addition, it’s believed that cats like these bring good luck to fishermen—fitting for a seaport, isn’t it?  


Hemingway House Key West Florida

It felt only right to pick up a copy of “The Old Man and the Sea” at the Hemingway bookshop for a little perusal. I went for the Spanish edition in keeping with Key West’s Latin-speaking heritage. Image by Michelle Raponi via Pixabay.


Restaurants on Duval St

Having finished perusing through highbrow literature, my wife notified me that it was time for lunch. We were roughly half-way up Duval Street at this point, so depending on your hunger level, there are plenty of great cafes and bistros to nip into for a coffee or snack, like the Croissants de France Bakery & Restaurant or Moondog Cafe. We wanted something a little heftier to carry us the rest of the way and ended up at DJ’s Clam Shack

We took the opportunity to take some selfies at Mile Marker 0 on Fleming and Whitehead. Continuing our journey nor-nor-west along Duval Street, we took a trip to Nancy Forrester’s Secret Garden, a sanctuary for rescued parrots run by the eponymous Nancy. 

Zig-zagging our way back across Duval, we ended the shopping portion of our day at the Key West Shipwreck Museum, which bears an astonishing resemblance to something from the Pirates of the Caribbean film series. 


Key West Shipwreck Museum, Key West, Florida

Step inside to discover how the (ship)wreckers — effectively salvagers — made their living off the coast of Key West in the mid-1800s. Image by Brian Urso via Unsplash.


Mallory Square

Finding ourselves at the north end of Duval Street, and hearing loud music and cheering in the distance, we followed the throng and ended up at Mallory Square. Jugglers, acrobats, street performers, and musicians vied for peoples’ attention as the sun set behind them, creating a stunning backdrop. A little to the north, you’ll find Sunset Pier: a tropical bar that doubles as a great place to take some romantic selfies.


Also, as we found out later, walking the full length of Duval Street equates to having crossed from the Gulf of Mexico to the Atlantic Ocean. Pretty good for our first day in Key West, I reckon. 


Mallory Square At Sunset With A Cruise ShIp In The Background

Every evening huge crowds gather in Mallory Square to watch the sunset and street performers in a nightly ritual. Image by Yinan Chen via Pixabay.


As a reward for covering all that distance, it was time for a romantic dinner at El Meson De Pepe’s Restaurant & Bar, which serves mouthwatering Cuban tapas. This meal, and a brief visit to Sloppy Joe’s, a bar famous for having Ernest Hemingway drink in it, concluded our first day in Key West.  



Sunday: Mangrove Kayak Tour, Rum Tour, And An Evening Surprise

Mangrove Kayak Tour

Having explored Key West the town, we were eager now to explore Key West the nature sanctuary. Accordingly, we’d booked a mangrove kayak tour, assuming that was the best way to see the isle’s natural beauty up close. By 10:30 we were out paddling among mangroves that formed a warren of alleys and tunnels. Through the crystal-clear, warm water, we saw coral reefs, sponges, sea anemones, all shapes and manner of fish, and even a spotted eagle ray that drifted idly by.

This video gives you a pretty good idea of what to expect while out kayaking:



In keeping with the Key West alternative lifestyle, our guide informed us not to be alarmed if we saw people watching us through the mangrove branches. “All sorts come to live out here,” she said casually, “some looking to leave their problems behind, others to be in tune with nature, and some just cause they like the peace and quiet.” My wife and I peered through the mangroves, a little apprehensively, but never once did we see a face peeking back at us (that we noticed). 

DON’T MISS!  The Most Fun Things To Do In Sarasota With Family


Key West’s First Legal Rum Distillery

After the mangrove trip and a spot of lunch at Pepe’s Cafe, we took a tour of Key West’s first legal rum distillery. The tour was free and required no reservation, and we even got to try some samples afterward at no extra cost. If you have the time, definitely check out at least one rum tour while you’re in Key West. It’s a fun and informative excuse to enjoy the island’s most famous alcoholic beverage. 


Pepe's Cafe In Key West, Florida Keys

As the sign says, Pepe’s is the oldest eatery in the Florida Keys. Don’t let the rustic exterior fool you, this is a quality restaurant with delicious pub fare and cocktails. Image by Mary Hartman.


Schooner Champagne Sunset Sail

With the afternoon growing late, it was time to spring the surprise I’d prepared for my wife in honor of our anniversary. Without telling her, I’d booked us a berth on a Schooner Champagne Sunset Sail. From the deck of this two-masted sailboat, we got to sip champagne, fresh shrimp hors d’oeuvres, and enjoy the romantic Key West sunset practically to ourselves.

For dinner, we went to El Siboney, one of the best restaurants in all of Key West. We’d also heard awesome things from our tour guide about the Green Parrot Bar and decided to check it out for ourselves.

Arriving back at the hotel, we discovered that our flight that was due to depart at 8:30 AM tomorrow morning had been delayed until 6 PM—meaning we had a whole other day to spend in Key West! My wife and I hastily booked a dawn snorkeling trip: something we’d wanted to do but hadn’t had the time for with our tight schedule.


Monday (Bonus Day): Dawn Snorkel And Afternoon At Smathers Beach

Morning Snorkel Trip

At the crack of dawn, we were out on the water for our morning snorkel trip. Never in all my life have I seen water so clear or fish so fearless as off the coast of Key West. Even a nurse shark came to say hello, which was terrifying and exciting. 

We got back a little after midday, and after a quick wardrobe change, got lunch at the Hog’s Breath Saloon. As the name suggests, this swine-centered eatery has out of this world pulled pork sandwiches, as well as live music, excellent cocktails, and a quirky gift shop. 


Don’t Miss! Discover Hidden Gems in Florida With Kids


Smathers Beach

Later, with time left before our flight, we headed out to Smathers Beach. (The hotel was kind enough to hold on to our luggage while we sunbathed.)  The seashore itself is so large, It felt like we were alone on our own private beach. 


Sunset On Smathers Beach, Key West Florida

As you can see, that coastline just seems to stretch on forever, making you feel like a castaway on a remote tropical island. Image by Mary Hartman.


With time running short, we grabbed a quick drink at Margaritaville Beach House, saddled our luggage, and hot-tailed it over to the airport to catch our flight back home, full to bursting with island tranquility. 


When You Go 



Getting To Key West From Los Angeles

Key West’s airport is conveniently located near the town’s center. Although, to be honest, the island’s so small that even if it was on the extreme periphery, it still wouldn’t take more than fifteen minutes to reach downtown. As it’s a smaller airport, tickets are pricey, and you’ll have to make a connecting flight since there aren’t any direct flights from LAX. Nevertheless, with foresight and a little creativity, you could score a good deal flying out to Key West. We find Cheap’OAir to have the best flights most of the time and this is a good start for your search for the best deal.



Where To Stay

As far as waterfront resorts go, the Hyatt Centric Key West Resort & Spa is the best in town.  From fine dining to spa treatments to e-vehicle charging and free wi-fi, the Hyatt provides great service and modern amenities while retaining the laid-back vibe of its island surroundings.

If boutique is more your jam, I encourage you to check out the Heron House Court. Situated in a lush tropical garden, this adorable bed-and-breakfast is ideal for a romantic couple’s weekend getaway. With a fine porch on the street-side and an outdoor pool retreat behind, Heron House mixes nostalgia with modern accommodations to bring you a uniquely Key West-style stay.  

Aptly named Not Your Average Hotel, NYAH excels by offering adults-only accommodations that’ll fit any party. Whether traveling alone with friends or your sweetheart, NYAH has an affordable and comfortable option waiting for you. Offering a complimentary happy hour, breakfast, and bike rentals, NYAH guarantees that your stay in Key West will be anything but ordinary. 

As you can see, Key West is simply overflowing with romance, color, and excitement. Its romantic mood and laid-back lifestyle inspired the words of such famous authors as Ernest Hemingway, Robert Frost, and Truman Capote to name a few. It’s the perfect romantic retreat for busy people looking to leave the world behind for a bit and return to a simple life of sand, sun, rum, and romance. 



Key West Pin #2


Matthew LaMourie II is a freelance writer and photographer based in San Francisco, CA. He is a regular contributor to a number of online publications, where he covers such diverse topics as travel, lifestyle, cooking, and classic short stories. When not writing, Matthew likes to explore new and interesting places together with his growing family.


Pin It on Pinterest

Share This