15 Things to Do in Key West for Couples

Looking for things to do in Key West for couples? This fun and quirky town is made for romance, with sunsets that stop you in your tracks, cocktails by the water, and adventures around every corner.

Check out some of the best things to do together, whether you’re planning a romantic getaway or just a fun day in port.

Where is Key West?

Key West is the southernmost island in the Florida Keys, sitting closer to Cuba than to Miami. You can get there by car along the famous Overseas Highway, a scenic drive that takes you over turquoise waters, past Key Largo, and across countless bridges.

It’s about a four-hour drive from Miami, though you can also fly into Key West International Airport or arrive by cruise ship at the Key West Cruise Port.

There’s also a ferry from Fort Myers Beach or Marco Island. We haven’t done it yet, but I’ve heard it’s a fun option. Boarding begins at 7 a.m., so that would be a very early morning for us as we’d have to make a two-hour drive to get there. If you’re staying in one of those cities, it’s a nice option if you don’t want to drive.

Why We Love To Visit Key West

It doesn’t take long to figure out that Key West has its own rhythm, and that’s exactly what makes us love it. The streets are lined with bright cottages and roosters that wander wherever they please.

There is a nightly sunset celebration at Mallory Square, with people gathering and cheering as the last bit dips below the water. It’s the little things you do in Key West that make it so special.

We stopped for mojitos while street performers juggled and played guitar, shared slices of tart key lime pie, snacked on crispy conch fritters, and followed the sound of live music drifting out of open doors on Duval Street. It’s the kind of place that’s just as fun your first time as it is on a return visit, and that’s why we keep coming back.

I’ve made the drive from Bradenton to Key West before, and it’s a long one. Once you hit Miami, there are still four more hours of highway driving ahead. Though it is one of the great American road trips, once you’ve done it, you really don’t get too excited about doing that part of the trip again, unless you make a few stops.

My suggestion is to stop and stay at the best luxury hotel in Naples for a night. With so many things to do in Naples, try to spend a couple of days.

After Naples, you could stop at Wilson Key for a bite to eat and some shopping. You can’t miss it if you look for the giant lobster.

Once you get to Key Largo, make a short stop to see the African Queen, that famous steamboat from the movie with Humphrey Bogart. You can even take a cruise as long as you book ahead of time.

Finally, about two hours after Key Largo, you’ll arrive in Key West. From the moment you arrive, it feels alive in a way that’s hard to describe. It’s simply a vibe you won’t find anywhere else. Key West is definitely on island time.

It’s not about rushing from one sight to the next, but about savoring the food, music, and little surprises around every corner. That’s what makes it such a great place for couples, and this guide shares some of the top experiences that will help make your trip unforgettable.

Depending on how long you’re staying, you may have time to do everything on this list. If you’re planning to take the family, check out my list of things to do in Key West with kids.

And on the drive back, you could spend a couple of days at Hawks Cay Resort in Duck Key. It’s only about an hour and a half from Key West, but it’s a great place to chill and be pampered for a couple of days.

Experience the Festivities at Sunset at Mallory Square

In the evenings, locals and visitors gather at Mallory Square for the nightly Sunset Celebration. The pier comes alive with entertainers like jugglers, guitar players, acrobats, and even fire eaters.

You’ll see local artists setting up their tables along the walkway with paintings, handmade crafts, and jewelry. Food vendors serve favorites like conch fritters, Key lime pie, and frozen drinks in case you want a snack as you wander from act to act.

We joined the crowd one night and watched as the last streaks of pink and fiery orange slipped below the horizon. It’s one of the most beautiful sunsets I’ve seen, and the crowd’s energy made it even better.

This is a very popular daily festival that’s been running for decades. If you go, I suggest that you arrive at least half an hour early to enjoy the entertainment and to grab a good spot by the water before the sunset show begins.

Explore Key West by Conch Tour Train or Hop-on Hop-off Trolley

Exploring the island is easy with a ride on the Conch Tour Train or the Old Town Trolley. The Conch Train has been running since 1958 and offers a 75-minute narrated loop through Old Town, passing highlights like Mallory Square, the Hemingway Home, and the Key West Lighthouse.

There is also an Old Town Trolley that offers 13 stops across the island, and you can hop on and off all day to explore places like the Southernmost Point, Fort Zachary Taylor, or Duval Street.

Both tours give you a guided look at Key West’s history, colorful architecture, and hidden corners. We hopped on the Conch Train for a loop and liked that it gave us ideas for places to go back to later at our own pace. I recommend booking one of these tours early in your trip so you’ll know which spots you want to explore more.

Share a Piece of Pie from Key Lime Pie Bakery

No trip to Key West is complete without a slice of Key lime pie. We sampled it more than once, and the tart, creamy filling with a graham cracker crust was worth every bite.

The Key Lime Pie Bakery on Greene Street is a favorite stop, just steps from Duval. You can order a slice on the spot or pick up a whole pie to take back to your hotel or cruise ship. They also sell Key lime cookies and candies, which make fun souvenirs or snacks for later.

I loved the pie so much that when I got home, I worked on creating my own Key Lime Pie Recipe to bring a little piece of Key West back with me.

Visit the Hemingway Home

Literary fans and history buffs will love the Hemingway Home and Museum, with its lush gardens and the famous six-toed cats that wander the property. The cats are descendants of Hemingway’s own pet, Snow White, and you’ll spot them lounging everywhere from the porch steps to the flowerbeds.

Inside, you can walk through the rooms where Hemingway lived and worked. During his years here, he wrote some of his most popular works, including To Have and Have Not, his only novel set in Key West. You’ll also see his typewriter, fishing trophies, and other pieces of daily life from his time on the island.

We enjoyed the guided tour that shared plenty of interesting stories. After the tour, we had time to explore the shaded gardens at our own pace and imagine what life here must have been like during Hemingway’s years here.

Order the Pancakes at Blue Heaven

Talk about heaven, Blue Heaven is the spot for your first meal of the day. You can have breakfast with the roosters until 2:30 p.m., but those fluffy pancakes are only served until noon, so get there in time to order their famous pineapple recipe.

There are a plethora of other breakfast options, from a simple fruit bowl with the best banana bread you’ve ever tasted to seven varieties of egg benedicts. Note: No counting calories allowed. You’re on vacation!

You can also get lunch starting at noon, offering a variety of salads and sandwiches. Their chicken salad is legendary.

Dinner begins at 5 p.m., and believe it or not, this spot where you can eat with roosters in the morning has a wine list that will knock your socks off. With choices from local fish to filet mignon to creative vegan options, there really is something for everyone. Order dessert!

Go Shopping at the Shops at Mallory Square

Right next to where the sunset celebrations take place, you’ll find the Shops at Mallory Square. It’s a cluster of boutiques and small stores where you can browse for souvenirs, local art, and island-inspired gifts.

We wandered through after an afternoon in Old Town and loved that it was an easy stop before heading to the pier for the sunset show. The shops stay open late enough to catch the evening crowds, so it’s a convenient place to pick up something last minute before heading home or back to your ship.

Take a Coffee Break at Cuban Coffee Queen

Cuban Coffee Queen is a little counter-service spot with a big reputation. It’s known for strong Cuban coffee and quick bites like breakfast sandwiches and pressed Cuban bread.

We stopped in for iced café con leche, and it was the perfect pick-me-up on a hot Key West afternoon. The bright murals make it hard to miss, and since there are a couple of locations around the island, it’s easy to fit a stop into your day.

Visit the Key West Butterfly Museum

One of the most unexpected stops in Key West is the Butterfly and Nature Conservatory. Inside the glass-domed habitat, you’ll see hundreds of butterflies, with dozens of different species fluttering around. Two resident flamingos also wander the paths that are almost as much fun to watch as the butterflies.

The walk doesn’t take long, and since the space is air-conditioned, it’s a refreshing break from the heat and easy to fit into a day on Duval Street. Before you leave, you can stop in the small gift shop for butterfly-themed souvenirs.

When I visited, I ended up staying longer than planned, just watching the butterflies (and flamingos), and it turned into one of the most relaxing stops of the trip.

Visit a Favorite Watering Hole of Ernest Hemingway

Captain Tony’s Saloon was originally built in 1851. It may have started out as an icehouse that doubled as a morgue, but it gets lively on the weekends and is a must when visiting Key West.

There’s a lot more history in the walls of Captain Tony’s. In the 1890s, the building became a wireless telegraph station that was used during the Spanish-American War.

Later, in 1912, the building became a cigar factory and a brothel. A few years later, it became the Duval Club, known for lavish gay parties before it was acceptable. It’s said the Navy put out the word that Duval Club was “off limits”, eventually causing it to close.

The story goes that in 1938, the landlord decided to raise the rent by $1.00 per week, prompting Joe to move his entire bar overnight, and his customers with it, to the current location at 201 Duval Street. Don’t worry, it’s still there. See the next thing to do!

In 1933, Joe “Josie” Russell bought the bar at 428 Greene Street and named it Sloppy Joe’s. There was live music, dancing, gambling, and of course, plenty to drink. When Captain Tony Tarracino bought the bar in 1958, it was renamed Captain Tony’s. It’s also where Jimmy Buffett got his start, being paid in tequila for entertaining the crowd.

Have a Beer at Sloppy Joe’s

Still at 201 Duval Street, after all these years! You have to stop in and see it. The food is good, the beer is cold, and there is entertainment all day long.

We had so much fun at Sloppy Joe’s! Put this at the top of your list for things to do in Key West for couples.

Stop for an Ice Cream at Mattheessen’s

After all the walking and sightseeing, nothing hits the spot like ice cream, and Mattheessen’s is the place to go. The scoops are huge and creamy with many flavors to choose from.

If you’ve got a sweet tooth (like my husband!), you’ll also find cookies, fudge, and slices of Key lime pie. For something different, try their Key lime pie on a stick dipped in chocolate.

There are a few locations around Old Town, including one right on Duval Street, so it’s an easy stop while exploring. A little tip, a “single scoop” is massive, closer to three normal scoops, so sharing is smart unless you’re really hungry. They don’t take cash, so bring a card, and if you want to avoid the long evening lines, swing by earlier in the day.

Spend a Day at Dry Tortugas National Park

A visit to Dry Tortugas is one of the best day trips you can take from Key West. You can get there by ferry or seaplane, and both options give you a chance to enjoy incredible views on the way.

Once you arrive, you’ll find Fort Jefferson, a massive 19th-century fort that sits right on the water. It’s huge, taking more than 16 million bricks to build it. Walking around the old cells and cannon openings gives you a sense of just how important this place once was.

The real draw of the park for many visitors is the snorkeling, because the waters here are some of the clearest you’ll find, with coral, colorful fish, and even sea turtles. Keep in mind, there aren’t any food or drink services on the island, so bring a day pack with plenty of water and snacks.

It’s a longer excursion that takes up most of the day, but if you’re looking to mix history with outdoor adventure, this one is worth putting on your list.

Visit the Southernmost Point

No trip to Key West is complete without snapping a photo at the Southernmost Point buoy. The brightly painted marker shows you’re just 90 miles from Cuba, and it’s one of the island’s most recognizable landmarks.

It does get busy, especially midafternoon, so if you want a picture without a long wait, try going early in the morning. But even if there’s a line, it moves quickly, and it’s worth it for the classic Key West souvenir shot.

Spend the Day at the Beach (Smather’s Beach)

When you’re ready for a beach day, head to Smather’s Beach. It’s the biggest public beach in Key West, running about a half mile along the Atlantic Ocean.

This is a great place to stretch out on a big beach towel, and the water stays shallow and calm. There’s plenty of room whether you want to swim, sunbathe, or just relax with a book.

Go in the morning if you’re into a quieter vibe, or later in the day if you enjoy more of the action and people-watching. Either way, it should be a must on your list of things to do in Key West for couples.

You’ll find chair and umbrella rentals plus vendors with kayaks and paddleboards if you’re feeling more active. Food trucks and snack stands often park nearby, so you won’t have to go far for lunch or a cold drink. Parking is available along South Roosevelt Boulevard, making it easy to spend a few hours or make a whole day of it.

Take in the View at the Top of Key West Lighthouse

For one of the best views in Key West, climb to the top of the Key West Lighthouse. It’s 88 steps to the top, and once you’re there, you get a sweeping look over Old Town, the ocean, and the colorful rooftops below.

The climb is short but a little steep, so take your time. Trust me, the view is worth it. The lighthouse was built in the 1800s, and the keeper’s quarters have been turned into a small museum that shares what life was like for the families who once lived there. Between the climb, the view, and the history, it’s an easy stop to fit into your day of sightseeing.

Key West is the perfect place for couples, with plenty of ways to relax, explore, and enjoy time together. From quiet mornings with coffee to evenings by the water, it’s a destination made for two. I hope this guide gives you the inspiration you need to start planning your own Key West getaway.

FAQS

More Florida Destinations

Best Beaches in Naples Florida
Things To Do in Siesta Key Florida
Affordable Things To Do in Orlando
Hawks Cay Resort Duck Key Florida