Tucked into the southwest tip of Key West, Fort Zachary Taylor Historic State Park is where history meets horizon—and it’s hands-down one of the most magical places on the island. You enter through the quiet Truman Annex, and as soon as you pass through the shaded gate you’re surrounded by whispering pines, sunbaked trails, and the quiet anticipation of discovery.

The centerpiece of the park is, of course, Fort Zachary Taylor, a pre-Civil War fort completed in the mid-1800s to defend the nation’s southeastern coast. Named after President Zachary Taylor, it played a strategic role during the Civil War and Spanish-American War and now stands as a massive brick time capsule overlooking the sea. Walking through its thick stone corridors feels like stepping through a portal—there are old cannon mounts, historic displays, and plenty of nooks and crannies for curious minds to explore. History nerds, rejoice.

Just beyond the fort lies the beach, which locals and in-the-know visitors agree is the best on the island. Unlike the flatter, sandier spots on the southern shore, Fort Zach’s beach is rocky and natural, made of coral fragments and hugged by clear, blue-green waters perfect for snorkeling. Schools of colorful fish dance among the rocks, and if you’re lucky, you might spot a sea turtle or two cruising past the reef just offshore. There are shady picnic areas nestled in the Australian pines, making it a great spot to cool off and refuel between dips in the water or fort-exploring sessions.

But if there’s one reason I keep coming back, it’s the sunset. While most tourists crowd into Mallory Square for the nightly celebration (which has its own festive charm), Fort Zach offers a quieter, more intimate front-row seat to the same golden show. You can sit on the rocky jetty, listen to the waves crash gently, and watch as the sun melts into the Gulf in a spectacular wash of color—reds, oranges, and purples reflected on water and stone. It’s peaceful, a little haunting, and incredibly beautiful.

Whether you’re in it for the history, the snorkeling, the quiet trails, or the pure romantic drama of a Key West sunset, Fort Zachary Taylor State Park is a must-visit gem. It’s a place where nature and nerdiness blend effortlessly.

601 Howard England Way
LINK: floridastateparks.org

Nestled inside the crumbling, vine-covered remains of the West Martello Tower, the Key West Garden Club is one of the island’s most unexpectedly enchanting spots. The Garden Club is one of those places that doesn’t feel real until you’re standing in it. Admission is free (though donations are appreciated—DO IT!), and it’s absolutely worth carving time out of your trip to explore it.

The West Martello Tower was originally built as a defensive structure during the Civil War, part of a ring of coastal fortifications designed to protect the U.S. from Confederate threats. Though it never saw battle, its thick, weather-worn bricks hold a quiet gravity—and the transformation from military outpost to flourishing botanical haven is poetic in the best way. A place once built for war now hums with life, color, and peace.

But the land itself holds even deeper layers of history. The West Martello Tower, one of three historic fortifications on this small 2×4 mile island, was part of a larger plan to secure the Atlantic and Gulf coasts after the War of 1812. Though construction didn’t begin until the Civil War had already started in 1861, the location was chosen carefully—desirable for its position, but complicated and sobering for another reason: it was the burial site of nearly 300 African refugees who had died after being rescued from illegal slave ships in the early 1860s. Despite Florida being a Confederate state, Union forces controlled Key West and Dry Tortugas, making the island both a strategic military post and a place where many refugees arrived in hopes of freedom and safety.

Today, the site honors this layered legacy not only through its peaceful gardens but also through art and remembrance. Scattered throughout the grounds are six striking statues, carved by free Black artisans and gifted to the Garden Club. Each one is quietly powerful—part of a deeper story that threads through the site’s beauty, resilience, and transformation.

The Garden Club has been lovingly maintaining and cultivating this space since the 1950s, transforming the once-abandoned fort into a lush, serene oasis filled with native and exotic plants, arched pathways, orchids clinging to old masonry, and quiet corners where butterflies flit through beams of sunlight. Every twist and turn reveals something new—a koi pond here, a tucked-away gazebo there, a butterfly garden, bursts of bromeliads and succulents everywhere.

They sometimes have plants or little gifts for sale to help support the space, and the volunteers are knowledgeable and welcoming without being pushy. You don’t need to be a plant nerd to enjoy it either—it’s just a good, peaceful spot to recharge, maybe take a few photos, and soak in the slower side of Key West.

1100 Atlantic Blvd
LINK: keywestgardenclub.com

Tucked along the southern shoreline of the island, just off Atlantic Boulevard, the Key West Nature Preserve is one of those blink-and-you-miss-it kind of places—but if you don’t blink, and you follow that unassuming wooden boardwalk past the sea oats and into the green, you’ll find yourself stepping into a whole other world. This compact preserve is a protected fragment of coastal wilderness, where thick mangroves stretch their tangled roots into the saltwater and native vegetation hums with life. It’s a quiet, often overlooked haven—and a dream come true for nature nerds and beachcombers alike.

At its heart, the preserve is all about the mangroves. These incredible, salt-loving trees are the unsung heroes of coastal Florida—acting as natural storm buffers, fish nurseries, and vital carbon sinks. Walking through the preserve, you’ll see their roots arching above the water like ancient fingers, providing shelter for crabs, juvenile fish, spiders, and wading birds.

For me, it’s a treasure trove—sometimes literally. After storms or strong tides, the beach here becomes a canvas for sea-swept surprises: coral fragments, intricate shells, driftwood with wild patterns, maybe even a sea bean or two. It’s a place to slow down, scan the shore, and let curiosity lead the way. There’s no admission fee, it’s a garbage in-garbage out kinda place – and *be warned* sometimes the no-see-ums can be FEISTY here!

The Key West Nature Preserve may be small, but it’s a mighty, resilient patch of wilderness.

1700 Atlantic Blvd

Tucked away on the northwest edge of Old Town, Simonton Beach is one of Key West’s more low-key oceanfront spots—and that’s exactly what makes it so good. It’s a small stretch of sand, but what it lacks in size, it makes up for in chill vibes and local character. You’ll usually find more island regulars here than tourists, soaking up the sun or slipping into the water for a quick snorkel.

There’s a little beach bar (Simonton Street Beach Bar) right on-site, making it a great place to grab a drink and watch the boats drift by. The beach faces toward the Gulf, and thanks to its tucked-in position, it tends to stay calmer than other beaches when the wind’s up—especially if there’s a breeze from the north. It’s one of those easygoing places that feels like a bit of a secret, especially on a sunny afternoon when the rest of the island is buzzing.

End of Simonton Street (Gulf side)

This little coastal spot sits at the southern end of Duval, near the Southernmost Point. It’s technically a public beach, but it has more of a pocket-park feel: a tiny green space with palms, benches, and a view of the open ocean that feels a lot bigger than the beach itself. It’s breezy, and a perfect pause point if you’re exploring the southern stretch of the island.

Right next to the beach, the Duval Street Pocket Park and Pier extends out over the water, offering a little lookout where you can see pelicans dive, boats pass, and waves roll in. It’s rarely overly crowded, and it’s a perfect example of how Key West tucks beauty into even its smallest corners.

1405 Duval Street

If you’re beach-hopping on the southern side of Key West, Smathers Beach and Higgs Beach are two of the easiest and most well-known public access points for sun and sea. They’re close enough to each other that you could easily visit both in one day, but each has a different vibe depending on what you’re in the mood for.

Smathers Beach is the longest stretch of beach on the island—wide, sandy, and usually full of activity. It’s where you’ll find beach volleyball games, jet ski rentals, parasailing, and people out on paddleboards. The sand here is soft (imported, actually), and palm trees line the beach like a classic postcard. It’s popular with tourists, especially spring breakers, but if you go in the morning or on a weekday, it’s pretty chill. There are bathrooms and food vendors around, and parking is easy to find along the road.

Just a short bike ride away, Higgs Beach has a smaller, more local feel. The beach itself is a little rockier in spots, but it has a long wooden pier, shaded picnic tables, and a dog park nearby. It’s a favorite for families and anyone looking for a quieter beach day. Higgs also has some unexpected historical depth—the African Burial Ground Memorial is right there near the sand, marking the resting place of Africans who died after being rescued from slave ships in the 1800s. There’s also a small garden and a Civil War-era fort nearby (now used for community events and exhibits).

Both beaches face the Atlantic, so you’ll get good sun all day and some beautiful views of the turquoise water. If you’re looking to swim and play, Smathers is probably the better pick. If you’re in the mood for a more relaxed atmosphere with a bit of history and space to breathe, Higgs is a solid choice.

Smathers Beach
2601 South Roosevelt Boulevard
LINK: www.cityofkeywest-fl.gov

Higgs Beach
1000 Atlantic Boulevard (right next to White Street Pier)
LINK: www.cityofkeywest-fl.gov

Tucked away in Old Town, Nancy Forrester’s Secret Garden is easy to miss if you’re not looking for it—which somehow makes it even better when you find it. This little sanctuary is all about rescued parrots, conservation education, and a deep love for animals and the natural world. It’s not a big flashy zoo or a polished exhibit. It’s a backyard haven run with heart and a whole lot of care.

Nancy, an artist and environmentalist, and the volunteers (Sean was AMAZING!) that work there, have been caring for parrots here for decades—many of them surrendered or rescued from bad situations. The garden gives them space to live out their lives with attention, enrichment, and, honestly, a surprising amount of sass (some of these birds have opinions). Visitors can meet the birds, learn about their stories, and hear about the long lifespans and complex needs parrots have—things most people don’t realize before bringing them home as pets.

The space itself is lush and leafy, like walking into a private little jungle. There are educational signs throughout, and volunteers are often around to answer questions or tell you more about the birds and their personalities. The entry is donation-based, and the money goes directly toward the care of the animals and keeping the garden going. The mosquitoes bite because of the lushness of the area, fair warning.

If you’re into animal welfare, nature, or just want to meet a parrot who might say hi (or call you out), this place is absolutely worth the stop. It’s calm, quirky, and quietly doing important work—very much a reflection of the island’s slower, stranger, more soulful side. Move slowly, and be respectful.

518 Elizabeth Street
LINK: nancyforrester.com/

If you only visit one indoor attraction in Key West, let it be this one. The Key West Butterfly & Nature Conservatory is pure magic—easily one of the most peaceful, immersive, and photogenic experiences on the island. I’ve been twice now, and honestly, I’d go again in a heartbeat. It’s that good.

From the outside, it might not look like much. But step through the entrance, and you’re suddenly in a climate-controlled glasshouse filled with tropical plants, waterfalls, and hundreds of free-flying butterflies. They flutter around you like you’ve wandered into a fairy-tale—or a scene from Animal Crossing, but in real life. You’ll also find flamingos, turtles, colorful birds, and small quail running through the foliage. It’s calm, warm, and surprisingly meditative. You could easily spend an hour just sitting and watching.

The Conservatory is also designed with conservation and education in mind. There’s an exhibit area before you enter the glasshouse that goes into butterfly life-cycles, anatomy, and global species diversity. The displays are approachable and informative without being overwhelming—great for kids, but interesting for adults too. And yes, there’s a gift shop at the end (and it’s actually good). Think butterfly-themed everything, from home decor to art prints and sustainable gifts.

A standout moment: the flamingos. Their names, Rhett and Scarlett. They’ve become kind of a local sensation. If you’re lucky, you’ll catch one of their very vocal conversations echoing through the glasshouse.

1316 Duval Street
LINK: keywestbutterfly.com

Whether you’re into literature, architecture, history, or just really into cats, the Hemingway Home and Museum is a must-see. Located right in the heart of Old Town, this iconic house was home to author Ernest Hemingway during the 1930s, and it’s packed with stories—some true, some probably embellished over the years (in very Hemingway fashion).

The house itself is beautiful: Spanish colonial style with wraparound balconies, lush gardens, and tons of original furniture. You can take a guided tour or explore on your own, but either way, there’s a ton to absorb—from Hemingway’s writing studio (still intact) to the famous urinal-turned-garden-fountain that has its own wild backstory. The place is full of quirky details and a lived-in feeling, like the writer just stepped out for a drink and might be back any minute.

Of course, it wouldn’t be the Hemingway House without mentioning the cats—about 50 of them live on the property, many of them polydactyl (they’ve got extra toes). They roam freely and are well cared for, each with a name that reflects their celebrity lineage. It’s hard not to get attached to at least one of them while you’re there.

The tour guides are great at painting a picture of Hemingway’s Key West life—his work, his travels, his complicated relationships—and how the island influenced his writing. Even if you’re not a huge Hemingway fan, there’s a lot to appreciate about the history and preservation of the home. And if you are a fan? It’s basically a pilgrimage.

907 Whitehead Street
LINK: hemingwayhome.com

Right across the street from the Hemingway House, the Key West Lighthouse is easy to miss if you’re not looking for it—but definitely shouldn’t be skipped. Built in the mid-1800s, it’s one of the oldest lighthouses in Florida, and a literal highlight (pun fully intended) if you’re up for the climb.

And yes—the climb is real. 88 iron steps in Florida humidity? It’s a bit of a workout. But once you get to the top, that panoramic view of Key West is absolutely worth the effort. You can see the treetops of Old Town, the glint of the water all around you, and even the rooftops of places you’ve probably already walked past without realizing. On a clear day, it’s kind of unreal.

At the base, the Keeper’s Quarters Museum is also worth a look. It gives a solid sense of what life was like for lighthouse keepers and their families—quiet, isolated, and full of responsibility. There are old tools, photos, and logbooks that help paint the picture of what it meant to keep the light on back in the day. It’s not a huge space, but it’s well-curated and atmospheric.

Fun fact: this lighthouse was originally staffed by a female keeper, which was pretty rare for the time. Her name was Barbara Mabrity, and she held the job for over 30 years.

938 Whitehead Street
LINK: kwahs.org

If you’re into maritime history, weird treasure stories, or just love a bit of theatrical flair with your museum visit, the Key West Shipwreck Museum is a total gem. Tucked just off Mallory Square, this place dives into one of the island’s lesser-known (but super important) chapters: the golden age of wreck salvaging.

Back in the 1800s, shipwrecks were big business. The reefs around the Keys were treacherous, and when boats went down, Key West “wreckers” would race to salvage the goods. It wasn’t looting—it was a legal, government-sanctioned economy, and for a while, it made Key West one of the richest cities in the U.S. Wild, right?

The museum leans all the way into that history. The staff are fully in costume and in character—think salty sailors, sea captains, and early wreckers telling you stories like they just got back from the reef. It makes the whole experience feel more like a historical play than a typical museum walkthrough. There are artifacts from real wrecks, old diving gear, cannons, treasure chests, and a bunch of interactive stuff too.

Don’t miss the tower climb—this one’s easy compared to the lighthouse, and when you get to the top, you get to ring the ship’s bell with a satisfying clang. The view’s great, especially around sunset, and you get a nice look over Mallory Square and the harbor.

1 Whitehead Street
LINK: keywestshipwreck.com

If you’re looking to dig a little deeper into what makes the Keys so ecologically special, the Florida Keys Eco-Discovery Center is the spot. It’s a low-key (pun intended) but incredibly informative center run by NOAA and several local partners, and it’s all about the unique ecosystems of South Florida—from coral reefs and mangroves to seagrass meadows and beyond.

This isn’t a flashy place, and that’s kind of what makes it great. It’s free to visit (yes, really), well air-conditioned (a huge plus), and full of interactive exhibits that explain the biodiversity of the Keys in a way that’s super approachable for both kids and adults. There are models of reef structures, displays about local marine life, and short films that give a great overview of conservation efforts in the area.

One of the highlights is the replica underwater lab, which gives you a peek into what it’s like to study reef systems from below the surface. There’s also a small but legit live aquarium section with native fish and coral, which adds a nice visual pop to all the learning. It’s the kind of place where you walk out feeling a bit smarter and a lot more appreciative of what’s happening just below the waterline.

Bonus: it’s located right near Fort Zach, so it’s easy to pair with a beach or park day if you’re already in that area of the island. It also doesn’t get crowded, so it’s a nice chill break from the buzzier tourist spots.

35 Quay Road
LINK: floridakeys.noaa.gov

If you’re into art, history, lush gardens, or all of the above, the Audubon House & Tropical Gardens is a standout stop. Tucked just a couple blocks from the hustle of Duval Street, this beautifully preserved 19th-century home offers a quiet, shady retreat—and a peek into both Key West’s past and the legacy of famed naturalist John James Audubon.

The house itself was built in the 1840s by Captain John Geiger, a harbor pilot and wrecker, and it’s been restored to reflect the elegant style of the time. Inside, you’ll find rooms filled with antiques, period furniture, and original Audubon prints—all curated with a lot of care. It’s got that lived-in museum vibe where everything feels authentic without being overly polished. You actually get the sense of what daily life might have looked like here when Key West was booming.

And the gardens? Absolutely beautiful. Tropical palms, orchids, bromeliads, and butterflies everywhere. It’s not huge, but it’s incredibly peaceful—easy to lose track of time while wandering the paths or just sitting on a shaded bench with a breeze coming off the ocean. You can definitely see how Audubon was inspired here. While it’s debated how much time he actually spent at the house itself, it’s believed that many of the birds he illustrated for “The Birds of America” were observed right in this area.

This stop feels quieter than a lot of other attractions on the island, which makes it a great place to take a breath, absorb some history, and appreciate the beauty of the Keys’ flora and fauna from a different angle.

205 Whitehead Street
LINK: audubonhouse.org

The Key West Aquarium might not be the biggest or most high-tech aquarium you’ve ever visited—but it is one of the oldest in Florida (built in the 1930s!), and it packs a surprising amount of charm, history, and hands-on fun into its space. Right next to Mallory Square, it’s super accessible and definitely worth a visit, especially if you’re into marine life or traveling with curious kids (or just a curious inner child).

Inside, it’s a mix of classic exhibits and open-air tanks. You’ll find everything from local reef fish and lobsters to stingrays, jellyfish, and even sea turtles. They do scheduled feeding times and educational talks, where the staff shares facts about the animals, conservation efforts, and the importance of the Keys’ fragile ecosystems. There’s also a touch tank, which is great for hands-on learning—featuring things like sea stars and horseshoe crabs you can gently interact with.

The shark exhibit is one of the highlights. You can watch feedings and learn about different shark species native to the area, along with the challenges they face in the wild. It’s clear the staff here care deeply about these animals, and they’re always up for answering questions or pointing out hidden creatures you might have missed.

It’s a relatively quick stop—you can explore the whole place in under an hour—but it’s dense with cool info and makes a great break from the heat or a lead-up to sunset festivities at Mallory. Plus, supporting places like this helps fund wildlife rescue and education programs in the region.

1 Whitehead Street
LINK: keywestaquarium.com

It’s not a trip to Key West without at least one photo in front of the iconic Southernmost Point Buoy—that big, brightly painted concrete marker that declares you’re standing just 90 miles to Cuba. It’s one of the most photographed spots in all of Florida, and while it might seem like a simple landmark, there’s a lot more behind it than meets the eye.

The buoy itself was installed in 1983, replacing a series of smaller signs that had been frequently stolen or damaged. The city decided to go with something a little more permanent—and harder to walk off with. Since then, it’s become a true Key West symbol, instantly recognizable in photos and postcards.

Despite the name, it’s not technically the southernmost point of the continental U.S.—that title actually belongs to a spot on nearby Navy property that’s not open to the public. But honestly, that’s part of the charm. The buoy is more about the spirit of being almost at the edge of the country, where land gives way to ocean and the Caribbean begins.

The spot has become more than just a landmark—it’s a gathering place. People come at all times of day, but if you want the best light (and a shorter line), try early morning. And don’t be surprised if there’s a street musician playing or a rooster strutting across the sidewalk mid-photo. It’s still Key West, after all.

Fun fact: during hurricane season, the city often boards up the buoy to protect it from storm damage—and yet it’s withstood quite a bit over the years, including being partially scorched by a fire in 2021 (which, don’t worry, has since been fully restored).

Check out the WEBCAM link below, it’s fun to watch.

1400 Whitehead Street
LINK: southernmostpointwebcam.com

Located right on the corner of Simonton and South, Ana’s Cuban Café is a walk-up style window attached to Southernmost Grocery—and it’s a gem. Whether you’re in need of a strong coffee fix, a hot breakfast, or a sandwich that’ll change your life a little, this place is a must-stop.

I tried multiple versions of their breakfast sandwiches, with all different meats- pork by far was my favorite. Also amazing: the sausage (think a spicy maple YUM), and the bacon (plentiful and thick). This place was a favorite for sure. The egg was soft and folded between homemade Cuban bread… it was heaven.

The Cuban coffee is the real deal—rich, sweet, and exactly what you want first thing in the morning (or anytime, honestly). The ice tea is amazing (and free refills!). Their Cuban sandwiches? Easily the best on the island. Full stop. THE PICKLE SLICES. The café itself closes after lunch (around 3PM), but the grocery store keeps making sammies (and more) til they close around 8.

It’s casual, unassuming, and absolutely beloved by locals (especially the local hospitality staff). Perfect for a quick bite or to-go fuel before hitting the beach or wandering Duval.

The Tipsy Rooster is part bar, part outdoor hangout, part liquor store—and all fun. Located on Simonton Street in Old Town, this spot is great for a housemade fruit infused drink, a bottle to-go, or just kicking back for some live music under the palm trees.

They’ve got a solid bar menu, super friendly bartenders, and outdoor tables that sit in a literal sandbox (yep, like barefoot beach bar style). It’s casual, relaxed, and has live music most nights that adds just the right amount of buzz without being overwhelming.

Inside, the liquor store side has a surprisingly good selection—perfect if you want to stock up your hotel room or grab something unique to bring home.

That blue and silver trailer parked right next door? Rooster Treats. In the next sandbox over, you’ll find a cutie little treats truck serving up homemade soft-serve ice cream and freshly made mini donuts—obviously, with a huge assortment of toppings. This place is adorable.

If you’re looking for a low-key hangout spot that doesn’t try too hard but still delivers, this is the Rooster for you.

Corner of Simonton St and South St
the bar LINK: tipsyroosterkw.com
the treats LINK: roostertreats.com

If you only hit one food truck on the island, make it Marlin Café. Located on Simonton Street in the Blue Marlin Hotel lot, this low-key gem dishes out some of the best tacos I’ve had anywhere—no exaggeration. The flavors are bold, the ingredients are fresh, and the portions hit just right after a morning of exploring (or recovering from a night out).

I’ve had birria before – but THOSE birria tacos… my life is forever changed.

They’ve got a small but mighty menu that rotates a bit, but everything I’ve tried has been a win. The breakfast sandwiches are also legit—hearty, flavorful, and exactly what you want with a strong coffee in hand (the Chorizo by far- THE BEST). There’s a shaded seating area if you want to linger, or you can grab and go if you’re mid-adventure.

Blue Marlin Hotel
LINK: marlincafekw.com

This is the sushi spot. Origami has been around since 1995, and it’s easy to see why. The fish was fresh, the rolls were amazing, the sashimi delicious. The whole vibe felt very authentically Japanese, down to the Buddha and Lucky Cats. Sitting outside was lovely, but the inside sushi bar? That’s where the energy’s at.

Reservations are a very good idea, especially during busy seasons. The staff is super friendly and really knowledgeable. End the night with the green tea ice cream— DO IT— it’s the perfect sweet, cold finish. Loved the meal and my whole experience here.

Located in Duval Square, Old Town
LINK: sushibarorigami.com

Le Creperie is that fun, flirty breakfast spot that makes you feel like you’ve slipped into a tiny Parisian corner café—if that café served mimosas by the bucket and had roosters strutting by. Expect a menu packed with sweet and savory crepes, fresh juices, and fruity bubbly drinks that make brunch here feel like a party.

The space is bright, colorful, and full of charm, with a staff that brings good vibes all around. Just a heads up: it does get busy (because it’s that good), and they close at 3PM—so it’s a breakfast or brunch-only kind of stop.

300 Petronia Street – Corner of Duval & Petronia
LINK: lacreperiekeywest.com/

If you’re looking for oceanfront dining with serious vacation vibes, Seaside Café at the Mansion is one of the best spots on the island—especially if you can snag a table right by the water. The setting is hard to beat: breezy, beautiful, and totally laid-back. The servers and staff are super fun, and nice – it’s a vibe on this island that you don’t really get bad service anywhere.

Now let’s talk food—because the food here is fantastic. The Honey-Butter Lobster Biscuits are ridiculously good (borderline addictive), and the Lobster Pizza lives up to the hype. Everything feels fresh, well-made, and just indulgent enough to feel like a splurge without being over-the-top. The seafood was always fresh – fresh Lobster dolloped on a green salad with candied pecans, strawberries, and Gorgonzola – ohhhh myyyyyyy.

Drinks, though? Meh. Despite what the staff shirts say (“Island’s Best Mojitos & Margaritas”), the cocktails are the one weak point. Multiple visits, multiple bartenders, multiple letdowns—think overly poured, poorly mixed, and just not doing the food any justice. If you’re heading here (which you definitely should!), stick to the food and maybe a beer or glass of wine if you’re looking for something to sip.

Still, between the view and the menu, it’s well worth a visit. Just… maybe pass on the mojito and double down on those lobster biscuits instead.

At The Mansion – off the Duval Street Pocket Park & Pier
LINK: themansiononthesea.com

Location? Fire. Vibe? Casual-beachy. Consistency? Ehhh… hit or miss.

Southernmost Beach Café has one of the best views in Old Town—right on the sand and steps away from the Atlantic. It’s attached to the Southernmost Beach Resort and just across from Seaside Café, so it’s in a super convenient spot. That said, dinner here often felt rushed and kind of bland (I gave it multiple tries). Definitely overpriced for what you get.

BUT! Go for lunch. Big difference. The sweet & spicy slaw alone was worth the visit—I still think about it. Drinks are strong, staff is friendly, and the view doesn’t quit. Just maybe skip the dinner crowd and opt for a breezy midday meal.

At the Southernmost Beach Resort – off Duval Street Pocket Park & Pier
LINK: southernmostbeachresort.com

If you’re in the mood for a classy oceanfront dinner with a view that actually delivers, Four Marlins hits the mark. Located inside The Reach Resort (yep, you walk through the Hilton to get to it), this place gives off subtle-lux vibes without being too stuffy. The seafood-forward menu is full of standout dishes—like the ultra-decadent lobster mac ‘n cheese and a legit award-winning Key Lime Pie that might ruin all others for you.

It’s on the pricier side, but the setting—right on the water—is hard to beat. Perfect for a special night or if you’re just craving some fresh-caught flavor in a gorgeous setting.

The Reach Key West, Curio Collection by Hilton
LINK: reachresort.com/menus/

This place has a reputation, and the setting is pretty—oceanfront, multi-level, indoor-outdoor dining—but honestly? It didn’t live up to the hype for me.

Parking is a nightmare in this area, with tons of “No Parking” signs and limited options, so if you’re going, plan to walk, bike, or Uber. Definitely make a reservation too, because it books up fast. That said… even with all that buildup, both the food and the drinks came across as just meh. Not bad, but certainly not memorable, especially when you compare it to the island’s vibrant food scene.

Louie’s has been around for a long time, and maybe we hit it during an off time, but their “What People Are Saying” section is oddly outdated—highlighting a Herald review from the 1980s by Lucy Cooper as if it were recent. As someone who cares about honest, up-to-date marketing, that rubbed me the wrong way.

With so many other exciting and delicious places to eat on the island, I’d skip this one for now. The views are nice, but the hassle of getting there and the underwhelming flavors just don’t justify it.

700 Waddell Avenue
LINK: louiesbackyard.com

We didn’t get into the food here (though the dishes flying past us looked incredible), but we did sample their beer flights—and they were totally worth the stop. This spot is actually located on the original site of Pan American World Airways’ first office, and they leaned into that aviation history in the best way. The place is surrounded by orchids, airplane propellers worked into the décor, and tropical charm all around.

The vibe is relaxing, almost hidden-away-feeling even though it’s in a busy area, and everything we tried beer-wise was crisp, cold, and creative. First Flight is definitely going on the list for a longer visit next time. Bonus: it’s just steps from the Audubon House, so it’s easy to pair with a daytime wander.

301 Whitehead Street
LINK: firstflightkw.com

I wanted to love Sushi Song. Sushi is top-tier comfort food for me, and this place looked like it had potential—but the experience didn’t match the hype. It’s styled to feel upscale (lots of red, black, and camo), but the vibe still had a weird “former fast food joint” energy that just didn’t land.

There’s no outdoor dining, and inside it was freezing —which I get for seafood safety, but it was uncomfortably cold (ladies bring a jacket or sweater). Our server seemed sweet, but he didn’t know the menu well (including which dishes included eel). And the rolls? Cream cheese overload. Like… shockingly so. If you love California rolls or fusion-y takes with heavy ingredients, you might really enjoy it. However, if you’re like me and into more of a classic, traditional, cleaner sushi—head elsewhere.

925 Duval Street
LINK: www.sushisong.com/

If you’re in Mallory Square and looking for a casual, lively hangout, Salty Frog’s hits the spot. The walls (and ceilings and rafters) are covered in signed dollar bills—yes, I left two of them myself! It’s got that slightly chaotic, beach-bar energy with an open-air breeziness that’s hard not to love.

Live music often drifts out from a tucked-away corner stage, and the vibe stays chill even when it’s busy. Menu-wise, you’ll find classic bar fare: sandwiches, oysters, and (for the adventurous) frog legs. I tried them—once. It was an experience, but probably a one-time deal for me 😂. Drinks are fun, service was solid, and the overall atmosphere is just pure Key West energy.

Corner of Front & Duval, Mallory Square
LINK: saltyfrogskeywest.com

This place brings the Cuban flavor and flair. While Ana’s still takes my personal crown for best Cuban bites on the island, El Meson de Pepe definitely holds its own. It’s got a super lively vibe, especially in the evenings when the live music kicks in and people start dancing as the sun dips over Mallory Square. It’s loud, it’s fun, it’s full of life—and yes, the Key Lime Pie here is fantastic. Worth it for the energy and people-watching alone, and a solid stop for anyone craving flavorful Cuban food with a festive backdrop.

410 Wall Street, near Mallory Square
LINK: elmesondepepe.com

An Old Town legend, and for good reason.

It’s got that gritty, no-fuss local bar feel, with live music that pulls a real-deal crowd. Drinks are strong and well-priced (hallelujah), the bartenders don’t play games, and even when it’s packed wall-to-wall, you kind of don’t want to leave. It has that “your favorite band’s about to take the stage” kind of magic.

601 Whitehead Street
LINK: greenparrot.com

If you’re looking for a party that checks every box—this is it. Housemade Mai Tais on tap (yes, on tap) loaded with fruit, karaoke in one corner, dancing in another, and food flying out of the kitchen—it’s a whole scene.

The space is massive, multi-leveled, and easy to get lost in… which is part of the fun. It’s a full-on choose-your-own-adventure kind of night here, and I loved every minute of it.

618 Duval Street
LINK: empouriumkeywest.com

Tucked down a side alley off Duval, this is your classic, gritty late-night dive bar—but like, the good kind. There are multiple bars to grab drinks from and at the very end—BAM—a stage with live music blasting. It’s dark, loud, and a little chaotic, but that’s exactly what makes it awesome.

Great for a “let’s see where this night goes” kind of stop.

202 Duval Street (Tucked inside Rick’s Bar complex)
LINK: ricksbarkeywest.com

Mallory Square– how I love thee. During the day, it’s a hub for souvenir shopping, boat tours, and meandering-filled-wandering. You’ll find all the usual tourist-friendly goods: seashell trinkets, tropical T-shirts, conch shell noisemakers, ocean sponges, and an endless supply of key lime-flavored snacks. It’s a funhouse of tropical kitsch and laid-back browsing.

Come sunset, the square transforms.

Every evening, people gather for the Sunset Celebration—a long-standing Key West tradition. As the sky melts into shades of orange and pink, a crowd begins to gather at the waterfront—locals, visitors, families, free spirits, and more than a few folks who seem like they just stepped out of a Jimmy Buffett lyric. It’s chaotic in the best way: joyful, slightly weird, and totally captivating.

Street performers set the stage—jugglers tossing flaming clubs, magicians pulling off close-up tricks, artists laying out their handcrafted wares, and musicians filling the salty air with everything from steel drum rhythms to acoustic ballads… and yes, even bagpipes. (There’s something oddly perfect about hearing “Amazing Grace” as the sun slips into the sea.)

And then, that moment—everyone collectively pauses to watch the sun dip below the horizon. A stillness followed by an erupted clapping, filled with awe. Sunsets on the island are something magical, they should never be missed.

It’s loud, it’s crowded, but it’s also completely unforgettable. Mallory Square isn’t trying to be polished or curated—it’s messy and real and full of life.

The Key West Cruise Port is like the gateway to the island for thousands of visitors every day. If you’re docking in Key West on a cruise, this is your first stop. Located just a short walk from Mallory Square, the port is where you’ll find cruise ships lined up next to the island’s colorful shops, bars, and eateries. It’s buzzing with activity—people hopping off the boats and heading into town, locals hustling to welcome the newcomers, and a whole lot of friendly faces sharing the island’s warm energy.

The port itself has a few things going on, like small shops offering island-inspired souvenirs and a spot where you can grab a quick drink before you head out. But the real action happens when you step off the dock and into the heart of Key West. From here, you’re just a stone’s throw from Duval Street, the waterfront, and all the classic spots that make the island so special. It’s a little touristy, yes, but also part of the island’s vibe—tourists and locals alike flowing in and out, keeping the place lively and vibrant.

The area around the cruise port also gives you a chance to peek at Key West’s nautical side. You’ll see ferries, fishing boats, and even kayaks all coming and going from the waterfront. Whether you’re just starting your adventure or wrapping up a day in paradise, the cruise port is a bustling entry point that leads right into the colorful chaos of island life.

One of the coolest things about Key West is that art isn’t just confined to museums or galleries—it’s woven into the fabric of the island. Stroll down Duval Street, and you’re practically tripping over galleries and studios showcasing local talent. The main drag is lined with vibrant spots where you can pop in, browse unique paintings, sculptures, photography, and so much more. It’s not just the established galleries that make the island’s art scene so special; you’ll also see local artists setting up on street corners, selling their creations directly to passersby. Whether it’s a painting, handmade jewelry, or a hand-carved wood sculpture, the whole island is a canvas.

Walking down Duval, you’ll find everything from contemporary pieces to art that draws on the island’s rich history and natural beauty. Each gallery feels like a reflection of the eclectic energy of Key West itself—playful, creative, and always welcoming. The best part? You can easily stroll from one gallery to the next, taking in the art while soaking up the island atmosphere. The variety is incredible, and you’ll probably discover something unexpected in every space you visit.

And the art scene doesn’t stop at Duval. All around Key West, there are little hidden gems—like murals on alley walls, art booths at the waterfront, and local vendors selling one-of-a-kind pieces. The whole island feels like a giant open-air gallery. It’s one of the things that makes Key West stand out—art and creativity are part of the island’s DNA, and whether you’re a casual observer or an avid collector, there’s no shortage of beauty to explore.

When the sun dips below the horizon, Duval Street transforms into a whole different animal. By day, it’s a bustling, colorful hub; by night, it turns into a neon-lit party zone where the energy is infectious, the drinks are cold, and the music spills out of every open-air bar. It’s a nightlife experience that feels a little wild, a little carefree, and totally full of life.

The street is lined with bars, clubs, and hidden spots that range from rowdy to relaxed, and there’s something for everyone. From live bands playing classic rock, reggae, or jazz to karaoke sessions where tourists and locals alike belt out their favorite tunes, you’ll never run out of entertainment. But the best part? The secret spots—tucked-away backyard bars, hidden courtyards with string lights overhead, and lounges where you can slip in and feel like you’ve found your own little corner of Key West. (Be a moth, always follow the stringed lights, you never know what little oasis you’ll find.)

Duval at night is where the island’s quirky, laid-back spirit truly comes alive. One bar might be packed with people dancing, while another offers a quiet, intimate setting with a chilled-out vibe. The mix of locals and visitors creates a sense of inclusivity, and it’s easy to strike up a conversation with just about anyone. You’ll also see plenty of street performers keeping the vibe alive—musicians, magicians, and some who are just out there for the fun of it. The vibe is always fun, a little chaotic, and thoroughly unforgettable.

It’s busy, it’s lively, and sometimes, it’s a little bit wild—but that’s the charm of Duval at night. It’s the kind of place where you can stumble into an impromptu dance party one minute and find a cozy, dimly lit bar to unwind in the next. No matter how many times you experience it, Duval’s nightlife always feels fresh, exciting, and full of surprises.