10 Things You Should Definitely Try at Key West
Close your eyes and picture Key West: the warm caress of a tropical breeze, turquoise water glittering like scattered sapphires, and the faint, citrusy perfume of key limes wafting through pastel-painted streets. Sounds tempting? Good—because the “10 Things You Should Definitely Try at Key West” on our list aren’t just activities; they’re sensory love letters to the island’s quirky soul. Whether you’re a first-timer chasing postcard sunsets or a seasoned Keys devotee hunting for fresh thrills, this guide is designed to slip effortlessly into your pocket (or phone) and whisper, “Hey, let’s do something unforgettable today.” Expect candid tips from locals, eco-friendly pointers, and vivid snapshots of life at the southernmost tip of the continental United States. Ready to taste the tang of an authentic Key lime pie, snorkel coral kingdoms, and sway to live island beats under neon-pink skies? Let’s dive in—paradise is waiting just beyond the mile-marker signs.
1. Catch the Sunset Celebration at Mallory Square
Why It’s Unmissable
Every evening, Mallory Square transforms into an open-air festival where nature’s grand finale meets a carnival of human creativity. Two hours before the sun slides into the Gulf, jugglers twirl flaming batons, folk guitar drifts through salt-sweet air, and the aroma of fresh conch fritters mingles with coconut-scented breezes. The crowd’s collective gasp the instant the sun kisses the horizon feels like a standing ovation for the day itself.
What you’re likely to encounter:
- Tight-rope walkers silhouetted against an apricot sky
- Tarot readers promising tropical fortunes
- Local artisans selling hand-painted seashells and recycled-glass jewelry
- Spontaneous applause that echoes across the water
Best Viewing Spots & Timing
| Arrive | What You’ll Experience | Pro Tip |
|---|---|---|
| 90 min before sunset | Performers warming up; easy parking along Wall St. | Grab a to-go mojito and wander the pier. |
| 45 min before sunset | Peak buzz; sailboats drift into view; sky shifts from peach to magenta. | Claim the pier’s western edge for an unobstructed horizon shot. |
| 10 min after sunset | Streetlights glow; impromptu encores; cooler breeze. | Stick around for the legendary (and elusive) “green flash.” |
Insider Tip for Fewer Crowds
Stroll past the main plaza toward the small jetty beside the Opal Key Resort. You’ll still soak up the steel-drum soundtrack but score elbow room for panoramic photos. Traveling with kids? Slip out via the Truman Waterfront path—ice-cream stands usually pop up there right after dusk.
Pack List: reusable water bottle, light sweater (breezes pick up!), small bills for tipping performers, and a wide-angle lens if your phone allows it.
Mallory Square’s sunset celebration isn’t just a photo-op; it’s a nightly reminder that Key West lives for the magic moment when day melts into night. Jot it in your itinerary—you’ll thank yourself later.
2. Snorkel the Vibrant Reefs of Dry Tortugas National Park
What You’ll See Underwater
Slip off the boat and you’re instantly inside a neon aquarium: brain corals the size of VW Beetles, purple sea fans swaying like lace curtains, and schools of silver grunt fish flashing in the sunlight. Keep an eye out for slow-gliding sea turtles and rainbow-painted parrotfish crunching on coral—soundtrack included. Visibility often exceeds 60 feet, so even novice snorkelers feel like National Geographic cinematographers.
Getting There: Ferry vs. Seaplane
| Option | Travel Time* | Vibe | Perks | Good to Know |
|---|---|---|---|---|
| Yankee Freedom III Ferry | ~2 h 15 min each way | Social & scenic | Breakfast, lunch, snorkel gear included | Book weeks ahead in high season; bring a light jacket—the A/C hums. |
| Key West Seaplane | ~40 min each way | VIP aerial views | Cooler of soft drinks, flexible departure slots | Strict 25-lb gear limit; afternoon glare better for reef colors. |
*From Key West to Garden Key, 70 miles west.
Eco-Friendly Snorkeling Etiquette
- Reef-Safe Sunscreen Only – Oxybenzone harms coral; mineral blocks keep both you and the reef protected.
- Look, Don’t Touch – A single kick can shatter centuries-old coral; keep fins horizontal and buoyancy neutral.
- No Souvenirs Except Photos – Shells and urchin tests belong to the ecosystem.
- Respect Wildlife Space – If a turtle changes direction, you’re too close.
- Leave It Better – Pocket any drifting trash you spot on the return swim.
Local’s Hack: After snorkeling, circle Fort Jefferson’s moat wall for a land-based “aquarium” stroll—the water is shallow, clear, and teeming with juvenile reef fish.
With every breath through your snorkel, Dry Tortugas delivers a technicolor postcard few tourists ever see. Add it to your Key West bucket list and you’ll float home with salt-tousled hair, sun-kissed skin, and a heart full of underwater wonder.
3. Taste an Authentic Key Lime Pie (and Learn Its Sweet Story)
Where to Find the Best Slice
Ask any local where to begin your Key West food pilgrimage and they’ll point you to a chilled display case glowing with sunshine-yellow wedges. Three spots top nearly every “must-eat” list:
| Bakery / Café | House Style | Vibe | Can’t-Miss Detail |
|---|---|---|---|
| Kermit’s Key Lime Shoppe | Classic graham-cracker crust, whipped-cream rosette | Breezy courtyard with fountains & parrot murals | Food Network and National Geographic both crowned it “best in town.” |
| Blue Heaven | Mile-high torched meringue towering over silky custard | Ramshackle Bahama Village patio, live jazz, free-roaming chickens | The meringue rises higher than a conch shell stack—yes, you’ll need two forks. |
| Old Town Bakery | Buttery pastry crust, tart filling, light whipped top | Locals’ coffee stop on Eaton St. | Arrive by 9 am; pies sell out faster than bike rentals. |
Pro Tip: Order a slice “on a stick, dipped in chocolate” at Kermit’s—the frozen-pie-pops come wrapped for beach strolls. Your taste buds will thank you, your swimsuit… maybe not.
Pie vs. Tart: Know the Difference
- Key Lime Pie: Graham-cracker crust, egg-yolk custard, baked just until set, topped with whipped cream or meringue.
- Key Lime Tart: Flakier short-crust pastry, thinner custard layer, served un-topped or with a whisper of zest.
Both rely on tiny, aromatic Key limes whose juice is more floral and tart than Persian limes. Tradition calls for sweetened condensed milk—an 1800s workaround when fresh dairy spoiled in the tropical heat.
The Flavor-Packed Backstory (Quick Bite-Sized Version)
Legend credits sponge fishermen who stirred lime juice, condensed milk, and eggs into a pail, letting the acid “cook” the custard at sea. Later, a house cook known as Aunt Sally supposedly refined the recipe in the 1890s at Key West’s Curry Mansion, though food historians debate whether Borden’s 1931 condensed-milk contest actually birthed the pie. Either way, by 1940 the dessert was island folklore—and today it’s the official state pie of Florida.
4. Explore Old Town on a Classic Conch Tour Train
Highlights Along the Route
Since 1958, the open-air Conch Tour Train has rumbled past pastel cottages and swaying palms, serving up a breezy crash-course in Key West lore. The 60- to 75-minute loop circles Old Town’s greatest hits—Hemingway Home, Mallory Square, Duval Street, and the Historic Seaport—while onboard guides sprinkle in pirate tales, railroad triumphs, and celebrity anecdotes.
Expect to roll by:
- The Little White House where President Truman escaped Washington winters
- Sloppy Joe’s façade, still echoing with 1930s rum-runner gossip
- Key West Lighthouse, framed perfectly for quick snaps from your seat
- Shady lanes scented with jasmine, punctuated by rooster crowing and ukulele chords
Ticket Hacks & Combo Passes
| Pass Type | Cost* | What You Get | Best For |
|---|---|---|---|
| Standard Loop | ≈ $44 adult | Narrated ride + souvenir map | First-timers on a tight schedule |
| All-Day Hop-On/Hop-Off | +$6 upgrade | Four stops, unlimited re-boarding | Photographers & café hoppers |
| Museum Bundle | +$12 | Free entry to Sails-to-Rails Museum | History buffs & rainy-day planners |
| Online Saver | –10 % | E-ticket, skip the kiosk line | Early planners who love a deal |
*Prices fluctuate with season—book online a week in advance for the best rate.
Ride-Like-a-Local Suggestions
- Board at Mallory Square’s first departure (9 a.m.) to snag a shady seat and cooler temps.
- Sit on the right side leaving the depot for prime views of Caribbean-blue water and Ernest Hemingway’s brick wall garden.
- Hop off at Stop #2 (Truman Annex) for Cuban espresso from the tiny café opposite the gate—your engineer will tip his cap when you re-board.
- Bring reef-safe sunscreen—the train is roofed but sunbeams sneak through every slatted window.
- Evening rides often feature balmy breezes scented with frangipani; perfect pairing with a frozen Key-lime-ade you can bring aboard (yes, drinks allowed!).
Quick mood-booster: As the engine bell clangs and you chug along Duval Street, wave at pedestrians—nine times out of ten they’ll grin and wave back, reminding you why the Conch Republic is famous for island-time friendliness.
Next stop in your Key West adventure? Keep reading—sunset sails and nightlife crawls await!
5. Meet the Six-Toed Cats at Ernest Hemingway Home & Museum
Literary Lore & Cat Legends
Step past the wrought-iron gate on Whitehead Street and you’ll be greeted by a sleepy feline doing a perfect stretch that shows off—count them—six toes per paw. These polydactyl stars are direct descendants of Snow White, the white ship-captain’s cat gifted to Ernest Hemingway in the 1930s. The author believed extra digits were good luck at sea; today, nearly 60 fur-clad “lucky charms” roam the tropical gardens, each named after celebrities (say hello to Marilyn Mon-Roe or Pablo Picatso). Guides weave tales of Papa’s writing marathons, rum-drenched evenings, and the way the cats still choose the coolest marble floor tiles for their afternoon naps.
Photo-Op Corners of the Estate
| Spot | What to Capture | Insider Angle |
|---|---|---|
| Front Veranda | Cats lounging on green-shuttered windowsills | Kneel low to frame paws + pastel facade |
| Writer’s Studio | Vintage Corona typewriter, cat sprawled on manuscript | Shoot through open doorway for depth |
| Jungle Garden Path | Giant bougainvillea arch, dappled light, prowling kittens | Late morning sun for floral glow |
| 20-Foot Pool Edge | Cats drinking poolside, emerald water reflections | Use portrait mode to blur background palms |
Tip: Keep a respectful two-foot buffer—Hemingway’s heirs prefer candid kitty portraits over forced cuddles.
Quiet Hours for Reflection
- Beat the bus tours by arriving with the 9 a.m. opening bell; the house is fragrant with night-blooming jasmine and the cats are wide-eyed from breakfast.
- Mid-afternoon lull (2–3 p.m.) brings shade and fewer footsteps; perfect for lingering by the pool Hemingway famously called “the most expensive $20,000 I ever spent.”
- Evenings are closed to the public, yet from the sidewalk you can still hear distant paw-pads tapping porch planks while stars wink on above the lighthouse next door.
Pack List: refillable water bottle (there’s a fountain by the gift shop), quiet-shutter camera or phone, and lint roller if you’re rocking dark clothes—those extra toes mean extra cuddle surface.
Spend an hour here and you’ll feel as if Hemingway might stroll out, tuck a sleeping cat under one arm, and invite you to share a story over mojitos. The spirit of creativity—and feline charm—lingers in every leafy corner.
6. Paddle Through Mangrove Tunnels on a Kayak or SUP
Wildlife You Might Spot
Glide into a jade-green corridor where arching roots knit together like a living cathedral. As your paddle slices the glassy water, keep watch for:
- Nurse sharks napping beneath limestone ledges (they’re docile—promise).
- Juvenile tarpon flashing silver in filtered sunbeams.
- Spotted rays fluttering across sandy patches like underwater butterflies.
- Snow-white egrets stalking minnows at eye level.
- If you’re lucky, a manatee surfacing with a soft exhale that ripples the mirrored surface.
Local guides often carry a waterproof identification chart; ask to borrow it and turn the tunnel into your personal nature bingo.
Guided vs. Self-Guided Routes
| Option | Duration | Vibe | Gear Included | Best For |
|---|---|---|---|---|
| Eco-Guide Tour | 2–2.5 hrs | Story-rich, relaxed | Kayak/SUP, dry bag, snorkel mask | First-timers & wildlife lovers |
| Sunset Paddle | 1.5 hrs | Golden-hour glow, floating jazz | Clear kayaks with LED lights | Photographers & romantics |
| Self-Rent (Half-Day) | Up to 4 hrs | Choose-your-own-adventure | Board/boat + paddle only | Independent explorers |
| Full-Day Adventure | 6 hrs | Picnic on remote sandbars | Cooler, anchor, tide chart | Seasoned paddlers wanting solitude |
Insider savings: Book a morning tour online and rental shops usually knock 10 % off a second activity—think reef-snorkel package after lunch.
Tide & Wind Safety Basics
- Check the tidal clock—low tide can strand kayaks on exposed mudflats; aim for mid-to-high water for easiest passage.
- Wind below 10 knots keeps tunnel turns gentle; anything above 15 knots can turn your board into a sail.
- Wear reef-safe sunscreen and a rash guard—branches hover low, and a clipped elbow leaves a mark.
- Follow the white PVC markers; they’re breadcrumb trails back to the launch if GPS fails.
- Pack a soft-shell dry bag with phone, snack, and mini first-aid kit. (Yes, mosquitos love mangroves too.)
Local Hack: Paddle silently for one full minute, then listen—crackling shrimp, distant gulls, and the heartbeat thump of your board against ripples compose the Keys’ most intimate soundtrack.
With every dip of your paddle, the mangroves breathe out earthy perfume and dapple you in emerald light. Add this watery labyrinth to your Key West “definitely-try” list, and you’ll return salt-skinned, soul-quiet, and carrying stories only the mangroves could whisper.
7. Pose by the Southernmost Point Buoy
Why This Iconic Photo Matters
Bold bands of red, black, and yellow shout “90 Miles to Cuba” from a 12-foot-tall concrete buoy planted at the corner of South & Whitehead Streets. Erected in 1983 to replace a repeatedly stolen wooden sign, the buoy has survived hurricanes, a small fire, and countless bear-hugs from first-time visitors—cementing its status as the island’s most photographed landmark.
Fun fact: the real geographic southernmost point sits a few yards away on restricted Navy land, but the buoy’s colorful charisma makes that technicality easy to forgive.
Timing Your Visit to Dodge Lines
| When to Go | Crowd Level | Lighting & Vibe | Quick Hack |
|---|---|---|---|
| Sunrise (6:30–7:30 a.m.) | 🟢 Sparse | Cotton-candy skies, ocean glitter | Bring coffee—most shops open at 6 a.m. |
| Late Morning (10 a.m.–Noon) | 🔴 Long queues (30–60 min) | Bright but harsh light | Snap from the opposite curb with zoom if you’re short on time. |
| Golden Hour (5:30–7 p.m.) | 🟡 Moderate | Warm glow, shorter shadows | Lines shrink after tour buses leave. |
| Weekdays vs. Weekends | Weekdays always lighter; cruise-ship days surge. | — | Check the port schedule online before planning. |
Locals swear by an early-bird selfie—sun still low, breeze still cool, and maybe a pelican gliding into frame.
Nearby Cafés for Post-Pic Refreshments
- Southernmost Coffee (½-block north) – Iced Cuban cortadito & guava-cheese pastelitos.
- Moondog Café (5-min walk) – Garden patio, legendary cinnamon rolls bigger than the buoy’s lettering.
- Café Moka (on Duval) – Nitro cold brew and shady sidewalk tables perfect for caption-crafting.
Traveler’s Heads-Up
- Renovation Alert: The city plans plaza-and-seawall repairs starting late August 2025; a replica buoy will stand nearby so photo-ops continue uninterrupted.
- Respect the Ocean: During high surf, keep a safe distance—rogue waves sometimes spray the seawall.
- Pack List: reusable water bottle, small umbrella for shade while waiting, and $1 bills for the street musician often serenading the queue.
One quick click beside this cheery sentinel and you’ve officially joined the ranks of Conch Republic adventurers. Ready for the next Key West must-try? Grab your flip-flops—sunset catamaran sails are up next!
8. Set Sail on a Sunset or Champagne Catamaran Cruise
Cruise Types & What’s Included
| Cruise Style | Duration | On-Board Treats | Vibe | Good to Know |
|---|---|---|---|---|
| Open-Bar Party Sail (Fury) | 2 hrs | Unlimited beer, wine, margaritas, live steel-drum band | Lively—dancing encouraged | Frequent sunset “green-flash” sightings |
| Champagne Catamaran (Sebago / Echo) | 1.5 hrs | Chilled bubbly, artisanal cheese platter | Intimate—max 40 guests | Crew snaps free photos for you |
| Premium Dinner Sail | 2.5 hrs | Fresh grilled mahi-mahi, Key-lime tarts, house wine | Date-night elegant | Jackets not required—just island chic |
| Private Charter | Custom | BYO playlist, chef upgrade | Whatever you make it | Book 4–6 weeks ahead in high season |
Budget tip: Prices start around $59 pp for basic sunset sails and climb with dinner add-ons. Booking direct online often knocks 10 % off walk-up rates.
Dress Code & Footwear Tips
- Barefoot bliss—most captains ask you to ditch shoes at the gangway; pack flip-flops in your tote for dockside.
- Lightweight linen or quick-dry shorts keep you cool when the Gulf breeze fades.
- Bring a lightweight layer; temps can dip once the sun sinks, especially in December–February.
- Polarized sunnies = crystal-clear dolphin spotting on the sail out.
Phone-saving hack: Slip your mobile into a clear zip bag; you can shoot photos through it while protecting against rogue spray.
Best Months for Calm Waters
| Season | Sea Conditions | Sunset Flavor |
|---|---|---|
| Apr–Jun | Glassy, mild trade winds | Long golden glow; ideal for drone photos |
| Jul–Aug | Warm bath-water temps; occasional squalls | Electric pink cloudscapes after brief showers |
| Sep–Early Nov | Shoulder-season serenity | Fiery horizons, fewer crowds |
| Late Nov–Mar | Cooler breezes, choppier days | Clear skies, rich crimsons; pack a windbreaker |
Captains cancel only for sustained winds above 20 knots—rare but possible during peak hurricane season (mid-Aug to Oct). Always keep your booking email handy for weather updates.
9. Join a Duval Street Nightlife Crawl
Must-Try Bars & Live-Music Venues
Duval Street packs more neon per square inch than almost any mile in America—think of it as Bourbon Street with flip-flops. Start your crawl at the legendary Sloppy Joe’s for grit, guitars, and a Hemingway vibe, then glide two doors down to Rick’s & Durty Harry’s for multi-level dancing and patio people-watching. Slide into Green Parrot (just off Duval) where locals jam under paper-lantern ceilings, and end at Virgilio’s for late-night martinis beneath a canopy of twinkling lights. A rotating roster of buskers and club bands means you can follow your ears from doorway to doorway—there’s live music seven nights a week.
| Stop | What Makes It Pop | Best Time to Arrive |
|---|---|---|
| Sloppy Joe’s | Classic rock, frozen margaritas, epic souvenir T-shirts | 6 p.m. for the first headliner |
| Rick’s Complex | Eight themed bars in one—dance, karaoke, tree-top deck | 9 p.m. when the upstairs opens |
| Green Parrot | No-cover blues & funk, “sound check” happy hour | 5 p.m. for $4 drafts |
| Virgilio’s | Craft cocktails, Sinatra-meets-salsa soundtrack | 11 p.m. for martini Monday |
Signature Cocktails to Order
- Papa Doble at Sloppy Joe’s – a nod to Hemingway’s daiquiri (double rum, no sugar).
- Key Lime Colada at Fat Tuesday – tart island twist on the classic piña colada.
- Parrot Punch at Green Parrot – secret-rum recipe served in a souvenir cup.
- Espresso Martini at Virgilio’s – because you’ll need stamina for round two.
Take a moment to inhale the mix of salt air, gardenia perfume, and charcoal smoke from street-side grills; it’s the olfactory anthem of Key West after dark.
Staying Safe After Dark
- Hydrate between rounds—the tropical heat works faster than the rum.
- Stick to the crawl corridor (Front St. to Truman Ave.) where pedestrian traffic and extra lighting keep things lively and secure.
- Use a pedicab or e-scooter for late-night rides back to your hotel; they’re plentiful till 2 a.m.
- Watch for Fantasy Fest or big-event weekends when crowds triple—secure dinner reservations and bar tickets in advance.
- Keep cash handy for street-musician tips and the $5 cover some venues charge after 10 p.m.
Local Hack: Start on the gulf side of Duval at sunset and slowly “crawl” toward the Atlantic; you’ll feel each bar’s soundtrack morph from laid-back acoustic to thumping dance beats as the sky shifts from peach to midnight blue.
Duval’s magnetic glow promises spontaneous sing-alongs, rooftop cheers, and new friends who swear they’ve known you for years. Add the crawl to your Key West bucket list, and you’ll carry home more than just a souvenir cup—you’ll bring back the island’s nocturnal heartbeat.
10. Reel In a Trophy on a Deep-Sea Fishing Charter
Target Species by Season
| Season | Offshore Stars | Typical Size | Why Go Now |
|---|---|---|---|
| Dec – Feb | Sailfish, King Mackerel | 20–60 lb | Cool fronts push pelagic predators closer to shore. |
| Mar – May | Blackfin Tuna, Wahoo, early Mahi-Mahi | 10–40 lb | Spring bait runs trigger frenzied surface strikes. |
| Jun – Aug | Mahi-Mahi (Dolphin), Blue Marlin | 15–50 lb (Mahi), 150-300 lb (Marlin) | Calm seas + floating weedlines = color-splashed action. |
| Sep – Nov | Grouper, Snapper, Late-season Wahoo | 5–40 lb | Post-storm reefs teem with hungry bottom dwellers. |
Quick scent memory: warm diesel mingling with salt spray, cut ballyhoo on the bait table, and that unmistakable zing as a reel screams to life.
Half-Day vs. Full-Day Charters
| Trip Length | Time on Water | Range from Shore | Ideal For | Price Ballpark* |
|---|---|---|---|---|
| Half-Day (4 hrs) | 3–3.5 hrs | 6–15 mi | Families, first-timers, quick trophy hunt | $750–$950 per boat |
| ¾-Day (6 hrs) | 5–5.5 hrs | 15–25 mi | Mixed surface & bottom fishing | $1,050–$1,300 |
| Full-Day (8 hrs) | 7–7.5 hrs | 25–40 mi (Gulf Stream) | Serious anglers chasing billfish | $1,400–$1,800 |
| Overnight (18 hrs) | Sunset-to-sunrise | 60 mi+ seamounts | Swordfish & deep-drop specialists | $3,000+ |
*Whole-boat rate for up to six passengers; bait, tackle, and ice included. Always confirm fuel surcharge and mate’s customary 15–20 % tip.
Catch-and-Cook Options Around Town
- Hogfish Bar & Grill – Hand your fillets to the chef; return 20 minutes later to citrus-butter perfection.
- Conch Republic Seafood Co. – Offers blackened, fried, or grilled “hook-and-cook” with two sides for under $20.
- Eaton Street Seafood – Will vacuum-seal the rest of your haul for the flight home (TSA-approved frozen block).
Charter-Day Checklist
- Lightweight sun shirt + reef-safe sunscreen (reflective water doubles UV).
- Polarized sunglasses to spot that neon-green mahi charging the spread.
- Small cooler with snacks—most boats supply water and Gatorade.
- Sea-sickness bands or ginger chews if you’re unsure of your sea legs.
- Camera or phone in a splash-proof pouch; mates will gladly snap hero shots.
Local hack: Book mid-week to dodge weekend demand, and ask your captain about planer trolling—a Keys favorite for razor-toothed wahoo lurking in the thermocline.
Hook up with a feisty sailfish or heft a technicolor mahi against blue-ribbon skies and you’ll carry home a salty grin—and maybe dinner – that no downtown souvenir can match. One rod bend is all it takes to understand why deep-sea fishing sits proudly among the 10 Things You Should Definitely Try at Key West.