Key West sits at the end of the island chain like a colorful exclamation point—closer to Havana than Miami, historically Bahamian and Cuban in flavor, defiantly quirky. Pirates and wreckers once ruled its reefs; later came writers, presidents, and bohemians. Today you’ll find conch-style cottages shaded by palms, roosters strutting Old Town, and a daily sunset ritual at Mallory Square that feels part festival, part poem.

Beyond Duval Street’s energy, Key West is a gateway to protected waters: the Florida Keys National Marine Sanctuary guards North America’s only living coral barrier reef. Snorkelers and divers drift above brain coral and gorgonians; dolphins slice silver arcs across the “dolphin playground.” On land, Hemingway’s six-toed cats still patrol his studio, while Truman’s “Little White House” tells of Cold War decisions made in flip-flops.

Practical notes: Park the car and rent bikes or a golf cart—streets are narrow, parking is scarce, and everything in Old Town is delightfully close. Book sunset sails, Dry Tortugas trips, and popular restaurants in advance, especially December–April. Bring reef-safe sunscreen, a light rain jacket, and an appetite for Cuban coffee and Key lime pie.

Key West

Key West’s Old Town is compact, walkable, and wildly photogenic—gingerbread-trim cottages, Creole verandas, and pastel shutters. History lives loudly here: the Key West Lighthouse climbs above the Hemingway Home; Fort Zachary Taylor guards a pocket of turquoise water and some of the island’s best snorkeling from shore.

Top sights and activities include the Ernest Hemingway Home & Museum, Truman Little White House, Key West Lighthouse & Keeper’s Quarters, Key West Butterfly & Nature Conservatory, Fort Zachary Taylor Historic State Park, the Historic Seaport Harbor Walk, and the nightly Mallory Square Sunset Celebration. For the water: reef snorkel sails, sandbar picnics, jet-ski circumnavigations, dolphin-watching, parasailing, and, for a grand adventure, a day trip to Dry Tortugas National Park and Fort Jefferson.

• Where to stay (handpicked):
• Oceanfront glam with a Duval Street address: The Ocean Key Resort & Spa (also via Expedia).
• Adults-only B&B vibes near the Southernmost Point: The Southernmost Inn.
• Resort ease across from Smathers Beach: Margaritaville Beach House Key West.
• Private-island tranquility a short ferry from Mallory Square: Sunset Key Cottages.
• Popular beachfront escape with multiple pools: Southernmost Beach Resort.
• Beachfront pier and private sand: The Reach Key West, Curio Collection by Hilton.
• Budget-friendlier, social courtyard scene: NYAH Key West - Adults Only.
• Browse more stays: VRBO Key West or Hotels.com Key West.

• How to get here:
• Fly into EYW (Key West International). Typical connections are via Miami, Fort Lauderdale, Atlanta, or Charlotte. Search fares and schedules on Trip.com Flights or Kiwi.com. From Miami, it’s ~1 hour by plane; fares vary ~$150–$600 round-trip depending on season.
• Driving the Overseas Highway (US-1) from Miami takes ~4 hours without stops, but it’s a scenic ribbon over teal water—allow extra time for traffic and photo breaks.

Day 1: Arrival, Duval Street Stroll, and Sunset Ritual

Afternoon: Arrive and check in. Shake off travel at the Historic Seaport Harbor Walk—watch tarpon laze under docks and charter crews cleaning today’s catch. Grab a late lunch at Eaton Street Seafood Market (buttery lobster roll; blackened mahi sandwich) or Fisherman’s Café for a Cuban mix and conch fritters.

Evening: Wander Duval Street’s art galleries and Bahama Village’s pastel lanes. Catch the Mallory Square Sunset Celebration: jugglers, live music, and that famous green flash. Dinner at El Siboney (Cuban roast pork, plantains, black beans) or Santiago’s Bodega (tapas—lamb lollipops, stuffed dates). Nightcap at the Green Parrot, a beloved locals’ bar with live bands.

Day 2: Old Town Orientation and a Sunset Sail

Morning: Cuban fuel at Cuban Coffee Queen (try the cortadito and Key Wester breakfast sandwich). Then loop the island’s landmarks with this narrated classic:

Key West Hop-On Hop-Off Trolley Tour

Hop off for photo stops at the Southernmost Point, the Lighthouse, and the Butterfly Conservatory. Your guide’s stories stitch pirates, poets, and presidents into one engaging loop.

Afternoon: Beach time at Fort Zachary Taylor State Park—snorkel from shore along rocky edges for sergeant majors and parrotfish; tour the Civil War-era brick fort. Lunch at the park’s beach café or head to Garbo’s Grill (Korean BBQ tacos) tucked behind Hank’s Saloon.

Evening: Set the tone for the week with a live-music sunset catamaran:

Key West Sunset Sail with Full Bar, Live Music and Hors D'oeuvres

Return glowing and hungry—book Nine One Five for porch dining (seared scallops, short rib gnocchi) or Hot Tin Roof at Ocean Key for Caribbean-influenced plates and harbor views.

Day 3: Hemingway, Lighthouse Views, and a Sandbar Safari

Morning: Breakfast under banyans at Blue Heaven (lobster Benedict; banana bread). Tour the Ernest Hemingway Home to peek into the studio and meet polydactyl cats, then climb the Key West Lighthouse for a sweeping island panorama. Stroll shaded lanes of Bahama Village for boutiques and murals.

Afternoon: Head out to the “dolphin playground” and a sun-splashed sandbar:

All-Inclusive Sandbar Safari with Dolphin Playground Encounter

Expect shallow turquoise water, floating mats, and frequent dolphin sightings—bring a waterproof camera and reef-safe sunscreen.

Evening: Sunset cocktails at Sunset Pier or on the waterfront at Truman Waterfront Park. Dinner at Louie’s Backyard (book the ocean deck; conch ceviche, grilled fish) or go sweet-and-sultry at Better Than Sex for dessert wines and decadent cakes.

Day 4: Dry Tortugas National Park Expedition (Full Day)

Rise early for the ferry or splurge on a seaplane to Dry Tortugas National Park and Fort Jefferson, 70 miles west in electric-blue water. Explore the massive 19th-century fort, snorkel over seagrass and coral heads where tarpon and tropicals cruise, picnic on the beach, then nap on the return ride. Pack a hat, long-sleeve sun shirt, and plenty of water. Ferry is ~2h15 each way; plan 8–10 hours total. (Reserve well ahead; seats sell out.)

Back on island, crack claws and dip into oysters at Half Shell Raw Bar, or grab a late bowl of Caribbean conch chowder at Conch Republic Seafood Company. If you have gas left in the tank, wander over to Smokin’ Tuna for live music.

Day 5: Do-It-All Watersports Day (Full Day)

Ready for adrenaline? This all-inclusive combo packs your day with floatplanes of fun—jet skis, parasailing, banana boats, a water park, and more, plus lunch and beer included:

Key West: All-Inclusive Watersports Adventure with Lunch & Beer

It’s a splashy sampler of everything that makes Key West’s waters addictive. Dry off, then cab ten minutes to Stock Island for dinner at Hogfish Bar & Grill—order the namesake sandwich, fried and piled on Cuban bread.

Day 6: Shipwrecks, Gardens, and Quiet Beaches

Morning: Coffee and a croissant at Old Town Bakery, then the Mel Fisher Maritime Museum to ogle Spanish treasure and hear wild tales of the Atocha. Prefer butterflies? The Key West Butterfly & Nature Conservatory is a dreamy glasshouse fluttering with color.

Afternoon: Seek serenity at Higgs Beach and the adjacent West Martello Tower & Key West Garden Club—a brick ruin draped in orchids and vines. Lunch at Salute! On The Beach (grilled fish salad, linguine vongole) or a vegan-friendly spread at The Cafe on Southard.

Evening: Golden hour along the Historic Seaport; consider a tasting flight at The Porch (craft beer, wine) before dinner. Book Latitudes (on Sunset Key via short ferry) for a special-occasion sunset, or stay in town for tapas-and-sangria at Santiago’s Bodega if you missed it earlier.

Day 7: Slow Morning, Souvenirs, and Departure

Morning: Brunch at Banana Café (savory crepes; goat cheese omelet) or Moondog Café (house-made pastries, breakfast tacos). Browse White Street’s galleries and the funky boutiques along Petronia Street for local art and island-linen.

Afternoon: Before you go, grab a frozen chocolate-dipped slice at Kermit’s Key Lime Shoppe for the plane. If time allows, tour the Truman Little White House or pop into Pepe’s Cafe for a farewell Key lime pie. Depart with a sun-kissed grin.

Optional Swap: Reef Snorkel Cruise or Dolphin Watch

If the water calls for one more spin, consider swapping in one of these during Days 2–6:

Key West Reef Snorkel – Morning Mimosas or Afternoon Margaritas

Getting around and tips: Rent bikes (~$15–25/day), scooters (~$40–60/day), or a golf cart (~$90–120/day). Sun is strong year-round; pack reusable water bottles, brimmed hats, and UPF layers. Hurricane season runs June–November—keep an eye on forecasts. Respect wildlife: give dolphins, turtles, and sharks their space, and always use reef-safe sunscreen.

Flight home: For your departure, check updated schedules and prices on Trip.com Flights or Kiwi.com. If you’re driving back, depart in the morning to beat afternoon traffic along US-1.

In a week, you’ll have traced wrecking lore and presidential hideaways, tasted the island’s Cuban and Caribbean kitchens, and sailed into sunsets brilliant enough to hush a crowd. Key West is a small place with a big personality—plan to come back in a different season to meet it again.