Key West—America’s southernmost city—has long lured free spirits, writers, and sea captains with sun-washed cottages, roosters crowing, and sunsets that feel choreographed. Once a sponge-diving and cigar-rolling hub, it declared itself the “Conch Republic” in 1982 with tongue-in-cheek independence and never lost that playful defiance.

Today, Key West blends historic lanes and Caribbean color with water adventures: snorkeling on North America’s only living coral reef, dolphin sightings, and sandbar days on gin-clear flats. Duval Street delivers music and merriment, while Bahama Village and the Historic Seaport reward lingerers with stories—and stellar seafood.

Practical notes: parking is tight—walk, bike, or trolley when you can. Wear reef-safe sunscreen; the sun is strong. Conch cuisine rules here (think Key West pink shrimp, conch fritters, and Key lime pie). You’ll arrive on Day 1 afternoon and depart Day 2 afternoon, so we’ll maximize golden hours and cool evenings.

Key West

Why go now: Reliable sunshine, easy access to reef adventures, and nightly sunset rituals at the waterfront. You’ll find historic homes (Hemingway’s six-toed cats), Civil War-era forts, and spontaneous street music near Mallory Square.

• Top Sights: Ernest Hemingway Home & Museum, Key West Lighthouse, Fort Zachary Taylor beach, Truman Little White House, Key West Cemetery’s quirky epitaphs, Southernmost Point (best at sunrise).
• Local Vibes: Bahama Village’s pastel porches and peppery Caribbean flavors; roosters strutting down Petronia Street; live music at pocket-sized bars off Duval.
• Food to Try: Cuban coffee, Key West pink shrimp, blackened grouper sandwiches, mojo pork, and tart Key lime pie.

Getting there (Flights): Most visitors fly into EYW (Key West International). From Miami, it’s ~1 hour by air; nonstop flights from major hubs commonly run ~2–3 hours. Typical fares range from about $150–$450 roundtrip depending on season.

• Search flights on Trip.com (check multiple airports for the best deals).
• Compare fares on Kiwi.com (great for multi-airline combos).

Driving: If you already have a car, the Overseas Highway (US-1) is a spectacular 165-mile drive from Miami—plan ~3.5–4 hours without stops, longer if you pause for Keys scenery.

Where to stay: Midrange budget picks close to the action with local character.

• NYAH Key West - Adults Only — Social, budget-friendlier lodging with pools in Old Town.
• The Southernmost Inn — Historic adults-only inn near the quiet end of Duval, great for walkers.
• The Reach Key West, Curio Collection by Hilton — Private beach access; breezy, beachy design.
• The Ocean Key Resort & Spa — Steps from Mallory Square; balcony sunset views if you want to splurge.

Browse more stays: VRBO: Key West rentals | Hotels.com: Key West hotels

Day 1: Old Town Welcome, Trolley Stories, and a Legendary Sunset

Afternoon (Arrival): Drop bags and shake off travel with a cafecito at Cuban Coffee Queen (try the buccaneer sandwich or a cortadito). Walk the Historic Seaport boardwalk—watch shrimp boats and tarpon under the docks. If you’re hungry, grab fish tacos at Garbo’s Grill (a beloved food truck) or a lobster roll at Eaton Street Seafood Market—both locals’ favorites with fair prices.

Afternoon Activity: Get your bearings with the classic Key West Hop-On Hop-Off Trolley Tour—great for history, breeze, and easy transport. Expect fun commentary on pirates, poets, and presidents, plus convenient stops for later exploring. Book here: Key West Hop-On Hop-Off Trolley Tour.

Evening (Sunset on the water): Celebrate your first night with a live-music sail—few places do sunset like Key West. The Key West Signature Sunset Sail with Live Music, Open Bar & Food includes appetizers and open bar on a brand-new catamaran—festive but relaxed, with postcard views of Mallory Square’s “sunset celebration.” Book here: Key West Signature Sunset Sail with Live Music, Open Bar & Food.

Night (Dinner & music): For a classic harbor meal, try Half Shell Raw Bar (stone crab in season, steamed shrimp, cold beer at picnic tables). Prefer Cuban comfort food? El Siboney’s roast pork with mojo and yellow rice is hearty and affordable. For live music under the stars, wander to Schooner Wharf Bar or pop into The Green Parrot for a high-energy local set.

Day 2: Sunrise Strolls, Reef Snorkeling, Bahama Village Flavors, and Night Kayaking

Morning: Early light at Higgs Beach or Smathers makes for quiet photos and pelican-watching. Breakfast at Blue Heaven—banana pancakes, Benedicts, roosters, and shady banyan trees—feels quintessential Key West. After, swing by the Southernmost Point for a quick snap (shorter line in the morning) or climb the Key West Lighthouse for island views.

Late Morning Activity (Water time): Join a reef cruise to see parrotfish and elkhorn coral. The Key West Reef Snorkel – Morning Mimosas or Afternoon Margaritas pairs a smooth catamaran ride with reef snorkeling and drinks—good value and beginner-friendly. Book here: Key West Reef Snorkel – Morning Mimosas or Afternoon Margaritas.

Afternoon (Local lunch & neighborhoods): Refuel in Bahama Village: try jerk chicken or conch fritters from casual spots nearby, or grab a blackened mahi sandwich at a pet-friendly patio. If you’d rather something quick, pop into Moondog Café for salads and pastries or Fisherman’s Café for Cuban-influenced sandwiches near the seaport. Stroll Petronia Street’s pastel cottages and peek into small galleries.

Evening (Unique night on the water): Cap your trip with a rare after-dark adventure: the Guided Night Kayak Adventure Tour in Luminous Lagoon. Glide through mangrove mazes as guides spotlight nocturnal life and the water glows around your paddle—quiet, mesmerizing, and distinctly Key West. Book here: Guided Night Kayak Adventure Tour in Luminous Lagoon.

Night (Farewell bites): For a laid-back final meal, Off the Hook Bar & Grill does creative local seafood at fair prices; or keep it simple with grilled Key West pink shrimp at a harbor-side joint. Save room for a slice of Key lime pie—try it frozen, chocolate-dipped, or classic with graham crust.

Only Have Four Hours in Key West? (Bonus Blitz)

• Hour 1: Start at the Historic Seaport with a Cuban coffee; stroll the boardwalk and watch tarpon swirl beneath the docks.
• Hour 2: Hop on the Hop-On Hop-Off Trolley for a narrated loop past Hemingway’s, the Lighthouse, and Truman’s Little White House.
• Hour 3: Quick photo at Southernmost Point, then zip to Bahama Village for a snack—conch fritters or a fish taco.
• Hour 4: End at Mallory Square for street performers and sea views, or if timing fits, join a sunset sail departure.

Alternative/extra activities (if you extend time or swap):

• Sunset Sail in Key West with Beverages Included for a quieter, uncrowded cruise.
• Key West Glass-Bottom Boat Tour for reef viewing without getting wet.

Eating & drinking cheat sheet (local favorites):

• Breakfast/coffee: Cuban Coffee Queen (cafecito), Blue Heaven (Benedicts, banana pancakes), Old Town Bakery (fresh baguettes), Glazed Donuts (small-batch treats).
• Casual lunch: Garbo’s Grill (tacos, Korean BBQ burrito), Eaton Street Seafood Market (lobster rolls), Fisherman’s Café (Cuban sandwiches), Sandy’s Café (late-night Cuban staples).
• Dinner: El Siboney (Cuban classics), Half Shell Raw Bar (seafood on paper placemats), Off the Hook (creative, midrange seafood plates).
• Drinks/live music: Schooner Wharf Bar (harbor breezes), The Green Parrot (legendary local bar), The Porch (craft beer & wine in a Victorian house).
• Sweet finish: Key lime pie—classic, frozen-on-a-stick, or chocolate-dipped.

Pro tips: Book water tours in advance in peak season. Aim for sunrise at Southernmost Point to skip lines. Bring reef-safe sunscreen, a light long-sleeve for the sail, and water shoes if you’ll explore shallow flats.

In two days, you’ll trace Old Town’s history, toast a painted sky at sea, and slip through mangroves by moonlight—very Key West. With this plan, you’ll feel less like a visitor and more like a temporary Conch, already plotting a longer return.