Florida has been a crossroads of cultures for centuries—from Indigenous peoples and Spanish explorers to Bahamian wreckers and Cuban exiles—shaping a coastline that hums with music, food, and maritime lore. Today, Miami’s skyline rises like coral out of Biscayne Bay while the Florida Keys stretch seaward in a silver chain of bridges and mangrove islets.

This 5‑day Miami and Key West itinerary pairs big‑city energy with island time. You’ll wander the Art Deco District, taste pasteles and cafecito in Little Havana, skim across Everglades sawgrass on an airboat, then sail into Key West’s legendary sunset with a glass in hand. Along the way, expect powdery beaches, fresh seafood, and sultry evenings that never seem to end.

Practical notes: late summer and fall bring hurricane season—monitor forecasts and consider flexible bookings. Pack reef‑safe sunscreen, a sun hat, and lightweight layers; reserve key tours ahead in peak months (Dec–April). Renting a car is handy, but flying between Miami and Key West can save time; rideshares work well in Miami, and Key West is delightfully walkable.

Miami

Miami is a mosaic: pastel Art Deco on South Beach, Afro‑Caribbean beats in Little Haiti, Cuban coffee and dominos in Little Havana, and world‑class art in Wynwood and the Design District. The Atlantic glitters on one side; Biscayne Bay frames yacht wakes, manatees, and island neighborhoods on the other.

• Top sights: South Beach’s Art Deco Historic District, Wynwood Walls, Pérez Art Museum Miami (PAMM), Bayfront Park, Coconut Grove’s banyan‑shaded streets, and the Design District’s public art.
• Signature flavors: Cuban sandwiches at ventanitas, stone crabs (in season), Peruvian Nikkei ceviche, and Miami’s cocktail craft scene.
• Stay via VRBO Miami or Hotels.com Miami. Consider South Beach for car‑free beach time, Brickell for skyline views and dining, or Wynwood for artsy lofts.
• Getting there: Search flights to MIA/FLL on Trip.com or Kiwi.com. Typical nonstop times: NYC ~3h, Chicago ~3h, Dallas ~2h 45m, LA ~5h 30m; $120–$350 roundtrip off‑peak.

Day 1: Arrive in Miami, Art Deco Glow, and Biscayne Bay

Afternoon: Touch down and check in. Grab a pick‑me‑up at Panther Coffee (Wynwood) or All Day (Downtown)—both roast meticulously and pull balanced espresso shots. Stroll Ocean Drive and Collins Ave to admire the Art Deco Historic District’s neon trims, porthole windows, and streamline curves; Lummus Park is steps from the surf.

Evening: Sunset in the bay is pure magic. If you’re up for a gentle first night, book the Miami Sunset and City Lights Cocktail Cruise for skyline views with prosecco and frozen cocktails as the lights flicker on across Brickell and South Beach.

After, dine at Stubborn Seed (creative, Michelin‑starred tasting menu; reservations recommended) or La Mar by Gastón Acurio on Brickell Key for modern Peruvian and bay breezes. Nightcap at Sweet Liberty Drinks & Supply Co. (award‑winning cocktails) or Jaguar Sun (pasta + martinis) if you’re still energized.

Day 2: Wynwood Color, Little Havana Flavor, and a Millionaire’s Row Sail

Morning: Breakfast at Zak the Baker (Wynwood)—go early for fresh babka, sourdough, and shakshuka—or GreenStreet Café in Coconut Grove for fluffy pancakes and people‑watching. Explore Wynwood Walls and the surrounding murals; galleries and indie boutiques dot NW 2nd Ave.

Afternoon: Taste Miami’s Cuban heart on the Little Havana Food and Walking Tour—expect guava pastries, picadillo empanadas, sugarcane juice, a cafecito lesson, and salsa rhythms on Calle Ocho while guides unpack exile history and neighborhood traditions.

If you prefer casual lunch, Versailles (classic Cuban) and El Mago de las Fritas (Cuban burger) are beloved institutions.

Evening: Head to Bayside/Brickell for a golden‑hour boat ride: the Miami Millionaires Sightseeing Cruise glides past celebrity mansions, the Venetian Islands, and glittering high‑rises—great for photos of Biscayne Bay.

Dinner in the Design District at Michael’s Genuine Food & Drink (seasonal American) or Mandolin Aegean Bistro (Greek‑Turkish plates in a 1940s house). For dessert, The Salty Donut in Wynwood stays open late.

Day 3: Everglades Wilds and a South Beach Evening

Morning: Fuel up with a cortado and pastelito at Enriqueta’s Sandwich Shop (Wynwood). Then trade skyscrapers for sawgrass on the Everglades Small-Group Tour from Miami with Transportation. An expert guide leads an airboat ride through the River of Grass with chances to spot alligators, herons, and turtles; hotel pickup keeps logistics easy.

Afternoon: Return to South Beach for a swim at South Pointe or 21st Street Beach—soft sand and turquoise water. Grab a late lunch at La Sandwicherie (classic French‑style subs and smoothies) or Los Félix (heritage corn and wood‑fired dishes) back on the mainland if you’re exploring Coconut Grove.

Evening: Dinner at Uchi Miami (elevated Japanese, pristine sashimi and makimono) or Macchialina (handmade pastas, intimate vibe) on the Beach. If you want one last toast to the skyline, the Miami Sunset & City Lights cruise from Day 1 is a relaxed repeat favorite; otherwise, sip a nightcap at Broken Shaker’s garden bar.

Key West

At the end of the Overseas Highway, Key West feels like the Caribbean met Old Florida and decided to paint every porch the color of conch shells. Roosters patrol, gingerbread houses lean under palms, and sunset is a daily ritual on Mallory Square.

• Top sights: Ernest Hemingway Home & Museum (and six‑toed cats), Key West Lighthouse, Fort Zachary Taylor’s beach and fortifications, and the Southernmost Point buoy.
• Where to stay: For resorts and boutique inns near Old Town and the beach, browse VRBO Key West or Hotels.com Key West. Excellent specific picks: Ocean Key Resort & Spa (on the water, near Mallory Square), The Southernmost Inn (adults‑only, historic), and Margaritaville Beach House Key West (family‑friendly, across from Smathers Beach).
• Getting from Miami: Drive the Overseas Highway (Miami to Key West 3.5–4.5 hours without long stops) for epic views, or fly MIA→EYW (~1 hour, often $100–$250 one‑way) via Trip.com or Kiwi.com.

Day 4: Miami → Key West, Old Town Treasures, and a Sunset Sail

Morning: Depart Miami after breakfast for a scenic drive down US‑1 (stop on Islamorada for a quick café con leche if you’re hungry), or take a morning hop to EYW. Aim to arrive by midday to maximize island time.

Afternoon: Check in, then lunch at Garbo’s Grill (Korean BBQ tacos from a beloved food truck) or El Siboney (Cuban comfort staples—ropa vieja, black beans, and sweet plantains). Walk Old Town: tour the Hemingway Home (peek at the six‑toed cats), climb the Lighthouse for views, and snap the Southernmost Point buoy.

Evening: Celebrate your arrival with the Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres—a classic way to watch the sky ignite as sails fill and the Gulf turns molten.

After, dinner at Louie’s Backyard (waterfront fine dining; book ahead) or Half Shell Raw Bar (icy oysters, peel‑and‑eat shrimp, and Key lime pie in a laid‑back harbor setting). Finish with live music at the Green Parrot, the island’s quintessential bar.

Day 5: Sandbars, Dolphins, and Farewell

Morning: Get on the water early with the All-Inclusive Sandbar Safari with Dolphin Playground Encounter. You’ll skim over shallow flats to a secluded sandbar, then look for wild dolphins in the marine sanctuary—snorkel, sun, and swim time included.

Prefer staying dry? Consider the Shark and Wildlife Viewing Adventure to see nurse and lemon sharks from a catamaran.

Afternoon: Quick bite at DJ’s Clam Shack (lobster rolls) or Cuban Coffee Queen (for one last cortadito and a pressed Cuban). If time allows, swim at Fort Zachary Taylor State Park’s rocky‑clear beach and peek at the Civil War-era fortifications. Depart in the afternoon—fly from EYW or begin the scenic return drive.

Evening: Travel home. If you have a late flight, an early dinner at Blue Heaven (Caribbean‑inspired plates under banyans; famous for Key lime pie) makes a memorable finale.

Where to Stay (Quick Picks)

• Miami: South Beach for car‑free beach days; Brickell for upscale dining; Wynwood for artsy lofts. Search deals on VRBO Miami and Hotels.com Miami.
• Key West: Ocean Key Resort & Spa (right by Mallory Square sunsets), The Southernmost Inn (quiet adults‑only stay), or Margaritaville Beach House Key West (steps to Smathers). Browse more on VRBO Key West and Hotels.com Key West.

Logistics & Tips

• Getting in/out: Compare fares and times on Trip.com and Kiwi.com. For Miami↔Key West, flying saves ~3 hours compared to driving.
• Budgeting: Expect $15–$25 breakfasts (for two), $18–$30 casual lunches, $35–$70 dinner entrees at top spots, and $35–$85 for most boat tours.
• Seasonality: Stone crab season runs Oct–May (Joe’s Stone Crab is iconic). Winter/spring are dry and mild; summer brings heat and storms—plan midday breaks.
• What to pack: Reef‑safe sunscreen, water shoes for rocky beaches at Fort Zach, a light sweater for breezy cruises, and a compact rain jacket in summer.

Alternative/Optional Experiences

• Private boating in Miami: Charter your own captain‑guided bay day on the Best of Miami: Private Top-Rated Boat Charter for sandbar time and skyline swims.

  

• Jetski adrenaline: Zip across Biscayne Bay on the Miami Jet Skis Adventure for a high‑octane hour with skyline views.

  

In five brisk days, you’ll trace Florida’s contrasts—from Miami’s neon and Cuban soul to the Keys’ blue horizons and sunset rituals. Whether you’re here for beaches, wildlife, or bites and boats, this itinerary sets an easy rhythm: mornings of discovery, afternoons by the water, nights under warm stars. You’ll leave plotting your return for stone crabs, street art, and one more sail into the sun.