Florida has long been a frontier of reinvention: Spanish explorers arrived in the 16th century, Henry Flagler’s rail ambitions reshaped the southern coast, and 20th-century dreamers turned beaches, mangroves, and coral islands into some of America’s most recognizable holiday landscapes. In one week, you can feel those layers distinctly—from Miami’s immigrant-built neighborhoods and Art Deco heritage to Key West’s seafaring stubbornness at the end of the Overseas Highway.

There is also a pleasing strangeness to Florida that makes it ideal for a 7-day itinerary. You can sip a cortadito in Little Havana, scan the horizon for dolphins in the Keys, pass banyan trees older than many buildings around them, and watch the sky turn sherbet pink over the Gulf before dinner. The contrast is the point: tropical ease, deep local culture, and a touch of old American myth.

Practically, March is one of the best times to visit Florida, with warm weather, busy beaches, and strong demand for hotels and tours, so booking ahead matters. Expect driving to be the most logical way to connect Miami and Key West, and note that Florida sunshine is intense even on breezy days—pack reef-safe sunscreen, light clothing, and one smarter outfit for waterfront dinners and sunset cruises.

Suggested arrival: Fly into Miami and compare options on Trip.com or Kiwi.com. For this itinerary, plan on landing in Miami in the early afternoon.

Miami

Miami is not merely a beach city; it is one of America’s most layered urban mosaics. Cuban, Haitian, Colombian, Venezuelan, Caribbean, and Jewish histories all leave marks here, and the result is a city where architecture, food, music, and language feel gloriously alive.

Its greatest strength is range. You can spend the morning among Art Deco landmarks in South Beach, the afternoon in a serious art collection or on the water in Biscayne Bay, and the evening eating some of the best Latin food in the country. It is stylish, yes, but the more rewarding Miami is the one found in family-run bakeries, old-school seafood spots, and neighborhoods with stories to tell.

Where to stay: Browse vacation rentals on VRBO Miami or hotels on Hotels.com Miami. South Beach suits first-time visitors who want walkability; Brickell works well if you prefer polished high-rises, strong dining, and easy rideshare access.

• Top sights: South Beach, Ocean Drive, South Pointe Park, Wynwood Walls district, Pérez Art Museum Miami area, Little Havana, Biscayne Bay.
• Food worth seeking out: Cuban sandwiches, croquetas, stone crab in season, citrusy ceviches, and strong cafecito served at a counter with no patience for dawdling.
• Fun fact: Miami Beach’s Art Deco Historic District holds one of the world’s largest collections of 1920s and 1930s resort architecture.

Viator activities in Miami to consider:

• Little Havana Food and Walking Tour in Miami — a smart early-trip choice because it gives cultural context, neighborhood history, and excellent bites in one go.
• Everglades Eco-Adventure Tour — ideal for travelers who want to balance city time with Florida’s wild interior.
• Miami Millionaires Sightseeing Cruise — classic Biscayne Bay sightseeing with skyline views and a playful dose of local real-estate theater.
• Miami Sunset and City Lights Cocktail Cruise — best for a relaxed evening on the water after a day on foot.

Day 1 – Arrive in Miami and Settle into South Florida

Morning: Arrival day assumes you are in transit, so keep this block open for your flight into Miami. Review transfer options and flight timing on Trip.com or Kiwi.com.

Afternoon: After checking in, ease into the trip with a stroll along South Beach and Ocean Drive. This is the postcard Miami many travelers imagine: cream-and-mint Art Deco hotels, palm-lined sidewalks, and a broad sweep of sand where the Atlantic seems to start just beyond the lifeguard towers.

Afternoon: Walk south toward South Pointe Park, which gives you excellent people-watching, views of cruise ships slipping out to sea, and a cleaner, calmer atmosphere than the busiest beach blocks. If you want a late lunch, try Joe’s Take Away for a streamlined version of the city’s famous stone crab institution, or head to South Pointe for Smith & Wollensky’s outdoor setting if you want a classic waterfront meal.

Evening: For dinner, choose Macchialina for deeply satisfying Italian with a Miami following; its handmade pastas and thoughtful small plates are exactly the sort of place locals book in advance. If you prefer seafood in a more relaxed setting, CVI.CHE 105 downtown is a strong bet for bright Peruvian flavors, polished service, and dishes that feel refreshing after a flight.

Evening: If energy allows, take a short post-dinner walk along Española Way. Its Mediterranean revival styling is a little theatrical in the best sense, and the lane comes alive after dark without demanding a full late-night commitment on your first evening.

Day 2 – Little Havana, Bay Views, and Miami After Dark

Morning: Start with breakfast and coffee in Little Havana. A cortadito and pastelito from Versailles Bakery or a Cuban coffee stop at La Colada Gourmet will put you in the city’s true rhythm much faster than a generic hotel buffet.

Morning: Then dive into the Little Havana Food and Walking Tour in Miami. This is one of the best orientation experiences in Florida: you get neighborhood history, cigar culture, Cuban exile stories, and a sequence of bites that illuminate why Miami’s food scene is inseparable from migration and memory.

Afternoon: Spend the afternoon around Bayside and Biscayne Bay. If you want a seated sightseeing option, the Miami Millionaires Sightseeing Cruise offers skyline perspectives and a peek at celebrity mansions, but the real pleasure is seeing the city from the water, where Miami’s glass towers and low islands make visual sense.

Afternoon: For lunch, try El Rey de las Fritas if you want an iconic Cuban-style burger, or Sanguich de Miami for one of the city’s most consistently praised Cuban sandwiches. Both are rooted in local flavor rather than scenery, which is exactly why they are worth your time.

Evening: For dinner, reserve a table at Michael’s Genuine in the Design District for seasonal American cooking with Florida brightness, or choose Mandolin Aegean Bistro for a Greek-Turkish menu in a blue-and-white courtyard that feels transportive without feeling contrived. Either works especially well if you want a meal that is stylish but grounded in substance.

Evening: Cap the night with the Miami Sunset and City Lights Cocktail Cruise if you prefer a softer ending to the day. Miami’s skyline after sunset has a glamorous glow, and seeing it from the bay is one of the few experiences here that fully deserves its reputation.

Day 3 – The Everglades and a Different Florida

Morning: Have an early breakfast at All Day in downtown Miami, a favorite for carefully sourced coffee, excellent breakfast sandwiches, and pastries that feel considered rather than ornamental. Then set out for the Everglades Eco-Adventure Tour or the Everglades Airboat, Wildlife Exhibit, & Roundtrip Bus from Miami.

Afternoon: The Everglades are one of the most misunderstood landscapes in America: not a swamp in the cartoon sense, but a vast, slow-moving river of grass supporting alligators, wading birds, mangroves, and delicate ecological balances. A guided outing adds context you simply will not get on your own, especially if you are curious about restoration efforts, invasive species, and the region’s unusual hydrology.

Afternoon: Back in Miami, keep lunch casual with a seafood stop at La Camaronera, a beloved counter-service institution known for its fried snapper sandwich and no-nonsense freshness. It is one of those places that reminds you Florida’s best meals are often the least ceremonial.

Evening: Spend the evening in Wynwood. The murals made the district famous, but the greater pleasure lies in browsing the streets at golden hour, when warehouse walls catch the light and the neighborhood’s restaurants begin to hum.

Evening: For dinner, choose KYU for wood-fired dishes with Asian influences, or opt for Coyo Taco if you want something lively and more casual. If you still have room, Zak the Baker is more often thought of for daytime, but if you can visit earlier for pastries, it is one of Miami’s most admired bakery operations for very good reason.

Day 4 – Drive the Overseas Highway from Miami to Key West

Morning: Depart Miami after breakfast and make your way to Key West by rental car. The drive typically takes about 4 hours without long stops, though 5 to 6 hours is more realistic if you pause for views, coffee, or lunch; it is one of America’s great road journeys, linking islands and mangrove flats by bridges that make the sea feel almost level with the road.

Morning: For travel planning, check flights into Miami on Trip.com or Kiwi.com; for this leg itself, driving is the most sensible option. Estimated one-way car rental/fuel/tolls costs vary widely, but budget roughly $70-$160 for the day depending on vehicle type and rental structure.

Afternoon: On the way, stop in Islamorada for a relaxed lunch at Lazy Days, known for straightforward local seafood and water views, or Robbie’s if you want a lively roadside-Keys atmosphere. Even a short stop helps break up the drive and introduces the middle Keys before the finale of Key West.

Afternoon: Arrive in Key West, check in, and take an easy orientation walk through Old Town. The island is compact, eccentric, and immediately legible: pastel conch houses, roaming roosters, banyan shade, and a sense that mainland urgency has finally failed to follow you.

Key West

Key West has worn many identities—wrecking port, cigar town, military outpost, literary hideaway, bohemian refuge—and somehow kept them all. It is the southernmost city in the continental United States, but it often feels psychologically farther away than geography should allow.

The appeal lies not only in beaches or sunsets, though both matter. It is the island’s scale, walkability, and sly self-awareness that make it irresistible. Here, history is close at hand: Ernest Hemingway drank and wrote here, President Truman worked from here, and Bahamian and Cuban influences still shape local architecture, food, and speech.

Where to stay: Search broadly on VRBO Key West or Hotels.com Key West. Strong specific options include The Ocean Key Resort & Spa for harborfront views, The Southernmost Inn for an adults-oriented Old Town base, and Margaritaville Beach House Key West for travelers wanting more resort-style space.

• Top sights: Duval Street, Mallory Square, Ernest Hemingway Home area, Southernmost Point, Truman Little White House, Key West Historic Seaport.
• What to eat: Key lime pie, pink shrimp, conch fritters, Cuban coffee, and very fresh fish served with less fuss than on the mainland.
• Fun fact: The island’s famous six-toed cats at the Hemingway Home are descendants of a polydactyl cat once given to the writer.

Viator activities in Key West to consider:

• Hula Hank's Key West Tipsy Tiki Sunset Cruise — playful, casual, and tailor-made for travelers who want a breezy social evening.
• All-Inclusive Sandbar Safari with Dolphin Playground Encounter — one of the best ways to experience the marine environment beyond the island streets.
• Key West Signature Sunset Sail with Live Music, Open Bar & Food — classic Key West atmosphere with less kitsch than the words “sunset sail” might suggest.
• Key West Sunset Cruise: Dinner, Live Music & Drinks Included — a good all-in-one option if you want evening entertainment and dinner wrapped together.

Day 5 – Old Town Key West, Literary History, and Sunset on the Water

Morning: Begin with breakfast at Blue Heaven, a Key West institution where the shady courtyard, Caribbean-leaning menu, and famously towering meringue-topped Key lime pie capture the island’s offbeat personality. If the wait is too long, Cuban Coffee Queen is the better quick option for strong coffee, breakfast sandwiches, and a notably local feel.

Morning: Then explore Old Town on foot. Walk past the Ernest Hemingway Home area, the leafy lanes of Bahama Village, and the Southernmost Point. Even without entering every museum, the architecture tells a story: wooden conch houses built for heat and hurricanes, set behind porches and tropical gardens.

Afternoon: For lunch, try Garbo’s Grill for excellent Korean-inspired tacos and burritos from a tiny but beloved setup, or Eaton Street Seafood Market if you want lobster rolls, pink shrimp, and a more classic fish-market lunch. These are the kinds of places people remember because the food is specific to the island rather than dressed up for tourists.

Afternoon: Spend some time at the Key West Historic Seaport, where schooners, fishing boats, and marinas preserve a little of the working waterfront that existed before the island became shorthand for sunset leisure. Stop for a drink or light snack rather than overprogramming; Key West rewards unhurried wandering.

Evening: Book the Key West Signature Sunset Sail with Live Music, Open Bar & Food or the Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres. Sunset is the island’s nightly civic ritual, and while Mallory Square is famous, being on the water offers a calmer, far more memorable view as the sky folds through gold, coral, violet, and blue.

Day 6 – Sandbars, Dolphins, and a Proper Key West Night

Morning: Have breakfast at Sarabeth’s for polished American fare in a historic building, or choose Keys Coffee Co. if you want something lighter and more casual before a boat excursion. Then head out on the All-Inclusive Sandbar Safari with Dolphin Playground Encounter.

Afternoon: This outing is one of the best ways to understand why the Keys are special beyond Duval Street. Shallow turquoise water, marine sanctuary landscapes, and the chance to encounter dolphins in their natural environment reveal the ecological side of Key West that many visitors miss if they stay entirely on land.

Afternoon: After returning, take a break at your hotel or wander through shops and galleries off Duval. For a late lunch, Pepe’s Cafe is a strong choice; it is one of the island’s oldest restaurants and still offers the sort of unpretentious seafood and island staples that suit the setting better than anything too polished.

Evening: For your final full evening, book dinner at Latitudes if you want a special-occasion waterfront meal, or choose Nine One Five for a more intimate Old Town dinner with a stylish but easygoing tone. If neither fits your mood, Santiago’s Bodega remains one of the island’s most reliable dinners, with Spanish-inspired small plates that encourage lingering rather than rushing.

Evening: If you prefer a more playful send-off, substitute dinner with the Hula Hank's Key West Tipsy Tiki Sunset Cruise or the Key West Sunset Cruise: Dinner, Live Music & Drinks Included. Key West at dusk has a talent for making even skeptical travelers sentimental.

Day 7 – Final Morning in Key West and Departure

Morning: Enjoy one last slow breakfast at Cuban Coffee Queen or Banana Cafe, where French-Caribbean touches and a relaxed porch setting suit the final day nicely. Use the rest of the morning for souvenir browsing, a short harbor walk, or simply sitting somewhere shaded and letting the island linger a little longer.

Afternoon: Depart in the afternoon. If you are driving back toward Miami for a late flight, allow roughly 4 to 5 hours of driving time minimum, longer on busy weekends; if you are arranging onward air travel elsewhere, compare options on Trip.com or Kiwi.com.

Evening: This block is reserved for travel. Keep snacks, water, and patience close at hand if returning by road; the Overseas Highway is beautiful, but it does not reward tight scheduling.

This 7-day Florida itinerary gives you two of the state’s strongest contrasts: Miami’s cosmopolitan pulse and Key West’s sun-faded island character. Together they offer beaches, Cuban and seafood dining, Everglades wildlife, historic streets, and some of the finest sunset boating in the United States—an excellent first taste of Florida, and one that leaves room to return for more.