The Complete Florida Travel Guide: Miami, the Florida Keys and Key West
- The Anonymous Hungry Hippopotamus
- Jun 27
- 7 min read
Florida is not one place. It is a collection of entirely different worlds, connected by highways and coastline but separated by atmosphere, culture, and pace in ways that can surprise even experienced travelers. Miami hums with an energy that is equal parts Latin America, Caribbean, and international metropolis. The Florida Keys unfold southward in a slow, sun-drenched procession of islands that seem to exist outside ordinary time. And Key West, at the very end of it all, is a place so singular that it has developed its own mythology.
I have spent time across all of it — from a food tour through Little Havana to tarpon feeding on the docks of Islamorada to standing at the southernmost point in the continental United States as a rooster wandered past. This guide collects everything I have written, organized so you can plan your own version of the journey.
Miami
The best place to begin any visit to Miami is not South Beach. It is Little Havana, the neighborhood along Calle Ocho where Cuban culture has been rooted since the 1960s and where the food, the music, and the people tell a story that no museum could replicate. This post covers a full food tour through the neighborhood — the Cuban sandwich, the croquetas, the fresh-squeezed guarapo, the cafecito, and the particular pleasure of eating food that has been made the same way, by the same families, for sixty years.
South Beach is where Miami performs. Eight hundred Art Deco buildings were erected along Ocean Drive in the twenty years between 1923 and 1943, making this the largest concentration of Art Deco architecture in the United States — a fact that becomes tangible the moment you walk the street and realize every building you see belongs to the same extraordinary moment in design history. This post covers the architecture in depth, the beach itself (two miles of white sand against genuinely turquoise water), a boat cruise past the celebrity mansions of Star Island, and the particular electricity of a neighborhood that has always known it is being watched.
Wynwood was a neighborhood of abandoned warehouses until artists arrived and covered every wall with color. Today it is one of the world's most concentrated open-air galleries — 80,000 square feet of murals by international artists including Dan Kitchener, Kenny Scharf, Dasic Fernández, Shepard Fairey, and Bordalo II, whose large-scale animal sculptures are constructed entirely from recycled trash. This post also covers the Wolfsonian Museum in Miami Beach, whose collection of 200,000 objects from 1885 to 1945 — posters, machines, paintings, furniture, and a piano that won Grand Prix at both the Paris Exposition Universelle and the St. Louis World's Fair — tells the story of the modern world through the objects that made it.
Miami was named Food City of the Year by Bon Appétit, and the restaurants confirm why. This post covers Stubborn Seed in South of Fifth — the Michelin-starred creation of Top Chef winner Jeremy Ford — alongside Gianni's at the former Versace Mansion, where dining on a patio of a murdered fashion legend adds a layer of atmosphere that no other restaurant in the city can offer, Hoja for tacos built from twelve varieties of freshly ground corn, and Mister 01, a Michelin-recognized pizzeria hidden inside an office building and seating fewer than twenty people.
The Florida Keys
The Florida Keys stretch 120 miles south of Miami in a gentle arc of more than 800 islands connected by the Overseas Highway and 42 bridges. The journey itself is part of the experience — this post covers the drive south from Miami, the first stops along the Overseas Highway, and arrival in Islamorada, where ocean breezes, wind chimes, and the tangible slowing of pace announce immediately that this corner of the continental United States is like no other. Including one of the most unexpectedly charming activities in the Keys: feeding wild tarpon directly from a dock.
Islamorada is a serious food destination despite its relaxed exterior. This post covers Islamorada Fish Company — the original location, set directly on Florida Bay, where the grouper is caught that morning in the adjacent waters — and Pierre's, one of the most romantic restaurants in the Keys, where dinner ends with Key lime pie served with berry compote and graham cracker crumble, and which first planted the seed of the key lime quest that culminates later in this series.
Key Largo sits at the northernmost tip of the archipelago, where the mainland releases its grip and island life takes over. Known as the Diving Capital of the World, its clear turquoise waters and mangrove forests offer a completely different experience from the more developed islands to the south. This post covers a solo kayaking excursion through the mangroves, a wedding celebration that ended watching the sun set over Florida Bay, and the particular feeling that Key Largo produces — that quiet, insistent sense that you are in a place worth being.
Key Largo's bar scene is less about velvet ropes and more about character. This post covers three standouts: The Armory Speakeasy, a hidden military-themed bar requiring a passcode to enter; the Salty Pecker beach bar; and the Caribbean Club — the oldest bar in the Upper Keys, opened in 1938, built as a fishing retreat, turned gambling hotspot, turned movie location for the Humphrey Bogart film Key Largo, and today a beloved local haunt sitting right on Blackwater Sound.
The food in Key Largo rewards those willing to look past the obvious. This post covers the finest meals I had on the island — fresh seafood, local catches, and the particular pleasure of eating well in a place that prioritizes water views and ocean breezes over formality.
The drive from Key Largo to Key West along the Overseas Highway is one of the most spectacular road trips in the United States. This post covers the essential stops: Bahia Honda State Park, where powdery white sand and turquoise water create a scene so beautiful it feels staged; the 7 Mile Bridge, one of the longest segmental bridges in the world, where the road appears to continue endlessly into the horizon suspended between sky and water; and the remote pier at West Summerland Key, where standing over the open ocean with wind in every direction somehow makes the world feel quiet.
Key West sits at the very end of America — closer to Cuba than to Miami, marked by a boldly painted buoy at the Southernmost Point of the continental United States, where roosters wander freely and the pastel houses glow in the afternoon light. This post covers the Hemingway Home and Museum, the Southernmost Point marker, the story of Albert "Bishop" Key who greeted visitors and sold conch shells at that corner for decades, and the particular atmosphere of a city that has made an art form of not taking itself seriously while being, in fact, quite serious about beauty, history, and the good life.
Key West feeds you well if you know where to go. This post covers Bagatelle — a French-influenced restaurant on Duval Street with balcony dining and the finest hogfish sandwich I encountered in the Keys, the fish caught fresh that morning and grilled with Cajun seasoning — alongside The Conch Shack directly across the street for the island's signature shellfish, and the other essential dining stops in a city that takes its food as seriously as its sunsets.
No single dish is more associated with the Florida Keys than key lime pie. This post is devoted entirely to finding the best one — a quest that took me across multiple islands, through bakeries, restaurants, and roadside stands, and ended with a definitive conclusion that I will let the post deliver. If you eat only one thing in the Florida Keys, this should inform what it is.
Planning Your Florida Trip
Getting there: Miami International Airport (MIA) and Fort Lauderdale-Hollywood International Airport (FLL) both serve the Miami area with direct flights from most US cities. Key West has its own small airport (EYW) with limited direct routes — most visitors fly into Miami and drive south.
Getting around: A rental car is essential for the Florida Keys. The Overseas Highway is the only road connecting the islands and driving it at your own pace — stopping for sunsets, detours, and whatever catches your eye — is part of the experience. In Miami, rideshare is the most practical option within neighborhoods; a car is useful for getting between Wynwood, South Beach, Little Havana, and Coral Gables.
How long to spend: Miami deserves a minimum of three days to do it justice. The Keys, if you're doing the full drive from Key Largo to Key West, are best spread across three to four days. Key West alone warrants at least two nights. The full Florida itinerary — Miami plus the Keys plus Key West — works beautifully over eight to ten days.
Best time to go: November through April is peak season — dry, warm, and busy, with hotel prices to match. May through October brings summer heat, afternoon thunderstorms, and significantly lower prices. Hurricane season runs June through November; September and October carry the highest risk. The shoulder months of November and April offer the best balance of weather and value.
Coming Soon: West Palm Beach and Palm Beach — the final piece of the Florida picture, combining world-class art museums, extraordinary dining, and the particular splendor of a town that has been doing luxury quietly and very well for over a century. Those posts are coming. Subscribe here to be notified when they go live.
Florida keeps surprising me. I thought I knew what it was. The Keys convinced me I didn't. Key West confirmed that some places resist easy definition and are better for it.
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