4-Day Florida Road Trip Itinerary

Even the most pressed for time road trippers can get a good dose of Florida favorites starting with Miami, heading through the Everglades, and capping it off in Key West. Four days are better than none, and here’s how to get it done without wasting a single minute of your vacation.

Days 1-2: Miami

Start your day exploring the art deco architecture of South Beach by walking along Ocean Drive as the morning sun blasts the pastel buildings and makes for some stunning scenery. Grab breakfast or brunch at one of the several al fresco restaurants along Ocean Drive. The earlier you get here the better, as parking is easier in the morning, and the crowds have yet to arise from their post-party slumber. Take an hour or two to soak in some rays at nearby Lummus Park.

Be prepared for the throngs-in-thongs to show up on the beach in earnest by around noon. That’s as good a time as any to towel off and start exploring the sights of central Miami. Hit the Design District and Wynwood Art District at the northern end of downtown first, to check out the galleries, boutiques, and restaurants that have sprouted up around these creative outposts. From there, keep the arts vibe rolling with a walk through the brand-new Pérez Art Museum Miami, one of the few real “sights” in downtown Miami. After that, head back to South Beach for a stylish night of dinner and drinks. Sleep it off in a tiny room in one of the several boutique hotels that are housed in vintage art deco buildings here.

Shake off the previous night’s festivities with a café cubano in Little Havana. Take a little while to stroll through this Cuban-American enclave, making sure to make the tourist-required stop at Maximo Gomez Park, where you can watch Cuban senior citizens play dominoes. Sure, it may sound boring and weird, but it’s sort of a must-see.

From there, it’s just a few minutes’ drive into Coral Gables, where you can shop along the Miracle Mile or take a dip in the 1920s-era Venetian Pool. Nearby Coconut Grove offers more shopping. But, the beautiful Vizcaya Museum & Gardens is a far better way to spend the rest of your day. Treat yourself to an excellent, upscale Spanish dinner at Coral Gables’ Xixón Spanish Cuisine and then head back to your South Beach hotel for one more night.

Day 3: The Everglades

Pack some bug spray and sunscreen and head off for a day’s adventure into Everglades National Park. On your way, stop by Coral Castle in Homestead. An exquisitely weird and deeply romantic slice of Old Florida, the castle was constructed out of locally-quarried coral-stone in near-complete secrecy by a Latvian immigrant mourning a lost love.

From Homestead, it’s just a half-hour drive to the main entrance of Everglades National Park. Make sure to stop into Robert Is Here fruit stand and farm to grab some provisions and a fresh fruit smoothie. There’s only one road in and out of Everglades National Park. Visitors can make the circuit to the southernmost point of the park, Flamingo Visitor Center, and back in four or five hours. Although Flamingo is something of a destination (it’s here that you can take guided boat tours), there are several stops and smaller visitor centers along the route that are well worth exploring.

Make the hour-long drive (from the main entrance of Everglades National Park) to Key Largo and book a room.

Day 4: The Keys

There’s no way on Earth you can see all that the Florida Keys have to offer in just one day. Plan on heading straight for Key West. Take in some of the major sights along the way, including a photo-op on the Seven Mile Bridge, the gorgeous beach at Bahia Honda State Park, and Key deer-spotting on Big Pine Key.

Arrive at Key West in time for a late lunch and a drink. You’ll still have time to take in must-see spots like the Southernmost Point buoy and the shops and bars of Duval Street. Make sure you head to a good spot to catch the sunset (try the Crowne Plaza La Concha Hotel) and then prepare to partake in Key West’s raucous nightlife. Make sure you’ve got a room reserved, as you won’t want to be driving anywhere afterward. This itinerary doesn’t allow for the two things the Keys are best for—relaxing and fishing—but it does give a pressed-for-time traveler a good taste of the basics.

Jason Ferguson

About the Author

Florida native Jason Ferguson has yet to find a corner of his home state that doesn’t hold some sort of surprise. With a background in alternative journalism and arts and culture reporting, Jason enjoys finding surprises and unusual sights in some of Florida’s most well-traveled destinations. As a father, he certainly enjoys the pleasures of the beaches and outdoor opportunities, but also likes to dig deep into the nightlife, arts, and cultural scenes.

Jason has written for publications ranging from Time Out, Travel + Leisure, and Caribbean Travel & Life to Florida newspapers such as the Orlando Weekly and Miami New Times. He enjoys sniffing out the beauty of Florida’s natural history as well as the oddness of its quirky present. He, his wife, and their kids utilize their home in Central Florida as a launching pad for weekend adventures that take them to points of interest throughout the state. Although their favorite spots change from week to week, there’s a general consensus that the white-sand beaches of southwest Florida aren’t just the best in the state, but are possibly some of the best in the world.

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