There are so many beautiful places in Florida covering more than 65,000 square miles that it can be hard for a visitor to know which to hit on their trip! Luckily, this 5-day Florida road trip itinerary will take you to—and through!—the best places the Sunshine state has to offer.

Day 1: Miami

Start in Miami and spend your daylight hours exploring the Design District, the Cuban American community of Little Havana, and the galleries and historic sights of Coconut Grove and Coral Gables. Grab dinner at one of the many excellent restaurants at South Beach and spend the night enjoying a drink or two along Ocean Drive.

Day 2: Miami

Once you’ve shaken off the night before with a café cubano, hit Miami Beach, where the sunbathers next to you might be famous. In the afternoon and evening, hit the sidewalks of Collins Avenue and Ocean Drive to shop, eat, and gawk at the art deco buildings.

Day 3: Miami – Fort Lauderdale, approx. 30 Miles / 45 km

Fort Lauderdale

Fort Lauderdale travel tends to peak in the winter, thanks in large part to the many flights arriving filled with people fleeing the cold Northeast. But unlike some beach towns, this city never shuts down. You can visit Fort Lauderdale at the peak of summer, take advantage of off-season rates, and find all the bars and restaurants are open.


  • Sawgrass Mills—with over 300 shops, it’s Florida’s most extensive outlet mall.
  • Breakfast at the Floridian, a beloved old-school diner adorned with celeb photos that’s open round the clock.
  • Escaping to the whimsical 35-acre Bonnet House Museum & Gardens, a 1921 Carribean-style plantation-cum-artist residence.


Hilton Fort Lauderdale Beach Resort

505 N. Fort Lauderdale Beach Blvd., Fort Lauderdale, FL 33304

Opened recently within the last several years, the Hilton Fort Lauderdale Beach Resort is an all-suites venture with ocean-view balconies. Don’t forget to wing by the spa for a lush treatment.

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Day 4: Fort Lauderdale – Key Largo, approx. 90 Miles / 144km

Key Largo

Key Largo is the First of the Keys, given its northernmost perch within the chain of islands below the tip of Florida.  But the largest of the Keys also has the rightful claim of being the Diving Capital of the World, thanks to the coral reefs and its huge underwater state park. When you travel to Key Largo you’ll find an accessible island getaway, with plenty of chances to dive, snorkel or just enjoy the beautiful sunset and the islands’ namesake pie. 


• John Pennekamp Coral Reef State Park
• Key Largo National Marine Sanctuary
• Dagny Johnson Key Largo Hammock Botanical State Park
• Florida Keys Wild Bird CenterDay


Coconut Palm Inn

198 Harborview Dr., Key Largo, FL 33037

A 1940’s fishing camp that has been transformed into a tranquil retreat with just the right amenities and an authentic old Florida Keys feel. The 20 rooms spread across two low-slung, bay-facing structures have hand-carved wooden furniture from Bali, sisal rugs, and sage-green walls. Outside, a palm-shaded swath of sand has Adirondack chairs for lounging.

5: Key Largo – Islamorada, approx. 17 Miles / 27 km


Islamorada is comprised of six small islands in the Florida Keys, located between the saltwater wilderness, barrier reefs and Everglades National Park. If you visit Islamorada, you’ll also be treated to a selection of fine dining and some of the best seafood imaginable.


• History of Diving Museum
• Theater of the Sea
• Indian Key State Historic Site
• Michelle Nicole Lowe Art Gallery
• Windley Key Fossil Reef Geological State Park


Postcard Inn Beach Resort & Marina

84001 Overseas Hwy, Islamorada, FL 33036-3408
This newly refreshed Florida Keys resort getaway is an iconic property that offers the retro, throwback feel of a nostalgic American beach vacation, combined with modern amenities, designer furnishings and a touch of whimsy. 

Each of the boathouse chic guest rooms showcase a waterfront style of white woods and sand-colored stripes, daybeds, large flat-screen televisions and Wi-Fi service. Following the tradition of the Postcard Inn style, each room and suite at  this resort has been personalized with amusing quotes from ocean lovers that have been hand-stenciled on the walls.

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Day 6: Islamorada – Key West, approx. 80 Miles / 128 km

Key West

Four miles long, two miles wide, and loaded with quirky charm, the southernmost city in the continental United States feels like a Caribbean getaway. Travel to Key West, and you’ll still find that freethinking sensibility today. The city’s location—closer to Cuba than to Miami—results in an eclectic cultural mix. This is a place where people go barefoot, chickens roam the streets, and epitaphs like “Devoted Fan of Julio Iglesias” are found in the cemetery. 


• Watching the sunset (and theatrics) at Mallory Square
• Seeing the cats and literary relics at Ernest Hemingway Home and Museum
• Exploring the Eco-Discovery Center
• Seeing the underwater life while snorkeling, or taking a dolphin or glass-bottom boat tour
• Catching a cabaret drag show at La Te Da
• Eating an authentic slice of key lime pie
• Taking a day trip, by boat or seaplane, to Dry Tortugas National Park


Hyatt Key West Resort & Marina

601 Front St., Key West, FL 33040

Designed to resemble a large plantation-style home, this resort has 118 rooms, each with tiled-entry foyers and private balconies providing at least partial ocean view. The open-air piazza overlooking the Gulf of Mexico has a heated outdoor pool, whirlpool, and access to the hotel docks with jet skis and other watersports. Decorations include brightly-colored, tropical print upholstery and pillows, wooden lounge chairs, and oversized bath fixtures like a large tiled shower. 

Gardens Hotel

526 Angela St., Key West, FL 33040 

Something between a classic B&B and a modern boutique hotel, the Gardens Hotel, an 1870 plantation-style mansion-turned-luxury accommodation in the heart of Key West. The hotel offers orchid-filled gardens, fountains, and winding brick walkways.

Florida Miami Roadtrip Randomwaterbeats Travel Guide
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Florida Miami Roadtrip Travel Guide Randomwaterbeats
© Randomwaterbeats

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