Plan a lavish East Coast road trip from Orlando to Key West
Indulge in a sophisticated East Coast road trip by exploring Florida’s most enchanting experiences in style, starting in Orlando and ending in Key West.
By Elizabeth Wellington | June 25, 2021 (Updated March 26, 2026)
There's never been a better time to take a scenic drive and head south for an East Coast road trip from Orlando to Fort Lauderdale, Miami, and the Florida Keys. Florida’s stunning beaches, lush mangroves, and legendary sunshine light the way for a vacation filled with fun, relaxation, and pampering.
In this article: Best places in Florida to visit on an East Coast road trip
Take a drive to sunny Fort Lauderdale
Make a splash in Orlando
As one of the most popular tourist destinations in the world, Orlando is the ideal launching point for a road trip in the U.S. Start your vacation off by skipping the airport baggage claim. Drive to Waldorf Astoria Orlando and experience first-class accommodations and service, as well as a personal concierge to ensure that your every need is met. With easy proximity to theme parks, you can plan ahead with the concierge for easy access to the best attractions. Relish in resort-style swimming pools with private cabanas, or have the littles ones enjoy the Kids Club, while you relax in the award-winning Waldorf Astoria Spa. Walk over to play a round of golf at Waldorf Astoria Golf Club, a stunning golf course within the Bonnet Creek nature preserve. During your time in Orlando, don’t miss the charming college town outside city limits. Winter Park, home to Rollins College, charms visitors with brick-laden streets and some of the area’s best restaurants. Visit Rifle Paper Co., an Orlando-based stationery brand, for authentic items to bring home with you before returning to your resort for dinner at Bull & Bear.
Take a drive to sunny Fort Lauderdale
A three-hour drive from Orlando brings you to the blue umbrellas and balmy beachside breezes of Fort Lauderdale. The “Venice of America,” this city boasts waterfront as far as the eye can see, with 300 miles (482.8 kilometers) of canals and 24 miles (38.6 kilometers) of beaches. Stay at Conrad Fort Lauderdale Beach, which overlooks the Atlantic Ocean with panoramic views and unparalleled access to one of the destination’s most beautiful stretches of beach. Just steps from North Beach, experience five dining options, a pool with private cabanas, Conrad Spa, and a fitness center with professional trainers. Begin your day with a sunrise paddleboarding tour and a yoga class, all before enjoying a green juice at Cornucopia, the hotel’s in-house market. In the late afternoon, head up to the sixth-floor sky deck for a fun game of cornhole with the ocean as your backdrop. Book a private water taxi to take through the canals to a seaside restaurant or charter a yacht for the evening to toast on the open water.
Experience local culture in Miami
In just under an hour’s drive from Fort Lauderdale, you’ll be weaving through Miami’s bustling streets, preferably in a vintage convertible with the top down. Although South Beach, which sits on an island off the coast about a 45-minute drive from Miami Beach, is famous for its Art Deco architecture, downtown Miami has its own cultural legacy to behold. The stunning Vizcaya Museum & Gardens, the crown jewel of Miami, is always worth a visit. Wander through a 50-acre paradise of botanical gardens and learn about priceless art in a stately villa. Next, head to lunch at Miami's Doce Provisions in Little Havana, where you can dine on chorizo croquettes and ahi tuna tacos — all handmade with local ingredients — at picnic tables in a tucked-away tropical garden before heading back to South Beach for a later afternoon stroll along the Miami Beach Boardwalk.
Embrace adventure in Key West
After you visit Miami, drive along Route 1 to Key West — it's one of the most scenic drives in the country. After you pass over the Southern Glades, which are part of Everglades National Park, you hit Key Largo and make your way along the string of islands that lead you to Key West. Rather than hustle to your Florida Keys destination, turn up the car radio and enjoy the ride, particularly when you drive over the famed Seven Mile Bridge. Travel to Casa Marina Key West, Curio Collection by Hilton to stay at an iconic resort that’s on the National Register of Historic Places in Key West. Tucked away between the Atlantic Ocean and the Gulf of Mexico, guests benefit from spectacular views and a peaceful ambiance that’s missing in the heart of town. The resort’s private beach and two oceanfront heated swimming pools are a slice of paradise. If you’re traveling without children, enjoy the calm oasis of the adults-only pool with a cocktail in hand. The resort’s legacy as a glamorous getaway in the 1920s is a fitting jumping-off point for exploring the country’s southernmost city, which is known for its culture. Take a literary walking tour and visit the Ernest Hemingway Home & Museum before experiencing fine dining sand-side at Dorada. Yearning for more adventure? Arrange a ferry trip to Dry Tortugas National Park, off the coast of Key West. Bring some snorkeling gear because the reefs are spectacular here at one of the most underrated national parks.
Road trip to Key West
When you avoid the airport and buckle up for road trips through Florida, you’ll experience an authentic mix of adventure, culture, nature, and delectable dishes that take you to the end of the road in Key West. Keep this road trip planner handy when you plot your summer vacation and be open to the spontaneous detours that may lead you somewhere unexpected.
Elizabeth Wellington is a travel writer and brand copywriter whose work has appeared in Vogue, Condé Nast Traveler, Travel & Leisure and BBC. When not writing in her Vermont farmhouse, she's usually en route to a new destination with a notebook in hand.
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