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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
It’s never been a better time to head south for an East Coast road trip from Orlando to the tip of Key West. Florida’s beautiful sites — and legendary sunshine — light the way for a holiday filled with fun, relaxation and pampering. Here are a few reasons to plan your own road trip from Orlando:
  • Family-friendly fun: Give the kids something to remember at the country’s most iconic parks and white sand beaches. These memories serve as the best souvenirs.
  • Exclusive experiences: Savor the locally inspired itineraries thoughtfully planned just for you, all against the backdrop of Florida’s beloved palm trees and blue skies.
  • Relax in luxury: The state’s laid-back pace and five-star accommodations mean that you can balance the excitement of your trip with ample rest (and lush indulgence) along the way.

Beat the Crowds 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. When you think of the city, your mind no doubt jumps to the theme parks that help bring the magic of everyone’s favorite films and characters to life.

Waldorf Astoria Orlando

Experience an ambiance of stylish sophistication with celebrated amenities and impeccable personalized service.
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Start your trip off with first-class accommodations and service at Waldorf Astoria Orlando, where your personal concierge will ensure that your every need is met. With easy proximity to Walt Disney World, you can plan ahead with the concierge, giving you access to the best attractions. The Team Members at Waldorf Astoria Orlando expertly help guests plan hassle-free visits to the parks and make the most of their time in sunny Orlando, from complimentary transportation to Walt Disney World to private cabanas by the pool. When you need a break from the parks, 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 trip to 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. Walk over to Rifle Paper Co. (558 W New England Ave, No. 150), an Orlando-based stationery brand, for authentic items to bring home with you before dining al fresco at award-winning restaurant Prato (124 N Park Ave).

See Fort Lauderdale by Boat

A three-hour drive from Orlando brings you to the blue umbrellas and balmy sea breezes of Fort Lauderdale. The “Venice of America,” this city boasts waterfront as far as the eye can see with 300 miles of canals and 24 miles of beaches.

Conrad Fort Lauderdale

Just steps from North Beach, experience five dining options, pool with private cabanas, Conrad Spa, and fitness center with professional trainers.
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Make a reservation at Conrad Fort Lauderdale, which stands overlooking the Atlantic Ocean with panoramic views and unparalleled access to one of the city’s most beautiful stretches of beach. Begin your day with a sunrise paddle boarding 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.
After you valet your car at arrival, give yourself a break from your road trip from Orlando and embrace an alternative mode of transportation. Here, boats are the go-to mode of transportation. 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 Downtown Miami

In under an hour 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, is famous for its Art Deco architecture, downtown Miami has its own cultural legacy to behold.
The stunning Vizcaya Museum & Gardens (3251 S Miami Ave), 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 Doce Provisions (541 SW 12th Ave) in Little Havana, where you can dine on chorizo croquettes and shrimp enchilado — all handmade with local ingredients — at picnic tables in a tucked-away tropical garden.

Embrace Adventure in Key West

The Key West road trip along Route 1 is one of the most spectacular in the country. After you drive over the Southern Glades, which are part of Everglades National Park, you hit Key Largo and make your way along the string of breathtaking islands that lead you to Key West. Rather than hustle to your destination, turn up the car radio and enjoy the ride, particularly when you drive over the famed Seven Mile historic bridge.

Casa Marina Key West, A Waldorf Astoria Resort

Home to Key West’s largest private beach, two outdoor pools, and a spa. Duval Street and The Ernest Hemingway Home and Museum are a mile away.
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Casa Marina Key West, A Waldorf Astoria Resort welcomes you to an iconic property that’s on the National Register of Historic Places in Key West. Unlike other luxury properties, this gem is tucked away along the Atlantic Ocean, where guests benefit from spectacular views and a peaceful ambiance that’s missing in the heart of town. The resort’s private beach and two heated swimming pools are a slice of paradise for guests. If you’re traveling without children, you can enjoy the calm oasis of the adults-only pool with a cocktail in hand.
The hotel’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 dining at a white-tableclothed table on the sand at Latitudes. On an island and accessible only by boat, the restaurant is a beautiful location to feast on grilled lobster tails and rum cocktails while the sun sets.
If you’re still yearning for more adventure, arrange a ferry trip to Dry Tortugas National Park, off the coast of Key West. Bring some snorkels because the reefs are spectacular here at one of the most underrated national parks.

Make Your Florida Road Trip Memory

When you buckle up for an East Coast road trip through Florida, you’ll experience an authentic mix of adventure, culture, nature and delectable dishes that takes 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.
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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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