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Best of Florida Road Trip
A four-stop road trip that takes you to all the must-see locations across the Sunshine State
Start with a whirlwind time in Orlando, then leave the frivolities behind as you search out Florida’s finest East Coast beaches and the endlessly fascinating Everglades before arriving in Miami. Sip Cuban coffee and mojitos and soak up the beach scene of this scintillating city before driving one of the world’s most famous routes — the 42 bridges that make up the incredible Overseas Highway all the way to the USA’s most southerly point at Key West.
Ideal for
Pairing Orlando with Florida’s amazing beaches and scenic diversity.
Current offers
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Best of Florida Road Trip
From £1,575 per person
11 nights- Board Basis Room Only (unless specified)
- 4 nights Embassy Suites by Hilton Orlando Sunset Walk - Kissimmee (Room & Breakfast)
- 2 night Hyatt House Naples/5th Avenue - Naples
- 3 nights The Gates Hotel South Beach - Miami
- 2 nights The Reach - Key West
- 11 days economy car rental
- Fly with Virgin Atlantic from London Heathrow
- Flights available from other UK airports - contact us for details
- Based on selected September 2025 departures
Itinerary overview
Orlando
Thrills, then chill?
You’ll start in Orlando, ready to take on the incredible theme parks. Whether you want to experie...
Naples
Unwind on sandy shores
You’ll collect your hire car and hit the road, heading south to Naples on Florida’s southwest coa...
Miami
Get swept up in the city’s energy
Take the 130-mile drive to Florida’s east coast. The journey takes you directly through Big Cypre...
Key West
The southernmost point of the USA
Driving from Miami all the way to Key West is an incredible day on your holiday. It’s a four-hour...
Set sail
Add a cruise to your holiday
Miami is the largest and busiest cruise ports in the USA, with ships leaving for the islands of t...
Orlando
Thrills, then chill?
You’ll start in Orlando, ready to take on the incredible theme parks. Whether you want to experience the sheer magic of Walt Disney World’s four parks or dive into Universal Orlando to meet the Minions and take an adventure to the Wizarding World of Harry Potter, make sure you allow enough time to experience it all. Hit the parks, but linger longer to relax by the pool in your hotel, allow enough for a round or two of golf on the region’s pristine courses, or head to the outlet malls to pick up some bargains?
Recommended Hotel
Rosen Plaza Hotel
Rosen Plaza Hotel is centrally located on International Drive, the main thoroughfare running through Orlando.
Naples
Unwind on sandy shores
You’ll collect your hire car and hit the road, heading south to Naples on Florida’s southwest coast. It’s a good idea to head west to Tampa, then drive down the West Coast, perhaps calling at Sarasota and pausing at sugar-white beaches. The drive alone will take around four hours, but you’ll want to plan a whole day for the journey to allow for stopping along the way. Stroll along Naples’ 1888 pier, shop for trinkets in little boutiques on Fifth Avenue, and find a bayside bar for drinks with a sunset view. The white sands of the Gulf Coast will likely prove irresistible during your time here.
Recommended Hotel
Hyatt House Naples 5th Avenue
Set in downtown Naples, this waterfront hotel features spacious suites with kitchens, and a leisurely lagoon-style pool.
Miami
Get swept up in the city’s energy
Take the 130-mile drive to Florida’s east coast. The journey takes you directly through Big Cypress National Preserve and the Everglades. Pause and take an airboat adventure through the water, or continue straight to Miami, where glamour awaits. Miami is a sultry, sub-tropical beauty fringed by swathes of beach, infused with a vibrant arts scene, spiced up with Hispanic heritage, and crowned by Art Deco elegance. Hang out with the hip crowds in Wynwood, catch the aroma of Cuban coffee in Little Havana, browse endless galleries and shops, and sip cocktails on a rooftop over lively Ocean Drive.
Recommended Hotel
Key West
The southernmost point of the USA
Driving from Miami all the way to Key West is an incredible day on your holiday. It’s a four-hour drive without stops, so plan to set off early. Along the way, there are clear waters and beaches to admire, plus you get to cross the remarkable Overseas Highway, a 113-mile road linking the Florida Keys. Key West blends tropical beauty, rich history, and a lively atmosphere. Take a sunset sail, visit Ernest Hemingway's house, or see the southernmost point marker of the United States. After a day of adventure, relax with a slice of the local key lime pie and an icy drink while watching the sunset over the Gulf of Mexico.
Recommended Hotel
The Perry Hotel Key West
This award-winning hotel’s peaceful home on Stock Island keeps it removed from the rowdiest Key West crowds.
Set sail
Add a cruise to your holiday
Miami is the largest and busiest cruise ports in the USA, with ships leaving for the islands of the Caribbean, the shores of South America and beyond. It's easy to add a voyage to the end of your self-drive; a couple of our cruise partners that feature round-trips from here (or 30 miles up the I-95 in Fort Lauderdale) include luxe line Celebrity Cruises, and Royal Caribbean International with its facility packed ships that are a real favourite with families.
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