Best of Florida Road Trip  

500 miles of sunshine

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.

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Orlando, Naples, Miami, Key West

Ideal for
Pairing Orlando with Florida’s amazing beaches and scenic diversity.

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Best of Florida Road Trip

From £1,395 per person

  • tick11 nights
  • tickBoard Basis - Room Only
  • tickFly with Virgin Atlantic from London Heathrow
  • tick3-4* accommodation for 4 nights Orlando
  • tick2 nights Naples Beach
  • tick3 nights Miami
  • tick2 nights Key West
  • tick11 days intermediate car rental
  • tickBased on selected September 2024 departures

Recommended itinerary


Full on fun

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.

What to do in Orlando

Thrills, then chill?

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?

Where to stay in Orlando

Choose a convenient base

If most of your time will be spent in the Disney parks, Walt Disney World Swan Resort is a great option – you can walk to Disney’s Hollywood Studios and EPCOT. If you’d rather base yourself near Universal Studios, you’re spoilt for choice, with the Hard Rock Hotel, Aventura, Loews Royal Pacific Resort, Universal Cabana Bay, and Lowes Sapphire Fall Resorts all in the area.


Drive to Naples

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.

What to do in Naples

Unwind on sandy shores

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.

Where to stay in Naples

Fifth Avenue boltholes

Decide between Hyatt House Naples, a waterfront hotel with suites where families can enjoy some extra space and the convenience of a kitchen. Inn on Fifth has a more luxurious feel, and there’s a rooftop pool and full-service spa here.


Drive east

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.

What to do in Miami

Get swept up in the city’s energy

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.

Where to stay in Miami

Choose a South Beach resort

Stay in the heart of the action and opt for a contemporary hotel on South Beach – we highly recommend 1 Hotel South Beach. Families will love the pools and activities available at the Fontainebleau, whereas couples may be drawn to the elegantly tropical surroundings of The Betsy at the quiet end of Ocean Drive.

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.

What to do in Key West

Snorkelling, fishing, and diving

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.

Where to stay in Key West

A hotel with a sea view

Check-in somewhere suitably beachy for your final stop in Florida. At Ocean Key Resort & Spa, the pool overlooks the sea, or try The Reach Key West, set on the only private natural sand beach in Key West.

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.