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Driving The Florida Keys

Stretching in a graceful arc from mainland Florida south-west into the Gulf of Mexico, the Florida Keys are connected by the legendary 113-mile-long Overseas Highway, the stage for this laidback 11-day road trip from Art Deco Miami to the sun-and-sand playground of Key West, the southernmost point of the continental United States.

Number of days Prices from The itinerary includes

11

10 nights / 11 days from £2,650.

Prices are per person based on two people sharing standard rooms on room only basis plus economy flights from London.

  • Itinerary Starts In Miami & Ends In Key West
  • Compact car hire with insurance.
  • Hotel accommodation as detailed
  • Day 1

    Miami

    Arrive at Miami Airport, collect your hire car and make your way to Fontainebleau Miami Beach. The epitome of mid-century Miami glamour, the hotel reopened in 2008 after a $1 billion restoration and boasts nine different restaurants, 11 distinctive pools and one of the finest spas in town – perfect for recovering from the flight across the pond.

  • Days 2-4

    Islamorada

    One of the greatest pleasures of holidaying in the Florida Keys is driving the Overseas Highway, a modern marvel of concrete and steel that connects the Keys through a series of 42 ocean-skimming bridges. Some are so long there are moments you can neither see land ahead of you nor behind you, creating the surreal sensation that you’re driving across the ocean.

    The key to enjoying the drive is to take your time, stopping where and when you want to soak up the ever-changing land- and seascapes and get to know the communities that call the Keys home. You may well want to stop in Key Largo, the northernmost of the Keys and around an hour from Miami. It’s especially popular among divers and snorkellers, who come to explore coral-encrusted shipwrecks and see the sunken bronze statue, Christ of the Abyss.

    After Key Largo you’ll reach Islamorada and Cheeca Lodge & Spa, where you’ll stay for the next three nights. The hotel boasts a gorgeous stretch of sandy beach as well as three heated pools, a nine-hole golf course and the longest pier in the Florida Keys. Islamorada is known as the sport-fishing capital of the world and you’ll find expert fishing guides ready to lead you across the backcountry’s shallow flats for bonefish, snook and tarpon, or out into the deep blue for grouper and giant tuna. If angling’s not your thing, there are also wonderful opportunities for paddleboarding, kiteboarding, tennis, cycling, shopping and fine dining.

  • Days 5-7

    Duck Key

    Next is a three-night stay at the tropical Hawks Cay Resort on the small, secluded island of Duck Key. A haven of tranquillity fronted by a glorious natural lagoon, the hotel offers numerous chances to get out on the water to enjoy boating, swimming, snorkelling and other watersports. Should you wish to explore beyond the hotel, nearby Marathon’s Dolphin Research Center and Turtle Hospital are both great examples of the many conservation projects, animal rehabilitation centres and wildlife refuges found throughout the Keys. Also worth a visit is the museum on Pigeon Key, which depicts the life of the men who built the original Overseas Railroad from Miami to Key West at the turn of the 20th century – a remarkable achievement orchestrated by millionaire industrialist Henry Flagler.