Take a Florida Keys road trip

The Florida Keys dribble down from Mainland Florida with the laziness you might expect from someone pouring out the last dregs of their rum bottle. Starting from Miami, you can pick up a hire car, in partnership with Avis, and drive down the Keys in less than a day. Just use the States’ famous Highway One. The road strings the most important islands together like a tropical necklace – and, with 42 bridges, it doesn’t spend much time on solid ground. Instead, you’ll cruise over warm cerulean waters, past reefs, mangroves, motley locals and many perfect sunsets.

The drive looks short, but there’s no need to rush when you’re on ‘island time’. Besides, it’s better to savour your journey, breaking it up into smaller hauls over a couple of days. This will give you the time to admire the impressive span of Seven Mile Bridge or snorkel over dramatic Elkhorn Coral in the Florida Reef.

Your drive down will keep getting weirder and weirder the further you go. It starts innocently enough, when you see houses with mailboxes shaped like manatees. Next you’ll spot signs to an underwater music festival at Pine Key, starring ‘Paul McCarpney’. Soon you’ll pass cars covered in shells and dogs wearing life jackets. Keep going and you’ll eventually wash up at famous Key West, home to a host of lost souls and Hemingway fans. The LGBTQ community is hopping here, too.

Key Largo is many people’s first port of call on the Keys, and it shows. It’s busy, built up and touristy to the hilt. However, there are quiet spots if you go looking for them and fine snorkelling, too. John Pennekamp Coral Reef State Park makes up for Key Largo’s commercialisation: it contains the only coral reef in the continental United States and you can spend the day in a glass bottomed boat watching coral scroll past under your feet.

Ocean Pointe Suites has a selection of roomy waterfront suites in a pleasant Key Largo complex. Active types: strike out from here on a visit the Everglades or, after a walk along the private beach, hang out at the tennis court and play a few friendly games.

Make for Mrs. Mac’s Kitchen for a menu as long as the Overseas Highway. Mrs. Mac’s Kitchen is hokey, homely and holiday-ready, and (a case in point) has its own souvenir shop.

For a drink, sit out back at Gilbert’s Tiki Bar and hum along with visiting live bands. This joint does plenty of passing trade with motorists coming off the Overseas Highway for their first stop along the Keys.

There’s an underwater national park on your doorstep in Key Largo, named after a do-gooder newspaper editor from Miami. When you snorkel in John Pennekamp Coral Reef State Park, you’ll find a peculiar sight: an eight-foot tall bronze statue of Christ submerged underwater, his hands raised in supplication to passing swimmers. Don’t try and lift him out, though; he was placed here deliberately. Visiting the Everglades from Key Largo is easy, too, since the mainland national park is only 40 minutes away by car. Look out for crocs as you tread the easy boardwalked Anhinga Trail.

Islamorada is found just after Key Largo in the upper Keys. Islamorada is found just after Key Largo in the upper Keys. Make a stop in the ‘village of islands’ and bask on the blissful beaches and take a dip in the tropical waters.

If you’ve dismissed the Keys as far too kitsch, Casa Morada will make you do a double take. This adults-only, all-suite property is all class. Guests can enjoy their own warren of cool, calm rooms. Some suites have outdoor showers. To make up for the lack of beach, a freshwater pool and its all-important poolside bar entertain on their own mini-key.

Enjoy a pint of ale flavoured with local hibiscus flowers at the Florida Keys Brewing Company – the only micro-brewery on the Keys. When dinnertime rolls around you’ll need more than beer. You’ll find fresh seafood on every good menu in the area. Try juicy coconut shrimp or whole fish fry.

Join a guided boat tour and cruise across the turquoise ocean, or perhaps rent your own boat for a day out on the open waters. Remember to take some snorkelling gear and take a dip in the glistening sea – keep your eyes peeled for natural wildlife wonders.

In the middle of the Keys, totally tropical Duck Key makes for a quiet stop on your southbound journey. Take a breather on this tranquil island. With sandy beaches, gorgeous reefs and an abundance of seafood, you can truly unwind.

Hawks Cay Resort dominates Duck Key. This large, family-friendly property offers plenty of activities, including kids’ clubs, water sports and fishing charters. Once you're back ashore, leisurely explore the 60-acre property, dividing your time between the multiple pools, the spa and the on-site restaurants.

Look out for conch on the menu, a Florida Keys classic. Pronounced ‘konk’, you can eat this shellfish as a fritter (mixed with potato) or as ‘cracked conch’ – whole, chewy pieces deep fried in batter. You’re in for a special treat if you arrive during the area’s Marathon Seafood Festival in March. The weekend event features fresh local seafood in addition to live music and craft stalls.

If you want to explore the Keys by land, Duck Key is a great starting point. Nearby Marathon Key marks the half-way point on the Keys and runs a popular turtle hospital. Book in to their guided 90-minute ‘education program’ to meet the residents.

A little further on, you’ll reach the famous Seven Mile Bridge. Pack a picnic and enjoy lunch on the gorgeous beach in Bahia Honda State Park, overlooking the current bridge’s crumbling predecessor. Next up, you’ll reach the less-developed Big Pine Key, where you may spot tiny Key deer in the local refuge. Keep your eyes peeled and keep them low: this gentle animal is only 26 inches tall at the shoulder.

Ditch your car, the road runs out here. In Key West you can get to the beaches, the bars, and the island’s cluster of curious sights on foot or by bike. This punchline at the end of the Florida Keys is one of the strangest cities in the States. While you may spy nudity or hear far-fetched stories from drunken sailors, there’s no need for alarm: the Key West community is famously gentle and safe. If you feel out of place, there’s only one thing for it: join in.

The Southernmost Resort really is at the bottom of America. It’s a historic hotel on the seafront in the heart of Key West, with three pools and two beaches available for all your dipping and lounging needs.

Enjoy seaport dining at busy Turtle Kraals. Make sure you order a Cuban sandwich as soon as lunchtime rolls around. Afterwards, take to the bars of Duval Street. This sticky tourist trap will likely lure you in with live tunes, and soon you’ll be cheerily bouncing from one bar to the next – look out for Sloppy Joes and ‘Margaritaville’. You may even come across the rooftop nudist bar. Alternatively, head to Papa’s Pilar. Don’t let its 1870s frontage fool you; this is one of the world’s newest luxury rum distilleries.Guided tours on the hour begin at 11.00 am for ten bucks.

You aren’t the first people to discover the charms of Key West. There’s a new Tennessee Williams Museum on the island dedicated to the playwright, who was a long-standing fan of the Keys. If you prefer the stylings of Harry Truman, visit his ‘little White House’ on Front Street. Hemingway fans should embark on an amusing tour of his Key West home, where you’ll come toe-to-paw with its resident six-toed cats.

Resurface in time for the daily sunset celebration on Mallory Square with street performers and fortune tellers. (‘I see… I see… many more sunsets to come’.) There are more outlandish celebrations during the islands’ ten-day Fantasy Fest in October. However, if you’d rather not discover what this ‘fantasy’ entails, retreat to Smather’s Beach: it's one of the best in Florida.