Inspiration for your own tailor-made trip

Florida Road Trip Miami, Key West and Naples

United States - Florida - Miami - The Keys

Starting from between £3,295 to £4,555 per person for 11 days depending on the season of travel, advance booking time and the accommodation and activities chosen

Itinerary Highlights

  • Tour star-studded Miami with a local guide
  • Set off in a luxury hire car and road trip along the beautiful Florida Keys
  • Discover the charming city of Naples with a sailing cruise or airboat safari
  • Keep the beach theme going with South Beach, Key West and the Gulf of Mexico
Take the road less travelled on this epic Florida road trip. Discover the best the state has to offer, away from the hustle and bustle of amusement parks: we’re talking drives framed with pristine sandy beaches and lots of sun, with plenty of tasty local restaurants and trendy Art Deco districts thrown in for good measure.

Your 11-day road trip begins with a stay in Miami’s chic South Beach, before you head south to explore the iconic Florida Keys. Perfect for nature lovers, foodies and culture vultures alike, there’s never a dull moment here: beach enthusiasts can wade through the Gulf of Mexico, while water babies can enjoy a diving adventure in Key Largo. Experience unforgettable airboat rides in the Everglades, renowned bars and restaurants in Key West and wildlife watching in Naples – what better way to discover the ‘Sunshine State’?
Miami Beach - Florida - United States © Tono Balaguer/stock.adobe.com
Miami Beach - Florida - United States © Tono Balaguer/stock.adobe.com
House in Florida - United States © Droits reservés
House in Florida - United States © Droits reservés
Key Largo - Florida - United States © Randy Harris/REDUX-REA
Key Largo - Florida - United States © Randy Harris/REDUX-REA
Florida - United States © Albo/stock.adobe.com
Florida - United States © Albo/stock.adobe.com
Key West - Florida - United States © Droits reservés
Key West - Florida - United States © Droits reservés
Miami Beach - Florida - United States © Gabriel Pevide/Getty Images/iStockphoto
Miami Beach - Florida - United States © Gabriel Pevide/Getty Images/iStockphoto
Florida - United States © Droits reservés
Florida - United States © Droits reservés
Miami Beach - Florida - United States © Filippo Bacci/Getty Images
Miami Beach - Florida - United States © Filippo Bacci/Getty Images
Naples - Florida - United States © Nikolay Tzolov/Getty Images/iStockphoto
Naples - Florida - United States © Nikolay Tzolov/Getty Images/iStockphoto
Miami - Florida - United States © Gabriele Maltinti/iStock/Getty Images Plus
Miami - Florida - United States © Gabriele Maltinti/iStock/Getty Images Plus
Miami Beach - Florida - United States © Getty Images/iStockphoto
Miami Beach - Florida - United States © Getty Images/iStockphoto

Itinerary

100% customisable for you

Make sure alarms are set and bags are packed, because your Florida road trip begins today with an early morning flight to Miami. Head to the airport, whizz through security and enjoy a coffee in the lounge before boarding your ten-hour flight, which lands in Miami at midday.

Once you touchdown, hop in a private transfer to your hotel. You have four nights in this star-studded southern Florida city, so for today, unpack, relax and ready yourself for the exploration ahead. Or, if you’re raring to go, we can recommend the best places to wine and dine the night away. What better way to kickstart your holiday?

The spirited city of Miami boasts buckets of sun, sea and culture. Over the next three days, discover a labyrinth of trendy bars and restaurants set against a backdrop of pristine coastline and warm lapping waves.

To help you get your bearings, start your Miami adventure with a private tour. Spend the morning getting to know the city’s iconic beach neighbourhoods with a local guide, from the glitz and glamour of Ocean Drive to the culture and community of Spanish Village, complete with tapas and Mediterranean-style architecture.

Once you’ve found your feet, the next few days are yours for the taking. Overheating in the sun? Head to one of the many postcard-perfect beaches or the iconic Venetian Pool in Coral Gables to cool off in the sparkling water. Once you’ve worked up an appetite, venture to a local restaurant – there are plenty of mouth-watering spots for foodies, and our clued-up Concierge is on hand to share some hidden gems.

After a few days of touring and tanning in Miami, it’s time to collect your hire car and begin your Florida road trip. Today it’s onto Duck Key, a two-and-a-quarter-hour drive south that skirts Biscayne Bay and crosses the southern tip of the Everglades. Along the way, stop in Key Largo, best known for its John Pennekamp Coral Reef State Park – a snorkeller’s paradise.

Once you’ve soaked in Key Largo’s beauty, set off on the legendary Overseas Highway. This concrete stretch ricochets from island to island, offering dolphin spotting as far as Islamorada (cameras at the ready!). After driving through Layton, arrive at Duck Key and its marina, where you’ll hang your hat for the night.

Today, head down to Key West, a city whose Eden-esque beauty has long inspired famous writers like Ernest Hemingway and Tennessee Williams. Nowadays, this paradise between land and sea is home to plenty of bars and cafes that have retained a historic charm.

Head to Sloppy Joe's Bar, where Hemingway frequently enjoyed a rum daiquiri, and the terrace of La Concha Hotel, where Williams sipped perfectly-crafted cocktails while writing A Streetcar Named Desire. Spend the evening chasing the setting sun at Mallory Square’s nightly Sunset Celebration, or take to the waters and enjoy drinks on board a sunset cruise.

It's time to hit the road again today, so drive two hours back towards the mainland to the fishing mecca of the Keys, Islamorada. This coral archipelago comprises six islands and is one of the last coral reefs in the Straits of Florida, so it’s the perfect place for diving enthusiasts. If you’re a non-diver, don’t worry – you can still enjoy the waters on a fishing trip, or stay on land and walk through the botanical gardens. Once you’ve worked up an appetite, sample some fresh seafood specialities in a rustic quayside café, before settling in for the night.

Today, it’s time to say goodbye to Islamorada and hop back in the car for a three-hour drive towards Naples (no, not the Italian one), a sun-soaked city on the Gulf of Mexico. Once you arrive, we’ve arranged a private tour of the Everglades by airboat, so spend an action-packed hour with a local guide discovering these scenic wetlands. Crisscross through the park and get up close and personal with the incredible wildlife, including some skulking alligators…

It’s your final day in Florida, so it’s up to you how you spend it, whether you’d rather explore Naples’ beautiful beach and pier, wander through the old town’s trendy galleries and boutiques or leave the bustling centre behind completely. Those in search of secluded serenity can explore one of many nature reserves, where vast mangroves, swampy plains and walks down wooded paths await.

Fancy yourself an animal aficionado? Take a boat trip to Naples Bay in search of manatees. Thanks to dedicated conservation programmes, an estimated 7,000 to 11,000 of these 'sea cows' live in the warm waters of Florida, so keep your eyes peeled. End your evening with a tasty dinner and drink at a local restaurant, reminiscing on a road trip well spent.

Sadly, it’s time to head home today. There are two possible routes to take towards Miami, so it’s your choice for the final drive of your road trip – you can’t go wrong.

The first route is two hours and runs horizontally to the east of the Florida peninsula, heading towards Fort Lauderdale, a small ‘American Venice’. The second is 20 minutes longer, but 12 miles shorter – it follows the famous Tamiami Trail, running through the Big Cypress National Preserve and the Everglades, before arriving in the heart of Miami.

Once you’ve made the scenic journey, it’s time to return your hire car to the airport and head to the lounge for one last holiday tipple. It’s an overnight flight home, so you’ll arrive in the UK the next day, ready to research your next epic road trip.

Suggestions

Everything in this itinerary is entirely customisable, down to the smallest details. Here are some more suggestions of what could be included

ZODIAC BOAT TRIP IN MIAMI BAY

Head offshore to discover Biscayne Bay, a haven for nature lovers and diving enthusiasts. This two-hour boat tour takes you to some of the bay’s most beautiful coastal landscapes aboard a speedy Zodiac boat. While you’re gliding through the water, your guide will let you in on the history of Miami's monuments and landmarks that can be seen from the decks. This tour offers a beautiful glimpse of Miami and its coast, allowing you to discover the lesser-known places in the bay and delve into its rich history.

Optional



BOATING OFF THE NAPLES COAST

Fancy more coastal cruising? Head out on a private boat trip to discover Naples Bay’s beautiful scenery and resident manatees. Thanks to incredible conservation efforts, the number of these 'sea cows' living in Florida’s waters has increased from 2,000 to an estimated 7,000 to 11,000 – so it’s even more special when you glimpse this recently-restored population. These huge marine mammals are entirely harmless, approachable and present in large numbers in the Naples region.

Optional add-on

Why visit USA with Original Travel ?

Each of our trips is entirely tailor-made with originality, quality and cultural immersion in mind. Our team of destination specialists will craft itineraries based on your tastes, using their first-hand knowledge and the help of our in-country team of Concierges and guides. All trips are accompanied by a wide range of additional services, including a 24-hour helpline, the Original Travel app, fast-track airport services and much more.

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A few of the benefits of travelling with us to USA

  • Our local Concierges
  • The Original Travel app
  • Airport lounge access
  • Wi-Fi router and e-Sim
  • Destination Dossier
  • 24-hour helpline
  • Expert guides
  • 100% carbon absorption

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Estimated Price

Dependent on the season of travel, advance booking time and the accommodation and activities chosen

The prices shown here are merely a guide, as all of our trips are entirely tailor-made. Tailor-made travel involves multiple moving parts, and prices can vary hugely depending on the season of travel, the lead time before the proposed travel date (last minute deals are pretty much a myth), availability, your choice of accommodation and any additional activities you want to include. That means the only exact price will be the one we quote you, which we can adapt to suit your budget. The estimated starting cost for this trip is between £3,295 and £4,555 per person. The average starting price for this trip is £4,020 per person.
Included in this itinerary

  • International flights with a scheduled airline
  • Airline taxes and fuel surcharge
  • Airport/hotel private transfer on arrival in Miami
  • A convertible hire car for seven days
  • Three-night stay in Miami in double room (accommodation only)
  • Two-night stay in Key West in double suite (accommodation only)
  • Overnight stay in Islamorada in a garden suite (accommodation only)
  • Two-night stay in Naples in double room (accommodation only)
  • Two half-days with a Miami local, to discover the iconic neighbourhoods of Miami Beach and Wynwood
  • A sailboat and sunset cruise to Key West with wine and beer on board
  • A one-hour private airboat safari in the Everglades
  • Our local Concierge service

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