Florida Keys Road Trip • Miami To Key West • Key Largo & More
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Overseas Highway, Florida Keys
South Beach Miami
Miami Beach Lifeguard Towers
Aerial view of Miami Beach
John Pennekamp Coral Reef State Park, Key Largo, Florida Keys
Beach front, Dove Creek Resort & Marina, Key Largo, Florida
Overseas Highway, Florida Keys, USA
Florida Keys
Key West, Florida Keys
Dry Tortugas National Park, Florida Keys
Islamorada, Florida Keys
Islamorada Sandbar, Florida Keys
Aerial view La Siesta Resort, Islamorada, Flordia
Ocean Drive, South Beach. Miami, Florida

Florida Keys Road Trip

11 day Fly Drive – from £1425

With flights from £2045

Experience the dynamic energy of Miami, before sampling the little slice of paradise that is the idyllic Florida Keys. Enjoy stunning beaches and coral reefs, exhilarating watersports, a vibrant food and drink scene and interesting history on an all-encompassing road trip across the Overseas Highway.

Highlights:
  • Tour the urban artwork at Miami’s Wynwood Walls
  • Wildlife encounters including dolphins, turtles and Lower Keys native deer
  • Enjoy a magical sunset, music and entertainment at Key West’s Mallory Square
  • Visit Islamorada Sandbar for a buzzing atmosphere and 360° views of the Keys

Your Itinerary

Expand All

You can customise your Florida fly drive by adding extra nights or stops along the way. Just let us know what you would like to do.

South Beach Miami

Day 1 – Welcome to Miami

Touchdown in Miami in the afternoon and collect your car, before making your way your way…

Touchdown in Miami in the afternoon and collect your car, before making your way your way to Miami’s famous South Beach.

Miami is an international city, rich with a multi-ethnic culture which is reflected in the cuisine and architecture. Miami’s South Beach is a particularly stunning: swaying palm trees, and the waves washing ashore act as a backdrop for pastel-coloured, Art Deco buildings.

    Miami International Airport > South Beach | 11 miles

    Gale South Beach or similar

South Beach Miami
Aerial view of Miami Beach

Day 2 – Explore Miami

On day two, you are free to explore this cosmopolitan city at your leisure. You may…

On day two, you are free to explore this cosmopolitan city at your leisure. You may choose to begin the day with a walk along Ocean Drive and the Miami Beach Boardwalk, or even cross the sands for a dip in the ocean.

Then you could head to Wynwood Walls, Miami’s outdoor street art museum. Stroll through the Wynwood Walls complex to see colourful murals and graffiti art by local and international artists.

You could choose to grab lunch at a Cuban bakery or café in Little Havana. Enjoy traditional Cuban pastries like pastelitos and a café con leche while soaking in the lively atmosphere. Then visit Domino Park to watch locals play dominoes and browse the shops selling Cuban cigars and souvenirs.

In the evening, you can watch the sunset from a beachfront bar or rooftop lounge while sipping cocktails and listening to live music. For dinner, indulge in fresh seafood at a waterfront restaurant overlooking Biscayne Bay or the Miami River. Try local specialties like stone crab claws, ceviche, or grilled fish prepared with Caribbean flavours.

Optional Experience Miami Hop-on Hop-off Bus Tour
This Miami Sightseeing Tour has been specially designed to show the best Miami has to offer. Enjoy it all from the comfort of the open-top buses; hop off wherever you like, then hop back on to continue your journey. You will see all the most interesting and attractive areas: South Beach, Downtown Miami, Coral Gables, Coconut Grove, Little Havana and more.

    Gale South Beach or similar

Aerial view of Miami Beach
John Pennekamp Coral Reef State Park, Key Largo, Florida Keys

Day 3 – Miami to Key Largo

Leave Miami behind and head towards the tropical paradise that is the Keys, cruising the Overseas…

Leave Miami behind and head towards the tropical paradise that is the Keys, cruising the Overseas Highway. Take in the incredible sea views through the network of 42 bridges, towering over the ocean.

As you arrive on Key Largo, spend the afternoon at John Pennekamp Coral Reef State Park, an underwater treasure trove of coral and marine life. The best way to experience the park is by diving right in, with a whole host of watersports on offer. Snorkelling or scuba diving is particularly spectacular, with the chance to spot sea turtles and dolphins amongst the coral. Alternatively, kayak or paddleboard through the mangroves, or you can take a glass-bottom boat tour.

After checking into your hotel, wander into the town to sample some local seafood, before finishing the evening enjoying some live music at Snappers Oceanfront Bar.

    Miami > Key Largo | 76 miles

    Dove Creek Resort or similar

John Pennekamp Coral Reef State Park, Key Largo, Florida Keys
Beach front, Dove Creek Resort & Marina, Key Largo, Florida

Day 4 – Key Largo

Enjoy a relaxed day exploring some of Key Largo’s beautiful beaches. Bring a picnic to Harry…

Enjoy a relaxed day exploring some of Key Largo’s beautiful beaches. Bring a picnic to Harry Harris Beach and Park, spanning 21 acres, and offering a number of facilities. Take advantage of the protected beach and swimming area, picnic tables, BBQs and sports fields.

There are also a number of watersports on offer from Key Largo. Perhaps try your hand at parasailing or jet skiing, or hire a paddle board.

    Dove Creek Resort or similar

Beach front, Dove Creek Resort & Marina, Key Largo, Florida
Overseas Highway, Florida Keys, USA

Day 5 – Key Largo to Marathon

Continue on the Overseas Highway, making your way to Marathon. On the way, stop off at…

Continue on the Overseas Highway, making your way to Marathon. On the way, stop off at the Florida Keys History and Discovery Centre on Islamorada. Learn about the Keys’ rich past, the people, places and events that have shaped its development through interactive exhibits.

Another worthwhile stop is the Dolphin Research Centre, a nonprofit organisation providing vital rescue and rehabilitation work, and educating visitors about these amazing creatures.

Finish the day watching the sun set at a waterfront restaurant.

    Key Largo > Marathon | 41 miles

    Hampton Inn Marathon or similar

Overseas Highway, Florida Keys, USA
Florida Keys

Day 6 – Marathon

Spend your second day on Marathon by exploring one of the most beautiful beaches in the…

Spend your second day on Marathon by exploring one of the most beautiful beaches in the Keys: Sombrero Beach. Relax on its pristine sands, embrace some watersports or even sign up for an Island yoga class, regularly taking place on the beach.

Marathon is also home to the Keys’ Turtle Hospital, carrying out vital conservation work. The hospital regularly carry out public releases of the rehabilitated turtles, as Sombrero Beach is a designated nesting zone.

    Hampton Inn Marathon or similar

Florida Keys
Key West, Florida Keys

Day 7 – Marathon to Key West

Continue your journey to the lowest of the Keys, taking in the views as you cross…

Continue your journey to the lowest of the Keys, taking in the views as you cross the iconic Seven Mile Bridge.

Key West has lots to offer. You may like to climb to the top of the Key West Lighthouse for panoramic views of the island and surrounding waters. Nearby you can also snap a photo at the Southernmost Point Buoy, a colourful landmark marking the southernmost point in the continental United States, just 90 miles from Cuba.

Take a tour of Ernest Hemingway’s Home and Museum, where the famous author lived and wrote during the 1930s. Explore the beautifully preserved house and gardens, home to descendants of Hemingway’s beloved six-toed cats.

Alternatively, immerse yourself in the tropical beauty of the Key West Butterfly and Nature Conservatory. Wander through lush gardens filled with exotic plants and hundreds of colourful butterflies fluttering freely around you.

    Marathon > Key West | 54 miles

    Key West Lighthouse Hotel or similar

Key West, Florida Keys
Dry Tortugas National Park, Florida Keys

Day 8 – Key West

From Key West you can catch the ferry to Dry Tortugas National Park, the historic site…

From Key West you can catch the ferry to Dry Tortugas National Park, the historic site of a fort, that now stands guard over a pristine beach and nature reserve. Well worth a day trip, the island is sensational for snorkelling or diving, but it is also incredible to explore on foot. You can even take a Seaplane to view Dry Tortugas in all its glory.

In the evening, explore Duval Street, Key West’s main thoroughfare, lined with shops, restaurants, bars, and historic sites. Take a leisurely stroll along the street, browse the unique boutiques and galleries, and soak up the lively atmosphere.

At Mallory Square, there is a nightly sunset celebration, with music and acts including jugglers and sword swallowers, putting on a night of entertainment.

    Key West Lighthouse Hotel or similar

Dry Tortugas National Park, Florida Keys
Islamorada, Florida Keys

Day 9 – Key West to Islamorada

On your journey back up the Keys, make sure to stop on Big Pine Key, at…

On your journey back up the Keys, make sure to stop on Big Pine Key, at the National Key Deer Refuge. This endangered species is the smallest subspecies of white-tailed deer, and is only found on the Lower Keys. Hike, bike or kayak through the reserve, keeping your eyes peeled for deer.

Check into your Islamorada hotel, then explore Morada Way Arts & Cultural District, a local initiative aiming to support the arts and the community in the Florida Keys. Enjoy a 6 block corridor of lively galleries, restaurants and studio spaces. Every Sunday, there is also a bustling farmers market, with art, food and gifts on offer.

The History of Diving museum is also worth a visit, telling the story of man’s attempts to explore under the sea.

    Key West > Islamorada | 80 miles

    Islamorada La Siesta Resort or similar

Islamorada, Florida Keys
Islamorada Sandbar, Florida Keys

Day 10 – Islamorada

Take a day trip to Islamorada Sandbar, accessible by boat or float (paddleboard or kayak). Enjoy…

Take a day trip to Islamorada Sandbar, accessible by boat or float (paddleboard or kayak). Enjoy the crystal clear waters, the pristine sands, panoramic views and electric atmosphere. Sometimes attracting 300 boats, it quickly becomes a boat party. Bob about with a cold drink in hand, and enjoy the views and lively energy.

Spend the evening sampling some local brews at Florida Keys Brewing Company. The artsy and colourful microbrewery has a tropical beer garden and often hosts live music.

    Key West > Islamorada | 80 miles

    Islamorada La Siesta Resort or similar

Islamorada Sandbar, Florida Keys
Ocean Drive, South Beach. Miami, Florida

Day 11 – Farewell to Florida

Head back to Miami, picking up a Cuban sandwich or some souvenirs on the way. Make…

Head back to Miami, picking up a Cuban sandwich or some souvenirs on the way. Make your way back to Miami International Airport in time to return your rental car and check-in for your return flight or to continue your America holiday.

    Islamorada > Miami International Airport | 81 miles
Ocean Drive, South Beach. Miami, Florida

Your Itinerary

You can customise your Florida fly drive by adding extra nights or stops along the way. Just let us know what you would like to do.

Day 1

|

Welcome to Miami

Touchdown in Miami in the afternoon and collect your car, before making your way your way to Miami’s famous South Beach.

Miami is an international city, rich with a multi-ethnic culture which is reflected in the cuisine and architecture. Miami’s South Beach is a particularly stunning: swaying palm trees, and the waves washing ashore act as a backdrop for pastel-coloured, Art Deco buildings.

    Miami International Airport > South Beach | 11 miles

    Gale South Beach or similar

South Beach Miami

Day 2

|

Explore Miami

On day two, you are free to explore this cosmopolitan city at your leisure. You may choose to begin the day with a walk along Ocean Drive and the Miami Beach Boardwalk, or even cross the sands for a dip in the ocean.

Then you could head to Wynwood Walls, Miami’s outdoor street art museum. Stroll through the Wynwood Walls complex to see colourful murals and graffiti art by local and international artists.

You could choose to grab lunch at a Cuban bakery or café in Little Havana. Enjoy traditional Cuban pastries like pastelitos and a café con leche while soaking in the lively atmosphere. Then visit Domino Park to watch locals play dominoes and browse the shops selling Cuban cigars and souvenirs.

In the evening, you can watch the sunset from a beachfront bar or rooftop lounge while sipping cocktails and listening to live music. For dinner, indulge in fresh seafood at a waterfront restaurant overlooking Biscayne Bay or the Miami River. Try local specialties like stone crab claws, ceviche, or grilled fish prepared with Caribbean flavours.

Optional Experience Miami Hop-on Hop-off Bus Tour
This Miami Sightseeing Tour has been specially designed to show the best Miami has to offer. Enjoy it all from the comfort of the open-top buses; hop off wherever you like, then hop back on to continue your journey. You will see all the most interesting and attractive areas: South Beach, Downtown Miami, Coral Gables, Coconut Grove, Little Havana and more.

    Gale South Beach or similar

Aerial view of Miami Beach

Day 3

|

Miami to Key Largo

Leave Miami behind and head towards the tropical paradise that is the Keys, cruising the Overseas Highway. Take in the incredible sea views through the network of 42 bridges, towering over the ocean.

As you arrive on Key Largo, spend the afternoon at John Pennekamp Coral Reef State Park, an underwater treasure trove of coral and marine life. The best way to experience the park is by diving right in, with a whole host of watersports on offer. Snorkelling or scuba diving is particularly spectacular, with the chance to spot sea turtles and dolphins amongst the coral. Alternatively, kayak or paddleboard through the mangroves, or you can take a glass-bottom boat tour.

After checking into your hotel, wander into the town to sample some local seafood, before finishing the evening enjoying some live music at Snappers Oceanfront Bar.

    Miami > Key Largo | 76 miles

    Dove Creek Resort or similar

John Pennekamp Coral Reef State Park, Key Largo, Florida Keys

Day 4

|

Key Largo

Enjoy a relaxed day exploring some of Key Largo’s beautiful beaches. Bring a picnic to Harry Harris Beach and Park, spanning 21 acres, and offering a number of facilities. Take advantage of the protected beach and swimming area, picnic tables, BBQs and sports fields.

There are also a number of watersports on offer from Key Largo. Perhaps try your hand at parasailing or jet skiing, or hire a paddle board.

    Dove Creek Resort or similar

Beach front, Dove Creek Resort & Marina, Key Largo, Florida

Day 5

|

Key Largo to Marathon

Continue on the Overseas Highway, making your way to Marathon. On the way, stop off at the Florida Keys History and Discovery Centre on Islamorada. Learn about the Keys’ rich past, the people, places and events that have shaped its development through interactive exhibits.

Another worthwhile stop is the Dolphin Research Centre, a nonprofit organisation providing vital rescue and rehabilitation work, and educating visitors about these amazing creatures.

Finish the day watching the sun set at a waterfront restaurant.

    Key Largo > Marathon | 41 miles

    Hampton Inn Marathon or similar

Overseas Highway, Florida Keys, USA

Day 6

|

Marathon

Spend your second day on Marathon by exploring one of the most beautiful beaches in the Keys: Sombrero Beach. Relax on its pristine sands, embrace some watersports or even sign up for an Island yoga class, regularly taking place on the beach.

Marathon is also home to the Keys’ Turtle Hospital, carrying out vital conservation work. The hospital regularly carry out public releases of the rehabilitated turtles, as Sombrero Beach is a designated nesting zone.

    Hampton Inn Marathon or similar

Florida Keys

Day 7

|

Marathon to Key West

Continue your journey to the lowest of the Keys, taking in the views as you cross the iconic Seven Mile Bridge.

Key West has lots to offer. You may like to climb to the top of the Key West Lighthouse for panoramic views of the island and surrounding waters. Nearby you can also snap a photo at the Southernmost Point Buoy, a colourful landmark marking the southernmost point in the continental United States, just 90 miles from Cuba.

Take a tour of Ernest Hemingway’s Home and Museum, where the famous author lived and wrote during the 1930s. Explore the beautifully preserved house and gardens, home to descendants of Hemingway’s beloved six-toed cats.

Alternatively, immerse yourself in the tropical beauty of the Key West Butterfly and Nature Conservatory. Wander through lush gardens filled with exotic plants and hundreds of colourful butterflies fluttering freely around you.

    Marathon > Key West | 54 miles

    Key West Lighthouse Hotel or similar

Key West, Florida Keys

Day 8

|

Key West

From Key West you can catch the ferry to Dry Tortugas National Park, the historic site of a fort, that now stands guard over a pristine beach and nature reserve. Well worth a day trip, the island is sensational for snorkelling or diving, but it is also incredible to explore on foot. You can even take a Seaplane to view Dry Tortugas in all its glory.

In the evening, explore Duval Street, Key West’s main thoroughfare, lined with shops, restaurants, bars, and historic sites. Take a leisurely stroll along the street, browse the unique boutiques and galleries, and soak up the lively atmosphere.

At Mallory Square, there is a nightly sunset celebration, with music and acts including jugglers and sword swallowers, putting on a night of entertainment.

    Key West Lighthouse Hotel or similar

Dry Tortugas National Park, Florida Keys

Day 9

|

Key West to Islamorada

On your journey back up the Keys, make sure to stop on Big Pine Key, at the National Key Deer Refuge. This endangered species is the smallest subspecies of white-tailed deer, and is only found on the Lower Keys. Hike, bike or kayak through the reserve, keeping your eyes peeled for deer.

Check into your Islamorada hotel, then explore Morada Way Arts & Cultural District, a local initiative aiming to support the arts and the community in the Florida Keys. Enjoy a 6 block corridor of lively galleries, restaurants and studio spaces. Every Sunday, there is also a bustling farmers market, with art, food and gifts on offer.

The History of Diving museum is also worth a visit, telling the story of man’s attempts to explore under the sea.

    Key West > Islamorada | 80 miles

    Islamorada La Siesta Resort or similar

Islamorada, Florida Keys

Day 10

|

Islamorada

Take a day trip to Islamorada Sandbar, accessible by boat or float (paddleboard or kayak). Enjoy the crystal clear waters, the pristine sands, panoramic views and electric atmosphere. Sometimes attracting 300 boats, it quickly becomes a boat party. Bob about with a cold drink in hand, and enjoy the views and lively energy.

Spend the evening sampling some local brews at Florida Keys Brewing Company. The artsy and colourful microbrewery has a tropical beer garden and often hosts live music.

    Key West > Islamorada | 80 miles

    Islamorada La Siesta Resort or similar

Islamorada Sandbar, Florida Keys

Day 11

|

Farewell to Florida

Head back to Miami, picking up a Cuban sandwich or some souvenirs on the way. Make your way back to Miami International Airport in time to return your rental car and check-in for your return flight or to continue your America holiday.

    Islamorada > Miami International Airport | 81 miles
Ocean Drive, South Beach. Miami, Florida

This Self Drive Includes

10 nights’ hotel accommodation
11 days’ car rental with unlimited mileage

Flights & More

Ask your FREEDOM Consultant to include Economy, Premium or Business Class flights for a complete ABTA and ATOL protected package.

They can also add extra nights and experiences in places you choose, to create the exact holiday you are looking for. Popular options include:

  • Extra nights in Miami, Islamorada, Key West or any other location along your route
  • An upgrade to your car to an SUV, 4×4 or electric vehicle
  • Speak to your travel consultant about adding in further experiences during your holiday

Next Step

Please get in touch with our America Experts to start planning your holiday. You’ll have a single point of contact from your first enquiry through booking.

Florida Keys Road Trip

11 day Fly Drive – from £1425

With flights from £2045

Price is per person, based on two people sharing a double or twin room and includes pre-booked accommodation, air-conditioned car and unlimited mileage. Hotels specified are subject to availability and may be substituted by one of a similar or higher standard.

Map

FLorida Keys Road Trip, Fly Drive Holiday, Route Map

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