The Florida Keys are a stunning archipelago of islands teetering on the edge of reality, boldly positioned off the southern coast of Florida, and commanding the title of the southernmost realm of the continental United States.

They begin at the South-Eastern coast of the Florida peninsula, about 15 miles South of Miami and extend in an arc Westward to Key West. The islands lie along the Florida Straits dividing the Atlantic Ocean to the east from the Gulf of Mexico to the Northwest and defining one edge of Florida Bay.

At the nearest point, the Southern part of Key West is just 90 miles from Cuba.  

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The Florida Keys are made up of so many islands they are often divided into several different groups. These groups are the Upper Keys, the Middle Keys, the Lower Keys. The Upper Keys are those located the farthest north and closest to Florida’s mainland and the groups extend out from there. The city of Key West is located in the Lower Keys.

Most of the Keys are uninhabited and are connected by an overseas highway. The drive is very easy if not slow due to the speed limit, along Highway 1, that will span roughly 97 miles. However, if you wanted to drive the entire length the you should get it done within roughly 3 hours. For my drive holiday through the Keys I decided to stay on various islands on my way down to Key West.   

In the breathtaking Upper Keys I found myself captivated by the charm of Key Largo and the pristine beauty of Islamorada. As I ventured into the Middle Keys the vibrant spirit of Marathon welcomed me with open arms, sealing my heart. Finally, I made my way down the iconic road to the captivating Key West in the Lower Keys, a journey that filled me with a sense of adventure and wonder.

THE UPPER KEYS

KEY LARGO

Key Largo is a warm sunny destination in the Florida Keys, and, the first major island in the Upper Keys. As the welcome sign reads it is the ‘Dive Capital of the World’ offering world-class diving, delicious cuisine, and thrilling water sports.

ACCOMMODATION

My arrival into Key Largo was courtesy of a short drive from South Beach in Miami that had me arrive at the hotel by mid-afternoon. I Stayed at the 3* Bayside Inn Key Largo. Prices are roughly US$210 (GB£200). One thing I have discovered is that Key Largo is not cheap!

There are a few quality places to dine and sit back and relax with a cocktail. One of my itineraries were to take the ‘African Queen‘ canal tour.  The African Queen Canal Cruise is a 90 minute adventure that takes visitors down the Port Largo Canals. Prices are $65 (GB£50). If booked in advance these cruises also offer dinner.

This steamship was the actual one used in the 1951 film of the same name, starring Bogart and Hepburn.

SHARKEYS BAR AND GRILL – sharkeysgalley.com

Head here for good food at decent prices.  They are open early serving breakfast until late evening.  It can be a little tricky to find but head to the harbour and you cannot go wrong. 

KAYAKING THROUGH THE MANGROVES

Choose to paddle solo or rent a tandem kayak to explore with a friend. There is a great 3 hour excursion delivered by Florida Bay Outfitters that cruise the mangroves costing $63 (GB£48) for the day. Launch from the beach and explore the mangrove estuaries or cruise out to a small island where you can stretch your legs. 

Pick up your kayak and leave the hustle and bustle of everyday life behind as you set out on your own expedition. After launching from the beach, glide along the serene blue waters and feel the ocean breezes while you paddle at your own pace. Keep your eyes peel for a manatee or stingray gliding through the shallow waters and have a waterproof camera handy to capture the action.

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ISLAMORADA ISLAND

Carry on down Highway 1 for roughly 30 minutes and you will reach Islamorada, also part of the Upper Keys. Known as the “Village of Islands”  it consists of 5 other smaller islands  – Tea Table Key, Lower Matecumbe Key, Upper Matecumbe Key, Windley Key and Plantation Key.

ALLIGATOR REEF

Get out your snorkelling gear and make tracks for Alligator Reef.  The Florida Reef’s northern end lies in Biscayne Key at Biscayne National Park and it spans all the way down the Atlantic side of the Florida Keys; it stretches approximately 220 miles along the coast. Apparently, the most fascinating part of the reef rests off of Key Largo near John Pennekamp State Park, but we still have yet to visit this part of the reef.

MORADA BAY BEACH CAFE – moradabaykeys.com

If you fancy watching the world go by over a cocktail or ice cold beer make your way to this little haunt. Based on the beach it offers good food at decent prices along with great views of the beach.

THE MIDDLE KEYS

MARATHON KEY

Continue along Highway 1 for another 45 minutes and you will reach Marathon that makes up part of the Middle Keys. Like pretty much every activity throughout the Florida Keys most involve the sea in some manner, whether it be kayaking, diving, fishing or simply sunbathing on the white sands.

I have to admit despite Key West offering its lion share of incredible sunsets Marathon Key can run as a close contender.  Watching the sunset with a cocktail was a mesmerising experience and one I still to this day have not forgotten.

ACCOMMODATION

Again, The Florida Keys are not cheap. I stayed at the 3* Blackfin Resort Prices are US$135 (GB£102).

BARNACLE BARNEYS BAR – barnacle-barneys-tiki-bar-marathon

Head over to the harbour where you find not only this great bar and grill for some great food. After dinner why not take a stroll along the harbour front and meet a large gathering of Pelican’s, or take some photographs of  Faro lighthouse.

Floridian Lighthouses

SEVEN MILE BRIDGE

One of the most beautiful parts of the drive through the Florida Keys is driving accross ‘Seven Mile Bridge‘. It begins on  Knight’s Key (part of the city of Marathon),  in the Middle Keys to Little Duck Key in the Lower Keys.

At the time it was Among the longest bridges in existence when it was built, it is part of the Overseas Highway in the Keys, which is part of the 2,369-mile U.S. Route 1.

LOWER KEYS

KEY WEST

Key West makes up the Lower Keys and is closer to Cuba than to mainland Florida. I spent three days here. Key West has a culture that is a bit contrary to the rest of the mainland United States.

Famed for their tolerant attitudes and laid back lifestyles. Liberal attitudes have stimulated a large gay influx, estimated at two out of five of the population. Although Key West today has been heavily transformed for tourists, the town has retained some of its offbeat character, especially away from the main drag of Duval Street, now a well-tended tourist strip of boutiques and beachwear shops (though it’s still a pleasant place for a leisurely stroll).

ACCOMMODATION

I stayed at the 3* The Palms Hotel Key West. Prices are roughly $220 p/n. It’s a great location within less than 10 minutes walk from Duval Street.

Key West locals have a love-hate relationship with the most famous road in Key West. Duval Street, Old Town Key West’s main drag, is a miracle mile of booze, tacky everything and awful behaviour. But it’s fun. The ‘Duval Crawl’ is one of the wildest pub crawls in the country. The mix of neon drink, drag shows, T-shirt kitsch, local theatres, art studios and boutiques is more charming than jarring.

ERNEST HEMMINGWAY HOUSE

Key West’s biggest darling, Ernest Hemingway, lived in this gorgeous Spanish colonial house from 1931 to 1940. Papa moved here in his early 30s with wife No 2, a Vogue fashion editor and friend of wife No 1. The Short Happy Life of Francis Macomber and The Green Hills of Africa were produced here, as well as many six-toed cats, whose descendants basically run the grounds.

MOST SOUTHERN POINT OF THE USA

Key West is famous for being the southernmost city in the continental United States.

When you visit it’s essential that you make it to the southernmost point on the island, found at the intersection of Whitehead Street and South Street. Here, you’ll see the landmark Southernmost Buoy.

MARGARITAVILLE

has been a major landmark on Duval Street for over three decades. “The Original Margaritaville” in Key West embraces the mythical world defined by the insightful lyrics of singer/songwriter Jimmy Buffett and creates an entertaining atmosphere that brings paradise to life. 

KEY WEST TROLLEY

Why not take some time to use the hop-on/hop-off trolley tour. This is a great way to learn some history as well as taking in the sights and sounds of Key West. For more information click here.

SLOPPY JOE’S BAR

As pictured in the above photo, I found that most of my evenings in Key West would end up at some point in here.  Located on Duval Street open since 1933, this bar offers live music & dancing plus a separate bar room for sports watching.

KEY WETS SUNSETS

I have to mention the incredible Sunsets that Key West Offers across the Gulf of Mexico. They are simply stunning! As soon as the sun begins to go down make your way down to the harbour on the Southern Coast and sup a drink, whilst watching street entertainers perform to entertain the crowds.

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