Road Trip: To the End of the Florida Keys

On a blue sky January day, we rented a car and drove 180 miles south through the Florida Keys. We didn’t realize there are 800 keys in total with 42 bridges that connect the main chain of islands.

With our windows down, we turned up the song Kokomo by the Beach Boys and sang along to the lyrics “…Key Largo, Montego, baby why don’t we go, to the Florida Keys, there’s a place called Kokomo, that’s where you wanna go to get away from it all…” We looked everywhere for Kokomo, but couldn’t find it on our 24 hour adventure south.

But here’s what we did find out on our road trip…

  • The Keys are a fishing destination and attract fishermen from around the world. The Overseas Highway south to Key West was lined with harbors, marinas and thousands of boats.
  • The longest bridge, called the Seven Mile Bridge, seemed to go on forever.
  • The Keys really are a skinny strip of land that’s surrounded by shades of turquoise waters.
  • There are marine sanctuaries that protect turtles, dolphins, and parks where deer are protected.
  • Stop for scenic views at Fort Zachary Taylor State Park in Key West and Pigeon Key, near Marathon and the Seven Mile Bridge. Visit Islamorada at the Chamber of Commerce to pick up maps and helpful information. Another great stop is Key Largo to visit the John Pennekamp Coral Reef State Park.
  • There are dozens of artificial reefs formed on sinking ships in the Keys and divers love to explore these areas that attract colorful fish.

We made it to Key West, the southernmost city in the continental United States. Key West is just 90 miles north of Cuba, and it’s closer to Havana than to Miami. Locals call Key West, the Conch Republic and some homes and businesses fly their own Conch Republic flag.

We are adding to this list, but for starters, sharing some of our recommendations on where to stay, dine & go in Key West.


Margaritaville Beach House – located on the eastern shores of Key West, and only a five mins drive to historic main street, this hotel is in a prime location.

We loved our hotel suite complete with a kitchen, living room and comfortable bedroom and large bathroom.

The hotel is just across the street from Smather’s Beach. We loved staying on this quiet side of the Key and being so close to a two-mile stretch of white sand to walk on at sunrise. You can rent beach chairs, umbrellas, kayaks, paddle boards and sailboats from vendors on the beach too.


Head to Duval Street for an array of pubs, cafes and restaurants. Most tourists walk along this historic street and either bar hop, people watch or souvenir shop.

Be sure to order a mojito to go along with some Cuban roasted pork sandwiches, conch fritters or a fresh lobster roll. Wake up to some Cuban coffee from Cuban Coffee Queen.

Sloppy Joe’s is a popular bar where Hemingway used to hang out after a day of writing or fishing. Or stop at the Bull and Whistle Bar along Duval Street.

Fine Dining – check out Latitudes where you can watch the sunset too.

Don’t Miss! Order a slice of Key Lime pie at The Cafe.


  • Route 1 runs 2,370 miles from the Canadian border and ends in Key West and you can see the marker at Whitehead Street and Fleming Street.
  • Ernest Hemingway’s Home and gardens that inspired his literary works in the 1930’s.
  • Visit the Key West Lighthouse just across the street from Hemingway’s home, and climb the 88 steps to the top with some of the best views over the town.
  • The Winter White House where President Truman resided
  • Mallory Square at the end of the day to watch the sunset
  • Visit the Nature Conservatory with butterflies, birds, tropical plants and flamingoes.
  • Explore the Shipwreck Museum
  • The Southernmost Point – get here early morning or be ready to stand in line.
  • Stroll along the historic seaport where yachts from around the world dock
  • Visit Dry Tortugas National Park where there are seven small islands with coral reefs and bird nesting grounds. The historic Fort Jefferson is also here.
  • Stroll the streets near Duval Street to see some of the historic homes – Whitehead Street and Greene Street.

On our drive back north, we rolled the windows back down, turned on some tunes. I removed my hair tie and let my flocks flow freely in the southernmost air. I was tapping my flip flops to some Cuban music and feeling more relaxed. It finally occurred to me that Kokomo found us.