The Upper Florida Keys–A Baby Boomer’s Road Trip

Jimmy Buffett’s 1974 A1A album cover photo said it all — with his surfer-dude look, sitting under a palm tree. If the Baby Boomers had not already taken a road trip to the Florida Keys on the famous highway, this album cover was surely the inspiration to travel to a laid back paradise.

Jimmy Buffett's A1A Album
Jimmy Buffett’s A1A Album

My first trek South on Florida Highway A1A was as a college student in a Miata convertible with very little money, a two-man tent and sleeping bags in the tiny trunk. In the ’70s, we didn’t even need reservations in campgrounds, and hardly anyone referred to us as Baby Boomers.

Key West is the ultimate destination for most travelers but my favorite of the Florida Keys are prior to getting there. Everyone should experience staying in and exploring the Upper Keys which include:

  • Key Largo
  • Tavernier
  • Plantation Key
  • Windley Key
  • Islamorada
  • Upper Matecumbe Key
  • Lightnumvitae Key
  • Indian Key
  • Lower Matecumbe Key

Water Adventures are a MUST DO

Driving south for the first time, you’ll see water everywhere, but not white sandy beaches.

The shorelines are typically rocky from the coral reef bottom or thick with vegetation. The first stretch of beach is at Bahia Honda State Park at Mile Marker 36 (more about mile markers later).

Rocky beach

To truly enjoy the splendor of the Keys, YOU MUST get out onto, into, or under the water.  It’s as crystal clear and is every shade of green, turquoise, and deep blue as found in the Caribbean.

John Pennekamp Coral Reef State Park in Key Largo is famous for snorkeling or scuba diving.  It was the first undersea park in the U.S., established in 1963. It is adjacent to the Florida Keys National Marine Sanctuary, and the two cover approximately 178 nautical miles of coral reefs, mangroves, and seagrass beds.

You can take snorkel and dive tours,  ride on glass-bottom boats or rent canoes, kayaks, and paddle boards  to explore the reefs and mangroves. The underwater park is well known for the Christ of the Deep statue, which is one of the most photographed underwater sites in the Keys. It stands in about 25 feet of water, but is visible to snorkelers from closer to the surface.

Christ of the Abyss

The statue is one of three bronze sculptures cast from the same mold in Italy and intended to be placed under water.  The Key Largo statue was placed  in 1965, after it was presented to the Underwater Society of America’s 1962 convention in Chicago by an Italian scuba entrepreneur. The other two statues are in the Mediterranean Sea and Grenada.

On one of my trips in the Florida Keys, my group, all in our 20s, snorkeled in the John Pennekamp underwater park.  We had been surface swimming with masks and flippers for some time, viewing the large formations of various coral and brightly colored tropical fish in schools.  We came upon the underwater Christ of the Deep statue.


Key Largo Diving
Christ of the Abyss-Key Largo Diving

Seeing the statue in the distance, I kept trying to dive down towards it for a closer look. Each time, REPEATEDLY,  I popped back to the surface… APPARENTLY a 7-month pregnant woman (or this one anyway) is very buoyant.

My sister and brother-in-law linked my arms through theirs with me in the middle and dove down. I had the thrill of seeing The Christ Statue, with up-stretched arms and His face looking up from the deep. This is a sight any diver will not forget.

Largo Sound-Cooling off

The statue viewing took place when we spent seven days island hopping aboard a 42′ long wooden motor sailer, a sort of self-guided saliboat cruise.  Beginning in Key Largo on the Atlantic side, we sailed or motored (on still days) over to the bay, into Largo Sound, to the historic Lignumvitae Key Botanical State Park, and on to Key West.

Sailboat Cruise
Sailboat Cruise

On our sailboat cruise, we stayed aboard the boat at night, anchoring offshore. On most nights, sleeping in the cabin bunks was suitable only to Dante himself, so we usually slept on the top deck. (Did I mention it was JULY?)

The night skies with no light pollution were like none other, stars alone lighting our nights.

As the winds shifted or died down, the mosquitoes found us, sounding like a Harley-Davidson rally in our ears. Our boat captain had to wake often and move the boat to the next anchor spot to keep the Harley’s away. Many thanks to my brother-in-law captain for that!

When choosing a dive or snorkeling service always keep in mind: SAFETY is of the utmost importance.  I recommend Quiescence Diving Services ( in Key Largo. They specialize in small group excursions with a maximum of six passengers. They cater to the group’s abilities and explore reefs and wrecks.

If you have a boating license, you can rent everything from a skiff to a deck-boat or pontoon boat and peruse the Atlantic Ocean side and the bay side of A1A.

On our last trip (decades after the first) we rented a nice deck boat on the ocean side on a beautiful day and the sea was rather calm. Locals anchor on sandbars and have ocean parties.

Islamorada Ocean Side

Depending on your experience navigating an ocean, you may prefer to head towards the bay side or rent from a vendor located on the bay.  The bay side is better protected with land masses to ensure a smoother ride.

Islamorada Bay Side

Individual rental prices are reasonable and offered on half and full-day rentals.  Canoes and kayaks offer up-close looks at the mangroves, rich in wildlife on top of and under the water.

Florida Keys Boat Rentals
Fishing Boat Rentals at Captain Pips

Fishing charters are more than abundant, with Islamorada boasting the title of Sport Fishing Capital of the World. Islamorada has over 100 fishing charter companies and offers trips in the Atlantic, Gulf of Mexico, and Florida Bay. Back country fishing trips in the Florida Everglades can also be arranged. With access to many different waterways, a fishing expedition can result in catches of Sailfish, Black fin tuna, Mahi Mahi, Bonefish, Snapper, Grouper, Swordfish, and more!

 A little further south from Islamorada, you’ll find a one of a kind area to explore. Lignumvitae Key State Park, described as an “island forest, “ is accessible only by boat — private or rented, canoe, kayak, or tour boat. The park offers guided Eco Tours  on the water and walking trails to view the vegetation and wildlife.

To call the vegetation in the Florida Keys unusual is an understatement, but consider the wet, humid, climate, salt air, and limited land mass, and it’s hard to imagine anything growing.

Mangrove trees grow in the waterways where their tangled roots hold onto sediments in the muddy bottom.  Air plants, like Spanish Moss and orchids, grow against the smallest tree limbs, so looking up into the trees can bring a pleasant surprise.  I love how tree roots wrap themselves anywhere they can grab on.

State Park
Lignumvitae Key Botanical State Park

Getting There-The Road South 

Navigating the trip is easy, U.S. Highway 1 is the longest north-south highway in the U.S. running 2,369 miles from Maine to Key West. Now that’s a ROAD TRIP !

Florida highway A1A, also known as the Overseas Highway, has small green mile marker signs indicating the distance north from Key West, which makes locating businesses and landmarks easy.

Mile markers begin with Florida City, at the end of the Florida Turnpike (toll road) at Mile Marker 127 . The first of the linked islands, Key Largo, is Mile Marker 106, then traveling south to Key West to Mile Marker 0, and the southernmost tip of the continental U.S.

Mile Markers

Being from the South, I’ve driven through the Florida Keys many times, but flying into Miami or Ft. Lauderdale and renting a car is my go-to option now, (now that I know I’m a Baby Boomer and have more funds at my disposal).

Florida Toll roads will be encountered between the airports and the Florida Keys. All-electronic tolling is in effect, meaning no more toll booths to slow you down.  A camera takes a picture of your license plate, you’re mailed a bill (if in a personal vehicle) for tolls plus a $2.50 service charge; or the credit card used for a car rental is charged for tolls used.  I like simplicity–and credit cards.

Shuttle options from the airports to the Florida Keys can be found here:

Things to Do on Land

I believe the water is the must see, must do experience in the Keys, but make no mistake…there are plenty of fun things to see, nifty little bars with plenty of personality, great restaurants, and other things to do on land.

NautiLimo Tours-Lorelei Restaurant and Cabana Bar

Seafood lovers are in heaven when eating out in any of the Florida Keys, knowing the seafood is fresh off the boat. Some restaurants offer the service of cooking your catch from your own fishing expedition.

In Islamorada, my favorite restaurants are Islamorada Fish Company and Morada Bay. Both offer plenty of outdoor seating and sunset viewing. Lorelei Restaurant and Cabana Bar is a lively fun evening with live music, where I found the pink NautiLimo, a boat/car available for shoreline tours.  Casual dining is the norm, with most restaurants offering outdoor seating, sometimes directly on the sand, as at Morada Bay.

Morada Bay Facebook Photo

As the decades pass, I still love going to the Florida Keys, with slight adjustments to earlier modes of travel.  My husband and I have traded in our sleeping bags for clean hotel rooms. Comfortable beds are preferable (if not necessary) to pallets on the deck of a sailboat.

All sorts of lodging options from small Mom & Pop motels to luxury resorts are available, selections to fit any budget. The Netflix series, Bloodline, was set in the Florida Keys, and the family’s “Rayburn House Inn” is actually part of Islamorada’s Moorings Village & Spa.


Captain Pip’s Marina & Hideaway

Since my first road trip in the mid-’70s, some things have changed (more restaurants and shopping, more tourists), but the atmosphere has not. The Florida Keys are still the same as in Buffett’s picture — chilled out.

As you drive through the Florida Keys, and if your goal is Key West, just take your time, don’t bypass the Upper Keys. Linger, stay a while, and see if you totally understand the last line of Buffett’s song Nautical Wheeler:

“That’s cause everyone here is just more than
contented to be living and dying in three-quarter time”

The end of A1A