Super Scenic Florida Road Trip: Key Largo to Key West

The Florida Keys Overseas Highway is a living corridor of reefs, bridges, history, and local tradition. We sit down with journalist and photographer Andy Newman, who spent 44 years with the Florida Keys Tourism Council, to build a true start-to-finish Florida Keys road trip.

We talk logistics: how long the drive takes, why the mile markers function like addresses, and when you can get away without hotel reservations. From there, we trace the story behind the islands themselves: Henry Flagler’s Overseas Railroad, the 1935 Labor Day hurricane, and how the modern highway opened the Keys to a different kind of traveler.

Then we start the itinerary. Key Largo brings John Pennekamp Coral Reef State Park and the Christ of the Deep, plus smart reminders about the Florida Keys National Marine Sanctuary and boating responsibly around shallow, sensitive habitat. 

Islamorada delivers sport fishing culture, the History of Diving Museum, and the simple joy of hand-feeding tarpon. Marathon adds the Dolphin Research Center, Aquarium Encounters, the Turtle Hospital, and a walk into history on Pigeon Key. The Lower Keys bring Bahia Honda beaches, key deer, and even an Underwater Music Festival. 

Key West rounds it out with the Conch Republic story, Hemingway Days, six-toed cats, sunset celebration at Mallory Square, and the option to reach Dry Tortugas National Park and Fort Jefferson.

If you love travel stories with practical tips, local food, and real history, this one’s for you. Subscribe, share it with your favorite road trip partner, leave a review.

Andy Newman is currently an avid fisherman and photographer, and lives in the Florida Keys.

Podcast host Lea Lane has traveled to over 100 countries, and has written nine books, including the award-winning Places I Remember  (Kirkus Reviews star rating, and  'one of the top 100 Indie books of  the year'). She has contributed to dozens of guidebooks and has written thousands of travel articles. Read her weekly essays on Substack.
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Our award-winning travel podcast, Places I Remember with Lea Lane, has produced over 130 travel episodes! New episodes drop on the first Tuesday of the month, on Apple, Spotify, and wherever you listen to podcasts. All episodes are also on her website: placesirememberlealane.com
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Transcript

Welcome To The Florida Keys

Lea Lane 0:00

The Florida Keys is a curving chain of small islands south of Miami, stretching for about a hundred miles from Key Largo to Key West. The Keys are connected by the famous Overseas Highway, making the drive between the Atlantic Ocean and the Gulf of Mexico one of the most scenic road trips in the United States. Our guest is journalist and photographer Andy Newman, former PR director of the Florida Keys Tourism Council for 44 years. Welcome, Andy, to Places I Remember.

Andy Newman 0:28

Lea, thank you so much for having me. It's an absolute honor and a pleasure.

Lea Lane 0:32

Great. Let's start with some tips about the drive itself. There are 42 bridges, including the seven-mile bridge. How long does it take without stops?

Andy Newman 0:41

If you're driving from Miami International Airport down to Key West, and you go straight through and the traffic flow is reasonable, it's about three and a half hours. Well, actually, most of the Keys runs east and west. That's why it's called Key West, by the way. Okay.

Lea Lane 0:57

That's very interesting.

Andy Newman 0:57

Yeah,

Driving The Overseas Highway

Andy Newman 0:58

yeah, it is.

Lea Lane 0:58

Well, you're driving south, sort of. Let's put it that way.

Andy Newman 1:02

Yes, yes.

Lea Lane 1:02

Let me ask you about the mile markers, because that's something people don't always understand. What do they represent?

Andy Newman 1:08

Mile markers are pretty much addresses throughout most of the Florida Keys. For example, you actually start in Miami Dade County in Florida City with mile marker 127. It is a spectacular drive. Before there was an overseas highway, there was actually an overseas railroad. And that was built by Henry Flagler, finished in 1912, and then the railroad ceased in 1935 due to a number of reasons. One was a 1935 hurricane, a Labor Day hurricane, which was a significant damage, damage the bridges. A lot of them are used for fishing piers. The railroad

Railroad History And Hurricane 1935

Speaker 1:48

also was actually failing from an economic standpoint. There was no way that it was actually going to get rebuilt. And by then, of course, the automobile had come in vogue ; instead of rebuilding old railroad, the officials built Florida Keys Overseas Highway. It opened up in 1940 from Miami down to Key West.

Lea Lane 2:09

Great information. Now, if you're driving along just for the day, you can get to Key West, but you're not going to get to see much. But if you want to have a last-minute accommodation, let's say you decide I want to see more. Is it a problem? Do you have to have reservations? Do you think, or can you perhaps depends on the time of year?

Andy Newman 2:26

Weekdays, I don't think you need to have a reservation, except during holidays, but weekends, I would really recommend that you have that reservation, and

When You Need Reservations

Speaker 2:35

especially during high season, between Christmas and Easter.

Lea Lane 2:39

Okay. I know it can get crowded on weekends any time of the year. Okay, so let's create a journey with the most special stops and attractions that you think, starting in Key Largo. Tell us what we would find in the significant attractions in the Key Largo area.

Andy Newman 2:54

John Pennacamp Coral Reef State Park, the United States' very first underwater preserve. One of the most famous parts of the park is the nine-foot tall bronze Christ of the Deep statue, which is an iconic for divers and

Key Largo Reefs And Snorkeling

Andy Newman 3:10

uh snorkelers. The park welcomes about 650,000 visitors annually who come to explore nature trails, beaches, and of course observe the abundant underwater life.

Lea Lane 3:21

I took a glass bottom boat tour there. I think if people don't want to get in the water, it can be a little cool. It's not the Caribbean, but it's fabulous to see this fish and the coral. It's something that's so much fun.

Andy Newman 3:32

Yes, you don't want to get wet. Uh there's actually several different options in terms of glass bottom boats in the Upper Keys. You know, besides the dive operators at the state park itself, there's a number of independent dive shops throughout the Key Largo area and the rest of the Keys, they take snorkelers and divers out there. Of course, you've got to be a certified diver. Several dive shops do dive certification. There's different ways to go ahead and do that. But the PennaCamp, by the way, is part of the Florida Keys National Marine Sanctuary. The sanctuary covers about 3,800 square miles of coral reefs, seagrass beds, mangrove swamp on both sides of the Keys Island chain. And so, really, protecting this natural resource, this treasure is super important. And we hope visitors who want to use the natural resources down here will take some time, look at the various websites. The Keys has a website, visit Floridakeys.com. The sanctuary does as well. And just familiarize yourself, especially, especially if you're bringing your own boat down. That's so important because navigating a boat in the sanctuary can be very challenging if you're not used to understanding the markers and also the different levels of shallow areas. We really must protect those areas that are so sensitive and so important to the marine habitats in the Florida Keys.

Lea Lane 4:56

Absolutely. So if we're going to go on a little further, we would go to Isla morada. It's a very charming chic village, known for its calm waters and its fishing. And I've heard it called a purple island. Why is that?

Andy Newman 5:08

There's all types of theories about that. Some people think that when the Calusa Indians discovered the islands and they saw these purple flowers on the shoreline. Of course, fishing is huge in Islamorada. It is known as

Marine Sanctuary Rules And Boating

Andy Newman 5:22

the sport fishing capital of the world. By the way, more saltwater world records established in the Florida Keys compared to any other saltwater fishing destination around the world. Yes, absolutely. And that's not according to me, that's according to the International Game Fish Association.

Lea Lane 5:39

Bone fishing is a great sport there. I know bone fishers love it.

Andy Newman 5:42

And I'm an angler. I mean, that's the reason why I continue to live in the Keys. I love fishing in the Keys. It's about the diversity. Okay. I can go offshore, okay, right now. I can catch black fin tuna. I can catch Mahi Mahi, which in the old days we called dolphin as in dolphin fish. No, we're not eating Flipper. Okay. Um, but I still call it a dolphin. Beautiful, beautiful fish. And then other species. And in the same day, I can come back if I can go on the bay side and I can catch a bonefish. So I can catch a tarpon, catch and release obviously, for those species. It really is about the diversity. Islamorada is also very close to Everglades National Park and the salt water habitats of Everglades National Park, where there's snook and there's redfish. It's really about the convenience and about the diversity. Some of the other highlights, by the way, of Islamorada, the History of Diving museum, it's absolutely a fascinating facility that talks about man's quest to explore the underwater. They have all these incredible artifacts ranging from the first diving bell to something much more sophisticated for not only commercial diving, but for deep water research. There's Lignan Vitae Key Botanical State Park, Indian Key Historic State Park. Fascinating, just fascinating historical stories to be told there. Robbie's Marina, by the way, where you can hand feed tarpon. You grab a bucket of fish. I call it the most cost-effective attraction in the Florida Keys. I think it's a couple dollars to get in. You buy a pail of bait fish for three bucks or so, then you hand feed these tarpon. It's just incredible.

Lea Lane 7:17

Fabulous. I know stone crabs are found there. Islamorada where you would get a boat charter and get out, get some stone crabs?

Andy Newman 7:24

As a resident, okay, I can have up to 10 traps. That usually takes like a week or so. Only legal size claws. A long-term stay thing. I know of one charter Islamorada that will take people out and try to dive for stone crabs.

Lea Lane 7:39

Well, it's a good reason to stay longer. I think that would be an excuse immediately. I know the Rain Barrel Village has a giant lobster statue. People notice that as they drive.

Andy Newman 7:48

It's Betsy the Lobster. That's her name. I remember when the artist that made her, and the artist actually lived in Marathon. By the way, Betsy was once in the Orange Bowl parade many, many years ago. Uh-huh.

Lea Lane 8:00

Don't remember that. Okay.

Andy Newman 8:01

Okay, but it is anatomically correct in terms of a Florida Key spiny lobster.

Lea Lane 8:07

Okay, so let's go on to Marathon. That's another scenic spot, another scenic key. Tell us about what we would look for.

Andy Newman 8:13

Absolutely. So I think one of the really great things about visiting Marathon, Marathon is in the heart of the Florida Keys. If you wanted to just go and stay in one place and not have to pack, unpack, and pack again, there's no place in the Keys that's more than about an hour and 20 minutes away. There's the Dolphin Research Center. It's one

Islamorada Fishing And Quirky Stops

Andy Newman 8:33

of several facilities in the Keys, an opportunity to learn about dolphins. And we're talking about mammals now, not the fish. They do a great job there at they are an acclaimed nonprofit marine mammal research and education facility. They offer a number of different swim encounter programs for visitors to really get in the water for an up close look at the beauty of the resident dolphins. There's also Florida Keys Aquarium Encounters. One thing about the Florida Keys National Marine Sanctuary is that you are not permitted to feed the fish within the sanctuary. That's the great thing about Florida Keys Aquarium Encounters, which is a 250,000-gallon tank, is that you are encouraged and you can feed the native species of fish. I love it. It's a really cool attraction. Activity there is not governed by the weather at all. The turtle hospital in Marathon is absolutely wonderful. They just marked their 40th anniversary, and it all started with a gentleman, Richie Moretti. He built this hospital on his own. Today, the hospital is funded by visitors that come and see the operating room, the various turtles that are being treated, and they're the real deal. Also, the old Seven-Mile bridge, taking a walk, taking a bicycle ride, going to Pigeon Key, which is about two and a half, three miles to the west end of Marathon, it's outstanding. That's something that you'll absolutely want to do. Pigeon Key was the base camp for the workers for Henry Flagler's Overseas Railroad for that Seven Mile bridge. When you step onto Pigeon Key, you're stepping back into time.

Lea Lane 10:12

Right. Fabulous. You're giving us little details that I I've been to the Keys since I was a child. I remember staying at a place called Jack Tar. I'm sure it's not there anymore.

Andy Newman 10:22

I don't believe so. Yes.

Lea Lane 10:25

Yes, way back when I was a child. So, but I didn't realize some of the history that's there as well. I was just looking at the beauty. Speaking of beauty, Bahia Honda Key is renowned for having the best beaches in the Keys and offering these spectacular sunset views. Tell us a little about Bahia Honda.

Andy Newman 10:43

Well, Bahia Honda is part of Big Pine and the Lower Keys. And so we're talking about the areas of the Keys between the Seven Mile Bridge and Key West. For the person that really, really enjoys nature,

Bahia Honda Beaches And Key Deer

Andy Newman 10:58

this is the place to be. Bahia Honda State Park. There's also wreck diving for divers to explore. [Tell us about the Key deer.] Key deer are small, diminutive sized deer. They're an offshoot species of the Virginia whitetail, the size of a very, very large dog. They are protected. At one time, the herd got to like less than 50 deer. The federal government came in and said, 'Hey, we need to protect this.' I believe that the size of the herd today is somewhere in the neighborhood of around 800. [Oh, that's wonderful. ] Yeah. And for you folks that may be hunters, you cannot hunt here. [Do they come on the road? ]There is a speed limit on Big Pine Key. Daylight hours are around 45 miles an hour, I believe. And then nighttime it's 35 miles an hour. And the speed zones are really enforced throughout the Keys. For most of the Overseas Highway, it's still two-lane, one lane going to the south, one lane going north. Our sheriff's office is very concerned about safety on the Overseas Highway. One of the most imaginative and significant events that the Lower Keys offers, it's the second Saturday in July, the annual Lower Keys Underwater Music Festival. And local radio station, US1, broadcasts four hours of continuous music without commercials, but they do have public safety messages about coral reef conservation. These are specially selected for the underwater

Underwater Music And Animal Farm

Andy Newman 12:29

listening experience. Now, how do they get the music down there, Lea? [Yes, how

Marathon Dolphins Turtles And Pigeon Key

Andy Newman 12:33

do they? How do they?] Underwater speakers. There's a number of boats that have these Lubell laboratories. I think they're still using them speakers, and they're strategically positioned above the reef at uh Luke Reef is exactly where it's at. So, and then also, this is a very unusual visitor activity, okay? And it's technically in the Lower Keys, not Key West. It is the Monroe County Sheriff's Office Animal Farm. It's mile marker five, Bayside. It's on Stock Island, it's on the grounds of the Monroe County Detention Center, and it's open on the second and fourth uh Sundays of each month from 1 to 3 p.m. admissions free. They have all kinds of traditional farm animals, but they also have exotic animals such as an emu, a zebu, an albino python, peacocks, and tropical birds. So basically a haven for animals that have been neglected.

Lea Lane 13:29

Now we're going to hit Key West, which is characterized by its very colorful Bahamian style architecture. It's free roaming chickens, it's literary history, sunset rituals, and vibrant water activities. You can snorkel the barrier reef and you can watch the sunset at Mallory Square. Now it's called the Conch Republic, and it's very interesting. It's a micronation, right? Key West was considered a micronation

Key West Conch Republic Vibe

Lea Lane 13:55

in April of 1982 in response to a very disruptive U.S. Border Patrol checkpoint. And so there's lots of festivities around that. And I think in April, isn't there a celebration called Conch Week, where there are bed races and parades and a 21 conch shell salute? I have seen that.

Andy Newman 14:12

There's hardly a weekend or a week that goes by without some kind of event. Some of them are culture related, some are just more fun. Cannot talk about Key West without talking about Ernest Hemingway and Six Toed Cats. And the Six-Teed Cats, of which there are still descendants at 907 Whitehead Street. Hemingway also offers an event called the Hemingway Days Festival. Of all the festivals and events that I've covered throughout the Keys in all my 40 plus years, which includes the Seven Mile Bridge Run and

Hemingway Festival And Famous Cats

Andy Newman 14:47

Fantasy Fest, I think my favorite is the Hemingway's Days Festival. And of course, the Papa Hemingway Look-alike Contest at Sloppy Joe's Bar. I've made many friends with the winners along the way. There are two rounds, two preliminary rounds. And then on the Saturday night, usually closest to Hemingway's birthday, the third week of July, July 21st, if my memory serves me correctly. That's the final round. And that's when the you know the new Papa Hemingway look-alike winner is crowned. It is an absolutely coveted title among these men. I know contestants that keep coming back for 25 plus years. Question. I have never seen, I'll tell you what, I've never even seen a woman enter the contest. Okay. But but understand this contest normally selects a winner of Papa Hemingway, the way that he looked as he got older, with a gray beard and that turtleneck sweater. When Hemingway actually lived in Key West throughout most of the 30s, he was much younger. There's been this movement, a couple of entrants over the past five to eight years or so have presented themselves emulating the actual Ernest Hemingway that lived in Key West, not the aged Papa Hemingway. That person has not won yet. They keep trying.

Lea Lane 16:10

They keep trying. What else? I mean, Duval Street obviously is the main artery, and there's galleries and all kinds of wonderful shops. There's a butterfly and nature conservatory. I know that. There's a Truman Little White House. Harry Truman used to come in the summer with very interesting original furnishings and historic documents. The Key West Lighthouse has uh 88 steps, I believe. You can climb it to get a lovely panoramic view. And the southernmost point, buoy, which is the most southern point of the continental U.S., just 90 miles from Cuba. So you can go and have your picture taken. That's a big Instagrammable moment, I guess, today.

Andy Newman 16:50

The southernmost point and the seven-mile bridge are probably the two most photographed icons in the Florida Keys. And certainly that southernmost point, you know, probably is like number one. It looks like an irradiated nun buoy is the actual navigation buoy. You've got to have your photo taken. You mentioned the the Key West Butterfly and Nature Conservatory, and it's a fabulous, fabulous attraction. I've been there many, many times. They have two flamingos there, Rhett and Scarlet. They offer an activity called flamingle. You actually go to the conservatory after hours, and you sit down on a bench, and Rhett and Scarlet will walk over to you and start feeling your hair and giving you little kisses and stuff like that. So that's certainly a lot of fun. I cannot go to Key West without experiencing sunset celebration at Mallory Square.

Lea Lane 17:43

And it lives up to its reputation mainly because of the people. It's just such a wonderful people place.

Andy Newman 17:49

Absolutely, absolutely. If you're really adventurous, you'll want to take the seaplane or the ferry over to Fort Jefferson. Fort Jefferson National Park. It's about 70 miles west of Key West. This is an incredible brick fort built during the Civil War, and it still stands today. Very important part of the National Park Service. Probably best known because Dr. Samuel Mudd, M U D D,

Dry Tortugas And Civil War Forts

Andy Newman 18:17

was incarcerated. People that know their history know that Dr. Mudd was accused of aiding the assassinant of President Abraham Lincoln. But there's a lot of debate about that. And Dr. Mudd's descendants over the years have tried to get his name completely clear. He was pardoned mainly because of his work helping to eliminate and treat people working on the fort that had contracted yellow fever.

Lea Lane 18:42

Yes. Well, Dry Tortugas National Park is one place, as you said, to go to, but there's a fort in Key West, Fort Zachary Taylor Historic State Park, and it has a Civil War era fort as well, and a very nice natural beach.

Andy Newman 18:57

But there's actually two more forts, East Martello Tower and West Martello Tower. Certainly not as significant as Fort Zachary Taylor.

Lea Lane 19:05

Right. I think people don't always assume history is down there. As I said, you think of fishing and beautiful scenery, but you have a lot of great history as well. Also want to mention local food, stone crabs, those beautiful claws that you eat. You can find them all over. Of course, there's conch chowder. Conch is another wonderful dish that they serve that's different. You don't have that everywhere, right?

Andy Newman 19:28

I'm all about honesty being uh perfectly transparent. Key West High School is known as the Fighting Conchs. There's a conch barber shop, there's conch this, conch this, conch town.

Stone Crab Conch And Key Lime Pie

Andy Newman 19:40

for probably close to 50 years. It is illegal to harvest conch in the Florida Keys. Okay, so all the conch that comes in for restaurants is actually imported from the Turks and Caicos and the Bahamas.

Lea Lane 19:53

But we have a very delicious thing that comes from the Keys. It's key lime pie. That doesn't come from anywhere else. And you can sample various takes at spots like Kermits or Blue Heaven or just walk around and try it all over. Anyone who has not tasted key lime pie, you're in for a treat.

Andy Newman 20:09

This is very important. There are a lot of places in Florida that endeavor to emulate and they serve key lime pie. If that filling is green, that is not done by a key lime. Clear about that. Yellowish, right? Yes, ma'am.

Lea Lane 20:23

Yep, and a little bit tart. It's absolutely delicious. Right. Okay, well, I'm ready. The name of the podcast is Places I Remember. So, Andy, will you please share a favorite story that you have revolving around the Florida Keys?

Andy Newman 20:36

There are so many after 40 years. Probably one of my most favorite was in the early 90s. Queen Elizabeth actually made a trip, a stopover for a couple hours at Fort Jefferson National Park. It's something that we helped to arrange. My father actually had suggested it

A Queen Visits Fort Jefferson

Andy Newman 20:53

to the British consul. We had our county mayor, the late Wilhelmina Harvey. She was Monroe County's very first mayor. We used to call her the Admiral of the Conch Republic Navy. The admiral was out there. She was beautifully dressed with a very wide red brimmed hat. The mayor was there to present the Queen with not only a conch shell, okay, but an honorary conch certificate. If you're in the Keys, you're born in the Keys, you're automatically called a conch. If you've been here for seven years or so, then you call it a freshwater conch. And then there's the honorary conch certificate. So Mayor Harvey was there to present the queen with an honorary conch certificate and the conch shell when she stepped ashore from the Britannia. I remember that I was there as part of the little press pool, and the press officer from the British consulate was very, very stern with us and also other videographers and photographers that were there. I said, You cannot talk to the queen. You cannot ask her to move, you cannot ask her to turn, you cannot say a word to her. That's absolutely strict. Well, when the queen came ashore. Okay, I could see Mayor Harvey perfectly, but all I saw was the Queen's back. And I'm sitting there thinking, oh, oh gosh, okay. I just gotta be able to see the queen, but and I should have asked her to turn toward us, but I didn't because I thought I was gonna encounter the wrath of the British consulate. So there's this wonderful picture that that we have of Mayor Harvey presenting the Queen with her conch shell. However, we don't see the Queen's face, but we know that it is the Queen. So okay.

Lea Lane 22:30

We know her back very, very well.

Speaker 22:31

Yes, we do.

Lea Lane 22:32

You've done this for so long, and you obviously know everything possible. And what is your proudest accomplishment of your tenure with the with the Keys?

Andy Newman 22:41

Most tourism promotional agencies, they're there to attract visitors to a destination. The Florida Keys are very low-lying islands, and the Keys are an absolutely great destination. But every once in a while, the Keys get threatened by a tropical cyclone, otherwise known as a hurricane. Back in 1998, I pioneered a program with Monroe County Emergency Management to

Hurricane Safety For Visitors

Andy Newman 23:07

help visitors during storms. We used to evacuate visitors a lot. But basically, the emergency management of Monroe County and ourselves, you know, made this little pact focus on visitor safety. We actually have a hurricane safety section on that Keys website.

Lea Lane 23:25

Well, thank you, Andy Newman, for showing us why the Florida Keys are among the most fun, weird, interesting, naturally beautiful areas, historic. It's just a great destination. I can't wait to drive down to Key West again and experience it all. Thank you so much.

Speaker 23:44

And we can't wait to have you back. Thank you.