Driving down, or up, the Overseas Highway should be on everyone’s bucket list.  If you fly into Miami or Fort Lauderdale, then you will truly enjoy your Key West road trip.  Flying into Key West directly?  No worries, you can either rent a car or check out Up the Keys, which can take you on a private tour of the lower keys. When you step out of Key West and explore the rest of the Keys you gain a new perspective and truly appreciate the beauty and uniqueness of these islands.

A bit of back story, our first trip to the Keys, we drove down.  Loved every minute of it, except most of the trip was after sunset… so, plan accordingly.  Make sure you can at least see most of the Keys during the day, to truly appreciate the beauty and maybe plan sunset in Marathon, at the Seven Mile Bridge.  We love to stop at Sunset Grille and have a bite to eat and stretch on our way down.  If we are lucky enough to time it for sunset… well all the better.

Did you know the Florida Keys Overseas Highway is 113 miles long?  It joins the mainland of Florida to Key West.  Once you get to Key Largo, it’s about 100 miles to Key West, which if traffic is light, should take you about 2 ½ hours.  But, this is a two-lane highway and if there is any traffic, then plan to be driving longer.  During busy weekends and lobster season, travel times up and down the Keys can easily double.  Watch the traffic conditions on your GPS or peek at the road cams to check on traffic.

Honestly, most of us are in a hurry to get to Key West, we don’t plan to stop very much and truly take in all of what the Keys offers.  Or for that sake, what the drive offers.  But, let me tell you what you are missing, and maybe, just maybe, you will plan your next trip to take advantage of these amazing places.  

Heading down from South Florida, you can plan a stop at the Everglades National Park.  It’s the perfect place to see the natural beauty of Flordia.  You can easily plan a day trip if you staying in Key Largo. 

Below are affiliate links to book your sunset sail.  I will earn a commission if you use these links to book your trip and I truly appreciate your support!

Everglades National Park

This park is a 1.5 million-acre wetland preserve.  Noted as a grassy, slow-moving river, the Everglades is made up of coastal mangroves, sawgrass marshes, and pine flat woods.  It’s home to hundreds of animal species including the endangered leatherback turtle, Florida panther, and West Indian manatee.  It’s the third-largest park in the lower 48.  I had seen pictures of the Everglades as a kid and they, in no way, did they show off how really cool this area of Flordia is.  We explored the area a bit, but, have plans to head back and really explore and take advantage of all the outdoor activities.  Stay tuned…. But, in the meantime…

What can you do here?  So many options… but to list a few:

• Biking
• Bird watching
• Boating
• Camping
• Kayaking and Canoeing
• Fishing
• Geocaching
• Hiking
• Ranger-leg programs
• Slough Slogging
• Tours
• Wildlife viewing

You can hit up the Everglades National Park website to plan your trip, and here is a link to the best hotels in the area.

As we drive on down the road, I always say we are heading home once I see the blue cement dividers… if you have driven the Overseas Highway, you will know exactly what I mean, but honestly, you cant’ miss them.  Thus our road trip begins with our first stop, Key Largo.  But, first, if you are heading down early in the day, take Card Sound Bridge and stop at Alabama Jacks for lunch.  Great food, live music, but watch the time… the place closes at 7 pm.

Key Largo

From this point forward, everything will be noted by mile marker numbers.  It’s the way the Keys gives directions.  Plus, once you get used to the system, it’s easier to figure out where you are in the Keys. Key Largo is at mile marker (MM) 100.  Which means… 100 miles until Key West.  But, still a whole lot of driving in store.  

What to do in Key Largo… well, let’s break this down.  Key Largo is the self-proclaimed Dive Capital of the World, so snorkeling and diving would be a must here.  If you are planning to spend a day or two here, plan to head out on the water.

MM 102.5

Snorkel John Pennekamp Coral Reef State Park and see Christ of the Abyss.  So, true confession time, I can’t swim.  So I don’t snorkel or dive, but the hubby loves to snorkel.  I usually sit top side and enjoy the water and sun.   So, if you are like me, there is still stuff to do here.

This is one of the most famous scuba diving sites in the world.  Divers come from all around the world to see the Christ statue.  Because of this, there is a high number of scuba divers and snorkelers.  There is an abundance of sea life to see here too.  You will see what the Florida Keys are known for such as grouper, snapper, grunts, angelfish, nurse sharks, moray eels.

This is the first undersea park in the United States.  Established in 1963 it is adjacent to the Florida Keys National Marnie Sanctuary and they cover approximately 178 nautical square miles of coral reefs, seagrass beds, and mangrove swamps.  This area protects the only living coral reef in the continental United States. The park is open daily 8am until sunset. There is a park entrance fee and reservations are recommended during peak season.  

In the park, you can camp, fish, swim, and picnic.  Plus tours to snorkel, scuba, and explore on a glass bottom boat are available.  Don’t forget to check out the kayaks and paddleboards too

MM 100

Cruise aboard the African Queen.  Honestly, we had been traveling down the Keys for several years and didn’t even know about this.  The actual African Queen boat from the movie, with Humphrey Bogart and Katherine Hepburn… right in Key Largo.  How did I find out?  A friend of mine was planning a trip and made sure to include a stop in Key Largo to ride the African Queen.  The boat has been there since 1982 and in 2012 she celebrated her centennial year.  This is a really cool thing to do while visiting the Keys, cruise a piece of history.

MM 92.2

Key Lime Pie Factory – Ok, don’t we come to the Keys to eat Key Lime pie?  Or is that just me?  There are many, many places to stop to enjoy a slice, but add this to your list. The co-owner uses a recipe passed down from her grandmother.  Stock up on everything Key Lime from the shop.  This probably will tide you over until you hit the next stop for pie.

MM 92

Florida Keys Wild Bird Rehabilitation Center.   Open daily from sunrise to sunset, the Center’s mission is to rescue, rehabilitate and release native and migratory wild birds that have been harmed or displaced.  Admission is free, but donations are greatly appreciated.  Explore the Laura Quinn Wild Bird Sanctuary and visit with non-releasable wild birds, take a walk along the boardwalk and watch sunset.

Florida Keys National Marine Sanctuary – As soon as you step foot into any of the waters around the Flordia Keys, you will have entered the National Marine Sanctuary.  This Sanctuary protects 2,900 nautical miles of water surrounding the Keys.  There are more than 6,000 species of marine life to see as well as shipwrecks and other treasures.

Best Places to Eat?

We, probably like you, have a routine when we drive down.  Hobo’s (MM 101) is one of my favorite places to stop for lunch or dinner.  It’s a great place to stop and stretch your legs and enjoy a meal.  Other places?  Key Largo Conch House, The Buzzard’s Roost, Mrs. Mac’s Kitchen to name a few.  

Looking for an amazing waterfront tiki bar with live music?  Check out Gilbert’s Resort (MM 107).  They have a marina and you can rent jet skis, kayaks, and paddleboards.  Want to stay the night?  They offer rooms that offer waterfront views just steps away from the Tiki bar and all of the action.

Islamorada

Islamorada is from MM 90 to 72.  It encompasses 6 of the Florida Keys known for their coral reefs.

MM 88

Old Road Gallery – This is a hidden gem in the Keys.  You can wander the property and explore the winding paths and check out the Sculpture Garden.

MM 87

Founders Park – This 45 acre park offers a swimming pool, splash pad, sports facilities, playgrounds, and ocean access.  The park hours are sunrise to sunset and there is a small admission fee.  On the beach, you can enjoy a picnic under a Tiki hut.  Want to stop and stretch your legs?  Head out on the fitness or walking trails.  Does your fur baby need a chance to run a bit?  They have a one acre fenced dog park.  This is a fun stop, or if staying in Islamorada great place to spend the day.

MM 86.7

Rain Barrel Village – If you have driven by and seen Betsy the Lobster (who is larger than life) then you know right where this place is.  This artisan village has places to shop and talk with the artists.  Plus you can stroll through the tropical gardens or grab a bite to eat.  But… don’t forget to get your picture taken with Betsy!

MM 85.5

 Windley Key Fossil Reef Geological State Park.  You are probably noticing a theme… lots of state parks to visit in the Keys.  But, each offers a different perspective of this amazing place.  Windley Key Fossil Reef was a former quarry used by Henry Flagler to help build the Overseas Railroad.  After the railroad was completed the quarry produced exquisite pieces of decorative stone called Keystone. Today you can walk through the quarry on this island.  Check out the self guided trails and enjoy a picnic.

MM 84

Theater of the Sea.  Everyone wants to swim with dolphins and at the Theater of the Seas… you can do that.  Here you will see dolphins, sea lions, sea turtles, fish, sharks, stingrays, alligators, and birds.  They are open 365 days a year and feel free to bring your well-behaved dog on a leash to enjoy the property.  They have a restaurant on site as well as a private lagoon side beach.

MM 82.9

Islamorada Brewery and Distillery.  One of my favorites stops is here.  I have never had a bad beer here… and I think you won’t either.  My go to is usually the coconut key lime Ale. It ranks as a 4.25 on my Untapped scale.  Grab some beers to stash in your cooler for your final destination.  I always suggest several options… again, the beer is really that good. In the same building is their distillery.  They have vodka (gluten free), dark barrel-aged spiced rum, and gin.  Don’t forget to grab some swag with there!  Our home bar has several of the small tasting glasses.  

MM 82.2

 Lobster Trap Art Gift Shop and Gallery.  Here you can buy unique frames and art from local artists.  A Florida Keys art print really should be shown off in a lobster trap picture frame… don’t you think?

MM 82.1

Keys History and Discovery Center.  This two story building is a great place to learn all about the history of the Florida Keys.  They have rotating exhibits so be sure to stop by because you will usually see something you didn’t the time before.  

MM 82

 History of Diving Museum.  If you are into diving, then this is a must see place.  Even if you don’t dive (remember I can’t swim?) this is a cool place to visit.  Interactive exhibits, On the third Wednesday of every month they have a free program covering special topics.  Want to dig deeper into the history of diving?  They have the Bauer Diving History Research Library.  It houses the largest collection of historic and rare literature about diving history.

MM 81.8

Hurricane Monument.  This is a monument to “The Great Hurricane”.  That was the category 5 one that hit September 2, 1935.  Many, many lost their lives and the Overseas Railroad was torn up and never rebuilt.  Hurricane Irma (2017) was the third strongest Atlantic hurricane behind the 1935 Labor Day Hurricane and Hurricane Dorian (2019)

MM 81.6

 Florida Keys Brewing Company.  If you enjoy beer and art… then this is your stop.  Located in Morada Way Arts and Cultural District you will be able to wander in and out of amazing galleries and enjoy a great beer in the beer garden.  The Florida Keys Brewing Company is the Upper Keys’ first microbrewery.  Around the corner and down the block are the galleries.  We didn’t even know the galleries were down the street until we went to find an artist the hubby follows on Instagram.  Then we saw the magic of this place.  Art and beer.  Great place to spend an afternoon for sure!

MM 81.6

Morada Bay.  Funny story… we found this place by accident.  But, what a wonderful accident.  This place serves amazing food and you can eat on white sand sitting at tables and chairs painted in rich tropical colors.  Add this to your list!

MM 77.5

Robbie’s Marina of Islamorada.  Voted the number one place in the Keys that every tourist should visit.  This is where you can feed the tarpon.  Imagine hand feeding massive tarpon!  There is a small fee to do this… just a word of caution… watch out for the pelicans, they will try to steal your tarpon food!  Want to simply watch others do this, that’s fine too.  They have an amazing restaurant on site as well as the perfect place to enjoy a signature cocktail.  They recommend the Trailer Trash Bloody Mary.

MM 77.2

Lignumvitae Key Botanica State Park.  This State Park is located on 280 acre Lignumvitae Key and can only be reached by private boat or boat tour.  Here you can experience island living 1930’s style.  You can take a self guided tour of the historic William J. Matheson house and hardwood hammock.  

Indian Key Historic State Park – In 1836 Indian Key became the first county seat for Dade County.  Today the island has an uninhabited ghost town. This is only accessible by boat.  Here you can swim, hike, and kayak (rentals available from Robbie’s or Backcountry Cowboys)

Alligator Reef Lighthouse.  Located 4 nautical miles east of Indian Key.  It was established in 1873 and automated in 1963.  You can usually see it as you drive the highway.  Great place to head to by boat to snorkel.

MM 73

Anne’s Beach.  This is a rare find in the Florida Keys.  It has a natural sandy beach and … it’s free.  The park has two parking lots and restroom facilities.  There is a boardwalk that winds through the mangroves as well. Perfect place for a picnic.

My favorite stop to eat?  Lorelei’s.  The views are amazing and they have outside seating and live music.  The Square Grouper is also an eatery place to check out.

Other places of note are the Green Turtle Inn, Islamorada Shrimp Shack, MEAT Eatery, and Taproom.  These we highlighted on the Food Network’s Diners Drive-ins and Dives. 

Marathon

Maraton is set on 13 islands, known for their beaches and barrier reef.  Marathon covers mm 60 to mm 47.  It’s located about 1 hour from Key West and Key Largo, which makes it the Heart of the Florida Keys.  

Don’t have a car and staying in Key West?  No problem take a guided tour with Up the Keys.  They will take you to see all that Marathon and the Lower Keys offers.  Consider the Tiki Bar tour… so many cool places to check out and fun drinks to try.

MM 59

Dolphin Research Center.  I love this place.  It’s a rescue, research facility that lets you see the dolphins up close.  Plan to spend time here.  You can meet the dolphins, and even book a time to swim with them.  Take time to learn the Center’s history they don’t have “shows” but let the dolphins play and show off for the crowds as they would in the wild.

MM 56.2

Curry Hammock State Park.  So, what is a hammock?  It’s a stand of trees, usually hardwoods that form an ecological island in a contrasting ecosystem… in other words, it’s a group of trees that are all by themselves in an area.  There are many in Florida and very cool to see.   This State Park is 1,000 acres and the largest uninhabited parcel of land between Key Largo and Big Pine Key.  It has large areas of Rockland hammocks and a mangrove swamp.  Great place to kayak and paddleboard.

MM 55.5

Crane Point Museum & Nature Center.  With your price of admission, you can get a free fish pedicure… interested?

MM 53

Florida Keys Aquarium Encounters.  This was voted the best place to take the kids 5 years in a row.  Plan a day trip and enjoy the touch tanks, feed the animals, and even feed the sharks.  Snorkel or dive the coral reef and experience the aquarium environment or check out the other encounters they offer.  They also have a great grill on site that serves beer and wine

MM 52

EAA Air Museum.  This place is small but nice.  Admission is free, but donations are greatly appreciated.

MM 50

Sombrero Beach.  A lovely sandy beach on the Atlantic Ocean.  It is a turtle nesting beach too so during nesting season some areas of the beach may be restricted.

MM 48.5

Turtle Hospital.  The mission is the rescue, rehabilitate, research, and release sea turtles.  You can visit the hospital and see current patients,  Go on the guided tour to learn more about them, and meet the turtles.  Reservations are recommended. 

MM 47.5

Pigeon Key.  Pack a picnic, bring your snorkel gear or your beach chair and a book.  This is a secluded island paradise.  Take one of the daily tours and learn the history of this island.  The ferry service runs three times a day.  From the ferry, you will get great views of the Old Seven Mile Bridge.  The visitors center is located at MM 47.5 and this is where you catch the ferry. 

Oceanfront Park.  This is a free public park.  It is dog friendly park. Great place to picnic, fish, or launch a kayak.

Thunderbolt Wreck Dive Site.  This is Marathon’s most popular dive site.  

MM 47

 Shady Palm Art Gallery.  The Gallery has items made by over 50 local artists.  If you are looking for a unique gift or something beautiful to bring home… this is the stop.

Seven Mile Bridge.  No trip on the Overseas Highway is complete without a drive over the Seven Mile Bridge.  Finished in 1982, it is the longest in the Florida Keys.  As you cross the bridge, the Old Seven Mile Bridge can be seen.  Of, course we all remember seeing it in the movie “True Lies”.  Plan to stop at Sunset Grille for a view of the bridge and an amazing Tiki experience.  

Fred the Tree  – Be sure to look for Fred on the Old Seven Mile Bridge.  He has a fan following on Facebook if you want to stay in touch!

Big Pine Key

Big Pine Key is at MM 34.  This place is home to the Key Deer, the Blue Hole, and No Name Pub. 

MM 37

Bahia Honda State Park.  I love this park.  Walk up and see the Old Bridge or plan a picnic or spend the day playing in the water.  Here you can see wildlife and birds.  If you are staying in Key West, this is a great day excursion.  We always plan to be there for sunset.  The view of the sun setting in the water with the bridge in view is amazing. The park has Calusa Beach on one side and Sandspur Beach on the other.  At the top of you can see where the Gulf and the Atlantic meet.  Pretty cool for sure.

MM 30.5

National Key Deer Refuge.  You must plan a stop to see the Key Deer.  We have driven around the Refuge, but honestly, the best way to see them is with Up the Keys.  They take you on all of the back roads and get you very close to the deer.  You will learn the story, which is amazing, about how the Refuge was created.  Plus, you can stop at Bahia Honda, and the Blue Hole all in the comfort of an air conditioned van.

MM 30.4

Blue Hole.  Blue Hole is a freshwater lake on Big Pine Key.  It is an abandoned rock quarry and the perfect geological environment to create this wonder.  The water is clear and you will see all kinds of fish, turtles, and a few alligators, who love the shade of the deck overlooking the lake. 

Best place for a drink?  Check out No Name Pub.

Our last stop?  Key West

Key West

At the end of the road, MM0.  A place that offers unique experiences to all who come.  Tour museums, experience the Key West sunset from the water, tip a few pints on Duval Street, and of course get your picture taken with the Southernmost Point Buoy.  Want to know the 25 top things to do in Key West?  Check out our video and link to what we say is the top things.