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Key Largo to Key West Florida Mile By Mile Guide

Key Largo to Key West A Mile by Mile Guide
Mallory Square Key West – Our Destination

We travel quite frequently and Florida road trips are our favorite. From the far reaches of the Florida Panhandle to the Southernmost Point in the Keys, we love it all.

Yet, there are few road trips we look forward to than our almost annual road trip from Key Largo to Key West. The beauty, the quirky sights, the craziness on Duval Street, and the serenity of beaches along the way – it is always fascinating, new and exciting travel.

We are tracing our steps over the years into a Key Largo to Key West Florida Mile by Mile Guide. We take you along on things to do in the Florida Keys, places to stay in the Keys and the fun things to do in the 100-plus miles of the Overseas Highway.

How Far is Key Largo to Key West

Technically, Key Largo starts at MM (mile marker) 107 and ends at MM 0 in Key West. The trip seems to start earlier when you enter the long highway to Key Largo at MM 126.

All of a sudden you are on a small strip of land with a four-lane highway surrounded by water and mangroves. It has a Florida Keys feel as you leave the mainland in Homestead Florida.

We should explain that our Key Largo to Key West Florida Mile by Mile Guide uses Mile Markers to denote our location as we travel through the Keys. Each mile is marked by a green and white mile marker along the side of the road.Key Largo to Key West Mile by Mile Guide Map

For instance, you will find the Jewfish Creek Drawbridge at MM 107.2 as you enter Key Largo. That means it is 2/10s of a mile past MM 107. You are traveling on the famous Overseas Highway, otherwise known last US Route 1 that travels over 2000 miles up the coast of the United States all the way to Maine and southwest to Key West.

If you want a complete list of 133 Mile Markers in the Florida Keys, the post is here.

Key Largo Florida

At MM 106, you will see the Key Largo Chamber of Commerce, but we would rather point out a more interesting stop at MM104.1, the Caribbean Club. If you are thirsty again, you might make a stop here. Their claim to fame is the 1948 old movie Key Largo was partially filmed here. Humphrey Bogart may have shared a bar stool with you here.

On down the road at MM 104 is a better stop if you like tiki bars. Jimmy Johnson’s Big Chill is owned by the former Dallas coach serves some rather good food and has a huge tiki bar built over the water on the bayside.

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Reefhouse Resort & Marina, Key Largo

If you are looking for a place to stay before you complete your journey to Key West, the Reefhouse Resort & Marina at MM103.8 is excellent. The Reefhouse sunset bar, Breezer’s’ is a fabulous place for appetizers and watching the sun creep into the bay. The photo at the left was taken from the landing at Breezer’s.

A mile down the road is the entrance to John Pennekamp State Park. There are a plethora of state parks in Florida and several along your way to Key West. What makes this one different is that 75 square miles of it is underwater!

things you need when flying
Key Largo to Key West Mile by Mile Guide John Pennekamp Park
Part of the view of the Atlantic Ocean from John Pennekamp State park.

There are hiking trails and things to see on shore, but this park is made for snorkelers and divers. It’s worth the stop just to see the park’s information center with information about the reefs, diving and snorkeling in the Keys.

By the time you get to MM 100, you may be getting hungry. If so, look for Skippers Dockside on the oceanside. It is a little off the main road, but the food is better than average. Try the shrimp ceviche for a good Florida appetizer.

If lunch is on your mind, we have an excellent suggestion. Key Largo Fisheries is three or four blocks off the Overseas Highway at 1313 Ocean Bay Drive on the oceanside. You can expect the best grouper sandwich in the Florida Keys here.

Best Things To Do in Key Largo

Best Places To Stay in Key Largo

Tavernier Florida

Back on the road as you enter the next town, Tavernier, Florida about MM 93.6 is the Florida Keys Wild Bird Center. These people do great work rescuing birds who have been injured or entangled by fishing lines or nets. You can see numerous species in their rehab center. A kind donation would help preserve the Key’s wildlife.

We must insert a note about things to see and do. The drive along US 1 in the Keys has all kinds of attractions, sights, unique shops, and places you may want to see. The ones listed here are just a few recommendations along the way. It’s over 100 miles of scenery, waterfront views and sights along the road!

If we listed every interesting site and attraction, you would not get to Key West until the following week. Our select items to see and do are included.

Places to Stay in Islamorada Three Waters Resort
Three Waters Resort & Marina is one of our favorite places to stay in Islamorada.

Islamorada Florida

At MM 91 you begin the islands of Islamorada, often referred to as the “Village of Islands,”. It is a picturesque destination located in the Florida Keys known for its stunning natural beauty, world-class fishing, and laid-back island atmosphere. Situated approximately halfway between the cities of Miami and Key West, Islamorada is comprised of several islands, including Plantation Key, Windley Key, and Upper and Lower Matecumbe Keys.
Visitors to Islamorada enjoy the clear waters of the Atlantic Ocean and Florida Bay, where they can snorkel among vibrant coral reefs, dive to explore underwater shipwrecks, or simply relax on sandy beaches and soak up the sun. The area is also renowned as the “Sportfishing Capital of the World,” offering anglers the chance to reel in trophy catches such as sailfish, tarpon, and mahi-mahi.
In addition to its outdoor recreational opportunities, Islamorada boasts charming waterfront restaurants, eclectic shops, and art galleries, making it a beloved destination for travelers seeking a true Florida Keys experience.
Islamorada, the sport fishing capital of the world, is renowned for fishing grounds on both the bayside and oceanside of the Overseas Highway.
On the right side of the road (north) is Florida Bay. The Bay is an estuary for many saltwater species including tarpon, bonefish, mangrove snapper, redfish and snook.
On the left side of the road (south) is the Atlantic Ocean. A few miles offshore, fishermen from all over the world angle for sailfish, marlin, swordfish, wahoo, kingfish, grouper, and yellowtail snapper, to name a few of the available trophy fish.      
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Theater of the Sea, Islamorada a must visit Florida Keys stop.

At MM 84.2 you will see a big sign advertising the Theater of the Sea. Try to plan a visit. The Theater is just that – a tropical stage to interact with dolphins, sea lions, sea turtles, fish, sharks, stingrays, alligators, and birds.

The surroundings are a lush tropical setting for learning about Florida’s aquatic wildlife. This attraction is a great place for kids and adults to learn about the magnificent creatures of the sea.

After leaving the Theater of the Sea, just ¼ mile down the road is the Three Waters Resort & Marina (formerly the Post Card Inn). The reason Three Waters is significant is the huge fleet of fishing charter boats anchored at their very new marina and the spectacular views from their oceanfront accommodations.

A little history – while the Keys are known for their beauty and tropical weather, they also are known for their hurricanes.

In 2017, hurricane Irma hit this part of the Keys with a vengeance, destroying the Post Card Inn, now known as Three Waters Resort & Marina.

They remodeled, rebuilt, and restored the entire property. Thus, the new marina, new tiki bar, and an oceanfront hotel are worth spending a few hours or a few days. While the Three Waters Resort is one of our many favorites, there are dozens of marinas, hotels, resorts, restaurants, and boat dealers along your journey.

Best Things To Do in Islamorada Florida

Places To Stay in Islamorada

Over Seas Highway and The Bridges in the Keys

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Robbies at Islamorada where you can feed the tarpon.

There are about 1700 islands in the Keys and only 42 bridges. Obviously, most islands are not connected by bridges but are a vital part of the estuary of the Keys.

One very special bridge is heading over to Matecumbe Key, at MM 77. Just at the base of the far west end of the bridge, you will see a big sign that says ROBBIE’S. Robbie’s has become a major attraction for travelers in the Keys.

Thousands of people stop to hand feed tarpon that weighs more than most teenagers! Robbie’s also has a collection of little tent stores that sell everything from baubles to beads and everything from “Florida” but mostly made in China! 

This is an obligatory stop for the traveling first-time tourist (at least once) to feed the tarpon – if you have kids from 5 to 105, they will love it!

Key Largo to Key West mile by mile guide to Long Key State Park.
Long Key State Park

On down the road about ten miles, at MM 67.5, is the Long Key State Park. What a great place to hike, swim, camp or just stroll around the park. This is one of Florida’s many state parks that is unique because of the Atlantic Ocean view and the rustic grounds!

Places to stay in the florida keys Hawks Cay
The view from our room at the Hawks Cay Resort near Marathon.

Before you get tired of walking the ocean side, save some energy for one of the most famous family-oriented fishing resorts in the world – Hawks Cay Resort is at MM 61.1.

If you have ever watched any outdoor shows, Hawks Cay has been featured many times showing the bounty of nearby waters. This is a place for good old-fashioned family fun.

The resort has every possible saltwater activity, with the focus on sport fishing. The kids will have fun too with a huge pool, paddle boards and daily planned activities. The food is exceptional, so lunch on the way down the Keys is a great stop at their Angler & Ale restaurant.

In our opinion, Hawks Cay is the best family resort in the Florida Keys. Find out about rates here.

If you have kids, 5 to 95, The Dolphin Research Center is at MM 58.9. This place is for family fun and they do great work to preserve our dolphin population. They have a research center and a large contained area in Florida Bay where they rehab and train dolphins. The kids love it (and adults too).

Dolphin Research Center
Dolphin Research Center is a perfect place for children to learn about dolphin.

By the time you get to MM 53.5, you will be in Marathon, Florida. A city of about 8500 people stretching over several keys (islands), Marathon is considered halfway to Key West and you will see the obligatory businesses that are named “Halfway Bakery”, “Halfway Cleaners, etc.”.

One large development in Marathon is Key Colony Beach – a community with over 400 homes on a large peninsula out in the Atlantic Ocean. Few communities exist in the Keys of this size. A quick drive-through might be an interesting glimpse of how people live in this part of paradise!

Perhaps the most interesting place of all the attractions we discuss is at MM 50. Crane Point Museum and Nature Center is one of the coolest places to find out about the Florida Key’s history, nature, and early life in the islands – all in one

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Crane Point Museum and Nature Center

place! This is a privately operated attraction that offers exceptional opportunities to see and feel how it must have been to survive on this strip of land a couple hundred years ago. Of the nature trails on these 63 acres is one that leads to the Adderley House, a home built about 1903 from materials found around Vaca Key. It survives today to remind us of the hardships faced by our forefathers. Make time for a couple hours here – it’s worth the visit!

Marathon – Half Way To Mile Marker 0

We are about halfway to Key West as we enter Marathon at MM 59.9 and some of the best traveling is yet to come! In fact, you will see in the next three miles places like the Stuffed Pig, a great little local’s place for breakfast and lunch, and then you will start seeing signs like the 7 Mile Pizzeria and the 7 Mile Bar & Grill – heads up!

You are coming to the most spectacular views on your entire trip – The Seven Mile Bridge!

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Stunning Seven Mile Bridge some people consider the 8th wonder of the world.

The current Seven Mile Bridge was completed in 1982 and was one of the largest bridges in the world at that time. Alongside the new bridge, you will see the remnants of a railroad bridge Henry Flagler completed to Key West in 1912.

Built against unbelievable odds and at the cost of a major portion of his fortune from his Standard Oil investments, his railroad bridge helped to build much of the lower keys.

Flagler’s Bridge brought tourists and products to and from Key West leading to twenty-plus years of prosperity until the Great Labor Day Hurricane of 1935 destroyed the bridge structure. In the face of this destruction, the United States bought the right of way from the railroad and made a bridge for automobile traffic from the remaining structure.

The back story and history of the bridge are fascinating, but the real story is in the spectacular views on both sides of the bridge. Florida Bay on your right and the Atlantic Ocean on your left make keeping your eyes on the road nearly impossible.

You will see ships on the horizon in the Atlantic and bay fishermen looking for snook and tarpon in the shallows. The sparkling blueish-green water laps the pylons of the bridge along with the waves produced by the boat traffic underneath.

Sunrises and sunsets are breathtaking! Seven miles is a long way to travel on a bridge, but the time seems but a small few minutes you hate to see the end.

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                                 Bahia Honda State Park

After about 7 miles (imagine that, on the seven-mile bridge), the bridge comes to an end! By now you are awestruck with the beauty of the Florida Keys. But as hard as it is to imagine, at MM 36.8, get ready for a whole new close-up experience at Bahia Honda State Park.

This park has all the normal things state parks have, hiking, camping, swimming and more. But Bahia Honda offers a unique chance to get in the water and snorkel over the shallows to see another whole world beneath the surface of the Ocean.

This park is a family favorite due to the relatively shallow water and the ability to give children more than a cursory education about marine life. Relax and look around, your next adventure may just be underwater! Our family tells stories about their first encounters with the creatures of the sea, and their memories as they became acquainted with the saltwater environment at Bahia Honda.

Things To Do in Marathon Florida Keys

Places to Stay In Marathon

Big Pine Key and Key Deer

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                                           Key Deer

We must move on since you can almost taste the margaritas in Key West in an hour or so away. Across the bridge going south you will start seeing warnings about one of the strangest animals in the Keys – the Key Deer.

These dog size animals can be seen day or night on Big Pine Key. They look exactly like their full-sized white-tailed cousins in the woods of the Midwest, but are just about one-third the size. The Key Deer is an endangered species and lives only in this area. Their biggest enemy is man and the cars they drive. That is why speed limits are reduced and so you can keep a watchful eye out for the deer on the island.

Things To Do in Key West - No Name Pub
Dollar Bills Everywhere at No Name Pub


Key largo to key west a mile by mile guide No Name Pub
Hard to Find No Name Pub

While you are on Big Pine Key, and if you aren’t late for happy hour in Key West, you may want to set your GPS for another part of the island where the No Name Pub resides. This is a dive bar that has become an institution by selling the idea they are an old bar littered with thousands of dollar bills covering every imaginable inch of its walls.

I admit it is a sight to see, but the sight is short-lived once you get on down the road to Key West with dozens of quirky bars!

If you need to make a stop somewhere you may want to try Boondocks around MM 27 or Mangrove Mamas down the road, but you are now just about 20 minutes from Stock Island, which we consider part of Key West.

There are a few bars, a naval air station and a couple sights along the way, but few people can bring themselves to stop when they know the excitement of Key West lies just minutes ahead. 

Key Largo to Key West Mile by Mile Guide Comes To an End – But The Fun in Key West is Just Begining

Key West Map of Attractions
Locations of major places in Key West tourists need to know.

We have been to Key West at least 30 times. We haven’t always driven, but time allowing, we prefer the drive. I try to cross those 42 bridges at least a couple times annually. No matter how many times I look out that windshield at that final little bridge over a canal that separates Key West from Stock Island, my level of anticipation peaks at a new level.

We always wonder, what has changed? Something always changes. Is there a cruise ship in town? Not as many as there were when cruise ships were allowed to go to Cuba.  Any new bars? There are always new bars! Are any old favorites closed? There are always a few that close!

Change seems to only affect the fringes in the Conch Republic, the local’s name for Key West. Key West got the name Conch Republic when Key Westers got tired of Custom’s officers blocking traffic to the island. The government claimed

conch republic flag
The Conch Republic Had Their Own Flag

they were looking for illegal aliens (better known as immigrants), but Key West residents swore it was drugs they were looking for. So all in one day in 1982, the mayor and a few of his cohorts decided the city should secede from the United States! They declared a secession, called the new country the Conch Republic, marched to the naval base, declared war, surrendered immediately to the naval commander in charge, and subsequently demanded one million dollars in reparations.

We don’t think they got the money, but they did get the attention of the international media which caused enough pressure on officials to stop the roadblocks. That’s how the Conch Republic got its name!

The Attractions of Key West

The first thing you need to know is there are about 190 bars on this two-mile by four-mile island – that’s about four times the number of churches – and that’s Key West! Picking the best bars becomes an occupation for some residents of Key West and an obsession for visitors. You can break “best” down into categories – ones you have visited and ones you haven’t! We are not convinced there is a BAD bar on the island – just different. 

Then there are the great restaurants of Key West that serve some of the freshest seafood in the world. We highlight the best.

Finally, we give you a list of the attractions, things to see, and things to do in Key West. Some you can consider a must-do for first-timers and others can help to bring you back again. We start with the bars of Key West.

Tourists Must See Iconic Key West Bars 

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Sloppy Joe’s has entertainment most of the day.

There are bars in Key West that have a worldwide reputation and your friends, neighbors and relatives might think you were strange if you didn’t visit the basic watering holes! The List includes:

This is just a few of the many well-known hangouts in Key West. Some lesser-known places we like include Shots and Giggles behind Sloppy Joe’s, The Chart Room in the Pier House Hotel, and The Bull at Caroline Street and Duval Street.

The Best Restaurants in Key West

Casual Restaurants we love:

  • Blue Heaven – the best breakfast in Key West!
  • Pepe’s – one of the oldest restaurants in Key West serving great food.
  • Jack Flats – a local’s favorite on Duval. Sports bar with good food.
  • Hogfish Bar & Grill – On Stock Island, a must-visit bar on the wharf.

Upscale Restaurants we think have the best food in Key West:

We could list dozens more, but these are the basics in Key West you need to know about.

Things You Must Do in Key West – Must See In Key West for First-Timers 
Hemingway Home in Key West
Hemingway lived in this home on Whitehead Street while writing some of his literature.

In Key West there are attractions and then there are oddities that are just as entertaining and interesting as the ones plastered all over the travel brochures. We will start with the ones every tourist usually sees and then move on to some of the less publicized attractions.

The Top Ten Things You Must Do in Key West
The Bucket List Things To Do in Key West
Fort Jefferson Key West
Fort Jefferson in Key West is a must-take adventure.
More things to do in Key West may be on that second visit:
The Watersports of Key West Things To Do

With water total surrounding the island, there are many opportunities to engage in watersports that you may not be able to do anywhere else in the country. Our suggestions for water sport things to do in Key West include:

Best Places To Stay in Key West

There are well over 150 hotels in Key West and another 50 or more bed and breakfast lodgings. Choices range from big chain hotels to local independent owners. Prices are as varied as amenities.

Bed and Breakfast Recommendation

The Conch House Heritage Inn.  The Conch House is in Old Town and is roomy and clean according to friends who have stayed there. Of course, breakfast is offered in the mornings there as well.

Hotels in Key West We Can Recommend

There are an abundance of hotels on every part of the island. Every chain has a location somewhere in Key West. You can spend time looking on the travel sites or below are the ones we have stayed in that we recommend. (There are others we have stayed in we won’t be mentioning.)

Places to stay in Key West - pier House
One of our favorite places to stay in Key West is the Pier House.

The Pier House – We have stayed here many times. Right at the foot of Duval Street. The Chart Room, one of our favorite Bars, is located inside. They are on the high end from a cost standpoint. The location, clean rooms and waterside bar make it worthwhile. They also have a small private beach and a nice pool.

All the way to the other end of Duval Street (south) is the Casa Marina, part of the Hilton Curio group of hotels. This gracefully aging beauty was opened in 1920 as part of the Henry Flagler group of exclusive hotels he was building along the coast. This hotel is immaculate, exclusive, and right on the Atlantic Ocean with their own private beach. We would highly recommend this facility, but the cost may not be worth it if you plan to spend your days off the property.

The Galleon Resort and Marina is a perfect location if you are planning on taking advantage of the many water sports in Key West. The hotel is on the Gulf side of the Island and has a 90-slip boat marina. They also are a time-share resort, so availability may be limited at certain times of the year. They are priced about the same as the Pier House year-round.

Maragaritaville Resort Key West is now the Opal Resort
Opal Resort Key West

Opal Key Resort & Marina says on their website they were ranked as one of the top resorts in the Florida Keys! We are not sure about this lofty ranking, but Margaritaville has a great location right on the entrance to the Key West Harbor. The hotel is also next to Mallory Square, with their own shops on property near their marina. This is a good hotel and will be priced as the Pier House and others.

Right in the middle of Duval Street is the Crown Plaza La Concha Hotel. We haven’t stayed here in several years, but the hotel has been remodeled recently and should be better than our last visit. The La Concha is one of the tallest buildings in Key West and has a great view of the landscape. The hotel has a large wine bar on Duval and very comfortable lobby. Pricing is just slightly less than waterfront properties.

Final Thoughts on the Key Largo to Key West Florida Mile by Mile Guide

Everyone experiences the Florida Keys and Key West a little differently. Some are attracted to the unrivaled rich history. Others just scratch the surface for a quick get-away, much like taking Key West as nature’s Valium! Many people come for the water sports that abound in the clear blue waters. Some people love the almost 24-hour-a-day entertainment.

Annual events like the Hemingway lookalike contest, Fantasy Fest, Song Writer’s Festival, multiple fishing tournaments, food and wine festivals, Super Boat Championships, and many more bring thousands of visitors. The natural setting of islands between two oceans offers experiences not found anywhere else in the world.

For whatever reason you visit the Keys, you will always create memories that are hard to duplicate. Our Key Largo to Key West Guide hopefully added to your memorable trip though the Keys.

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