abrunettetravels Last updated on August 30th, 2023 at 04:06 pm
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Chris and I have been to Key West several times and like many people, we thought this was the Keys. It wasn’t until moving down to Florida that we decided to make the drive down. We knew we wanted to take our time and enjoy the drive. Chris kept telling me, the journey is the destination. Here you will find a guide of 15 places to visit to make this the ultimate road trip from Key Largo to Key West.
Key Largo
The first town of the Florida Keys and the first to be reached by the Overseas Highway. Because the islands are narrow, all of the stops, except for Key West are located at their specific mile marker.
1. Caribbean Club
This is a must stop for fans of the movie Key Largo. Waterfront views, great drinks and movie memorabilia only add to the charm of this club that was used during the filming of the movie. Depending on your timing, this is an excellent place to watch a beautiful Keys sunset.
Location- Mile marker 104.1
2. African Queen
Humphrey Bogart fans will delight in having another piece of movie history to visit. Imagine being transported back to 1951 when the movie was filmed as you step aboard this iconic vessel. Next, you will sit back and relax on a 90 minute cruise down the Port Lago Canals. Cruises depart from the Marina del Mar. Check the website for booking information.
Location- 527 Caribbean Drive
Islamorada
The sport fishing capital of the world. Islamorada also encompasses 6 of the Florida Keys. It also has several stops on our road trip from Key Largo to Key West. The laid back vibe and great restaurants and bars makes this our favorite place to stay.
3. The Blonde Giraffe
The search for the best Key Lime pie ends here. Trust me, if you like this creamy, tart dessert, you need to visit the Blonde Giraffe. As you gaze over the perfectly cut pieces of pie, you will have the difficult task of choosing one. We chose Key Lime with whipped cream and chocolate Key Lime. After making our selections, we wandered out to the beautiful garden behind the shop. Enjoy your pie and reflect on the satisfaction of finding the best Key Lime pie.
Location- Mile marker 92.2
4. History of Diving Museum
Diving is one of the most popular activities in the Keys, so it’s no wonder the History of Diving Museum is located in Islamorada. You will discover the world’s largest collection of diving equipment and memorabilia that spans more than 30 countries. Additionally, you will learn about the museum’s founders, Drs. Joe and Sally Bauer. The museum features special exhibits and presentations so make sure to visit their website for an up to date schedule.
Location- Mile marker 83
5. Rain Barrel Village
Two words used to describe the Keys are funky and artsy. Rain Barrel Village embodies both of those. Here you will find an eclectic assortment of craft, art and souvenirs. But, don’t be deceived by the building, there is a sprawling area in the back with a variety of unique shops. Rain Barrel Village is easy to spot–just look for Betsy, the 30′ tall lobster standing at the entrance. She happens to be the 2nd most photographed spot in the Keys.
Location- Mile marker 86.7
6. Islamorada Brewing
Craft beer lovers, rejoice! There are 2 choices for local breweries in Islamorada. As you enter Islamorada Brewing Company, you order at the bar and then proceed to the outdoor beer garden to enjoy beer. Having trouble deciding which beer to try? Get a flight! This is the perfect way to sample their beer. Not a beer fan? Fortunately, Islamorada offers cocktail flights. If all of this drinking is making you hungry, order from the food truck located in their beer garden to satisfy your food cravings. Lastly, be sure to check their website for the live music schedule.
Location- Mile marker 82
7. Morada Bay
The Beach Cafe at Morada Bay embodies everything about the Keys lifestyle. It is Laid back, yet beautiful and tropical vibe creates a vacation vibe from the moment you enter. We had dinner here our first night and are glad we did. Arriving in time for a pre-dinner drink while enjoying a beautiful sunset was the perfect start to our visit. We opted for the fish tacos, and they were wonderful. A word of caution-the pepper on top is HOT!
Location- Mile marker 81.6
8. Florida Keys Brewing Company
The second brewery you will come to, the Florida Keys Brewing Co. is the Upper Keys first microbrewery. Additionally, it is located across the street from Morada Bay. Considering its location, it is a perfect stop either before or after dinner. Similar to Islamorada Brewing Company, you can choose your favorite pint or flight and head out to the beer garden. For those wanting food, there is a food truck located out front 7 days a week. Lastly, make sure to check out their website for live music and events.
Location- Mile marker 81.6
9. Robbie’s of Islamorada
Long considered a “must visit” in the Keys, Robbie’s offers a little bit of everything. Whether you ae wanting to rent a boat, take a jet ski tour, relax on a sunset cruise or feed one of the 100’s of massive Tarpons, it is all available at Robbie’s. Because of this, you will want to add it to your list of places to visit. Not feeling brave enough to risk your arm with the Tarpons? No problem! You can still experience it by watching others. Either way, it is a site to behold. Robbie’s website has a detailed menu of the activities available.
Location- Mile marker 77.5
Marathon
Marathon is a city that spreads over 7 Keys. It is also the area where Loggerhead turtles nest, thus one of the reasons the turtle hospital is located here.
10. Turtle Hospital
Everyone has their own list of what is a “must see.” For us, the turtle hospital is high on that list. Because this is a working hospital, you must go on one of their guided tours. Our tour lasted 90 minutes and was informative and fun. Of course, the best part is getting to visit all of their sea turtles. You will get an up-close view of these beautiful creatures. Just remember to keep your hands back as touching them isn’t allowed. Reservations can be made online. We made ours the same day, but the tours can fill up.
Location- Mile marker 48.5
If you enjoy sea turtles and their habitat, you might be interested in this.
11. 7 Mile Bridge
Beginning in Marathon, the 7 Mile Bridge will connect you to the Lower Keys. Interestingly, the drive isn’t just about the bridge you are driving across, but the structures that came before it. At the same time you are enjoying the water, sea birds, boats and swaying palms, you can also get a view of the old bridge. What originally was a railroad bridge that was completed in 1912 and destroyed by a Labor Day hurricane in 1935. You can see parts of the bridge that still stands today. If you are so inclined, read about the history of the 7 Mile Bridge. You will be amazed at the tenacity it took to make it happen and the sheer engineering genius. You will also be saddened by its untimely demise.
Key West
The most well known of the Keys. It is known more its coral reefs, diving and snorkeling than beach vacations. It is also the only Key that has a cruise port, thus the cruise crowds follow.
12. Ernest Hemingway House
Every old home has a story and Hemingway’s has a novel. Even if you aren’t familiar with his literary works, the Hemingway House is worth visiting. Your tour guide will spill some of the details of Hemmingway’s tumultuous life. As an added bonus, 90% of the furniture and artifacts are original, down to the flooring, which was imported from France. You can almost hear his typewriter snapping each key when you visit his office. If after visiting you get the urge to read one of his novels, you can purchase one at the bookstore located on the property. Chris bought The Sun Also Rises–one of Hemingway’s books he hasn’t read. Lastly, if you are a cat lover, you will surely feel a connection to Ernest. He loved cats and had several over the years. There are still cats on the property today. In fact, there were 57 when we visited.
Location- 907 Whitehead Street
13. Truman Little White House
For those who enjoy history, The Truman Little White House is a fun and informative visit. Even if you don’t consider yourself a history buff, it’s worth going by the grounds. A ticket is not required to walk the grounds, visit the gift shop or see the presidential limousine. Until visiting, I had no idea that official duties were conducted in Key West or the number of politicians and entrepreneurs who visited here. At the very least, it is worth a quick visit for the historic architecture and grounds.
Location- 111 Front Street
14. Southernmost Point
It almost seems unthinkable to visit Key West and not visit the southernmost point. In fact, it is the most photographed spot in the Keys. Quite honestly, there isn’t much to see other than the iconic red, black and yellow buoy with the “90 miles to Cuba” famously written across it. Still, it’s a great place to see when you are in Key West and you don’t want to miss out on that photo do you?
Location- 1400 Whitehead Street
15. Mallory Square
Last, but certainly not least, Mallory Square. This is the perfect ending for your road trip from Key Largo to Key West. Just like the southernmost point, it’s hard to imagine going to Key West and not watching a sunset from Mallory Square. The area comes alive as the sun starts to set as crowds of people slowly arrive to watch the colorful display. What is a more perfect way to end your day than casually strolling and admiring the local craft vendors, grabbing something to eat from one of the food trucks and choosing the perfect spot to watch the clear blue sky turn stunning shades of pink, purple and orange? I don’t think there is one.
Location- 420 Wall Street
Conclusion
I hope you enjoy this list for the ultimate road trip from Key Largo to Key West as much as Chris and I did. I also encourage you to look for other sites you think look like fun. There is so much to see and do in the Keys. I would love to hear about what your favorites are.
If you are planning a Florida Keys roadtrip and are looking for hotel options, try here for available resorts.
