The Florida Keys has everything an epic girls trip needs… Sun kissed oceans, pretty tropical drinks, amazing sunsets, and one gorgeous drive.
Michelle and I were super excited to meet in a tropical place that didn’t require a passport (being that we live in the U.S.) or needing to worry about any language barriers. We could get to the Florida Keys in a few hours and start enjoying our trip right away. That’s the best kind of vacation!
We drove from Miami to Key West and I’m going to walk you through our 4 day itinerary with all the stops we made and the information you need for your next vacation to the Florida Keys. Let’s dive in!
What are the Florida Keys?
The Florida Keys are not just one Key (island), but many Keys that form in a gentle Southwesterly arc from the Southern part of Florida.
The Keys are divided into five regions: Key Largo, Islamorada, Marathon, Big Pine and the Lower Keys, and Key West. All of which are connected by the Overseas Hwy, or Highway 1. A 113-mile Highway that starts at the Miami-Dade/Monroe County line and ends in Key West.
How to get to the Florida Keys
I need to tell you that renting a convertible to go down the Overseas Highway and the Seven-mile bridge is absolutely amazing.
Renting the Mustang was really reasonable for us, but the prices fluctuate based on the time of year that you go. For example, if you go during Spring Break (typically March) you may pay a pretty penny for a convertible.
One thing to note when getting your rental car, Florida has highway tolls. You can choose the option to pay all the toll costs ahead of time when you get the rental car. Here is more information on the tolls.
But seriously, any car will do if you are on a budget. I highly recommend that you do rent a car and fly into either Miami or Fort Lauderdale as the drive is one of the best parts of going to Key West. It’s about 3 hours and 40 minutes from Fort Lauderdale, or 3 hours and 10 minutes from Miami.
Alternatively, if you really don’t want to drive, you can fly right into the Key West airport.
Day one- Starting your Epic drive in the Florida Keys
Due to the late time in the day and not wanting to miss out on the drive in the daylight to Key West. We opted to stay at Holiday Inn in Key Largo the first night. Key Largo is only a one-hour drive away from Miami. Perfect amount of drive time after flying in the same day.
First night hotel at Holiday Inn in Key Largo
One of the cool things about the Holiday Inn is there is a marina right next door. In the Marina, The African Queen (boat from the movie African Queen, starring Humphrey Bogart and Audrey Hepburn) is docked here. Pretty neat to see.
We also stayed in Key Largo on the way back to Miami, more on this later in the post.
Dinner at Skippers dockside Key Largo
We chose to eat at Skippers Dockside for dinner as it’s walking distance from the Holiday Inn and has that perfect tropical ambience. Complete with a tiki bar and the nostalgic beachy decor to match.
We started with a tropical drink, ordered some peel and eat shrimp, and followed that up with some scrumptious shrimp tacos. Perfect start in tropical island eating if you ask me!
Things to do in Key Largo
Being that Key Largo is the self-proclaimed dive capital of the world, it’s the perfect place for some scuba diving or snorkeling. One of the cool things to see under water, besides the amazing fish and coral, is the Statue of the Christ of the Abyss. An underwater statue that is both neat and haunting to see. Plus, how often do you see an underwater statue?
You can find more information on the statue, and also dive and scuba information at John Pennekamp Coral Reef State Park.
Alternatively, if diving or snorkeling isn’t your thing, they have other options like a glass bottomed boat ride, or paddle boarding, kayaking and canoeing.
Day 2 – Continuing your drive down the Florida Keys
Breakfast at Doc’s Diner
Start the day with a local favorite for breakfast in Key Largo at Doc’s Diner. A hole in the wall diner with the perfect breakfast to start your epic drive. I loved the “tropical” add on option to my French toast. Bananas, shredded coconut, pecans, and powdered sugar. Delicious.
Time to start your drive!
First stop: Islamorada
When passing Islamorada, be sure to stop and say hi and take a selfie with Betsy the lobster! After your selfie, support the locals and do some shopping at the Rain Barrel Village right next door.
Also in Islamorada, is the History of Diving museum if you wanted to learn more about the origins of diving.
Or you could visit the Theater of the sea. Where you can watch sea life shows, visit exhibits, and you can even swim with the dolphins!
Second stop: Marathon
Arriving in Marathon, one of the first places you notice is the Turtle hospital. A fully functioning veterinary hospital that rescues, rehabs and releases injured turtles. The hospital also offers education on sea preservation. You can visit and take a tour of the facility and even feed the turtles.
Third Stop: Seven Mile Bridge
Next up is the beloved Seven Mile Bridge. There is a designated place to pull over and park so you can walk alongside the bridge on the pedestrian walkway and snap 1000 pictures.
Ahhhh. Just look at that pretty aqua water!
After we pulled ourselves away from looking at the dreamy water, we found some friends. See them?
Big Pine and the Lower Keys
After driving down the Seven Mile Bridge, you will go through Big Pine and the lower Keys. One of the most beautiful state parks resides here, Bahia Honda State Park. Be sure to make a stop here, even if it’s just to hang out on the beach for a little while.
One thing to watch for while you are in the lower keys, is the endangered Key deer. The interesting thing about the deer is that they are a subspecies of the white-tailed deer, but they are much smaller. They are miniature deer! And they only live in the Keys. Unfortunately, we never saw one. We definitely looked for them though!
Arriving in Key West- Where to stay
We chose to stay at Casa Marina resort due to the property having a sandy beach and hammocks. That’s one bummer about Key West, is unfortunately there’s not a whole lot of sandy beaches in the area.
We also liked this resort as it was a little farther from Duval Street and a peaceful reprieve from all the action.
Casa Marina has a sister resort, The Reach, which also has a sandy beach on their property and would be another great hotel option.
The Southernmost Beach Resort is another highly recommended place to stay. I love that the architecture of the resort is more cottage, beach house style.
Lady’s Tip: The resorts can vary widely on their prices day to day. I highly recommend using the flexible dates calendar directly on their website and finding the cheapest days possible. Keeping in mind that hurricane season is June – November. Prices may be cheaper, but it can be a gamble with the weather.
Casa Marina is a beautiful resort that has the ultimate relaxing outdoor space. From their outdoor Sun Sun restaurant, to swaying in their hammocks on the beach, you will be sedated into tropical bliss in no time.
We started off with a visit to the Sun Sun Restaurant for a mojito and to try the infamous conch fritters… They were surprisingly good!
Discovering Key West
The first thing you notice in Key West is the sound of the roosters clucking. Yes, roosters! They roam free around the town, ducking their little heads and clucking away. I tried to find a picture and I have none!? How is that possible? I’m sure it’s because they totally captivated my interest that I couldn’t be bothered to take a picture. Very neat to hear and see the roosters.
After walking a bit, we notice that the town is absolutely gorgeous. All these beautiful Victorian houses with the porches with swings on them, palm trees swaying. Just divine.
Southernmost Point in Key West
Our first stop was to the Southernmost point buoy. This point is the Southernmost point in the continental U.S.A. You can wait in line to get your picture with the buoy if you want, but we didn’t want to wait. We just quick snapped a few pictures from a distance.
Duval Street in Key West
One of the first bars that we stopped at on Duval Street was La te da. They had a d.j. and a dance hour and we joined in and danced our hearts out. These people were some of the happiest people I’ve ever seen. They were just free to be who they want to be and the only care they had in the world was dancing. It’s a moment that cheers me up whenever I think about it.
Next, we stopped at The Rum Bar for a drink called the painkiller… Yeah, painkiller is right. This drink has lots of booze in it and it’s sooooo good. Dangerous combo!
Our last stop of the night was at Martin’s for some tapas and wine.
Day 3 in Key West
We started the day with the hopes of riding in the trolley around town.
Little tip for you, those trolleys are jam packed full in the morning if it’s a cruise ship day. Especially if you are on the other side of town from where the ship docks, it’s going to take a while to get to you. You’ll have to decide if it’s worth the cost of using the trolley instead of walking. Uber is available as well.
Regardless, even though we waited over an hour, we hopped on the trolley when it finally came. It was a short-lived ride though, because we hopped off once we came up to the stop for the Ernest Hemingway house.
Ernest Hemingway house
We opted to do the tour at the The Ernest Hemingway house, and it was very informative. The glimpse into Ernest Hemingway’s life, seeing where he lived and worked, really brought him to life for us.
And the 6 toed cats… Now, I’m not a fan of cats (Michelle was in heaven) but I will say that the cats definitely made the place come alive. They were everywhere!
Mile Marker 0
There is something so satisfying about standing next to Mile marker 0. And just across the street is the other sign for the “start” of HWY 1 which also has Mile 0. Be sure to check them both out!
Museums in Key West
There are a few shipwreck and pirate museums as you get closer to Mallory Square. We visited the Shipwreck Museum, and it wasn’t really what we were hoping for. The Mel Fisher Maritime Museum has great reviews and would be worth checking out.
Mallory Square
Mallory Square is an outdoor area by the pier that hosts a sunset celebration every evening. There are magicians, fire jugglers, musicians, food vendors and pop up shops to make for lively night.
Be sure to come here about 2 hours before sunset to check out all the vendors and to save a spot to watch the sunset. Keep in mind that it’s popular and it does get pretty busy.
This is also where the cruise ship docs.
Just off to the right of Mallory Square is the Sunset Pier bar and eatery. We stopped here for some appetizers and drinks. Perfect place to hang out and watch the ships on the water.
Sloppy Joe’s Bar
Another fun bar close to the area is Sloppy Joe’s Bar. The live music and atmosphere is super fun. Grab a margarita and a pretzel and watch the band play.
Willie T’s Bar
Or a little further down Duval Street is Willie T’s bar, the mainly outdoor bar that has dollar bills stapled all around the bar.
Day 4- Last full day in the Florida Keys
We opted to drive back to Key Largo and stay here for our last night as there was a little fear of driving the full length of the Overseas Highway on the same day as our flight home.
To further explain, the Overseas Highway is only a 2-lane highway and traffic could be delayed for hours if there was an accident or some other unexpected issue that came up. We didn’t want to take that risk on our flight day and decided to stay in Key Largo for our last night.
Key Largo- Playa Largo Resort and Spa
We decided to splurge a little for our last night and we chose to stay at Playa Largo Resort & Spa. However, we didn’t go too crazy as we saved a little money by not having an ocean view room. This resort is absolutely beautiful. They even offered a welcome drink and met us by the car for valet and taking our luggage, which was a nice touch.
We had our last dinner in the resort at Las Olas restaurant for some delicious sushi and ceviche.
After dinner, be sure to hang out by the outdoor firepits on the beach to relax your night away.
Perfect end to a tropical girl’s trip in Key West
Being in the Florida Keys is a dream. If you are looking for a tropical vacation that has a gorgeous drive, palm trees, tropical drinks and amazing sunsets… The Florida Key’s has it all.
This tropical dream is even better with your bestie by your side, singing your hearts out in a convertible cruising down the Overseas Highway. Perfect way to make those memories!
If you liked this post, please share or save to your social media for future reference. Thanks for visiting!
