The Ultimate Florida Keys Road Trip

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With swaying palm trees over white sand beaches, crystal clear turquoise waters, and strong Cuban coffee in abundance, it’s no wonder that The Florida Keys have often been called America’s Caribbean.

They may be only a couple of hours from Miami, but I truly felt like I was on a tropical getaway as we made our way through the islands. Strung together by a single highway, each of the Keys has its own character and charm, making it a perfect road trip destination. With an endless supply of beach activities, fascinating history, scrumptious cuisine and Southern charm, The Florida Keys really have something for everyone.

After picking up our rental car in Miami and purchasing a bottle of reef safe sunscreen, we were on our way to discover all this archipelago had to offer!


The Upper & Middle Keys

The Upper Keys mark the start of any Florida Keys road trip, and encompass the islands that are further north and closest to mainland Florida. For the first two nights of our trip, we stayed in Marathon, right in the middle of The Keys, making it an ideal base for exploring the area.



Where to Stay

Banana Bay Resort & Marina We spent two nights at this resort, and could have easily spent the whole day on the property. They have two tennis courts, a freshwater pool, complimentary bike rentals and a beautiful private marina . You can also book nearly any kind of water excursion at the resort.


Where to Eat

The Key Largo Conch House- This charming restaurant in Key largo is a perfect place to stop for lunch once you enter the Keys. It’s right off the main road, but the lush setting feels like a peaceful oasis. I had the fish tacos and they were delicious! We also heard they make amazing desserts, but were unfortunately way too full to try any.

The Hungry Tarpon Restaurant & Bar – You can’t leave the Upper Keys without stopping at Robbie’s Marina to feed the tarpon. Once we finished feeding the fish, we grabbed a table by the waterfront for a perfect sunset view.


What To Do:

The History of Diving Museum- Even as a non-diver, this museum was SO interesting (not to mention a welcome break from the afternoon heat). They have an incredible collection of diving helmets from all over the world, vintage diving equipment and an array of treasures found in the sea. I’ve always been terrified to try diving, but I may need to conquer that fear after this visit!

Bike across the Old Seven Mile Bridge– Visiting the Old 7 Mile Bridge is a must-do on any Florida Keys itinerary. Locally referred to as the Old 7, this bridge was originally built in early 1900, as part of the Over-Sea Railroad. Today, pedestrians and cyclists can enjoy a portion of the bridge, taking in the stunning views of turquoise water (we even saw an adorable sea turtle swimming along). There are bike rentals all over the islands, we rented ours from Bike Marathon Bike Rentals.

Visit Pigeon Key- The Old Seven Mile Bridge takes you right to Pigeon Key, a small island with a very rich history in the Keys. In the early 1900’s, over 400 workers lived on the island while building the Over-Sea Railroad. Today, 8 historic buildings remain, as well as a museum with stunning old photographs of what the island looked like at the time. I went in knowing nothing about Pigeon Key, and had no idea how fascinating our tour would be. The island is also great for snorkeling, so don’t forget to pack your snorkel mask for after the tour!

Bahia Honda State Park- If you’re driving down from Marathon to get to Key West, make sure you spend some time in this stunning park. The park has three gorgeous beaches that are great for laying out or snorkeling. There’s also a quick trail up to the Bahia Honda Railroad Bridge, with gorgeous views of the whole island.


Key West

The final stop of any Florida Keys road trip and home to the Southernmost point in the US, Key West really is a world of it’s own. From a host of historical sites and museums, to Caribbean looking beaches, and an insane amount of chickens roaming the streets, this small Southern island is full of surprises!


Where to Stay

The Perry Hotel- Located on Stock Island, just above Key West, this stunning property feels like a getaway in itself. Next to a marina and featuring two pools, three restaurants, and a gym, there’s almost no reason to leave. I was especially fond of the champagne greeting and that our terrace led straight to the pool. The hotel also offers complimentary shuttles back and forth from downtown Key West (the drive is less than 15 minutes). Parking in Key West is not very easy, or cheap, so I definitely recommend taking advantage of the shuttle during your stay!


Where to Eat

Half Shell Raw Bar– If you’re going to dinner at the Key West Historic Seaport, then this is your spot! The walls of the restaurant are covered in over 3,900 license plates left by past customers, so come prepared with your own if you want to be part of the fun! We were seated by the window and had a prime view of the sunset over the harbor while indulging in all the delicious seafood.  This is also where we had the most incredible key lime pie- the restaurant has used the same recipe since the 70’s!

Fisherman’s Café Key West- Located right by the seaport, this colorful takeaway window offers a handful of seats and delicious lunch items. I got the fish tacos and they were amazing (also, portions were huge)!

The Docks Stock Island- Just across the marina from The Perry, you’ll find one of the island’s newest restaurants. Not only is their industrial chic décor right up my alley, but the food was one of the best we had during our visit. All their seafood is sustainably sourced, and after speaking a bit with the owner, we could really tell how much he cared about providing quality seafood. The tuna Carpaccio and ceviche were delectable!

Blue Heaven- While the lush garden setting and scrumptious breakfast are already noteworthy, my favorite part of Blue heaven is its fun history.  Back in the day, Ernest Hemingway would come here to referee Friday night boxing matches! 

Cuban Coffee Queen- A popular choice, but for really good reason. They made our favorite Cuban coffee of the trip, so we quickly became regulars here!

What to Do

Dolphin Watch & Snorkel Tour- I’ve been on an unlucky streak with dolphin watching for years, but that finally ended in Key West! We went on a morning tour with Honest Eco Tours and saw over 10 dolphins at once! The experience was more magical than I could have ever imagined, and was made even better by the sincere enthusiasm from our Captain.

If you book a dolphin & snorkel tour, I highly recommend Honest Eco. They’re so committed to being an ethical eco-tourism company, that they even built the SQUID- the first Lithium-Ion hybrid Electric boat in the US.

The Ernest Hemingway Home and Museum- Not only is this historic house absolutely beautiful (I mean, talk about a dream garden), but the tour guides are also incredibly informative. Hemingway may not have been husband of the year, but his life made for some incredible storytelling. Ninety percent of the home contains his original furniture, and all 61 cats on the property were born there and are descendants of Hemingway’s original cat, Snow White. My favorite part was probably getting to visit Hemingway’s old study.

Sip & Sail Sunset Cruise- While the town and beaches around Key West are beautiful, there’s nothing like being out on the water when you’re there. We went on a sunset sail with Danger Charters, and it was absolutely perfect. They served an array of wines, delicious cheeses paired with various fruits and meats, and the whole crew had an amazing energy. Plus, we even spotted a few dolphins (our luck really has changed)!

Beach hop- With so many things to do in Key West, we almost forgot to leave time to indulge in those white sand beaches! Our two favorites were Smathers Beach (probably the most popular choice, known for its pristine sand and palm trees), and Fort Zachary Taylor State Park. Fort Zachary is located at the Southern part of Key West, and perfect for a day of snorkeling and picnicking on the beach.


When we began planning our Florida Keys road trip, I wasn’t sure if 5 days would be too long. In reality, we barely scratched the surface. In Key West alone, there are so many places on our list that we didn’t have a chance to visit. Thankfully, given how easy it is for us to get to The Keys from NYC, I have no doubts that we’ll be back soon.


*Our Florida Keys road trip was done in partnership with the Florida Keys & Key West tourism board. As always, all opinions are my own.

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