Miami to Key West Florida

Miami Beach to Key West: A Scenic Journey Filled with Adventure and Relaxation

A quick getaway or a long weekend trip to Florida is a popular choice for Midwesterners seeking some fun in the sun. However, if you’re looking for a unique twist to add to your vacation, filled with breathtaking scenery and unforgettable experiences, I highly recommend embarking on the drive from Miami to Key West.

I had the pleasure of exploring this route with my two young adult children, and over the course of four days, we experienced the best of air, land, and water. We started our journey with a direct flight from Milwaukee to Miami, where we rented a car at the Miami International airport and relied on Google Maps (without tolls) to guide us to our first destination: Miami Beach.

After arriving in Miami Beach, we were ready to dive into the local scene. One of the highlights of our trip was indulging in a delicious dinner at STK Steakhouse South Beach which is conveniently located on the infamous Colins Avenue in South Beach.  The area is trendy, hip and ideal for a nice dinner out.  We sampled the Chefs tasting and  the flavors of the meal truly set the tone for our adventure ahead. The presentation of each dish along with the ambiance of the restaurant was more than we expected. 

I planned our visit for January, just after the New Year and between Christmas Break and the start of the new college semester. This timing worked out perfectly, as we found reasonably priced accommodations at a charming boutique hotel that made us feel like locals. Situated just blocks away from the beach and Lincoln Road, we had easy access to Italian bakeries and coffee shops for takeaway treats, as we wasted no time in heading straight to the beach to kick off our first day. 

Exploring the shops on Lincoln Road and enjoying a delightful dinner on Ocean Boulevard were also within walking distance, making it a convenient and enjoyable  experience without the need  yet for our rented car. 

Before embarking on our  driving journey to Key West, we spent a few hours exploring Miami’s vibrant art and design scene.  Miami Design District and Wynwood District were filled with captivating artwork and unique design pieces, and it was a creative experience for any art-enthusiast.  

Throughout our adventure, we discovered one fantastic surprise that I truly recommend. If you’re a coffee lover, musician or car enthusiast, don’t miss out on the delightful experience of visiting Cars and Guitars at Walt Grace Vintage, where you can enjoy a  brewed cup of joe while surrounded by a unique collection of musical instruments and  collector automobiles. The guitar and amplifiers are displayed as if you are in a museum next to collector Corvette’s and automobiles as if you are at an indoor car show. This was probably the coolest “museum” of passion, design and product I have ever seen all fit into a coffee shop. This is definitely a must- see. 

We then set off for Key West, strategically timing our arrival to coincide with sunset, which we had the pleasure of witnessing from the iconic Southernmost Point of the United States. The drive was stunning. Incredibly picturesque as you drive over the water and bridge, the view of the “old” bridge on either side, the drive is long and short at the same time. It is just one of those experiences that is  

For seafood enthusiasts, The Fish House is an absolute must-visit. Located in Key Largo, it was our goal to stop quickly in as many of the Keys we could fit in on our drive. This restaurant was recommended to us by other visitors on their way driving into Key West and we were so glad to make that stop. Their fresh catches and flavorful dishes and the themed decor really set the tone for our vacation.  Try the Smoked Fish Dip and Shrimp and Scallop Scampi!  

Once in Key West, I highly recommend getting the Flex Pass, which allows you to explore the best attractions at your own pace. A couple of our personal favorites were  Butterfly Museum and Key West Trolley of the “Doomed” Ghost  and Graveyard Tour. If you know you know. 

No trip to Key West would be complete without visiting the legendary Hemingway Home and Museum.This historical gem offers a glimpse into the life of the esteemed writer, and the beautiful gardens and resident 27 toe-polydactyl cats. This is another must-do. Visit the gift shop and take home an Ernest Hemingway book for a gift of reading for yourself. His works are classics. 

You can not go to Key West without the experience of also going on the water. Because Key West is not a traditional beach-y community due to the Coral Reef, be sure to schedule time with organized water sports or as we did, a cruise. We chose a Sunset Sail cruise (included int he Flex Pass and booked theDanger Charters Sunset Cruise.  We boarded a Schooner on the island’s West Coast and set off to sail into the sunset. With hand-passed snacks aboard, the 2 hour excursion was a perfect way to end the excitement of discovery of Key West that day.  

Another noteworthy attraction is the Harry Truman Little White House, which provides insight into the former president’s retreat and serves as a fascinating piece of American history.

Indulging in a slice of Key Lime Pie is practically a rite of passage when in Key West. Be sure to visit Blond Giraffe Key Lime Pie Factory for a taste of this iconic Floridian dessert. For true seafood lovers seeking a true culinary delight, The Lobster Shack is a hidden gem.

As for our accommodations, we stayed at the Southernmost Beach Resort, which offered a perfect blend of comfort, style, and convenience. With its prime location as the only resort located closest to the “Southernmost“ tip   of the United States, the stunning ocean views and Key West charm of the entire property was the perfect place to really indulge in Key West ambiance. Blocks from the famous Duval Street everything is very walkable. However, having a car is best if you want to tour the whole island. Don’t forget to capture a selfie at the nearby the Southernmost tourist attraction, which is within walking distance from the resort 

On the drive back to Miami, we found ourselves with a few extra hours of time before our flight  so we decided to make a pit stop at the Margaritaville Resort Hollywood Beach. We booked a poolside seats through the Resort Day Pass or a “daycation” and took a leisurely stroll along the beach, savoring the last moments of our trip. 

The journey from Miami Beach to Key West is a captivating and unforgettable experience. From the vibrant energy of Miami Beach to the laid-back island vibes of Key West, this road trip offers a perfect blend of adventure, relaxation, and cultural exploration. So, whether you’re seeking a getaway, a fun-filled family vacation, or a solo travel trip, I encourage you to embark on this scenic drive and create memories that will last a lifetime.