RoadTrippin: The Perfect 5-Day Road Trip Through The Florida Key
RoadTrippin
Rich in natural beauty, history and home to the only barrier reef in North America, the Florida Keys is a unique place. With a sort of sub-culture of its own, its a destination in its own right, and the best way to explore the keys is by taking a road trip through the small towns and sites and really immersing yourself in it all.
What to know before your visit
As mentioned, the Florida Keys are set amongst the only barrier reef in North America and there is a big focus on sustainability and preservation of the reef and diverse wildlife that calls it home. Reef friendly sunscreen is part of the culture in the Keys, and is an easy way you too can enjoy this unique setting while helping to preserve it. Reef-friendly sunscreen is easy to find at your local pharmacy or on Amazon.
Day 1: Drive to Islamorada
There are many different ways and destinations to start your journey from, with Miami being the closest and most convenient airport to fly into. As we were temporarily living in Naples, Florida, we embarked on the 3-hour drive to Islamorada late morning.
We arrive in Islamorada early afternoon and first thing on the agenda was lunch, so we pulled into Morada Bay Beach Cafe, but not by chance though, as I had my eye on this place. It has a sort of St. Tropez vibe going for it given its French owners, with a laid-back chic atmosphere set on a massive colourful beach front property.
Many hotels had minimum night requirements given we were travelling during COVID-19, so we didn’t have anything booked and pulled into a few places to take a look around.
Based on my investigative research, and yes we drove around and poked our heads in everywhere, I highly suggest The Moorings Village, for the most luxury and intimate stay. The resort is made up of cottage style rooms with an immaculate beachfront property. The Postcard Inn, is on the outskirts of the town, but is famous for its tiki bar and is a more upscale and modern option compared to most in the area. Cheeca Lodge & Spa is touted for being the best resort in Islamorada, although it seemed a bit dated to me, however chocked full of amenities. We ended up at Amara Cay Resort for the night, which was a cheap and cheerful option with a large pool area and beachfront and fantastic staff.
No hotel is really walking distance to anything as Islamorada itself isn’t a pedestrian sort of place so you will be driving, ubering or shuttling anywhere anyway so don’t let proximity deter you. And yes, I said shuttling as all hotels run their own shuttle to make it easy for guests to get around – genius right!
Islamorada is most famous for fishing. You can easily rent fishing rods most places with a dock or pier and most the hotels offer free access to such equipment and docks to fish from. If you want to arrange for a private fishing charter, here is your opportunity!
We enjoyed some afternoon sun at the hotel and then, with fish in mind, headed for sundowners at Lorelei Restaurant & Cabana Bar, situated perfectly on the gulf side of the island providing for picturesque sunsets, with a casual yet great seafood menu and live music that carries on late into the night. For a more upscale evening with an equally perfect vantage point for sunset, head to Pierre’s at Morada Bay, its perfection.
Day 2: Islamorada to Key West
There is plenty to do between Islamorada and Key West so we got up early and hit the road, bathing suits on. We made a quick takeaway stop at Midway Cafe & Coffee Bar for their famous egg sandwich on a croissant and iced coffees. Verdict – greasy but delicious, totally worth all the calories!
Our first stop was at the southern point of Lower Matecumbe Key at Anne’s Beach – there was free parking and a newly built boardwalk with little huts for bbq-ing or hanging out for the day, but the beach is shallow, not well maintained and was anticlimactic to be honest.
So, a little disappointed, we hopped in the car and carried on about 30 minutes down the road to Marathon where we stopped at Key Fisheries for their much acclaimed lobster rueben, which was perfection and easily feeds two! As you sit at the outdoor seating provided you can get a good look at all the fish and sharks that hover around the pier, probably due to the fish feed available for tourists to throw in the water, but it’s cool because you get a pretty up close and personal experience with tarpon, sharks etc.
We departed Marathon fairly excited as up next was the famous Seven Mile Bridge, stretching 7 miles over the turquoise water and something I was very excited for. The highlight here is the fact that as you drive along this newer bridge you can see the old bridge that was often referred to as the ‘eighth wonder of the world’ for being constructed over such a large open body of water with a sandy bottom and known for its two dangerously narrow lanes. I know its history but it was somewhat of an eyesore as it wasn’t what I had built up in my head, for some reason I thought we would be driving the one and only old bridge!
Shortly after we touched land on the other, we arrived at Bahia Honda State Park, known for its beaches, so I was hoping that this was going to me a much better stop than Anne’s beach. There was an $8 car entrance fee, but at least it guarantees parking and bathrooms!
Bahia Honda has three different beaches, kind of all unique in their own way. There is Calusa beach, which you can actually see from the highway south of the park entrance, as its tucked into an inlet at the base of the old railroad bridge. Calusa seemed to be the much busier beach, filled with families, most likely due ot the proximity to the camp ground in the park and the fact there are washrooms and a snack bar there. We spent our time at Loggerhead beach, located right off the parking lot when you first pull in. Loggerhead beach is essentially just a large sandbar with crystal clear water. People were just hanging out sitting on the sandbar enjoying the view of the Atlantic. As its so shallow, the water i swarm and inviting and the sand is powdery and white, quite beautiful to be honest. Up the Atlantic coast just north of Loggerhead is Sandspur Beach, which is supposed to be less crowded (as its relatively the least easy beach to access) and absolutely stunning however we did not make it there.
#TravelTip – It is very important to know that in the summer months, the whole Atlantic experiences a massive influx of seaweed. I have personally seen it all the way down the coast in Belize, Tulum, Holbox and now here in the Keys. Apparently its a function of warming waters caused by climate change, and it definitely makes the beaches look less appealing and ruins those pristine white sand beach photos you see online so just be aware. At hotels you will find they are proactive in getting rid of it, but in state parks and public beaches, that’s obviously not the case.
And I digress! After leaving Bahia Honda, we continued south about 8 minutes to Big Pine Key, our next stop. I did a lot of planning for this trip but nothing I read really indicated to stop here, but luckily we got an insider tip from a neighbor that stopped to chat with us as we were packing our car back in Naples. #HotTip – He told us to visit No Name Pub on Big Pine Key, which was a 10min diversion from the highway. He said that not only is the pub sort of famous, but that along the way we would be sure to see some Key deer. Well Frank, you did not disappoint with this tip, these adorable little Key deer just wander the streets and are not scared of humans or cars – they will come and eat right out of your hand!
After downing two glasses of the most delicious sangria I have ever had at the No Name Pub, we finally set out on the final 45min stretch to Key West. We decided to stay at the Parrot Key Hotel & Villas, a bit outside the core of Key West, but located on the water in a lush and quaint setting. I wanted to get the feel for both a resort type and a more city immersed property on the island so we only checked-in for one night. The hotel itself is quite new, sleek and chic, and with two pools and a waterfront beach type area and pier (you cant go in the water) it has an overall intimate feel!. The rooms were large and while cute were fairly basic, but every room has its own balcony with chairs.
With no real dinner option at the hotel, we headed into town to eat and a look around. Even during a pandemic, Key West, specifically Duval Street, has a sort of spring break feel, people of all ages are spilled out all over the sidewalks and streets drinking and hopping from one place to another. Open-air restaurants and bars with front patios, playing loud music, creating a very energetic environment. We ate at Nine One Five set in a century old Victorian style home with a wrap around terrace overlooking Duval Street. The food and service was fantastic and to note all their pastas are made in-house, definitely one of the nicer places along the strip but still a casual, relaxed experience. Oh and they had a great wine list as well!
Day 3: Key West
We got up in the morning and took the short drive to Cuban Coffee Queen. Not only is their coffee fantastic, they offer a great Cuban take on breakfast with their Key Wester sandwich, that ordered with the mojo pork on it is literally one of the best sandwiches I have had. You can probably split one but they are so good you will wished you order two for yourself.
We then set off to Key West hotel number 2, the newly debuted Kimpton Key West, a series of 5 hotels all unique in their own ways, yet all consistent in design and focus on proving a true boutique 5-start hotel experience, the only true luxury hotel in Key West. We stayed at Winslow’s Bungalows and the property was stunningly lush, and really hits the mark of true traditional vintage Floridian style with an extremely modern, sophisticated flare. The rooms are decorated in a bright and airy manner and the furniture is so unique and customized to fit the personality of the hotel with top of the line products and each room has its own outdoor space, some more private than others though. The hotel has 2 pools and numerous little nooks for guests to enjoy some quiet time in a bustling area.
We took some time to relax by the pool and then headed out for a little self-guided walking tour of the town. Just a short walk to the south you will easily stumble upon the lighthouse, Hemmingway’s House and the most southernmost point of the USA buoy. The buoy is a quick photo op, Hemingway’s House offers 30 minute tours for about $16/pp, and the lighthouse has a $12 admission fee. We enjoyed them from a distance and then made our way up Duval Street. During the day the restaurants and bars that line the streets were packed with people, sidewalks full of tourists hopping from one place to another, so many great boutiques as well so be prepared for some shopping.
Mallory Square is known for its famous nightly sunset celebration which includes buskers, musicians, artists, food vendors and a beautiful vantage point to watch the sunset over the lowest point in the USA. Given it was COVID times, that celebration was not happening unfortunately. But what I did learn is that its a giant public square where people just hang out. There is no designating sitting and there are no cafes or anything lining the square so head there with this knowledge in mind. An alternative, if you so choose, is to head to the Rooftop Cafe’s second floor patio to enjoy a more relaxing sunset experience. I like enjoying my sunsets sitting with a drink in hand, maybe I am just a bit lazy!
We then stumbled across a great patio with live music called Hank’s Hair of the Dog Saloon which is apparently an establishment considering the love and devotion locals show towards this place. It also houses Garbo’s Grill, a sort of famous food truck, serving absolutely amazing tacos, the hype is real and the Korean BBQ tacos are a MUST! This place is full of locals and tourists alike and the talent is spectacular you may just spend the whole night here.
Day 4: Key West to Key Largo
We woke up and headed to Pepe’s for breakfast, its an institution apparently so there was a bit of a wait. It was somewhat like an eclectic diner/cafe but the food was great! We headed back to the hotel packed up early and headed north to Key Largo for a few days of rest and relaxation.
On the way we stopped for lunch at Lazy Days, a super casual beach front restaurant that almost looks sort of like it took over an abandoned building, but the fish sandwich is phenomenal, the beer is cold and the homemade coleslaw is the best in the Keys! I still dream of this sandwich, but we all know I Live for food so sounds about right.
We finally made our way north and checked into Baker’s Cay Resort, a relatively new addition to the Curio Collection by Hilton and selected by yours truly for it’s beachfront location. Although it’s manmade, Baker’s Cay has a lovely proper beach, 2 actually, ( a rarity in all of the Florida Keys FYI) with beautiful Gulf of Mexico views. (see my full review of the property here).
I consider sunset an attraction so heading off the resort, about 10 minutes north, to Snook’s Bayside Restaurant, which is perfectly situated offering unobstructed and unparalleled sunset views. I have never seen a better sunset than the one I saw here and I have seen A LOT. While the food was good, the crowd seems to dwindle a bit post sunset and many onlookers head to Snappers for dinner for its live music and well regarded menu, a migration I support and highly suggest.
Day 5: Key Largo
Taking a few days in Key Largo was strategic as per its proximity to John Pennekamp Coral Reef State Park, (just 15 mins) which offers a variety of activities to visitors including hiking, snorkeling, diving, fishing, kayaking, canoeing or just relaxing on the beach.
If you are more adventurous like my husband this is the perfect opportunity to go diving. Key largo is a preferred departing point for diving given the proximity to a variety of coral reefs and shipwrecks. The resort suggested he use Rainbow Reef Dive Center which was a great option with nice boats, helpful and informative instructors and quality gear. (so I was told)
After out morning of separate adventures we spent a bit more time relaxing on the beach and then made our way home happy we ticked off something we had been wanting to do for a while.
Overall the keys are for activities, eating, exploring and soaking up the culture of it all. Its more about ‘doing’ than ‘seeing’.
#HOTTIP – if you are passing by Tavernier in the morning or around lunch time a stop at Cafe Moka for their coffee (I would say its almost the best in the Keys) and either one of their tomato, pesto and cheese croissants or one of their homemade sandwiches on fresh French baguettes.
Hope this guides and inspires you!