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An Incredible Road Trip Along the Overseas Highway from Miami to Key West and Back
One of my favorite kinds of trips to take is a long meandering road trip. Usually I prefer to bring our old vintage trailer, Rapunzel. But for this particular trip, we didn’t want to make the cross country drive with her in order to reach the starting point of Miami. (Also, the campgrounds in the Keys are really not that much less than staying at hotels during the busy spring and winter season) I did recently spoil myself with a new vintage trailer purchase though. I have always wanted to upgrade to a fiberglass camper but wasn’t planning to make that dream a reality anytime soon. However, our friend Dan was selling his sweet, completely tricked out 1979 Boler and I knew I could not let that opportunity pass me by. So who knows, maybe Gilda, our “new to me” old trailer will join us on the next road trip.
But let’s get back to our incredibly beautiful journey from Miami down to Key West and back! I know not everyone has the luxury of taking longer vacations due to their jobs, but definitely one perk of working for yourself is you can design your workload to allow longer trips. I definitely have to pace these kinds of trips and can’t do them every year but nothing beats being able to truly slow down and stay longer in each location. I think this is vital for a good road trip that leaves you feeling relaxed and not stressed or rushed.
Why road trip through the Florida Keys?
Quite simply, it’s one of America’s most beautiful road trips. As you drive along US Route 1 you’ll see mile after mile of turquoise blue and sometimes jewel green seas along both sides of the road. As you drive southwest along what is also known as the Overseas Highway, you’ll see the Atlantic ocean on your left and the Gulf of Mexico on your right. This highway covers 113 miles and you’ll travel over 42 bridges (including the famous seven mile bridge) sometimes without even realizing you are on a bridge. It was declared one of our nation’s “All American Roads” by the National Scenic Byways committee and in my opinion is well deserving of being a part of that program. It’s a place that I never gave much thought to until I saw the Netflix series Bloodline and thought it looked like it might be a nice place to visit someday. It’s also been on my mind that it might be a good idea to visit some of our nation’s vulnerable coastal areas that could see big changes due to climate change. Basically, I wanted to experience Key West before it gets decimated by another hurricane. Plus it boasts a warm tropical climate perfect for us Denverites trying to get a break from our winter wonderland in the Rockies for a little bit!
Stop 1: Welcome to Miami!
Am I the only one who can’t get that damn Will Smith song out of my head when first arriving in Miami? You know the one where the girls sing in that sultry voice “Welcome to Myyyyahmeeee”…. Btw, I just realized that we ate at that diner that is featured at the very beginning of the music video. It’s called the 11th Street Diner and you sit inside an old vintage art deco dining car.
Geoff and I have both been to Miami before but not together. I visited with my sisters briefly years ago and felt that I didn’t get to fully experience it as much as I wanted to while he got to go with his artist friend Ravi for Art Basel a couple of years ago. I decided that this time we’d stay our first couple of nights right in the heart of South Beach at the Whitelaw Hotel which is one of many gorgeous old buildings that Miami was smart enough to preserve. (Hot tip, the Whitelaw includes a free happy hour from 7-8 every night which they share with the hostel around the corner and was a fun place to chat with other travelers from all over).
Staying in South Beach
Wandering around South Beach I was struck by how beautiful their collection of art deco buildings is and marveled at the power of historic preservation. I don’t want to sidetrack too much into the pros and cons of historic preservation when it comes to cities but when done right it can really be a wonderful thing. I wish Denver would take a stronger stance on protection of some of its historic architecture. Surely there is some sort of happy medium between totally demolishing old buildings while being reasonable about the changes that property owners must make due to the passage of time?
While we were staying in South Beach we went on a little self guided tour of the various cool old art deco buildings and took some photos of some of my favorites below. I was also so completely stoked to roller skate along the sidewalk all up and down South Beach! We bought super cheap airfare and could only take one carryon each for this trip and I made sure to fit in my roller skates at the expense of everything else just so I could skate along South Beach. I was completely in heaven doing that. My only beef was that the sidewalk where you can bike and skate didn’t go further north so that we could go up and down the beach even longer. There are certain spots once you hit the boardwalk up at 24th street where you can’t take your bike (Geoff was on a Citibike while I was on my rollerskates) which left us to fend with traffic on Collins Ave which is not nearly as enjoyable. Still, skating around South Beach was a highlight on the trip for me!
The Road Trip Portion of the Trip Officially Begins….
We were smart enough to realize that it made zero sense to rent a car directly after landing at the airport since we knew parking in South Beach is an expensive nightmare and we wouldn’t be needing a car during our stay there anyway. So after a couple of nights at the Whitelaw Hotel we checked out and took a lyft back over to the airport area to pick up our car for the road trip portion of our trip.
On our way toward the Florida Keys we stopped at the Vizcaya Museum and Gardens which I had wanted to visit on my last trip but couldn’t fit in. It’s this crazy enormous old mansion estate place that I had in my head was done by some sort of eccentric local Miami rich dude but was actually just the summer estate for some rich dude from Chicago I believe. It was built right on the edge of the Bay of Biscayne and uses all of this soft coral rock in the gardens and is essentially this crazy beautiful Italian style estate in South Miami. It’s been a little roughed up by the ocean and the hurricanes throughout the years and has this cool decayed feel to it. It’s clearly a favorite photo spot to use judging by the insane amounts of photographers there with their quince clients. I wouldn’t mind doing a photography session there someday for sure!
Second part of our Florida Keys Road Trip continued with Key Largo
I don’t have many photos from this part of the trip because we were busy spending time in the water. We stayed at this great little hotel called Drift Hotel which still uses actual real metal keys to get into the rooms (I don’t know why, but I just have a soft spot in my heart for small, one story, old-school hotels that remind me of places we would stay when I was a kid in the 80s/90s). They have their own little beach area with canoes/kayaks and a covered dock with chairs for enjoying the sunset there. We definitely spent some time lounging around on the beach chairs reading and napping.
Don’t miss John Pennekamp Coral Reef State Park!
We made sure to spend a day at John Pennekamp Coral Reef State Park. The day we were there, the seas were a little rough for snorkeling so we opted to skip it and do a glass bottomed boat tour instead. I’ve never been on one before and it was nice to finally get out onto the water on our trip but I can’t say it beats actually being in the water snorkeling.
We also rented a double kayak and meandered through the mangroves hoping to spot a manatee (sadly, no manatee sightings for us on this trip). We did see some awesome birds and some sort of gross crabs crawling all over the mangroves, haha.
We made sure to stop in at the Carribbean Club which is this cute little dive bar where they filmed the movie Key Largo back in the day. We enjoyed our happy hour rum and coke while looking out at the Gulf of Mexico. We also stopped by the History of Diving museum at mm 83 on our way down to Key West. I personally have no desire to ever get into scuba diving because snorkeling is enough adventure for this girl who grew up landlocked in Colorado and has a completely reasonable fear of the ocean. (Also, have you ever seen Open Water?) But I did enjoy seeing some of the old techniques and weird contraptions that braver souls than I used to explore the depths of the sea.
Next stop, a full week in Key West!
I had read from many places that it’s easy to spend your entire trip in Key West. Even though I was a little skeptical that such a small island could keep us entertained for so long, I decided to book us at the Key West Bed and Breakfast in Old Town for a full week. A full week was pretty perfect for us lazy, easy going vacationers. I have photos and descriptions of some of the highlights from that below.
Key West Bed and Breakfast on Williams Street in Old Town
I really enjoyed staying at the Key West Bed and Breakfast. We stayed in the Bella room and it was full of natural light and had a comfy bed. I was kind of nervous about it being a shared bathroom at first, but the prices in Key West are not great for your pocketbook so we opted to go for it anyway. Guess what? It ended up being totally fine and I never felt like I was locked out for too long. Plus, they had this adorable white cat who just started coming around after Hurricane Irma who they named “Temporary.” Turns out “Tempy” wasn’t so temporary after all. I enjoyed petting her (only on her head, thank you very much) while enjoying that front porch of theirs. Another huge bonus is that they share the pool with the Island City House next door and there were some afternoons after biking and skating around all over town where we just had to have a cool pool to jump in. Speaking of skating, I would say if you are a seasoned skater it wasn’t so hard skating around town but know that it’s not a smooth sidewalk type of place all over. Luckily, I never ate shit although I was expecting to at any moment!
More Scenery from around Key West
Key West Butterfly and Nature Conservatory
We visited the Key West Butterfly and Nature Conservatory which was pretty and neat but maybe a tad overpriced, imo for the size of it. Plus it was a little crowded with not much seating or places to hang out quietly and sit still to see if you could get a butterfly to land on you.
Sebago All Day Adventure
I had it in my head that I really wanted to ride a banana boat and spend a day just swimming around and doing water stuff. So we decided to splurge on an all day trip with a company called Sebago which has a water sports and snorkeling package. They take you out to a place on the water where you can parasail, jetski, jump on a water trampoline, ride the banana boat and more. We weren’t really interested in the parasailing so we stayed and tried the jetskis. Turns out I kind of suck at driving those and learned that it’s a good thing that I’ve never spent tons of money to rent one for 20 min at a time as it would be a complete waste of money for me. However, I did like the banana boat and the trampoline. In fact, thinking back on how much fun we had on this day makes me want to block off a date this summer to head to WaterWorld here at home!
One of the other highlights of this trip for me ended up being with Sebago on this all day trip. They took us out to the reef and as soon as we arrived one of the tour operators was like “Oh yeah, I see a shark already.” If you had told me that this sentence would not completely freak me out before I went on this trip I would not have believed you. But he said it so calmly and like it was so cool that I didn’t even think twice about jumping into the water for some snorkel time. One of the other trip goers ended up pointing out the reef shark to me while we were in the water and I swam overhead looking down at it for a little bit. It was one of the coolest parts of the whole trip! Unfortunately, Geoff happened to be fiddling around with his mask and completely missed seeing the shark.
Key West Garden Club in the Martello Tower
On one of the days we biked and skated over to the thrift shop to see if there were any good deals on snorkel gear or swim shirts like there are sometimes good deals on winter gear in our mountain towns (alas, it was a total bust) so we spent the rest of the day just biking and skating. We tried to check out the covered roller hockey rink where the Key West Roller girls practice, but sadly, it was locked. However, we made our way over to this pier called the Edward B. Knight pier with this huge painted circle and that ended up being the most kick ass place in all of the Keys that I found for skating! It was windy which kept me cool and the ocean was crashing around on the sides making it a very unique roller skating experience for me!
That same day we also walked around enjoying the gardens of the Key West Garden Club which is located in the Martello Tower which is a National Historic site. I just want to put it out there that this would make a really pretty spot to get married in the Keys and whoever reads this and agrees should hire me to photograph their wedding there!
We also stopped to check out the Key West Nature Preserve. Turns out it was just this tiny little boardwalk that popped you out at the ocean and didn’t seem like much at first. But, we slowed down and just started observing over the sides of the boardwalk and ended up seeing a black snake hunt down a lizard or a mouse (it was so quick we couldn’t tell!) and steal it away.
Another tip I have is to avoid Mallory Square unless you like a touristy Pearl Street Mall style atmosphere with performers because it’s incredibly crowded and has nasty security people yelling at tourists who are just trying to watch the sunset. You may also avoid some wanker showing off with his dumb flyboard right in front of the pretty sunset you’re trying to enjoy. Instead, pay the reasonable fees to get into Fort Zachary Taylor State Park and watch the sunset there. We spent a whole day hanging in a hammock (provided by Key West Bed and Breakfast, thank you!) reading and snorkeling at that awesome place. The cafe there even has fairly decent nachos for a small concession stand.
Dry Tortugas National Park
Also, make sure to make reservations well in advance to get on the ferry for Dry Tortugas National Park. I had it on my calendar to make a reservation around 6 weeks before our trip but then got lazy and forgot to do it until around a month before and there was only one day left from the entire week with space on the ferry! We almost missed out despite booking a month in advance. The only other way to get there is via private boat or plane charter which is way more expensive.
Shout out to the tour guide named Hollywood who made military history come alive for me in a way that I’ve never experienced before. We snorkeled all around the fort and it was pretty sweet. My only complaint is that the park service doesn’t allow enough time for the ferry to be at Fort Jefferson. It takes 2 hours just to get there since it’s 70 miles west of Key West and they only allow 4 hours at the fort. I could have used an extra hour or two to explore and snorkel for a little longer. If you know you’re like me and appreciate more time, it might even be worth looking into camping out there although it sounds like those reservations get snatched up super fast a year in advance.
Restaurant and Bar Highlights
My favorite happy hour was probably at Bagatelle and The Sandbar. They both had happy hour and specials going on for more than just beer and well drinks which I appreciate. Also, Turtle Kraals was silly fun with their turtle races. Geoff was so close to winning the big money payout but ended up losing when he didn’t take the deal from the announcer running the show (we probably would have taken the deal offered, but we were leaving Key West the next morning and likely wouldn’t get to use a gift certificate so we went for it instead). Also, the Key Lime martinis at the White Tarpon are as good as they say they are!
Moving along to Marathon and Knight Key
Unfortunately, the week went by fast and we found ourselves needing to pack up and move along on our trip back to Miami. For this part of the trip I booked us at the Knights Key Inn which is just down the street from the Sunset Grille and Raw Bar. This ended up being such an awesome thing because that place is so fun! It’s located right at the north side of the 7 mile bridge and has this awesome pool area and tiki bar. Of course they serve ridiculously enormous tropical drinks and we definitely enjoyed one of their giant Miami Vice drinks. The food was great and this place had awesome sunset views too. Everything you’ve heard about the Florida Keys having the best sunsets is true!
Prior to sunset though, we ended up spending a day hanging out at Curry Hammock State Park where we rented a double kayak again and paddled our way under some incredibly tight mangrove trails and into a somewhat choppy sea around Deer Key and back. There were a ton of kite surfers at this location and it looks hella fun but also kind of terrifying. Marathon and Knights Key Inn was a really great last stop for us in the Florida Keys. The hotel had a nice size studio apartment style feel and I could see it being a really great option for a traveler who wants to stay in one spot for a while and have access to a kitchen for making their own meals. They also have a small pool which was nice for a day of cooling off and reading.
Last leg of the trip, one more night in Miami
On the last leg of our epic road trip we found ourselves with two full days and one night in Miami. The first day I was toying with visiting Jungle Island but then we determined that maybe just visiting the Miami Zoo might be a better option. Holy smokes, this zoo blows Denver’s zoo out of the water. (Sorry Denver Zoo, but I may be ruined for you now) We got to see so many cool animals and the zoo is incredibly large and pretty too. I would say it’s a worthwhile place to visit with or without kids. That night, we ended up staying at an Airbnb in the Wynwood area of Miami. I had heard that this place is cool and full of street art and painted wall murals which I wanted to wander around and check out.
That night we walked over to The Wynwood Yard where we chowed down on some delicious bao buns from Tum Bao Bao food truck as well as enjoyed an extended Monday night Happy Hour at the bar. We liked the variety of food options so much that we came back the next day for some more food from the Poutine truck.
The day we had to leave for Denver our flight was moved later and we ended up spending the entire day just wandering around Wynwood enjoying all of the fantastic murals and street art. I took tons of photos but just have some of my favorites below. (I did my best to try and find each of the artists to give them credit but I wasn’t always successful) Even with walking around this area all day I know that there were still a ton of places we didn’t even see because it’s so full of art. This day ended up being a cloudy day and it even rained on us. But, I had a little sunburn already so I totally didn’t mind a cooler cloudy day for walking around. When the rain got bad we stopped in at the first place we saw which was called “Growler USA” which is apparently a franchise. They had a bunch of Florida beers in here though and I tasted a bunch of local IPAs and found the bartenders there to be quite friendly. The bartender recommended that we stop over at J. Wakefield as well where I enjoyed the Hops 4 Teacher ipa along with some good tunes they were playing at the bar.
Sadly, we knew we needed to wind down our time in Miami and head out to return our car and head on out to the airport. But, it was a fantastic last day of one our best road trips so far!
I want to know, have you ever been to the Florida Keys or to Miami? What were your highlights?
Want to see more travel photography from other road trips I’ve done? Check out this spring time road trip through the deep south that my husband and I went on a few years ago!
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