Taking the iconic US Highway 1 road trip in the off-season from Miami through the Florida Keys ending on Key West.
Ed and I have always enjoyed traveling and taking vacations both here in the U.S. and abroad. When I first met him, he owned a timeshare in Florida. At the time, I dismissed it and thought we would never use it. After taking a few trips to timeshare destinations, my thinking evolved. I quickly realized it was a pretty nice thing as long as we took advantage of all it could offer.
We have used and enjoyed it for 35 years. Since starting the blog 10 years ago, I have shared photos from trips where we stayed in a thatched roof cottage in Ireland, an oceanfront villa on the Riviera Maya, and two other Mexican vacations.
What To Do On a Road Trip Vacation Through the Florida Keys
In early December, Ed and I celebrated our 35th wedding anniversary and decided to take a weeklong vacation to the Florida Keys to celebrate. Neither Ed or I had ever been and have had it on our bucket list of travel destinations.
What we were looking forward to the most about the trip was taking the iconic drive along the Overseas Highway (U.S. Highway 1).
The highway starts in Miami and passes through some 40+ islands before reaching Key West. The journey time is approximately 4 hours. We didn’t drive it all in one day, but spent a week exploring the chain of keys.
Road Trip Tip: Ed’s car is a convertible. If you don’t have one, I would highly recommend renting one in Miami to thoroughly enjoy the scenic drive and beautiful weather.
Listening to Yacht Rock, Channel 4 on Sirius Radio with the top down on the car made the scenic drives we took every day to explore all the keys, delightful. Stopping along the way to take photos, as well as for local cafes, bars, and restaurants were made even sweeter by a margarita or two and a shared slice of Key Lime Pie. :-)
Where We Stayed on the Florida Keys?
The Keys themselves are broken into three categories: the Upper Keys, Middle Keys, and Lower Keys.
After doing online research and talking with friends who know the Keys well, we chose to stay on Marathon at The SkipJack Resort and Marina. It is in the lower middle of the chain.
The resort was recently remodeled after being damaged during Hurricane Irma. As you can see the parking lot was empty as the first week in December is in the off-season.
We stayed on the 4th floor with a view out to the marina.
Our suite had been recently redecorated with a modern farmhouse vibe. I liked the bathroom vanity with pull out drawers under the sink instead of cabinet doors. The tile floor throughout the suite looked like wood planking. I didn’t get a photo of the kitchen and living area, but it was all brand new, white, bright and nice.
Staying on Marathon allowed us to travel to the other keys each day in either direction – west or east without having a long drive on any one day. We also liked that Marathon was less touristy and more residential…
… off the beaten path, laid back and 2 miles to Sombrero Beach where we spent a lot of time reading and relaxing.
We also took a fascinating and educational tour of the Marathon Sea Turtle Hospital.
Why December is a Great Month to Visit the Florida Keys
The weather is generally sunny and warm, with low humidity in late November and early December. Hurricane season is over. In the high season in the spring and early summer, it is too crowded and gets very hot and humid. In the off-season of early December there were no crowds. Even in Key West, we were seated right away at restaurants. No lines for any of the tours, we got right into everything we wanted to do or see.
During the day, the temps were in the mid 70’s. It did cool down in the evening and I wore a lightweight jacket. We went to the beach a few times wearing bathing suits. Although the water was a little too cold for my liking to go swimming, there were people in the water having a good time.
One thing I wasn’t expecting to see EVERYWHERE and on every key were power lines. I have gotten so used to never seeing them on the mainland since they are buried. It was hard to take photos without power lines in them. In some spots along the highway we could hear them buzzing.
Are Florida Keys Back to Normal After Hurricane Irma?
We learned that after Hurricane Irma, many of the resorts and businesses on the keys still have damage and are in the process of reconstruction. We saw damage in areas, but it did not negatively affect our vacation at all.
What Are The Best Waterfront Restaurants On the Florida Keys?
We ate dinner out every night. Our resort had a continental breakfast every morning. Then we grabbed sandwiches and drinks from the nearby supermarket to cover lunch for the days we spent on the beach.
Since Ed and I are all about water views, we only ate at restaurants that were on the water, but there is no shortage of places to eat on any of the keys. We asked the concierge at our resort for a few recommendations. Since we were there in the off-season we walked right into every restaurant without the need of a reservation.
Our favorite restaurant to eat dinner and enjoy watching the sunset was not far from our resort on Marathon. It was called the The Sunset Grille 7 & Rawbar. We ate dinner there 3 nights. The weather and sunsets were perfect every night.
We also liked Marker 88 on Islamorada. We ate there twice. Ed only wishes he could catch a fish this big. :-) It is a fake fish… a place for photo ops at the restaurant.
The restaurant we enjoyed the most was Morada Bay Beach Cafe, also in Islamorada. The food was delish and eating on the beach watching the sunset was magical.
Is Key West Worth Visiting?
We went to Key West for a day. We left Marathon early in the morning for the hour-long drive so we could eat breakfast in Key West. Parking was not easy, but we eventually found a parking garage and paid the day rate.
After breakfast, the first thing we did was climb to the top of the Key West Lighthouse, where I took this photo looking down on Key West.
We then took the Hop on Hop Off Trolley that goes around the whole island.
This gave us the overall feel of the town. It is a city and a crowded one with lots of tourists, bars, restaurants, cruise ships, t-shirt and souvenir shops… and roosters roaming free throughout the whole key.
We toured the Papa Pilar’s Rum Distillery...
… and the Hemingway House.
In between taking tours we ate lunch at The Hard Rock Cafe, had margaritas at Margaritaville (which was a disappointment) and walked around the main sections of the town.
I am glad we took a day to check out Key West so I could check it off my list of “places I have been”, but it really wasn’t a place I would ever want to go back. It is a city buzzing with people and not what I was expecting. I thought it would be more laid back and breezy. It was too overdeveloped, loud, and touristy for me.
We liked the quieter, relaxed vibe of Marathon where our resort was located.
The best part of our week on the Florida Keys was driving on the open road with the car top down. It made us feel like one with nature and the ocean views all around.
Seeing the fantastic sunsets is a key wide event that we took part in every night. The bars and restaurants on the water were filled with patrons there to watch. It was truly a happy hour with drinks in hand, good music and food. Truly the perfect way to relax after a day out exploring.
Taking the road trip vacation was totally enjoyable and like most vacations went by way too fast.
If you like to drive and explore new places, I would recommend a road trip vacation for a few days or a whole week. It is the perfect antidote for a too-crowded, too-stressed world.