Road Trip Vacation Through the Florida Keys

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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.

Things to do in the Florida KeysWhat 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.

Rt 1 in the Florida Keys

What we were looking forward to the most about the trip was taking the iconic drive along the Overseas Highway (U.S. Highway 1).

Map of the Florida Keys

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.

Ed standing along road with view of one of the Florida Keys bridges in the background

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.

SkipJack Resort on Marathon Key Florida

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.

4th floor view from Skip Jack Resort on Marathon Key in Florida

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.

Pretty home in Marathon Florida

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…

Sombrero Beach on Marathon Florida

… 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

What to do in Key West-

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.

Where to Eat in the Florida Keys

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.

Sunset off Marathon Key Florida

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.

Fishing in the Florida Keys

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.

Where to Eat on Islamorada

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?

Key West lighthouse

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.

View of Key West from the top of Lighthouse

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.

key west on off trolley

We then took the Hop on Hop Off Trolley that goes around the whole island.

Street in Key West, Florida

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.

Papa Pilar's Distillery in Key West Florida

We toured the Papa Pilar’s Rum Distillery...

What to do in Key West

… and the Hemingway House.

Hard Rock Cafe in Key West

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.

Key West Tour building

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.

Bridges over water near Key West

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.

Sunset on The Florida Keys

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.

Two people standing next to convertible car on Highway 1 in the Florida Keys


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  1. Hi Diane…great post, and reminds me of a few visits to the Keys when our kids were younger. We stayed just south of Marathon at Key Colony Beach, in a 2 bed duplex on a canal, and close to the beach. Our son ( now 25) still talks about it and wants to go back. He and my husband went on a private fishing charter, just the two of them and the captain, and had an awesome day, bringing back the catch for dinner.
    We also did the Turtle Hospital and swam with dolphins at the Dolphin Research Centre….great. I like to go off the beaten path, so we also drove to an out of the way pizza pub, inland a bit where the “ key deer “ roam free…and money bills are plastered all over the walls…great fun ! I think it was called the “ No Name Pub”
    Saw Key West….once was enough ! Thanks for rekindling those sweet memories ! And yes, next time it will be a convertible!

  2. Hi Diane!!! What a fun beautiful getaway!! It’s 3 degrees here in NJ! Wish I was in the Keys!!!
    Happy 35th!!!

    1. Thanks Nancy – My sister in PA told me it was 6 there today. It was 26 here this morning which is super cold for the region. I hope you are staying warm and cozy.

  3. Hello,
    What a handsome couple! Congratulations to you! We also celebrated our 35th anniversary in 2018. Time flies!

  4. Welcome to my part of the world Diane.

    I love Islamorada and Marathon and we have our favorite places to stay when we drive through the keys.

    We live about 150 miles from Miami in Cape Coral on the gulf of Mexico. Lately, we have been taking the Key West Express boat up and back when our guests want to go to Key West. It is easier than driving the two lane highway all the way to Key West especially if there is road construction which there usually is.

    You gave a good assessment of Key West…and if you are there on week-ends…in my opinion, there are too many parades, mostly protesting or promoting a way of life. AND way tooooooo touristy. But everyone has to go at least once, or so they think, so we accommodate our guests. LOL

    The Captain and I have stayed at cute little cottages on the beaches of Islamorada and Marathon and ate at some of the same restaurants you recommended and I have posted about them.

    You did good girl, and by the way, my car is a steel blue Chrysler 300 convertible….perfect for driving around SW Florida.
    Good post.

  5. Diane, we took the family and several friends to Key West last year in December for my husband’s 70th birthday. It was on his bucket list as well. I agree, I’m glad we went, but I don’t think we’ll go back. For one thing we’re in California and it’s a LONG trip. We did enjoy going to the the Dry Tortuga NP, the Hemingway House and the Truman WHite House. We didn’t stay right down town which helped. It was an easy bus ride into town from our spot over the bridge. We really liked the drive down the Overseas HIghway as well but it was drizzly the day we drove it–no convertible for us.