Florida Keys Sunset

Road Trip through the Florida Keys

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Our road trip through the Florida Keys was a fun week-long getaway, which was the perfect amount of time to spend travelling with family. I am so grateful that my parents and brother still enjoy hanging out together – we always have the best time (as you will see from the images in this post, lol).

I’m lucky to have an easy-going family that is okay to go with the flow, and not worry about having plans set in stone. For this trip, we booked several Airbnbs, and that’s it. We took it day by day and decided what we wanted to do that day an hour or so before we did it!

If chilling your way through tropical vibes sounds like your idea of a good time, read on!


Day 1:
My brother and I flew to Fort Lauderdale via WestJet, and my parents met us there about an hour or so after we arrived (just enough time for us to watch Zach Galifinakis in the airport – sooo funny). We rented a Chevy Impala from Enterprise, and started our trip!
We drove to our first Airbnb which was a cute house on the Intercostal. It was close to the Hollywood Broadwalk with restaurants and stores (and Margaritaville) within walking distance.

road trip through the florida keys

We ate dinner at Le Tub and we all attempted their famous 13-ounce burger which provided us with enough food for breakfast the next morning. This quirky restaurant was the best place to watch the sun set!


Day 2:
We didn’t even realize that the Miami International Boat Show was the same weekend that we were in Miami, so naturally, we went. My family are huge boat people, so this was the perfect way to spend the Saturday.


After wandering around looking at and testing the latest and greatest lines, engines, lights, jet skis, sunglasses, sails, life jackets, and just about every other boat related thing you could think of, we stopped at a group of food trucks for some lunch. (I had pulled pork tacos.. yummm).


After eating, we wandered around some more and found the ferry that would take us back to our rental car.
From there, we drove to our next Airbnb, Vintage BnB Inc. This place was amazing. As soon as I walked in and met the owners, it felt like my family had reunited with old friends. The vibe of this place was welcoming, warm and vibrant. And the best part – this BnB features old airstreams that guests get to sleep in, and a private outdoor washroom. The airstream we were in seemed to have so many stories to tell. I could only imagine the unique people it has seen. Our hosts at Vintage BnB prepare dinner every night for their guests (based on donations), and so we grabbed some food and settled in for the night.

Day 3:

After a delicious breakfast at Vintage BnB, we started the morning with a trip to the highly recommended R.F. Orchid Farm. It was breathtaking, and I was absolutely in heaven. There were so many different species, kinds and colours of orchids floating around me, everywhere. It was magical, and I felt like I really grasped the history of this farm after a tour of the property.


We ate lunch at a small restaurant called Casita Tejas, which featured a good selection of Tex-Mex food that definitely filled us up!


From there, we continued on to the Florida Alligator Farm… This part was a little sad. I hate to see captive animals caged in with little space to move around and be free. The reason why my family and I decided to support this place was to go on a famous air boat ride in the Everglades (again, we’re boat people). The air boat ride was fast and exciting, and I am happy that I got to experience it. My hope is that one day the Alligator Farm will shut down, and the air boat rides will continue to show travellers the natural beauty of the Everglades.


We headed back to Vintage BnB for the afternoon, and relaxed by the pool and hot tub before grabbing dinner and getting ready for the next day.
Day 4:

We sadly had to leave our new friends at Vintage BnB, but we were excited for the unknown adventures that were yet to come. We slowly drove down towards the Keys and stopped at several points along the way, including marine stores, thrift shops, souvenir locations, and the History of Diving Museum. This museum seemed to be a small building, but upon entering, we quickly realized that it was home to years and years of diving innovations and experiments that helped to develop how we view marine life today. My family are all divers, and so learning about these important initiatives was informational and relatable in some ways.


We asked for a recommendation for lunch, and were told to visit the “hole in the wall” Key Largo Fisheries cafeteria. It was much more than what we expected after hearing that recommendation! The food was fast and fresh, and the atmosphere of the place was relaxing and breezy.


From there, we had to make a stop at Robbie’s to feed the tarpon (and pelicans) right off the dock. I had read several different reviews about this activity so it was fun to try it out! This was a cute spot to walk around and take a little break from driving.
We packed up and headed to our next Airbnb – a house boat in Mangrove Marina, Tavernier.
After eating our way through the Florida Keys, we decided to keep the good food vibe going, and visited Marker 88 for dinner by the sea. The sunset over the water was bright and warm, and as scenes of Bloodline wandered around in my head, the sun slowly faded out.

Day 5:

We received a recommendation to visit Harriettes for breakfast, and so we did just that. We ate till we were stuffed, and even picked out homemade muffins to take on the road with us. We took it easy on this day, and slowly drifted down the Keys while making various stops along the way at shops and restaurants.We arrived at our next Airbnb – a 2 storey apartment tucked in on Duval Street.Day 6:
After waking up, we wandered down to Panini Schemini for breakfast and got some refreshing smoothies to start the day. We walked around Duval Street and organized what they call a “Land and Sea Tour” which included a tour on the famous Conch Train, and a sunset cruise the night after with a live band on board.
We took the Conch Train to all the touristy areas of Key West including along Duval Street, Mallory Square, Ernest Hemmingway’s house and the Southernmost Point of the USA. Before visiting Key West, I had no idea about the history that it holds. It was quite interesting to learn about the different styles of architecture that this town is made up of. In the middle of our tour, we of course had to stop for chocolate dipped Key Lime pie, which was a refreshing snack on this hot day.


We stopped at the Half Shell Raw Bar for lunch and literally sat right in the marina while mucking some fresh oysters and shrimp. We hopped back on the Conch Train and after checking out a few stores along the way, we checked in to our next Airbnb which was another small apartment on Duval Street, about a block further than the previous one.


After an hour or so of down time, we walked through the cute stores to Mallory Square to check out the world-famous buskers that gather here to celebrate each sunset. It was crazy! The buskers were so entertaining and actually very talented – they really knew how to keep the crowd engaged and laughing! This was definitely a must-do in Key West, and even though I wasn’t watching the time, I would guess that we spent a few hours walking around and enjoying the atmosphere here.
On the way back to our place for the night, we stopped in at the Gas Monkey for a much needed greasy meal that put us all right to sleep.
Day 7:

In the morning, we drove right up to the marina to find parking for our sunset boat cruise, prepared to spend the entire day in Old Town Key West. We found the first bike rental place we could, and rented bikes for $10US for the entire day. The bikes were in great shape, and we had fun biking around the island. We explored smaller neighbourhoods, revisited the Southernmost Point, and discovered super cute shops and restaurants completely by accident. We went to Turtle Kraals for lunch (and just in time, since it started to pour rain as soon as we locked our bikes up!). The food here was great, and the view of the marina was compelling – I don’t think my family will ever get sick of looking at boats.


We continued to explore and check out various shops after lunch. After picking up a few souvenirs for friends and family, we decided to return our bikes and head to the marina to get on the sunset cruise we had organized. We chilled for about an hour or so enjoying the sun at the marina, and then it was time to board! The crew on the boat were friendly and fun, and the live band on the bow set the vibe perfectly. This sunset cruise featured a buffet of appetizers and of course, free alcohol (would my family say yes to an activity without food/alcohol? Not so sure…). We really enjoyed that boat ride, and after the sun set, we headed to one of our final hotels.

Day 8:

We woke up early on our last full day in the Keys, and decided to drive up through the islands to hit all the spots we felt we missed, including the Green Turtle Inn Restaurant for lunch, and Stone Age Antiques. Stone Age Antiques was a great final place to check out. It features thousands of antiques from old ships and marinas, and tons of cool collectable items that must have seen many days. Stone Age Antiques really summed up our cozy, familiar, boat and family oriented vacation.I really love to be with my family, and this trip combined everything that we all share a love for – boats and food, mainly!If you have been to the Keys, let me know if there is anything we missed – I think we need another reason to go back!
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I’m Sydney. Obsessed with travel, food, dogs and adventure, I spend my days finding new ways to appreciate life.

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