So I’m a little late with this but I just hadn’t gotten around to doing this until now plus I just finished the vacation video last week and wanted to wait for that to make this post. Our original plans for the summer didn’t include a family vacation. Wade and I had our 15-year anniversary trip to Jamaica booked for July, but once I started thinking about it, I realized it would be better to take the kids on a trip and do our anniversary trip when they were in school. A friend of mine had taken her whole family to Key West on Spring Break and while it was never a place that was on my radar, their family photos looked amazing! I talked to Wade about it … well, I just mentioned “Key West” and he said, “Yep, book it.” So that’s how this began.
We are not luxury travelers so I’m often planning these trips on a bit of a budget. Originally, we were going to drive, making some stops along the way throughout Florida. I started to realize just how long the drive was going to be and with gas being as high as it was over the summer, flying may be a better option. This is when I discovered a tip that I now pass on to anyone looking to go to Key West. The Fort Lauderdale airport and the Miami Airport, both large, international airports, are only twenty minutes apart. Did you realize that? And the flights? HALF THE PRICE. Literally. We were able to fly into Fort Lauderdale and rent a car for the same amount as it was to fly into Miami.
The next step was to find places to stay and after some more research, I decided on 3 stops throughout the Keys. I found AirBNBs at all 3 of them (one of the was actually a hotel booked through Airbnb) and we were all set!
If you are thinking about a Key West trip and just want some recommendations, just scroll to the very end for links to everything we did, everything we ate, and every place we stayed!
So here we are at the New Orleans airport, around 5 am, waiting for our flight to Fort Lauderdale. And this is the day I discovered that I should either 1. Not plan flights this early or 2. Not make any plans for the rest of the day.
By the time we landed in Fort Lauderdale and got the rental car, we were all GRUMPY. We were hungry and exhausted and it was way too early to check into the hotel. After driving around pretty aimlessly for a while, a stop at McDonald’s for very expensive sausage biscuits and an attempt to see some of the sights I was excited about … we were finally able to check into our hotel and we all crashed. All four of us slept for hours, straight into dinner time.
When in Miami, there’s just no other option but to eat Cuban food, right? Next time, I’ll consult people who know better way in advance. We found this place, Cafe Versailles, which had great reviews and was mentioned on all kinds of (tourist) blogs and websites. It was just OK … definitely not my cup of tea and I was later told by a friend that there are much better places to eat. La Carreta is one of the places recommended – let me know if you try it! After dinner, we stopped at a Cuban market for fruit and snacks, then headed back to the hotel to rest up for the next day.
First stop, Key Largo! Note to anyone interested or curious – you can skip Key Largo. Or at the very least, don’t spend 2 nights here like we did. They do have a great state park that is a great place to spend the day, especially if you like snorkeling or scuba diving. A large portion of the park is water and there is a beautiful coral reef. You have to book tours through the park in order to see the underwater park, which we didn’t do. You can also do canoe, kayak and paddleboard tours. Wade and the kids like to just snorkel on their own, so we found some places off the shoreline of Cannon Beach for them to explore. The other thing to note about Key Largo is that the water isn’t pretty yet. It’s very clear but it’s not that pretty blue/green color that you get further down in the Keys.
This guy scared the crap out of me when I went to grab our towel and he was right by our stuff! There are iguanas all over the Keys!
After they were finished snorkeling at Pennenkamp State Park, we found this other little park called Rowell’s Waterfront Park that was kind of neat. It had a large, deep lagoon-like area with ladders into it where you could swim. It was very calm and the water was very clear. We wound up going back later that evening to watch the sunset since it was on the Gulf side of Key Largo.
We stopped for dinner at Tacos Jalisco, a taco truck next to Keys Chocolates. While we waited for our tacos, we found some things to take photos of! We took our tacos back down to the waterfront park and watched the sunset.
Day two, we decided to take a ride down to Islamorada – I was ready for some fun, touristy stuff and to see some pretty blue water! Our first stop was the Rain Barrel Village to take a photo with Betsy and check out the shops. This was a fun stop and if we were hungry, we could have had lunch and drinks here as well. We just walked around a bit, took our photo with Betsy and headed south to our next stop!
And there it was … we hit that first bridge on the Overseas Highway and the blue-green water was all around us! It’s so beautiful!
Robbie’s is a marina in Islamorada that is well known for one thing – feeding the tarpon! You can buy a bucket of fish and hand feed these huge fish that jump out of the water to snatch it right from your hand. Only Hayden and Wade did it and they both loved it – even though they both walked away with bloody hands.
Robbie’s also has shops and restaurants as well as all kinds of rentals – boats, paddleboards, kayaks, etc. You can also book charters that leave from Robbie’s. We had a drink and walked around a bit, looking at the shops. We were starting to get hungry, but we were also ready to get in the water. We stopped at a Publix to grab a picnic lunch, some snacks and drinks, continuing south to see what we could find.
We started to notice people fishing and swimming off the sides of the highway, so Wade found us this quiet little spot (literally on the side of the highway, it’s right on the other side of that grassy area.) We stayed there swimming and snorkeling for a while until we were all tired and ready to head back home. It was about a 30-minute drive back north to Key Largo, where we had one more night at the Airbnb. Wade had caught some lobsters and fish, so he cooked dinner for us that night. The next day, it was time to move on further south to our next Airbnb, which was in the Faro Blanco Resort in Marathon. This is about when we started to notice how bad the seaweed was. I’m so glad I read about this before our trip because it would have been a huge disappointment if I wasn’t prepared. One thing that everyone will tell you is that you don’t go to the Keys for the beaches. They have some nice ones but it isn’t the place for long stretches of white sand and beautiful clear water. The Keys are nothing like Destin or Panama City. A lot of the shorelines are made of sharp coral and at this time of year, the beaches were COVERED in seaweed.
This was one of the beaches I had read about when doing my research. Anne’s Beach in Marathon is supposed to be one of the nicer, swimmable beaches with shallow water and sand. The area was really nice with this long board walk and a small parking area. I’m sure it’s beautiful when it isn’t covered in brown seaweed!
We arrived at our resort after eating breakfast at the Wooden Spoon (great simple place for breakfast). The resort turned out to be a yacht club with a large marina. We explored a bit, pointing out all the boats we could dream of owning one day.
After some rest and probably a meal, we headed to check out Sombrero Beach. This was another smaller beach that I had seen when doing research. It was also full of seaweed, but it’s on kind of a peninsula, so one side was a bit more protected and had a lot less seaweed. Once you got passed a little of it on the beach, there were clear, shallow areas in the water to hang out in. 
We spent the rest of the afternoon here, the kids and Wade snorkeling and swimming, of course. They found some neat things while snorkeling – I don’t remember what this thing is called, though.
The sunset from our resort was really pretty!
The next day, we headed to a taco truck for lunch. The place is called Takeria La Palapa and I highly recommend it. We wound up stopping there again on our way back to Miami on our last day. The street tacos were SO GOOD. We all really enjoyed it!
Heading south on the Overseas Highway, the water just gets prettier and prettier. In my opinion, the water was the prettiest in the middle of the keys around the Marathon / Islamorada area! If you are into water sports – diving, fishing, snorkeling, etc. – this is where you want to go when you head to the Keys!
Bahia Honda State Park was our favorite beach/state park of the trip. YOu can see from the photo above, it stormed a few minutes after we got there, but as soon as the rain stopped, the sun came out and we had a perfect beach day. The rain ran off most of the people on the beach, which was pretty crowded at first, and by the time it stopped, there were hardly any people left!
Bahia Honda is right underneath the old railroad bridge. The history of the bride and the Overseas Highway, in general, is pretty interesting, but basically, before it was a highway, you could only get to the Keys by railroad. This was the original bridge, which then had a highway for cars built on top of it. It was later replaced by a new 4-lane bridge and now you can walk on the top for some beautiful panoramic views of the area.
There are a few main beaches in the State Park and we wound up on Loggerhead Beach. It was shallow with a soft sand bottom and crystal clear water. Absolutely perfect for relaxing (not so great for snorkeling) but I was relieved to finally have an area where I could just enjoy sitting in the water. If you are looking for a beautiful beach to spend the day at in this area, I highly recommend Bahia Honda State Park. I would get there early if you are planning to spend the day there, or get there later in the afternoon, maybe around 3-4, after everyone has started leaving. Wade loved it so much that he has a trip booked for next summer with some friends to stay in the cabins at the state park. It took us about 2 weeks of trying every morning before we were finally able to get a reservation – they book up that quickly!
With a view like this, who would have thought that our charter for earlier in the day had been canceled? First, it was postponed until after lunch and our guide recommended a great place for breakfast. The Stuffed Pig in Marathon was really good, we all loved it. It was pouring rain at this point but it cleared up fairly quickly. The guide called again and postponed our charter to the next day, I think he was getting a fuel delivery or something. That was going to be a little inconvenient because we were headed to Key West the next day, which gave us a 45-minute drive back to our charter, but there wasn’t much we could do. He did, however, tell us about some amazing places to stop on our way down to Key West. They were local favorites that are off the beaten path and we loved every second of it! The first is called Horseshoe Beach, which can be found on the map. It’s a horseshoe-shaped area, almost completely closed in, surrounded by rock. I read somewhere that they used to do scuba certifications here. It was such a neat place! The day we were there, there weren’t any dry places, the water was up over the rock all the way around. It looks like sometimes the rock is dry and you can hang out there. There were lots of fish in the shallow areas, so it was fun for me to just walk around while Wade and the kids snorkeled. There were some storm clouds rolling in, though, so we didn’t stay very long.
I cannot remember the name of the next place we went to but it was WAY off the beaten path. I think it was on Ramrod Key. It was a local swimming hole and just a really neat place. There were tons of parrot fish that I could see just standing at the edge of the water (this wasn’t anything new for the kids and Wade, but I was amazed!) Just look how beautiful this little place was!
You can kind of see the parrot fish above and they also had these little upside-down jellyfish called cassiopea. After stopping at both of these places and having a quick lunch at a local sandwich shop, we headed south to Key West.
After checking into our Airbnb and getting our bike rentals. We rented from Fury Bike Rentals, they were great to work with, even when I had to change our rentals a couple of times, and they delivered the bikes right to our Airbnb. Our Airbnb was located in the perfect spot – I would definitely stay in this area again. We were a block off of Duval Street (the main street for bars and restaurants in Key West) and a few blocks from the water. It was quiet but still close to everything. We were even able to bike to a grocery store. I don’t think we used the car while we were in Key West, except to drive back to Marathon. 
We got lost trying to bike to Sunset Pier (the map took us through a gated community and we couldn’t get out without going back the way we came in). So by the time we reached the pier, the sun had gone down, but it was still pretty. We stayed for a few minutes, then headed back to the house to get everything ready for our charter the next day.
As usual, I was up before everyone else, so I took the time to bike around the area of our Airbnb. The Southernmost Point marker happened to only be a few blocks away, it was an accident that I even found it! There is usually a line of people waiting to take photos with it, but it was early, so there were only a couple of people there. The seaweed was bad all around this area too, that large black lump in the photo above is all seaweed!
Our charter was postponed AGAIN, but only until lunchtime, so we FINALLY made it out on the water! We were all so excited about this; it was the one big thing we splurged on! Our charter captain was a man named Kendall and it was just him and his dog on his boat. We had booked him to take us snorkeling on the reef, hang out on a sandbar and then go fishing. The water out in this area is a gorgeous emerald green – I’ve never seen water like it before! The kids got the best seat on the boat – at the very top!
We passed through some canals in between some really nice houses before heading out into the harbor and then the ocean. We headed out to Looe Key reef to do some snorkeling. Not really my thing, but since we paid a lot for this charter, I decided to suck it up. I cannot believe that I completely forgot to grab the Go Pro before I jumped in. Hayden and I had to stick together, so I spent the whole time trying to keep up with him, but it was amazing. We saw some of the coolest stuff – lots of fish, including a huge parrot fish. I have no idea what else we saw, but it was really neat. I did start feeling a little seasick by the time we got back to the boat, so I was glad it was only a short ride to our next stop.
Picnic Island is this tiny little stop in the harbor that only has a couple of chairs and a grill on it. It’s a popular place for boaters to stop because there is a shallow sandbar all around it and you can just hang out in the water. We had to put all of our things in a dry bag and we waded/ swam/ walked over to the island to eat lunch and hang out.
Next to Picnic Island, there’s a houseboat permanently docked and Kendall told us there are some docile nurse sharks and a 5-foot barracuda that hang out there. Wade and the kids jumped right in and saw both – they were face-to-face with that barracuda! I just watched from the top of the houseboat. No part of me felt the need to swim with sharks and barracuda.
The final part of our day was fishing for Wade and Hayden. They had a great time – Hayden caught a barracuda and a shark (both were thrown back) and they caught a bunch of these small fish that Kendell then fileted for us and Wade fried later that night. They were delicious. This is when the day took a turn … I would love to recommend Kendall and his company. He was an amazing guide all day, was great with the kids, we loved his dog, and he was very knowledgeable and nice (in a gruff kind of way). He reminded me of someone we would know from the camp – he would totally fit in with the Cajuns around here. However, when you mention gratuity several times throughout the booking process and then when someone hands you a tip, you tell them it isn’t enough – well, let’s just say it puts a damper on the entire day. It was one of the most awkward moments I’ve experienced as Wade just turned around and walked away and I fumbled with my phone, trying to Venmo Kendall the rest of the money he was asking for. We understand inflation and the need for more money, but if you are needing $1200 per charter, charge $1200 per charter. Don’t charge $1000 and expect a $200 tip – that’s just ludicrous. We would have willingly paid $1200 for the trip if that’s what the initial cost was. He works for himself and there was no one else on board, so there wasn’t a crew to pay or a percentage that went to an employer. Every bit of that money went to him. I have owned my own business for over 14 years and I have never once expected a tip from someone – that’s just not how things work!
Despite that, it really was a great day, one of my favorites of the trip and something we will remember forever. That night, Wade and I had a date night on Duval Street! Duval Street is very much a cleaner version of Bourbon Street in New Orleans – there are even a lot of the same bars. The next day, Emelyn and I decided to bike over to Ernest Hemingway’s house to check out the 6-toed cats.
LIterally, all we did was hunt for the cats! They were all over the place and I can’t remember now how many we saw, but we took photos and video of all of them (There’s a video over on my TIkTok of all of them!) Do you see their unique paws??
Here’s Em standing in the front hallway of the home as well as in front of the whole house. It was extremely hot that day and pretty miserable!
We couldn’t do a trip to Key West with out getting some fresh seafood and some Key Lime pie! I found this Caribbean restaurant right off of Duvall Street where we met up with Hayden and Wade to have lunch. We ordered a few different things to share and every bit of it was delicious! We had coconut shrimp, jerk chicken wings and fried mahi mahi. We finished it all off by sharing a slice of Key Lime pie – YUM!! I can’t remember the name of the restaurant but I’ll look it up and post a link to it when I find it!
And that was the end of our Key West road trip! There was one place left that I had read about and wanted to visit, Fort Zachary Taylor Park. This is said to be another really good beach in the Keys. It was pretty but we were pretty much wiped out and tired of beaches at this point. Wade, Hayden, and I walked around a bit, but we didn’t stay very long. Hayden’s wallet apparently fell out of his pocket at this point. We got a phone call weeks later saying they had found it!
The next day, we turned our bikes in, packed up the car, checked out of the Airbnb, and began heading back north toward Miami. This time there were no stops, just the straight 4-hour drive back to Fort Lauderdale to catch our flight the next morning. We booked a hotel close to the airport so that it would be easy to wake up and head home the next morning.
If you’ve stuck with me this long, I hope that I’ve given you some inspiration to plan your own road trip through the Keys. If you’ve only been to Key West and haven’t explored the other Keys, you have really missed out on the best parts! There is still so much that we didn’t do and I hope to one day go back there!
AC Miami Dadeland – Nice hotel located towards the south of Miami. Attached to a mall, quiet area, clean and comfortable. Not super convenient to any major attractions, though. We chose it b/c it was on the outskirts of Miami, on the way to Key Largo
Key Largo Bungalow (Airbnb) – 1 bedroom bungalow located on a canal, oceanside of Key Largo with full kitchen. Quiet area, very clean and comfortable. The bathroom didn’t have a door, so everything, including the glass shower, was open to the bedroom. The canal didn’t smell great and there aren’t any nice views, but it was very convenient to everything we did in Key Largo. There are 2 units in the building.
John Pennekamp Coral Reef State Park (Key Largo)
Rowell’s Waterfront Park (Key Largo)
Taco Jalisco Food Truck (Key Largo)
Rain Barrel Village (Islamorada)
Robbie’s Marina (Islamorada)
Anne’s Beach (Islamorada)
Faro Blanco Resort and Marina (Marathon) – we booked through Airbnb, listing here. – Typical hotel room, a bit outdated, looks older in person than the photos. The resort itself was nice as well as the marina and pool. There were on-site restaurants but we didn’t try any.
The Wooden Spoon (Marathon) – simple diner with a great, quick breakfast
Sombrero Beach (Marathon)
Takeria la Palapa Food Truck (Marathon) – we stopped here twice!
Bahia Honda State Park (Big Pine Key)
The Stuffed Pig (Marathon)
Horseshoe Beach (Big Pine Key)
Ramrod Key Swimming Hole (Big Pine Key) – no link but you can google map it!
Key West House – located one block off of Duval on the quieter end of Key West. One bedroom, two baths with a full kitchen. The living area has a day bed. Very clean and comfortable. 2 units in the building.
Fury Bike Rental (Key West)
Ernest Hemingway’s House (Key West) – no reservations, walk-ins only, cash only. We had to wait in line for about 15 minutes.
Kaya Island Eats (Key West)
RIck’s Bar Key West – if bars and/or live music are your thing, we really enjoyed this place. There were themed areas with different kinds of live music. We watched a one-man show first, which was amazing. Upstairs there was club music in one area and another had a metal cover band playing. Something for everyone here!