Not long ago, Em and I took our first trip down to the Keys. We’ve been in Florida for a little over two years now, and in South Florida for a little over a year, so we decided it was finally time to make the trip. It was a combo birthday trip as well, my 30th and her 27th, and my fam all pitched in as a birthday gift to help send us on our way! What a great gift! We decided to make the full trek all the way down to Key West, the southernmost point in the continental United States. We only planned for a weekend trip, and we knew that time would fly, so we tried to do a little looking around online and also talk to some people who had been several times to get an idea of places to see and things to do. This particular review on TripAdvisor was quite helpful, as it was “3 Days in Key West.” So below is our own 2-3 Days in Key West (Friday – Sunday).
We decided to go with airbnb instead of going with the traditional hotel or bed and breakfast. To stay in downtown (historic) Key West in one of those places will get awfully pricey, awfully quickly. Most of the places that we looked at were going to cost over $250/night. That quickly adds up to a very expensive trip before you’ve even done or seen anything. Airbnb provides a great alternative, with lots of different options. We ended up choosing a listing on Sugarloaf Key at Mile Marker 19 for $125/night, about a 25-30 minute drive into downtown Key West. Friday and Saturday we drove into Key West, paid for public parking for the afternoon, and used our bikes to get around the island throughout the day. Important Tip: You will absolutely want a bike or scooter to explore the island. Bring your own if you have one; if not, there are plenty to rent!
Friday (Day 1):
We left Friday morning around 10am. We wanted to avoid morning traffic through Fort Lauderdale and Miami, and we also wanted to time our arrival to be close to the 3pm check in time. Our commute was a bit over four hours, so we knew we would want to try to stop some place in one of the northern keys for some lunch. We wanted to find a neat/local place to stop. We ended up at a place called Alabama Jack’s – a true dive bar/establishment that is off the beaten path and right on a swamp in Key Largo. We both had specials of the day – I had Mahi Mahi fish tacos, and Em had a dolphin reuben sandwich. My tacos were good, not great; and Em’s sandwich was very good. The atmosphere was very cool.
We did a quick check-in at our house, and made it into downtown Key West around 4pm. We parked our car at a public lot, and began to explore Duvall Street – the main drag in Key West. We could not have been happier that we brought our bikes to get around…it’s so quick and easy, and there are bikes and scooters everywhere, so drivers are generally very careful and patient for those on bikes. The bikes are not only easier and quicker, they also help to provide a bit of a breeze while you’re riding instead of slogging all over the island by foot under the hot sun! Our first little pop-in was at Vinos on Duvall where we enjoyed $5 sangrias. This is a great spot to sit on the front porch and people watch for a bit! We liked both, but agreed that the white sangria was tastier than the red.
After that, we biked up and down Duvall Street a bit longer and eventually found our way to Mallory Square – where a lot of the sunset action happens. We were looking for a place to eat where we would be able to watch the sunset as well. We ended up at Sunset Pier, appropriately named. This place is kind of an island bar and grill style place. So the food is a little more casual (although not necessarily price-wise), but the view and atmosphere are what you are really there for, and that cannot be beaten. We did get there a bit early (around 6pm), and that ended up working out well because as the sunset time approached (8:15pm), the place was packed, and we already had our oceanside seats!
The food at Sunset Pier was good, not great. We ordered crab cakes, conch fritters, and a Mahi sandwich to split. We were not huge fans of the conch fritters (conch in general – but we had to try while in Key West!), but the crab cakes were very good, and the sandwich was good. Again, you’re here for the view and atmosphere first, food second. After the sun went down, we decided we were done for Day 1, so we packed our bikes and drove the thirty minutes back to our place to watch a little tv before bed (what a treat that we were flipping back and forth between Over the Top and Rocky IV – big Stallone night!).
Saturday (Day 2):
We woke up Saturday morning and went to get breakfast at the local diner/bar about a mile and a half up the road from where we were staying, Mangrove Mamas. Let me tell you that the breakfast we had here was absolutely delicious. It is great diner breakfast food, if you’re into that – and we are! We have this thing that no matter where we go for breakfast, one of us always tries the eggs benedict. They were delicious here. [Important Tip: When ordering eggs benedict anywhere, substitute the Canadian bacon that usually comes with bennies for sausage patties. So worth it!] This place also seems to be the place to go for evening drinks and live music if you’re staying on Sugarloaf Key. (We never made it here for the evening drinking / entertainment.)
After breakfast, we decided to take advantage of one of the little perks that cam with our airbnb location that we picked out – kayaks. We decided to take the kayaks out (to the bay side for a much easier ride!), and really enjoyed some time out on the water. We went by some pretty neat houses that were right on the water, saw several boats on the water, and just enjoyed being on the water under the sun. The water itself was very shallow where we were – probably only about 3 feet deep in most places and even more shallow than that in others!
We were told by people to make sure that we do some type of excursion while, whether it be snorkeling, a sunset cruise, or something else (Fury came highly recommended by a friend). We absolutely considered some of those options, but we decided to enjoy the kayaks as our own little excursion since we already had access to them and we both enjoy that activity.
We then cleaned up a bit and headed back into Key West a bit after noon. We parked using public parking, and were once again so glad that someone had told us ahead of time how handy bikes would be on the island. Our very first stop was the public library. It was a fairly small library and we didn’t really do anything here, but whenever possible Em likes to stop in and visit libraries of places we go. As a children’s librarian, she is always interested to see the children’s space and pick up some fliers and handouts to see what kind of programming they are doing.
Then we popped over to Sloppy Joe’s, a favorite bar on Duvall Street. We split a famous sloppy joe for a late lunch / snack, and grabbed a beer while enjoying some live music in the middle of the afternoon. Yes, the sloppy joe really was quite delicious, a worthy name-sake for the bar. Fun fact, as the musician on stage was taking a short break, he grabbed his little puppy from his empty guitar case on stage and took him outside for a quick walk…the guy’s puppy was just napping in his guitar case on stage as he was up there playing and singing! Only in Key West…
We hopped on our bikes and traveled across the island to the Key West Garden Club and West Martello Tower (the same place). This is a National Historic Site, as it is actually the ruins of Fort Taylor. The fort was meant to be built in the early 1830’s, but work was started and stopped many times before finished in 1866. It was then used off and on before becoming home to the Key West Garden Club and now houses the gardens. The site is completely free, and it is an interesting place to walk through and also see some lovely views out over the ocean, and the gardens themselves.
One of the other nice things about visiting the gardens is that it gets you to the south side of the island. This is one of the famous picture spots in Key West – the southernmost point in the continental USA is just a couple of blocks away. Of course, we popped over on our bikes to get a picture. (We decided not to wait in line to get our own picture with the landmark – the nice looking couple below will do.
After this we headed to a little coffee shop, the Coffee Plantation Coffee House. It’s a fun little coffee house that offered a great place for us to sit out of the sun for a short bit while sipping on some iced coffee – just what the doctor ordered in the middle of a hot afternoon full of biking. After we enjoyed our brief respite, we decided to bop around a bit more as we headed towards the place we had decided on for dinner – Bien Caribbean Latino Restaurant. This place was ranked as one of the top restaurants to eat in Key West. But be warned – this is not a typical sit down restaurant. It almost operates as if it is a food truck. They have a very small inside area (no seating) where you order, and then just outside they have a few benches with small tables where you can eat. We decided to sit at one of the benches to eat, but we also saw plenty of people order theirs to go.
While it’s not the place you would want to go if you are looking for a nice/fancy, sit-down dinner, we both agreed that the food was incredible. They have a grilled corn on the cob that is possibly the most flavorful food item I have ever eaten – fire grilled with aioli, lime juice, cilantro, parmesan, and paprika. It was so good. They also have a list of incredibly flavorful sandwiches (Em got one – delicious), and also some island rice bowls (I got one – delicious). The food was absolutely delicious and packed with so many bright flavors – but again, it’s more food truck than fancy, so maybe not the place to go if you are wanted to get dressed up and go some place nice.
We were quite stuffed after all of the delicious food that we ate at Bien, but while getting there (near the coffee shop) we had passed another spot that I wanted to make sure we stopped at, Bo’s Fish Wagon. This was a dive bar for sure, and so Key West. There were roosters running around everywhere (yes, live roosters are a fairly common occurrence all over Key West), little chickens wandering around, a beat up (non-working) truck almost acting as a wall at one end of the place. We didn’t try the food as we had just eaten, but we definitely like the beat-up island bar feel, so we did stop in for a drink.
After our beer, we hopped back on our backs and went back to Mallory Square. We didn’t go into the restaurant area at Sunset Pier that we had eaten at the night before, but just to the side of that is a big open area with lots of street performers, and a great place to watch the sunset. So we enjoyed some fire juggling, handstands and acrobatics, some nice easy island singing, and even a nice hippy encouraging people to stay in love and spread the love. We found a little ledge to sit and enjoy the sunset while listening to some nice music. It was truly a lovely evening. Once again, we decided to head home after the sunset. [Note: Key West does seem like the kind of place that gets hopping at night with a fairly rowdy bar scene. Since we had a 30 minute drive – and were actually driving – we didn’t stick around for the late night action, but I’m sure it would be a good time.]
Sunday (Day 3):
On Sunday, we decided to take advantage of the close proximity and delicious breakfast options of Mangrove Mama’s once again, and then we begin our trip back north. We had decided ahead of time that we wanted to stop mile marker 37 at one of the state parks – Bahia Honda – that is supposed to have some of the prettiest beaches in all of Florida. We paid our $9 bucks to go in, hiked one of the trails up to where one of the original bridges was built (no longer in use) and saw some pretty incredible views. I’ll add here that the entire drive down to Key West was filled with spectacular views – the water glistens and has so many shades of blue and aqua that you would probably think it was all fake if you saw it in a picture. Not to mention that for much of the drive you can see the water on either side of you – look to the left – beautiful views, look to the right – beautiful views. [Note: The drive into and out of the Keys is a one lane, one road trip for much of the way. Be prepared that depending on the traffic and time of day, it will likely be slow going. The speed limit is also a bit slower most of the way (45-55mph) and I hear that the police strictly enforce those limits.]
Shortly after our hike, it started to sprinkle a bit. So we decided to pack up our things and make our way back home. We’re lucky enough that we are able to hit the beach pretty much whenever we want, so cutting the beach day a bit short in Bahia Honda was not a huge deal for us.
Overall, we loved our trip to Key West – thanks again to the fam who pitched in as a birthday gift! We felt like we got to see and do a lot in the limited amount of time there. I’m sure that we missed some things – maybe next time! – but we absolutely did love what we saw and did. The views along the way were fantastic, the food was really quite good at the places we ate, the sunsets were great, and it was all in all just a fun little town with its own style and quirkiness that we really enjoyed.