The Key West Express
Since we started living in southwest Florida, we have been bombarded by the Key West Express! They definitely have their advertising game down because we drove by several billboards, read over many newspapers’ ads, saw the pink logo in bathrooms, and heard about it countless times from patients and friends. When we investigated it, we found out we could cut down our travel time considerably to get to Key West if we took the boat route instead of driving- and trying to find a parking spot wouldn’t be an issue. We chose to depart from Fort Myers Beach early on a Saturday morning. The boat leaves at 8:30 a.m., but we recommend arriving by at least 7:00 a.m. in order to get a good seat. We were even able to snag a table! It’s roughly a 4-hour trip to Key West from Fort Myers Beach, but they play movies which makes the trip go pretty quick. In hindsight, we would have opted to depart from their Marco Island port because the boat ride is an hour less from there. We were lucky enough to get a calm day, but it can get choppy, so if you are prone to motion sickness, I would definitely recommend using your remedy of choice. There is no Wi-Fi on the boat and cell service is spotty, so bring other forms of entertainment. We were only able to do a quick weekend trip to Key West, so we hopped back on the boat on Sunday evening departing at 6:00 p.m. We arrived by 4:30 p.m. but weren’t able to get a table on the boat again. We did think ahead and carried a whole pizza onto the boat for dinner which everyone drooled at when we walked by. They do have food and beverage options on the boat too, but for a price. Prophylactically, we decided to take Dramamine for the ride back which totally knocked us out!
The Key West Express: our boat ride from Fort Myers to Key West!
We were lucky enough to snag a table on the boat! (Arrive 1.5 hours prior to departure for the best chance)
The Key West Express: our boat ride from Fort Myers to Key West!
We were lucky enough to snag a table on the boat! (Arrive 1.5 hours prior to departure for the best chance)
The Waterfront Brewery
Once we arrived at the island at noon, we were pretty hungry after our 4-hour boat ride, so we walked straight to The Waterfront Brewery located in the historic Key West Seaport and Bight. This was the perfect spot for lunch! We got a flight of beer while enjoying a view of the harbor, discovering our favorite pour was the Crazy Lady, a honey ale. The food was great too! We had delicious (and very filling) pretzel sticks with beer cheese for an app and then we both got some tasty seafood.
The Waterfront Brewery – not too far from the ferry terminal.
Waterfront view at The Waterfront Brewery!
Plenty of great seafood options – we created our own shrimp grilled cheese!
The Waterfront Brewery – not too far from the ferry terminal.
Waterfront view at The Waterfront Brewery!
Plenty of great seafood options – we created our own shrimp grilled cheese!
Azul
With food in our bellies, we began walking the paradise island which turned into a 20-mile day! Our first stop was to check into our hotel, Azul. We picked this place because it’s centrally located- as we wanted to check out as much of the island as possible. It is a remodeled heritage house built in the early 1900s, and it was one of the least expensive options left for this weekend! In general, it’s very expensive to stay on Key West, especially during the busy season (Jan-April). Azul considers itself a hotel, but it has more of a bed and breakfast feel. The same goes for nearly all accommodations we researched. It is a pretty clean place with helpful staff, and it was perfect for our needs!
Azul: our hotel (more of a bed and breakfast) in a heritage house in the middle of the island.
Our poolside room at Azul.
Azul: our hotel (more of a bed and breakfast) in a heritage house in the middle of the island.
Our poolside room at Azul.
Higgs Beach
After checking into our hotel and dropping off our Osprey backpacks, we walked south to Higg’s Beach. There’s a nice pier here and some nice white sand for lounging on a beautiful day. We walked west up the beach from here and made our way along the coastline to the southernmost point buoy! There’s always a line to take a picture with the landmark here, but it’s fun to be a tourist sometimes 🙂
Higgs Beach
The pier at Higgs Beach
The southernmost point!
Higgs Beach
The pier at Higgs Beach
The southernmost point!
Fort Zachary Taylor State Park
While we walked even further west to get to Fort Zachary Taylor State Park, we discovered the iconic Key West animal, chickens! They are considered “Gypsy Chickens” because they truly roam wherever they please. There are also roosters galore popping out of nowhere. Fort Taylor is one of the most beautiful and most visited state parks around. The entrance fee for walkers now is $2.50 and definitely worth every penny. It has some fun history to learn about in the fort, a few remote rocky beaches at the north tip of the park where Adam took a dip, and then a large main beach area/picnic area with lots of great trees for hammocks! You could probably spend a whole day here relaxing.
So many free ranging chickens everywhere!
The main entrance to Fort Zachary Taylor Historic State Park: $2.50 to walk in.
Fort Taylor info
The inside of Fort Taylor
Checking out some massive cannons!
Harbor view from the top of Fort Taylor.
Ocean views from the top of Fort Taylor!
One of the most remote beaches at Fort Zachary Taylor.
Had to get into those turquoise waters!
Several hammockable trees found at this state park!
The main beach at Fort Zachary Taylor!
So many free ranging chickens everywhere!
The main entrance to Fort Zachary Taylor Historic State Park: $2.50 to walk in.
Fort Taylor info
The inside of Fort Taylor
Checking out some massive cannons!
Harbor view from the top of Fort Taylor.
Ocean views from the top of Fort Taylor!
One of the most remote beaches at Fort Zachary Taylor.
Had to get into those turquoise waters!
Several hammockable trees found at this state park!
The main beach at Fort Zachary Taylor!
Mallory Square
After enjoying some beach time, we wandered to the far northwest part of the island to make sure we didn’t miss the sunset! We caught a few street performer acts in Mallory Square during the fading daylight before we headed over to Sunset Pier for some tasty frozen drinks! We were able to snag a table on the pier for dinner while we were watching the start of the sunset over countless sailboats. There was even a pirate ship gliding out there preparing to watch the end of another day. We wanted to experience the true Key West sunset celebration though, so as the sun got dangerously close to the horizon, we quickly made our way back to Mallory Square! There were now hundreds of people packed into the square waiting for that sun to officially set. Once it did, the crowd went wild and conchs were blown. The street performers all came alive again right after the sunset. Adam was even picked to help in a show!
Street performers in Mallory Square!
Frozen drinks at Sunset Pier!
Catching the start of the sunset at Sunset Pier!
Catching the end of the sunset at Mallory Square!
Where several other people are doing the same 🙂
Conch blows to celebrate the sunset!
Adam trying out to be a street performer!
Adam being trusted to keep this pole upright.
All sorts of cool tricks!
Street performers in Mallory Square!
Frozen drinks at Sunset Pier!
Catching the start of the sunset at Sunset Pier!
Catching the end of the sunset at Mallory Square!
Where several other people are doing the same 🙂
Conch blows to celebrate the sunset!
Adam trying out to be a street performer!
Adam being trusted to keep this pole upright.
All sorts of cool tricks!
Night Life
Now that the sun had officially set, it was time for nightlife to begin! We decided to grab one drink at each bar we got to. Our first stop was the Schooner Wharf Bar, back near The Waterfront Brewery. This place has a great outdoor vibe with jazzy live music. We then walked down Duval Street where there are at least 22 bars in total. We stopped at the famous Sloppy Joe’s for their signature drink, the Sloppy Rita, and found live music. We then went across the street to check out the Hog’s Breath Saloon, where we found a slightly older crowd rocking out to some Tom Petty and Johnny Cash. For a younger crowd, try the Green Parrot. It’s just a block or two off Duval to the west. This was our favorite live music venue of the night due to the high-energy almost head-banging tunes. What we came to determine was that live music was almost everywhere, and that’s where the most fun was happening. After all these drinks, we needed to switch it up with some sort of food, so we went to the dessert bar and restaurant, Better Than Sex. They really play up the romance here with dim lighting and private booths, and wow are the desserts spectacular! Due to this reason, we had about a 30-minute wait, and even once we got in, it took us awhile to peruse the electronic iPad menu. But we ended up choosing the Cookie Nookie Pie accompanied by the Milf Shake and both were delicious. You probably can’t go wrong with any decision here. If you do decide to pay this place a visit, you’ll enjoy scrolling through the other suggestive dessert titles. To end our night, we then danced the night away on the outdoor patio of the Hard Rock Cafe!
A fun outdoor atmosphere at the Schooner Wharf Bar!
The iconic Sloppy Joe’s!
You won’t be disappointed by the dessert you order at Better Than Sex.
A fun outdoor atmosphere at the Schooner Wharf Bar!
The iconic Sloppy Joe’s!
You won’t be disappointed by the dessert you order at Better Than Sex.
Blue Heaven
Blue Heaven had been recommended to us by several people and most said to go very early for breakfast as the line gets long, so naturally we arrived at 11:00 a.m. on Sunday morning. It’s such a popular place that it likely would not have mattered when we woke up. So, we had to wait an hour and a half to be seated, but they send you a text when a table is ready so you can go explore more while you wait. We sure were glad we waited and came back on time because we had one of our favorite breakfasts ever! We shared a great seafood omelet, pecan pancakes, banana bread, and Heaven’s Punch (a delicious juice cocktail). While we enjoyed this tasty meal, we were entertained by live music in this funky, open-air backyard garden setting, with chickens roaming all around our feet.
Blue Heaven: a mostly outdoor restaurant with live music all day!
We heard they have the best breakfast and now we agree!!
Blue Heaven: a mostly outdoor restaurant with live music all day!
We heard they have the best breakfast and now we agree!!
Conch Train Tour
It took me awhile to convince Adam to go on the touristy Conch Train Tour, but we were glad we hopped on. The cost is about $30. It was a good way to get a quick overview of the island and learn some interesting facts about Key West. We briefly saw the Hemingway House (though we didn’t pay to enter it); we learned that most of the roofs on the island are metal to avoid the spread of fires; we learned that US 1 is the longest north-south road in the US. Each train ticket lasts the whole day, so you can hop on and off as often as you like, and your purchase also includes a free tour of Papa’s Pilar Rum Distillery!
Had to be tourists and do the Conch Tour Train!
Most roofs in Key West are metal due to the history of fires on the island.
Did you know that US 1 is the longest north-south road in the US running from Key West to Fort Kent, Maine at the US-Canada border?
Papa’s Pilar Rum
Ended our time in Key West with a tour of Papa’s Pilar Rum!
Had to be tourists and do the Conch Tour Train!
Most roofs in Key West are metal due to the history of fires on the island.
Did you know that US 1 is the longest north-south road in the US running from Key West to Fort Kent, Maine at the US-Canada border?
Papa’s Pilar Rum
Ended our time in Key West with a tour of Papa’s Pilar Rum!
Key Lime Pie and Mr. Z’s
I’m not usually a fan of key lime pie, but we had to try some while in Key West! We went to the Key West Key Lime Pie Company (as seen on TV) and tried a couple different versions; Adam preferred the classic pie and I preferred the frozen chocolate covered version. We also picked up some fantastic pizza to go, per a local’s recommendation, from Mr. Z’s to take with us on the boat ride back home. We heard their philly cheesesteaks are also very good.
Had to get some famous Key Lime Pie in Key West!
There are several forms!
Had to get some famous Key Lime Pie in Key West!
There are several forms!
As you can tell, our 28 hours in Key West was pretty jam-packed! If we are able to return, we would definitely take a more relaxed approach- hanging at the beach longer and lingering at one bar to enjoy a band’s full set before moving on. But do whatever you want, whenever you want here. They call Key West the Tropical Vacationland for a reason – enjoy!