Day 1 : Miami Beach
Land at Ft. Fort Lauderdale-Hollywood International Airport
Flight was smooth and the airport was extremely easy to navigate. We. picked up our Jeep Wrangler from Hertz. Highly recommend their service as it was extremely painless and speedy!
Siri, Play – Miami by Will Smith
We then drove to Miami with all the Miami throwbacks we knew. We arrived at our first hotel, WATERSIDE HOTEL in Miami Beach. When the website said the rooms were quaint they meant it, our bags barely fit into the room with enough room to walk. We did get free parking on the street, the parking lot they offer can fit all of three cars. Wandered around by our hotel and found a quick and delicious gyro place to grab a bite before taking a quick nap before a night out in Miami.
If you didn’t take any photos, then you must have been having a damn good time
After getting ready for our night out we walked to “the best dive bar in Miami“. Dive bar was right! ON THE ROCKS had a locals only broken beer bottles on the floor kind of vibe and we loved it. Our friends picked us up and drove us into the nightlife of South Beach. We spent most of the night walking around grabbing drinks here and there before ending the night dancing at CLEVELANDER BAR. I loved everything about this place! Not overpriced and the hiphop throwbacks were flowing as heavy as the tequila.
Going to bed at 5:00am is a Miami Beach MUST
Back to the hotel to catch up on some sleep and jet lag. Say see you in a few days to our friends and fall asleep to the hopes of not waking up with a hangover.
Day Two : Islamorada
Pool Time, Nap Time, Sunset Time
After buying a four pack of beers from the brewery we head back to the hotel for some pool time. The pool was the perfect temperature, enough to cool you off from the Florida heat but not too cold. It was also like we were the only ones at the Inn we had the whole pool area to ourselves for over an hour before we headed in for a quick nap before heading to dinner. Dinner was spent at LORELEI RESTAURANT AND CABANA BAR. This was one of our favorite stops on our trip! Make sure to get there early as there are no reservations and it is the best sunset view in Islamorada. It is also first come first serve and you seat yourself so stay vigilant! We chose to just sit at the bar where we could see the live band and sunset at the same time. The coconut shrimp was out of this world. DON’T skip this restaurant if you are in the area.
Day 3 : Key West
Slow your roll on the way to Key West
We were sad to be leaving Islamorada, but excited to see what the further keys had to offer. Our first stop after leaving the inn was ROBBIE’S on the outskirts of Islamorada. We were told by friends that this was one of their favorite things in the Florida Keys and a quick stop was a MUST! We will be the first to admit that it lives up to it’s hype in every way. We highly recommend finding a table as close to the water as possible and order the Huevos Rancheros for breakfast. After breakfast we head out to the dock to feed the famous Tarpon. If you haven’t heard of these fish…google them now! Or save it for a surprise as you hand feed these monsters, but don’t worry they are harmless it’s the pelicans lurking near by that you have to worry about.
On the hunt for local legends
After doing some research on other travelers blogs we came across The Blue Hole and the creatures who live there. This hidden spot is located on Big Pine Key. Make sure to drive slow on the way out there with the windows down and the music off and you just might spot a Key Deer. Unfortunately we weren’t as lucky as others at finding any Key Deer or the Alligator who lives in the watering hole known as THE BLUE HOLE. Even though we didn’t find anything it was great to get off the beaten path and do some real adventuring. If you need a pick me up on the last stretch to Key West stop at BABY’S COFFEE best iced coffee we had and the metal straws made great souvenirs that we used during the remainder of the trip.
Make landfall in Key West
We stayed at THE SOUTHERNMOST INN. This location was in the middle of it all. We parked the jeep at a parking lot down the street from the hotel where it sat for over 24 hours because we were in walking distance of everything! We stayed in a room in the back building near the pools. Be warned…the reason one pool is packed and the other is empty is probably due to their vast difference in water temperature, choose wisely. Below we will list all of our stops in Key West in the order we enjoyed them. We knew we only had 24 hours in Key West and we were there to make the most of every minute. Feel free to pick and choose our recommendations or pack it all in one day Lindblad style.
✖ Visit the SOUTHERNMOST POINT in the continental US. Be prepared for a long line if you want a photo in front of it, also watch your back for sea spray!
✖ Grab Mahi Sliders and a Key Lime beer at JACK FLATS. One of our favorite eats we tried and the air conditioner was a life saver!
✖ Do it all at the infamous CAPTAIN TONY’S SALOON. One of the most interesting places we explored. We grabbed a Pirate Punch and an Amber Beer in their souvenir cups. Be sure to check out the name on your barstool.
✖ Spin the Shot Roulette at THE BULL. You’ll be back to this building later, so enjoy your shot and sway along to the live band on stage.
✖ Grab a quick luck at PANINI SHAMINI. We ordered the Cuban Panini and the Mediterranean Wrap. Best eaten back at the hotel pool side.
✖ After a quick nap rush down to MALLORY SQUARE for the Sunset Celebration. Make sure to bring some cash to tip the unique performers and buy the fantastic street food.
✖ Right outside of Mallory Square you will find KERMIT’S KEY WEST KEY LIME SHOPPE. Grab a slice and sit on the curb outside because you won’t want to wait another second to eat this!
✖ SLOPPY JOE’S BAR is right across the street. This is one of the oldest bars in Key West and has been open since 1933. The cocktail list is very unique and the bartenders are extremely friendly. We recommend squeezing onto a stool at the bar and sing along to the live band. Just a warning though this place gets packed!
✖ Next stop on your bar crawl is THE WHISTLE BAR. This is on the second floor right above The Bull Bar you were at earlier. The drinks were 2 for 1 and extremely strong. We loved sitting outside on the balcony watching the chaos below. We made up a drinking game where you had to take a drink every time you saw a golf cart, a selfie, a tacky tourist shirt, etc.
✖ Get ready for a bit of a walk because you are off to find the most local bar in Key West. Once you step into THE GREEN PARROT you will see why this is known for being a local dive. It is dark, the juke box is loud, and the drinks are almost too strong to drink. You will need the strong drink for your next stop.
✖ THE GARDEN OF EDEN is the last bar of the night. This bar is unique for a few reasons: it’s a roof top bar, it doesn’t allow the usage of phones, and it will be full of naked people. This was our first experience at a clothing optional bar and we weren’t going to completely let the opportunity go by. If being fully nude is far past your comfort zone, then we recommend the following: chat with the super friendly staff, order a shot, take off your shirt, drop your drawers, take that shot, throw it all back on, and walk down the three flights of stairs laughing the whole time. The best way to end a night in Key West.
Day 4 : Key Largo
Say Goodbye to Key West
Waking up after our bar crawl was a little rough. Our hotel had an amazing complimentary breakfast bar. After breakfast by the pool we packed up and checked out. Before saying farewell to Key West we recommend stopping by CUBAN COFFEE QUEEN. Specifically the one off Margaret Street. (If you want a picture of this amazing wall mural.) The Hangover Smoothie and Rehydrator Smoothie really helped bring us back to life.
Stops to make on the way to Key Largo
We did a lot of driving on this day with a lot of tempting stops along the way. Here are a few stops we would make again and ones that weren’t worth stopping. SANDAL OUTLET had a full parking lot, so our thoughts were this must be good! False, it was a tourist trap and the discounts weren’t that great. SOMBRERO BEACH is known for being the best sandy beach in the Florida Keys. When we got to the beach it wasn’t crowded which is great! The huge downfall of this place is the sea weed. We aren’t new to the beach life and we understand that beaches have sea weed, but we have NEVER seen this much sea weed on a beach in our lives! MARKER 88 was our favorite stop. It’s found on Plantation Key with a small parking lot and a great restaurant on the beach. They also offer various beach rentals but we got the pleasure of sitting outside watching a nasty storm roll in. Lastly, if there was a stop we wish we would have made time for it was the THE TURTLE HOSPITAL in Marathon. We only heard amazing things about it and will definitely stop on our next trip.
It’s not supposed to rain in paradise…
We chose to stay at THE PELICAN in Key Largo, solely because it was the cheapest room in the area we could find. Boy did we get lucky! This is a cottage style hotel with cabin like rooms all over the property. Also on the property is a private beach with kayaks and a few docks. Unfortunately a HUGE storm was coming in, so we grabbed our books and rushed out to the dock to enjoy some down time and watching the dark cloud roll in. Another great thing about this stay was the restaurant that was next door. MRS. MAC’S KITCHEN was the place where we finally decided to try the local delicatessen called Conch Fritters. Which were fantastic by the way!
Patios, Beers, Rain, Fish Tacos = Heaven on Earth
SKIPPERS DOCKSIDE will be a place we stop every time we go through Key Largo. The outdoor patio is right on the water and the covered seating area is the perfect place to watch a tropical storm. Splitting the fish tacos and fish sandwich was the best choice we could have made. One of our favorite meals we had the entire trip.
Day 5 : The Everglades
See You Later Alligator