The Florida Keys & Key West

The Ultimate Guide to a Florida Keys & Key West Vacation

Known as ‘America’s Caribbean Islands’ The Florida Keys & Key West are an incredible vacation destination, just a 3-hr domestic flight from most of the major East-coast cities.  If you’re looking to book a vacation, but don’t want the hassle of traveling internationally or taking a long flight, the Keys are the destination for you.  Having just returned from an activity-packed girls road trip through the Keys, I’m going to break down our trip- including the best places to stay, dine, drink, and explore- so you can book your flights & accommodations, relax, and enjoy!

 DAY 1

 Although Key West has it’s own airport that you can fly into, my friends and I didn’t want to miss the experience of driving the Overseas Highway and seeing the Seven Mile Bridge, so we decided to fly into Miami and take a little road trip.  We took an easy 3-hr flight from New York’s JFK Airport and landed in Miami the same morning.  We then rented a car and drove the hour long drive to Key Largo, which is the first part of the Keys.  We stopped for lunch at Sundowners in Key Largo, which is a beautiful restaurant right on the water with views of the Florida Bay from both the glass-walled dining room, and the giant outdoor patio. There are tons of photo opportunities (which we all took advantage of, since it was our very first stop in the Keys) including giant adirondack chairs and beautiful ocean views. Although we didn’t get to experience it for ourselves, Sundowners also apparently has some of the best sunset views on the Island. After lunch, we continued on to our first hotel located on Stock Island, right outside Key West. We stay at Oceans Edge Hotel & Marina and it was genuinely one of the most beautiful resorts I’ve ever stayed at. The hotel has 6 heated pools that all overlook the marina- it is absolutely picturesque. We stayed in suites that each had a private living room and a balcony overlooking the marina where we watched the sunrise & sunset almost every day. I would definitely recommend looking into this resort if you want to be near Key West, but also want to be right on the water in a quieter area of the island . We had a car, so it was an easy under-20 minute drive to the center of town, but the hotel also offers a shuttle service every hour that leaves from the resort and drops guests off in Key West. For dinner on our first night, we headed over to Matt’s Stock Island Kitchen & Bar at the Perry Hotel Key West. The restaurant is very cute and trendy, and the food was incredible- I started out with their Key Lime Martini- and then we shared the Admiral Sea Food Tower and I chose the Today’s Catch grilled Salmon with asparagus on the side as my entree (DISCLAIMER: I ate A LOT of seafood on this trip. All the seafood in the Keys is so fresh, I had to take advantage of it!) It was after dark before we got to Matt’s and they had an outdoor seating area with little fire pits going, but I also think eating here during the day would be beautiful, because the restaurant overlooks the marina.


We started off our second day with breakfast at Blue Heaven- in my opinion, Blue Heaven is a must-see when you’re visiting Key West. The cute little restaurant is located in historic Bahama Village and has a massive outdoor dining space, covered by a canopy of massive cloth sails, tree branches, and twinkle lights. There was live music when we visited (which is a favorite of mine), and the food is seriously good. I tried the Shrimp Eggs Benedict and was very impressed. Although this Celiac chick didn't get to try the blueberry pancakes, I have heard that they are incredible. A fun fact about this fun spot- in the 1930s, author Ernest Hemingway officiated boxing matches at Blue Heaven! We spent the rest of the morning exploring Key West, and stopped by the Ernest Hemingway Home & Museum. I had only been in the Keys once before- when I was 13 on a family trip- and at that time we took the full tour of the house (recommended), which was incredible. This time, we walked around on our own, saw six (6) of the many cats who live there, and took some beautiful photos on the second story wrap-around porch that faces the Key West Lighthouse (fun fact about this lighthouse: the U.S. Navy opened in in 1948 with a woman as it’s Keeper, which was unheard of for the time!) Our next activity of the day was a Reef & Ritas Snorkel Excursion with Fury Water Adventures which was so. much. fun. We headed out on the water on a boat for an afternoon of snorkeling and margaritas. The water was so clear and beautiful, the crew was a ton of fun, and a POD OF DOLPHINS SWAM UP RIGHT ALONGSIDE OUR BOAT WHILE WE WERE ANCHORED! I freaked out, it was incredible. * *If you do decide to do the Fury tour or go snorkeling at all, please remember to wear REEF SAFE sunscreen to help protect the reef itself and the other sea life living around it!!* * That evening, we went to the nightly Sunset Celebration at Mallory Square which is a charming little arts festival on the water that features local artist’s booths, street performers, food carts, and locals & tourists alike who gather to watch the sunset and applaud once it drops below the horizon. This sweet tradition is definitely something unique and worth seeing when you visit Key West. We headed back to Oceans Edge for dinner at their restaurant, Yellowfin Bar & Grill. It was so nice relax at our resort and eat overlooking the marina and three of the pools (the outdoor dining area also offers fire pits, which is such a nice touch. I had the Whole Fried Snapper, which wasn’t too pretty to look at, but tasted SO good. The desert menu was also incredible and we tried one of everything, because why not?


Our third day started off with breakfast at Kermit’s Café & Kitchen , which is yet another (shocker!) really cute local spot in Key West! Kermit’s has a rainforest patio and koi pond, amazing cappuccinos, and the adjoining Key West Key Lime Shoppe- imagine ANYTHING Key Lime flavored. . . this place probably has it! After breakfast, we headed over to The Key West Butterfly & Nature Conservatory. The conservatory is so beautiful, and features FLAMINGOS and other pretty birds as well as the expected (50-60 species of) butterflies! (NOTE: the conservatory is a pretty small space and can get crowded & very warm- this is one of the experiences that I would recommend getting to right as it opens for the day to minimize crowds.) Within walking distance of the conservatory is the Southernmost Point Buoy, which marks the southernmost point of the continental U.S. This can be a quick stop, just to say you did it- but note that if you want a picture in front of it, there tends to be a line! A little before sunset, we set off on a Wind and Wine Sunset Sail with Danger Charters. This excursion was probably my favorite activity on the trip (I’m a sucker for sailboats, wine, and sunsets so this really was the trifecta!) I have to say that a huge part of what made this experience so enjoyable was the crew- all of the members were so fun & nice, and they all made sure every single one of us on the boat had an amazing time. We sailed out into the sunset, with the option of trying 8 different wines (or 5 different beers), ate some amazing passed apps, took gorgeous photos, and watched the sunset over the water before heading back to shore. What more could we ask for?? After we docked, we went for dinner at Turtle Kraals which is considered ‘authentic Key West dining’, influenced by generations of settlers from nearby Caribbean islands. The most fun part? The BOX TURTLE RACING! Influenced by the Bahamian pastime, you can watch these cuties scurry from starting line to finish line twice a week in the evenings. The races are MCed by the Turtle Master and everyone gets a ticket and cheers on their turtle. You even have the option to win a treasure box prize! (NOTE: the turtles are treated very well, and only race 2x per week. During the warmer summer months, they do not always race due to the heat, so you must call for race hours) Overall, a 10/10 experience.


On day four, we checked out of Oceans Edge Resort (sad face) and started the drive back through the Keys to Islamorada (happy face!) On our way, we stopped at Bahia Honda State Park (MUST DO!!) and spent some time on the little beach looking out onto some of the clearest water I’ve ever seen! Then we continued on to Robbie’s Marina for lunch at The Hungry Tarpon. Robbie’s Marina has outdoor shops, food vendors, and they’re known for their tarpon feedings (we didn’t participate, but we watched from the dock!) Afterwards, we checked into our second hotel, Amara Cay Resort! Amara Cay is a beautiful resort on Islamorada with a huge pool, beach, tiki bar, and docks that allow you to walk out onto the water. The staff & manager are incredible and so accommodating and the rooms are great as well. We had a really amazing experience staying there. After settling in and a tour of the property, we headed to Key Largo for dinner at The Fish House. The Fish House is a local eatery with fresh seafood and a ton of character! Their seafood is amazing, and their Key Lime pie is award-winning.


We started out day five with breakfast at Key Largo Conch House, a quaint, family-owned, sustainable seafood restaurant located in a cute little house with a back garden. I got the Spicy Cajun Omlet and an Iced Almond Latte and was a very happy girl. Afterwards, we headed to Playa Largo Resort and Spa to relax by the pool for a bit and get a spa treatment. This gorgeous waterfront resort had a huge pool and pool bar, beachfront and a marina, as well as the spa. It was so nice to hang out by the pool here and soak up the sun. I got a Smoky Mule cocktail while we waited for our treatment, and it was to die for. At the spa, we got their signature Key Lar-GLOW Organic Brightening Facial and my skin was baby smooth and so clear for weeks afterwards! The spa featured giant showers & saunas, a dimly-lit relaxation room with daybeds to relax in before & after your treatment that offered snacks & a variety of tea. They offer a variety of standard treatments, as well as an Ocean Spa Body Bar featuring specially formulated scrubs from coffee grounds, sugar and salt with pineapple, coconut and honey where you can create your own customized, self-guided treatment. The staff was so friendly & welcoming, and my facialist was incredible. After our treatments, we headed to Florida Keys Brewing Co. for a tour & tasting. They brew up craft beers feating local flavors like Key lime, citrus, local honey, and pumpkin. We got a full tour of the working brewery, which was the coolest, and also got to hang out and do a tasting in their cute outdoor beer garden featuring colorful picnic tables and live music! Although I couldn’t taste test the craft beers (Celiac), my friends gave them 5 stars- and I tried an amazing pineapple cider! For dinner that night, we headed to Marker 88- a beachside dining spot that opened in 1967 and offers some of the freshest seafood around. We sat under a veranda on the water and I ordered one of my favorite meals of the trip- Key Lime Seafood: lobster, shrimp, and blue crab in a Key Lime-Tabasco butter with tomatoes and scallions, served over cilantro lime rice * *swoon* *


Our last day in the Keys started with watching the sunrise on the beach at Amara Cay- it was dreamy! Then we checked out of our rooms (super sad face) and headed to our final destination of the trip. Postcard Inn Beach Resort & Marina is a sister property of Amara Cay, and is home to the Holiday Isle Tiki Bar that invented the Rum Runner! We ate lunch at the tiki bar (and, of course, had a couple of rum runners) and then hung out by their gorgeous pool for the rest of the day before it was time to leave.

Looking back on this recap, it’s hard to believe that we fit so much into our 6-day trip! If I had to do the trip all over again, I would’ve left some time for water sports (would’ve loved to have gone paddle boarding, or snorkeling one more time) but overall, this trip was a total dream!

Thanks for reading! If you have any questions that weren’t answered in this post, feel free to leave a comment below!


* Special thanks to The Florida Keys & Key West for sponsoring this post, and to all of the local businesses & resorts that hosted us along the way*

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Ultimate Guide to FL Keys