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An Amazing Weekend in the Florida Keys + How to Find Cheap Flights for a Spontaneous Getaway

Updated: Apr 1, 2023

Looking to take a little weekend getaway, but don't know where? Check out these tips to make finding the perfect location super easy! Also, read more for the top things to do on a long weekend in the Florida Keys.


Google Flights

If you have ever had a long holiday weekend and wondered where to go, you should definitely be taking advantage of Google Flights’ search engine. I’m sure many of you have heard of Matt and Scott’s Cheap Flights, or watched countless Bachelorette participants taut Hopper, but have you been using Google Flights to find new places to explore? Their travel engine allows you to search for specific dates OR specific locations with flexible dates.

For example, in January I always try to enjoy Martin Luther King Jr.’s long weekend somewhere warmer. I used Google Flights to search from Nashville to ???? with just the dates listed. Google Flights will show a map of all the available flights from Nashville for that weekend. I can narrow down by zooming in on geographic locations or price points or non-stop options. It’s a great way to play Russian roulette for travel locations. And because of it, that’s how I ended up in the FLORIDA KEYS for MLK weekend!


Florida Keys: Transportation

If you’ve been to Florida, you know how long the state is… and if you’ve been to South Florida, you know Hwy 1 goes for 100+ miles through the Keys… that’s only one two-lane road. Getting to the Keys, you can fly into Miami (or Ft. Lauderdale) and drive south, or you can fly into Key West -- at the tip of the Keys and the southernmost point in the continental U.S.

I flew into Miami (MIA airport) and met up with a friend who drove down from north Florida. You will need to rent a car or have access to alternative transportation to get down to the Keys. Uber won't do it. It’s about an hour on Hwy 1 to Key Largo from the airport.


Accommodations

While there are several cute inns in Key West, I recommend staying more mid-island or up by Key Largo. This helps getting out for your Miami flights as Hwy 1 can get very backed up and one accident could mean you miss your flight home.


Dove Creek Resort (mile 94.5) sits on the ocean, with a pool and restaurant on site. A lower budget accommodation near Tavernier, our room overlooked the pool and had a nice, enclosed patio to watch the sunset. Snapper’s, next door, was a bustling bar with fresh seafood and live music. The local crowd was definitely great people-watching!


Scuba Diving

Key Largo is home to some of the best dive companies on the islands and a great starting point for new divers. If you are interested, Key Largo Dive Center and Rainbow Reef Diving are two of the largest organizations with several dive boats and daily site changes for all skill levels. Since I needed a small refresher on my last visit, I used Scuba Fun Florida, which allowed me to tag along to a dive group with a DM/Instructor to make sure I was fully comfortable in the water. You can usually do a half-day (two dives) tour with all gear for ~$150-$175. For beginners, Molasses Reef or Christ of the Abyss are great shallow reef dives where you can check out coral and sea life. For those more advanced, I’d recommend some wreck diving at Spiegel Grove.

John Pennekamp State Park


While Key Largo is largely a diver’s paradise, you can also visit John Pennekamp State Park (mile 102.5) and walk along the trails, kayak through the mangrove swamps, snorkel the Spiegel Grove shipwreck or do a glass-bottom boat over the reef then have lunch at Key Largo Conch House. We took some beach chairs and spent a few hours under a mangrove on the (small) beach reading and napping.



Heading South


North of Marathon Key is the Dolphin Research Center (mile 59), where you can learn about these majestic creatures, including cognitive behavior studies. You can also explore Marathon Turtle Hospital (mile 48.5), where the animals are rescued and rehabilitated before being released again into the wild.


We stopped at Sombrero Beach (mile 50) for a beautiful sunset. It’s one of the largest beaches in the Keys, and wheelchair accessible. It has a shady park with picnic tables and pavilions for a family picnic, along with public showers.


Sombrero Beach

Key West

From Marathon, head all the way down to Key West on the 7-mile bridge.


Visit Ernest Hemingway’s house in Key West – cash only, open daily for walk-ins and tours.


Eat Key Lime Pie at Kermit on Duval or have dinner at Blue Heaven.


If you need a little R&R, head to Fort Zachary Taylor Historic State Park and lounge on the beach.


Hemingway Rum Company Distillery Tour at Papa Pilar’s is a great historic site (1800s) and a cool way to learn about some local legends and Hemingway’s secrets. Be sure to do a tasting at the bar.

Have kids? Need a rest from all the walking and exploring? Check out the Key West Conch Tour, a 90 min train ride that talks about pirates, local artists, and other fun facts.


Day Trip to Dry Tortugas

If you have time, take a day trip to Dry Tortugas National Park (by ferry) for $200 pp which includes lunch/snacks. Explore the 19th century Fort Jefferson on the 100-square mile park. You can snorkel or scuba dive in the picturesque blue waters.


Now, jump on Google Flights and schedule your own trip to the Florida Keys. Enjoy!!

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