Florida Keys Weekend Road Trip Itinerary: Where To Go & What To Do in the Keys!
The Florida Keys have been an iconic vacation destination for multiple decades and each of these unique islands have their own personal charms that are just waiting to be discovered. From Key Largo to Key West and everything in between, this itinerary is designed to aid in planning the best weekend road trip down the Overseas Highway. Disclaimer: this itinerary id designed with the trip beginning in Key Largo, although it can also be flipped to begin in Key West if that is your arrival destination by plane.Quick Day-to-Day Summary:
Day 1: Key Largo, FL to Marathon, FLDay 2: Marathon, FL to Key West, FL to Big Pine Key, FLDay 3: Big Pine Key, FL to Islamorada, FL
Day 1: Key Largo, Florida to Marathon, Florida
As soon as you cross the first bridge from mainland Florida into the Keys, you already begin to feel like you’ve entered a unique and magical place. The water that now seemingly surrounds you on all sides is as blue as the sky above and the weather is a welcoming warm no matter what time of year you’re visiting. The first island, or key that you venture through is Key Largo, and the adventure and great food that await you in this island community are plentiful! Day 1 Activities & Stops:Mrs. Mac’s Kitchen (milepost 99 in Key Largo) – Arguably one of the best local restaurants in the Florida Keys as well as the longest running restaurant in Key Largo, Mrs. Mac’s is the place to go whether you’re looking for breakfast, lunch or dinner. Our stop here was for lunch and let me tell you guys, do yourselves a favor and try the fried shrimp and fish, but maybe start with some alligator tenders to get you in the Florida state of mind.John Pennekamp Coral Reef State Park (milepost 102 in Key Largo) – After your appetite has been satisfied, it’s time to try out your sea-legs and find your inner-explorer. This state park’s claim to fame is being the United States first undersea park, as it encompasses over 70 nautical miles. One of the most popular activities here is to embark on a 2 hour glass-bottom boat tour that allows you to view the Florida Keys beautiful coral reef. You are also able to schedule guided snorkeling and scuba-diving tours as well that allow you to get up close and personal with the reef and its inhabitants.Robbie’s Marina (milepost 77 in Islamorada) – Undeniably a tourist trap at its finest, you still must make a quick stop at Robbie’s Marina and take the most touristy of videos while you feed the massive tarpon off the marina docks. Robbie’s also offers a gift shop and restaurant for those of you who have extra time to spend here.Sombrero Beach (milepost 50 in Marathon) – You’ve finally made it to your first overnight destination in the Florida Keys and what better time to hit the beach! Declared one of the most beautiful beaches in the Keys, Sombrero Beach in Marathon is perfect for swimming and tanning in the summer or just simple sight-seeing if you’re visiting when the water might be a little cooler.Burdine’s Waterfront (milepost 48 in Marathon) – After a relaxing time at the beach and taking in the views, dinner and drinks probably sounds like a good idea now. Well look no further than Burdine’s Waterfront, a well-hidden, but easy to get to marina and restaurant. This place is a local hotspot through and through and serves up some of the best homemade hushpuppies you can find. Not to mention they serve North Carolina raised beef, so for me it felt like home! So before settling in for the night, grab a brew and burger and mingle with some islanders.
Day 1 Notes:Driving mileage: 63 milesCost & fees: Admission into John Pennekamp Coral Reef State Park is $10 per vehicle and the glass-bottom boat, snorkeling and scuba tours can range from $32 to $90, not including equipment rentals.Lodging: We chose to stay in an Airbnb located in Marathon, but there also plenty of hotels and other rental properties to choose from when booking your road trip.
Day 2: Marathon, Florida to Key West, Florida to Big Pine Key, Florida
I hope you didn’t stay out too late on your first night in the Keys partying with the locals, because today is full of activities. From trolly tours to historic bars to sunsets, it’s time to introduce yourself to the famous, and infamous Key West. But first, as always, breakfast… Day 2 Activities & Stops:The Wooden Spoon (milepost 50) – If a homestyle breakfast is what you’re craving, then The Wooden Spoon and their homemade biscuits is where you need to be! Locals and tourists alike frequent here, so make sure you arrive early to make sure and grab a table!Key West Trolly Tour (Downtown Key West) – After another hour drive, you’ve arrived in the beautiful Key West and I know what you’re thinking, “A trolly tour? Come on Justin, are you trying to be the biggest tourist ever?” But here me out, this trolly tour is 100% worth it. You can hop on or off the trolly as many times as you want throughout the day, and it has multiple stops that take you to museums, restaurants, and shops. Not to mention, driving all over Key West to do multiple different activities is nearly impossible due to the lack of parking. So, all aboard the trolly!Earnest Hemingway’s House – A staple of Key West, the famous writer Earnest Hemingway called the island home for several years and his house still stands and is open to the public for guided tours. The architecture and furniture of the home are beautiful and one of a kind, however you might find the main attraction are the six-toed cats! Yes, you read that right, cats with six toes and they are huge! Over 40 cats call the Hemingway House their home and they are all super friendly and eager to greet you.Southern Most Point – Next stop is for the photo op. This monument marks the southernmost point of the continental United States and on perfectly clear days, you can even see the outline of Cuba on the horizon. There plenty of gift shops in this area as well, but the view is what you should stop for. Be aware that lines to take a photo at the point can be long, so plan accordingly.Sloppy Joe’s Bar – After exploring the sights of Key West, it’s time to hit Duval Street and what better place to start than Hemingway’s favorite hangout. Sloppy Joe’s offers three full bars, live music daily and great food. Obviously if you’re going for the first time, you must try their sloppy joe sandwich, but make sure to get the conch fritters as well. Overall, this restaurant and bar is a very fun hangout, and the staff are great, however if you’re looking for a more local place to eat and drink, you may need to find another option.Sunset Party in Mallory Square – Probably the highlight of my Florida Keys adventure was the nightly Sunset Party that takes place in Mallory Square. This celebration features street performers, food vendors and of course one of the most beautiful sunsets you’ll ever see. It can get crowded, but it is totally worth it and such a great experience to be a part of. Plus, it’s free!No Name Pub (milepost 31 in Big Pine Key) – Once the sunset party in Key West begins coming to an end, it’s time to hit the road again and head towards Big Pine Key, your overnight destination for the day. But first you might need a late-night snack, but you definitely need a late-night drink, and this is the pub to find one at. The No Name Pub is the kind of bar that you can only find if you’re looking for it. You won’t see this little pub just driving down the street, you’ll need the exact address and be ready to make a few turns off the main highway. Another claim to fame this pub boasts is that it has the most $1 dollar bills hung on the walls and ceiling than any other bar in the United States. Now, whether you think that’s sanitary or not, it’s still a cool fact!
Day 2 Notes:Driving milage: 84 milesCost & fees: Ticket prices for the Key West Trolly Tour runs around $45 per person. The Earnest Hemingway Home cost $17 person, and this is regardless of whether you do the guided tour or not.Parking in Key West: One thing that anyone who has been to Key West will tell you is that it is expensive, and parking is no different. To park in the city of Key West for 12 hours cost around $60 and most parking lots we encountered charge by the day, not by the hour.
Day 3: Big Pine Key, Florida to Islamorada, Florida
Today is your final day in the Florida Keys and in a few hours, you’ll be on the next flight out of Miami. However, if your flight is later in the day or at night, you have plenty of time to make a few more adventurous stops in the Keys! Day 3 Activities & Stops:Mangrove Mikes (milepost 82 in Islamorada) – Once you’re packed up and ready to hit the road, you’ll drive about an hour to Islamorada and stop for another popular breakfast place among the locals. Mangrove Mike’s has an old-style diner feel to it that makes you feel welcome and ready to try their delicious pancakes and waffles.Café Moka (milepost 81 in Islamorada) – Well your last stop in the Keys is here and before you head to the mainland, it’s time to grab some coffee and maybe a muffin for your end of road trip snack. This little café is tucked away in a garden and serves up tasty baked goods and delicious beverages. Honestly, you should just try to go here every day of your trip!
Day 3 Notes:Driving milage: 71 milesOne weekend could never possibly be enough time to properly explore the Florida Keys, but it’s definitely a good introduction to what will no doubt become one of your favorite places to visit. As always, I hope this itinerary will help you in planning your next road trip and make it a great adventure. Leave a comment below if you think there are any stops and activities in the Florida Keys that I left out!