The Ultimate Florida Keys Roadtrip Itinerary

The Florida Keys are the perfect place to go for a little slice of paradise in the United States. It is also considered one of the most beautiful drives due to its highways over the ocean which is why it is the perfect place for a roadtrip!

We roadtripped the Keys for our honeymoon since COVID-19 changed our original honeymoon plans in Hawaii. We spent an amazing 7 days exploring the Keys and socially distanced as much as possible by wearing our masks and dining outside. All businesses and restaurants were following social distancing guidelines and the areas weren’t too populated. Tour companies were still operating at half capacity with sanitization protocols in place. Overall, we had a blast and were able to make the best out of our COVID honeymoon! So, let’s dive into what we did…

Where to Fly Into

Fort Lauderdale and Miami are the best airports to fly into for your starting point. Since we fly Southwest, we opted for FLL and rented a car. The drive from FLL to Key West is 3 1/2 hours so overall it isn’t too bad of a drive time, but we made stops along the way to break it up. We flew from the west coast so by time we landed it was super late with the time change and we decided to spend a night at an airport hotel and get a head start on the road in the morning.

Day 1: FLL to Key Largo

Roadtrip time! Drive time from FLL to Key Largo took up about a hour and half and we were able to check into our hotel early. We spent the first day enjoying the hotel since it was right on the beach and it had free kayak and paddle board rentals. There aren’t really “beaches” in the Keys and the ones that are there really aren’t anything spectacular. We specifically picked to stay at the Baker’s Cay Resort since it did advertise having a beach so we didn’t have to travel anywhere to have some fun in the sand.

Days 2-3: Exploring Key Largo

We stayed at our hotel in Key Largo for 2 nights and thought it was the perfect amount of time. I’ll list our favorite things we did below!

Robbie’s of Islamoralda

• This is a must do for your trip! You can feed the tarpons, shop at the stores, and eat some delicious food. They also have a beach area where you can rent jet skis, boats, paddle boards, and kayaks. Overall this is such a fun and unique spot where you can spend hours at!

Shopping

• There are so many amazing places to shop in Key Largo! You’ll see so many shops as you’re driving in so definitely take some time to explore them. My favorite was Shell World and it has EVERYTHING you could ever think of!

John Pennekamp Coral Reef State Park

• This state park is huge and you can spend an entire day here. There’s snorkel and scuba tours, beaches, water sport rentals, and more. We were signed up for a snorkel tour, but it was unfortunately cancelled due to weather. Still, it’s on the list since I was looking forward to it and will definitely come back again, but this time with my scuba certification to really explore some more!

Mrs. Mac’s Kitchen

• The restaurant that is so good there’s now 2 of them in Key Largo! Both serve the same menu, but the original is open for breakfast while the other opens for lunch. Definitely stop here for a meal and try the coconut shrimp!

Day 4: Key Largo to Key West

Next up, Key West! The total drive time was about 2 hours and we stopped for lunch along the way. This is the best part of the drive since you’ll be going over the Seven Mile Bridge which is an overseas highway. The drive was absolutely beautiful and peaceful. We stayed at The Perry Hotel in Key West which is on a marina and about a 15 minute drive to the downtown area. The hotel was really nice and we didn’t mind the drive, but when we go back I’ll book in the Margaritaville since we spent a lot of time in that area and the grounds were beautiful. The Perry does offer a free shuttle to downtown or you can rent scooters for a day to explore!

Days 5-7: Around Key West

We had such a great time exploring Key West. I’ll list all the activities and excursions we did below with reviews! Definitely customize it as you see fit!

Downtown Key West

• Duval Street: a Key West must! There are so many shops, restaurants, and bars that you can spend all day here. Definitely check out Mallory Square as well for a gorgeous ocean and sunset view.
• Southernmost Point: this concrete buoy is as south as you can go in the US. It’s a fun picture opportunity and there’s a beach and some restaurants nearby for you to go to afterwards.
• Rent a bike: rather than worry about parking, rent a bike and explore on your own! The island is super small which makes it easy to bike and find a lot of hidden gems.

Latitudes on Sunset Key

• If you make one dinner reservation, this is the one. Latitudes is located on a private island and you’ll take a boat to get to dinner. The only other way to get on the island is if you’re staying there so it is super private. Reservations fill up fast! I booked ours a month in advance and there were only 3 timeslots left for the dates we were going. It’s encouraged to go for your meal and then return, but if you do decide to walk around for a little bit please be respectful of the area and residents. Do not expect to pack a beach bag and use this as a ticket to their private beach.

Excursions

• Parasailing: we booked with Fury Key West and it was amazing! The total trip is about a hour long and there were 3 other parties with us on the boat. We each had about 15 minutes in the air and the ride was so smooth. They offer a photo and video package at the end for $40, but we brought our GoPro and got amazing footage.
• Snorkeling: again, we booked with Fury Key West for the double dip snorkel package so we got to go to 2 sites. The snorkel spots were great and we saw a lot of fish. They offered complimentary beer and wine afterwards on the boat! There were 25 people on our tour since they were operating at half capacity, but the only concerning thing is imaging 50 people on this tour due to the boat size. It’s possible they downsized they boat due to the smaller tour size, but I typically like smaller tours in general and don’t think I would’ve enjoyed myself in a tour group this large.
• Dolphin Safari Charters: we booked this tour through our hotel and lucked out by being the only 2 on the boat! This is a smaller size tour with a max of 6 people so it is super intimate and enjoyable. We saw so many dolphins and our boat was able to get pretty close. Afterwards we did snorkel, but the spot we went too wasn’t the greatest so definitely don’t book this if that’s your primary goal. They offered snacks and drinks to us as well and you could bring your own alcohol to enjoy!
• Lazy Dog Adventures: this is a must do! Seriously one of the highlights of our trip. This company offers paddle board and kayak tours through the mangroves and it is so beautiful and unique to Key West. If you don’t want to go with a group, you’re welcome to rent and explore on your own!

Day 8: Key West to FLL

Unfortunately all good things must come to an end and we had to make our way back to the airport to head back home! We booked a flight at 5:30 pm to give us plenty of time in case there was traffic.

Well there you have it! I hope you have the best time in Key West and please let me know if you try out these spots or tell me if you explored somewhere new!