Seven days in the Florida Keys will fix whatever ails you. If you need to relax, there’s miles of coastline, hundreds of charter boats to relax on, and some of the calmest waters imaginable running through mangroves. If you’re ready to adventure you can scuba, parasail, or take a back country tour.
So, whatever your mood is, you can have a fantastic time with seven days in the Florida Keys, but there’s so much to do how do you know which ones are for you? Don’t worry, we’ve got you covered, this guide will have you traversing the Keys like a pro.
Days One and Two of Seven Days in the Florida Keys: Key Largo and Islamorada
Day One: Unwind
Head over to the beach at John Pennekamp State Park, the first underwater park in the United States. There are two beaches to sunbathe and snorkel from, mangrove tunnels to kayak, boat tours to the reefs around John Pennekamp, and a visitors’ center with 30,000-gallon aquarium. Not to mention hiking trails and picnic areas while you enjoy that dreamy Key Largo weather.
After you’re done at the park, give yourself a treat and visit Keys Chocolate and Ice Cream. You can try some of their delicious chocolate truffles, enjoy an ice cream treat, or spring for one of their Frozen Key Lime Pie Bars.
For dinner stop by Snook’s Bayside for fresh seafood, cold drinks and beautiful sunsets!
Day Two: Hang With The Pirates
No, not those pirates, I’m talking about the pirates at Pirates Cove Watersports of course. Whatever you have on your Florida Keys Checklist, odds are they have it. If you want to tear it up on jet skis, they have them. Float in the clouds? Then you’ll want to reserve one of their parasail tours. If you’d rather be underwater, book one of their snorkel or scuba dive excursions. But hold on, they also have fishing charters and sunset cruises, hell, you can spend the whole seven days right here if you want to.
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Follow up all that adventuring with a quiet dinner at Buzzard’s Roost. It’s located at the end of a canal with views of the cove. Steaks, seafood, and homemade desserts are sure to hit the spot. Bonus, if you’re there on Sunday, check out their Sunday Brunch, there’s no better way to waste a Sunday early afternoon.
Days Three to Five of Seven Days in the Florida Keys: Marathon
Day Three: Head to Marathon and Take a Nature Walk
If you’re looking for some “crafty” souvenirs, t-shirts, or artwork, stop and see Betsy, the big lobster at Rain Barrel Village. Rain Barrel Village is a multi-building campus with tropical courtyard. The shops are filled with paintings and crafts by local artists, beach wear, and Florida Keys-inspired trip mementos.
On your way to Marathon, stop at Publix and hit up the deli for one of their fresh made subs, or better yet, grab some Cubanos (the sandwiches, not the workers) for the family at Sunrise Cuban Market and stop at Windley Key Fossil Reef Geological State Park. There you can take a shaded nature walk and enjoy lunch at one of their picnic areas. There are 1.5 miles of trails where you can learn about the tropical hardwood forest that used to be in abundance throughout the Keys. Plus, you’ll see firsthand cutouts of the ancient coral reefs that make up the islands.
Hang out with the locals for dinner at Dockside Boot Key Harbor. More than just bar food, they have ribs and chicken pot pie on their menu. Chicken pot pie! That’s all good, but you can’t go wrong with the Mahi Sandwich. They also have happy hours and live entertainment to get you through the night.
Day Four: Kayak Mangrove Tunnels, See Manatees, Fish
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Get together with Key Kayak and sign up for one of their eco-tours and kayak through the mangrove tunnels off of Sombrero Beach. Beat the heat under the cool canopy of the trees while you kayak on calm clear waters. See the birds and fish that make the mangroves their home while you learn about the importance of this delicate eco-system.
Another tour they offer is a combo mangrove and manatee tour where you can get up close to the manatees. No touching! If that doesn’t do it for you, you can sign up for one of their manatee search tours, spoiler alert, I think that you find them. Or you can rent a kayak for fishing, a SUP for paddling, or a jet ski for jet skiing. If you didn’t drive the Wagon Queen Family Truckster and you don’t have room to haul a kayak, you’re in luck, they deliver.
For dinner, pop on over to The Island Fish Company and belly up to the longest tiki hut bar in the Keys. Delicious seafood, steaks, and Mexican inspired bites are on the menu, and I haven’t even gotten to the raw bar yet. Do yourself a favor and order the Caribbean Special, seared grouper with pineapple sauce, you can eat it while you enjoy another spectacular sunset.
Day Five: Sea Turtles and Travel to Key West
Before you start your journey to Key West, make an early appointment at The Marathon Turtle Hospital and take a guided tour. Find out how a mechanic from Jersey turned an old hotel (and strip club) into a hospital that has saved over 1,500 sea turtles. You’ll get to meet the current residents and get a tour of the grounds with the pools and tanks dedicated to saving these seemingly fragile creatures.
When you first get on the 7 Mile Bridge, there’s a small island to your right, that’s the historic Pigeon Key. It was an important part of the building of the Overseas Highway and the Overseas Railway that came before it. It’s a great spot to spend an afternoon in the Keys, keep that in mind for your next trip.
Along the way you’ll also pass by the Blue Hole on Big Pine Key, it’s a good quick stop, not missing much if you don’t. You can also stop at No Name Pub and debate how many dollar bills are stapled to the ceilings and walls while you eat lunch (current estimate is almost $1 million). Other good lunch places along the way are Kiki’s Sandbar and Mangrove Mamas. Or you could just enjoy the drive.
For dinner Hogfish Bar and Grill is right on the water, literally. Not only that, but the seafood is also fresh and fantastic. It’s in a marina on Stock Island, so if you’re staying in Key West you’ll have to drive, uber, or pedicab there.
Days Six and Seven of Seven Days in the Florida Keys: Key West
Day Six: Head For Danger and Historic “Homes” Tour on Duval Street
Danger Charters that is. Danger Charters offers a few different tours, but the Sail, Snorkel, and Kayak tour is one of the best things to do in Key West. On it you’ll sail out to the Key West National Marine Sanctuary where you’ll snorkel a shallow reef in crystal clear waters. After that you’ll kayak around mangrove islands and through mangrove tunnels. You can do this tour in the morning, afternoon, or spring for the whole day tour. All tours include snacks and drinks, including beer and wine.
After you’ve had your day of sailing, jump on over to Duval Street and visit some “historic homes”. Historic homes of stories and fun that is, and they’re waiting to help make your next story.
Capt. Tony’s Saloon is where famous author Ernest Hemingway hung out as well as Truman Capote, Jimmy Buffet, and a list of other celebrities. Originally a combo icehouse/morgue in 1851, it eventually became the bar that it is today.
Another bar that started in the 1800s is the Green Parrot. They’ve been slinging drinks there since 1891. In the 2020s you can hang out and listen to live music. If you happen to be there on the first Wednesday of the month then you are in luck because that’s Ukulele night, don’t want to miss that.
Sloppy Joes is the newest bar on the list. In a colorful story typical of Key West, it was opened in another building in 1933 and moved to its new location in 1937. Ernest Hemingway also hung out here, he even had a hand in the name change from The Silver Slipper to Sloppy Joes. Today there is live music nightly and a festive atmosphere.
Day Seven: Hit the Beach, You’ve Earned It
Time to relax and rejuvenate before you have to go back to the grind. The Florida Keys aren’t really known for their beaches, but there are some nice ones if you know where to look.
Smathers Beach is a long strip on the southeast side of Key West. Sandy beaches look out over the Atlantic Ocean. If you’re up for it, check out Sunset Watersports and see Key West from the sky as you book one of their parasail tours in case you missed out on the parasailing in Key Largo.
Fort Zachery Taylor is a civil war era fort but it’s also on one of the best beaches in the Keys. It boasts a white sand beach, and has grills, picnic tables, and the concession stand rents beach chairs and snorkel equipment making it easy to spend the whole day there.
For dinner Old Town Tavern & Beer Garden has a fantastic pub menu along with two(!) happy hours. Plus, it’s a great spot to watch the foot traffic pass by on Duval Street.
Now that your memories are full and your wallet is empty it’s another week in the Keys done. So, you know what that means, it’s time to start planning the next one (you know you want too).
