Last updated on June 4th, 2021 at 03:08 pm
There are thousands of things to do in the Florida Keys, the 110 mile string of playful islands connected to Key West by the scenic Overseas Highway. Pleasant sub-tropical weather attracts millions of visitors from around the world in winter. In summer, Floridians flock here for the relief afforded by gentle ocean breezes.
Here are our bucket-list picks for the coolest things to do in Key West and the Florida Keys.
Paddling in the Florida Keys
There are paddle trails throughout the Florida Keys for you to explore from your kayaks, canoes and paddle boards. You can just pull off the Overseas Highway almost anywhere to launch your own boat, or patronize any one of dozens of outfitters for rentals of kayaks and standup paddleboards strategically located near the Keys’ finest paddle trails.
A few special spots we like are in the undeveloped back-country islands of the Lower Keys, and no kayak guide knows that area better than Bill Keough at Big Pine Kayak Adventures. You might also want to arm yourself with Capt. Bill’s excellent Florida Keys Paddling Guide or Bill and Mary Burnham’s Florida Keys Paddling Atlas.
Bicycling in the Florida Keys
The Overseas Heritage Bicycle Trail, when complete, will extend 107 uninterrupted miles from Key Largo to Key West. You can experience much of that trail today, and the most enjoyable sections span old bridges abandoned to bicyclists, walkers and fishing,
Peddling a bicycle through the quiet side streets of Key West may be the best way to explore this iconic destination, from historic Old Town to the Bahamian Village and everything in between — the storied Key West Cemetery, legendary author Ernest Hemingway’s house and haunts, and historic Higgs Beach.
Snorkeling & Diving in the Florida Keys
The most popular destination for snorkeling is John Pennekamp Coral Reef State Park in Key Largo, but that’s not all there is. The Great Florida Reef, the only coral reef in the United States, extends 170 miles four miles offshore in parallel to the Keys all the way to the Marquesas Islands, 20 miles west of Key West.
For a different experience than mingling with the snorkeling hordes of Key Largo, try a snorkeling expedition to Looe Key Reef from the Looe Key Dive Center on Big Pine Key, paddle a kayak or jet ski out to the lighthouse off Marathon, or hop aboard a schooner for a snorkel trip out of Key West.
Fishing in the Florida Keys
Islamorada is the legendary go-to destination for fishing in the Florida Keys with historic significance. This is where former President George H.W. Bush would frequently go bone-fishing on the flats of Florida Bay and adventuring author Zane Grey made his mark fishing in the ocean from Henry Flagler’s long-gone Long Key Fish Camp.
Fishing charters, including party boats, deep-sea charters and private flats guides, are available at marinas throughout the Keys, but no island has a higher concentration of fishing charters than Islamorada, which not coincidentally is also home to the Keys’ largest bait and tackle shop, Bass Pro Shops’ Worldwide Sportsman.
But you don’t have to charter a boat to find excellent fishing in the Florida Keys. Many of the old bridges that carried Henry Flagler’s railroad have been retro-fitted with fishing balconies, and these bridges draw anglers 24/7. We recommend trying the Channel 5 and Channel 2 bridges that link Lower Matecumbe Key to Long Key.
Less often fished, but certainly not lacking productive catches, is the back country of the Lower Keys.
Beaches in the Florida Keys
Visitors don’t often consider the Florida Keys as a beach destination, but there are more beaches here than you might think. Not all of them are natural, only a handful are in public parks, and few are as splendid as you might find along Florida’s Gulf Coast.
But they are here!
We especially love the award-winning beaches at Bahia Honda State Park, and I personally have an affection for the beach at Curry Hammock State Park. Sombrero Beach in Marathon is a fabulous beach, and the beaches of Key West — Smathers Beach, Higgs Beach and Fort Zachary Taylor State Park — are worthy.
Camping in the Florida Keys
Warm days and breezy nights make spring the ideal camping season in the Florida Keys. Savvy campers have already snapped up the campsites at the four state parks in the Keys, but there are dozens of private campgrounds from Key Largo to Key West that have sites available at reduced rates, whether your are in a tent or RV.
Related articles: Best Tent Camping in the Florida Keys;
Private options include Sugarloaf Key KOA and Sunshine Key Resort and Marina in the Lower Keys, the Jolly Roger Travel Park and Fiesta Key RV Resort in the Middle Keys, and Key Largo Kampground in the Upper Keys.
Sunsets in the Florida Keys
Sunsets in Key West and the Florida Keys are legendary. While you can see spectacular sunsets from land on almost any island in the Keys, the best way to enjoy the ritual is from a boat. You’ll find a sunset cruise in every community, from Key Largo to Key West, or just paddle your own kayak into Florida Bay.
Our favorite locations on land are the Bayside Grill and Sunset Bar on Key Largo, the Lorelei Cabana Bar in Islamorada, the Indian Key Causeway between Upper and Lower Matecumbe Keys (just before Robbie’s Marina), the Island Fish Company Tiki Bar in Marathon (MM 54) and the Niles Road kayak launch on Summerland Key.
Mallory Square in Key West is where all the tourists go to see the jugglers, magicians and tight-rope walkers, but you’ll have a better view from Fort Zachary Taylor State Park, where the locals go to see sunsets.
There’s a sunset cruise offered from every island in the Keys. Try something different and watch the sunset from motorized tiki bar in Key Largo, the Cruisin’ Tikis, which embarks from Snook’s Bayside. A catamaran named “Blue” can accommodate 100 passengers out of Robbie’s Marina in Islamorada. For $36, you can hop aboard Capt. Dale Mallory’s “Sirius” sailing catamaran out of the Marathon Marina.
When you get to Key West, you’ll find more than a dozen sunset cruises being offered on schooners, catamarans and party boats. Review your options on TripAdvisor or visit any of a dozen sidewalk kiosks offering to sell you passage.
Eat, Drink and Be Merry
Seafood restaurants and tiki bars dominate the dining scene in the Florida Keys, but travelers should not bypass the legendary pit stops and offbeat hole in the wall symbolic of the Keys lifestyle. From Mrs. Mac’s Kitchen and Hobo’s in Key Largo to Blue Heaven and the Hogfish Grill on Stock Island, you will find a happy place to graze.
A few of our favorite waterfront eateries are Skippers Dockside on Caribbean Drive in Key Largo, the Lorelei in Islamorada, Burdine’s Waterfront in Marathon, Kiki’s Sandbar on Little Torch Key, Hogfish Bar and Grill on Stock Island and the Half-Shell Raw Bar in Key West.
Kick it up a notch at these fabulous landlocked restaurants, the Fish House on Key Largo, Marker 88 or the iconic Green Turtle Inn in Islamorada, Frank’s Italian Grill in Marathon, the Square Grouper on Cudjoe Key and La Te Da in Key West.
Looking for fresh seafood to go? You’ll find none fresher than at Key Largo Fisheries on Ocean Bat Drive, Islamorada Fish Company in Islamorada, Brutus Seafood in Marathon, Fanci Seafood on Cudjoe Key and Fishbusterz on Stock Island.
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