Florida Keys Road Trip

Many of our customers end up flying into Ft. Lauderdale or Miami since the fares are often less than Key West. If so, you can take the Keys Shuttle, Greyhound bus, or rent a car and drive down. We've had requests for sights to see along the way, so we thought we'd post some of our favorites.

You’ll want to leave plenty of time driving down the 100-mile Route 1 Overseas Highway that island-hops the Florida Keys to Key West, the southernmost point in the Continental US. For one, it’s a gorgeous drive, recently named a Great American Road. For another, the speed limit is 45 to 55 with plenty of speed traps!

Historic Route 1 sign

Once you get off the Florida Turnpike in Homestead, you have a choice: the 18-mile recently redone “Stretch” or Card Sound Road, a toll road that costs all of a buck. If you take the Stretch, stop in at Gilbert’s tiki bar; if Card Sound, pull into Alabama Jack’s, a funky watering hole amid the mangroves. Keep your eyes fixed on the creek below for colorful fish and a manatee may even glide silently by.

Key Largo

You’ll start to notice numbered small green signs on the side of the road. These milemarkers start on the Stretch, around 112, and go down to 0 in Key West. It’s a great way to give directions in the Keys. There’s ‘bayside’ for Florida Bay, on your right if heading south, and ‘oceanside’ on your left, referring to the Atlantic Ocean.

At mm104 bayside is the famous Caribbean Club bar where portions of the Bogey and Bacall film Key Largo were filmed. Despite it’s claim to fame, it’s refreshingly un-touristy and family-owned for nearly a half-century. There’s usually some Harleys parked outside, dogs are welcome, and there’s a flock of wild parrots that perch above the waterfront picnic tables.

Pop into Florida Bay Outfitters next door, a really neat kayak shop that sells our “Florida Keys Paddling Atlas.” Tell them Mary and Bill sent you!

North America’s only living coral barrier reef draws divers and snorkelers from all over the world to John Pennekamp Coral Reef State Park at mm 102.5 oceanside. Even if you don’t take the boat out to the reef, the park is a great introduction to the flora and fauna of the Keys, with nature walks and kayaks trails through mangrove tunnels, a small aquarium, and two beaches.

Islamorada (pronouned eye-la-mor-ada)

While fishing is legendary throughout the Keys, Islamorada is the ultimate destination for a deep-sea sailfish adventure, fly-fishing for tarpon in the nearby Everglades or flats fishing for bonefish. World Wide Sportsman at mm 81.5 bayside is a fun place whether you fish or not. It’s one of the more unique in the BassPro Shop chains, where you can step aboard the "Pilar," sister ship to Hemingway's famous fishing boat, or dine at the elegant Zane Grey Lounge overlooking the marina.

Robbie’s Marina, mm 77 bayside, is the jumping off point for a boat or kayak trip to Indian Key, the island ruins of the first seat of Dade County. A visit to the Keys isn’t complete until you feed the giant tarpon that wait off Robbie’s dock.

Lower Keys
Once you cross the spectacular 7 Mile Bridge from Marathon, you've entered the Lower Keys. This is where we do our Backcountry kayak trips, and where you can see the endangered Key Deer. Stop in at the Key Deer Wildlife Refuge Headquarters on Big Pine Key to learn more.

Key West

Cats jumping through flaming hoops, fire-eaters, clothing-optional bars. There’s no place quite as “ultimate” as the southernmost city in America, from the nightly Mallory Square sunset celebration to the Duval Street “pub crawl”.

Sloppy Joe’s is one of the more popular tourist bars, with lots of Hemingway claims to fame. Some of our favorite bars are the Green Parrot, Schooner Wharf Bar, and the Bull and Thistle (there’s a clothing-optional bar on the roof if you are so inclined!)

Wherever you choose to stop on your Florida Keys road trip, shoes are optional and the sunset lingers.

For more information visit Florida Keys Tourism

Getting to the Keys: a Tip to Save on Flights

There’s still room on some of our March trips, but if you are checking airfares into Key West, you may get sticker shock! They were fairly low in January and early February, but now that Spring Break has kicked in, the fares have gone way up.

Here’s a tip that may help: Fly into Ft. Lauderdale, rent a car and drive down the Keys, and save up to half on your airfare. For example, we just did a quick search on cheapfares.com and SouthWest Airlines, and round-trip flights from Washington Dulles to Key West in March are over $500. Dulles to Ft. Lauderdale round-trip flights are starting at about $230 (plus taxes and fees, of course).

US 1 is a recent designee as a Great All American Road and a spectacular drive across historic railroad bridges and Caribbean-blue waters. Leave enough time, as the speed limit is 45 most of the way, and you’ll want to stop off at some famous—and quirky—places, like the Caribbean Club in Key Largo and Robbie’s Marina in Islamorada, home of the giant tarpon. Our Lower Keys kayak trips start around milemarker 25 in the Big Pine Key area.

In a future blog post, we’ll list some of our favorites stops on a Road Trip to Paradise!