Keys to the South: One or Two Days in the Florida Keys

“We’re going to the keys this weekend,” in the Miami lexicon means that the person is going to be 1. unreachable, 2. on a boat and 3. intoxicated. It’s more about a state of mind than an exact location, as the Florida Keys are made up of 1,700 tiny islands between Soldier Keys and the Dry Tortugas.

If you have a day or two to spare on your next trip to Miami, it’s worth it to add the keys to your itinerary. Below are a few ideas how:

Major Key

After landing at MIA, rent a car and get on the Turnpike South. There is no getting lost, so it’s the perfect starter road trip. You and/or your passengers can call out the fun names of each Key and get a glimpse of their personalities as you zoom by. After three-and-a-half hours (without stops and avoiding rush hour), you will literally be at the end of the road at the heart of Key West. Spend the rest of your day exploring hidden gems, like the Little White House or taking pictures at the Southernmost Point Buoy or bar-hopping down Duval Street or enticing Hemingway’s cats to let you pet them. Although it’s possible to drive back the same day, it’s best to spend the night and indulge in a few extra Rum Runners.

Keys to Success

If you have a little more time, you can certainly get a little more out of your southernmost adventure. Leaving Miami behind, you’ll be in Key Largo in an hour. There you must go on a snorkeling tour at John Pennekamp Coral Reef State Park.* Even if you’re not much of a swimmer, you can opt for a glass bottom boat ride over the sunken Christ statue.

Just 30 minutes from Pennekamp is Islamorada where all of Miami’s rich cousins have their second home. If you know someone with a “house in the keys” it’s here, but if you don’t know anyone, you can still stop at MEAT Eatery and Taproom for a delicious, post-swim lunch.

You’ll need this sustenance for your next stop (a mere seven minutes from MEAT) at the world famous Tiki Bar at Holiday Isle. The icon of Islamorada, here you can enjoy more swimming and you can also jet ski to your heart’s content. But really, you’re here for a Rum Runner.

While I’ve never personally had dinner or stayed at the PostCard Inn, those options are available to you in case you over do it.

From here, you can be in Key West in two hours…if you’re sober. If you’re drunk it will take you a bit longer after you inevitably plunge to your death off the side of the Seven Mile Bridge.

Kidding. No one is plunging because you’re saving your liver for Duval Street.

After taking in the Key West sunset, go to dinner at Seven Fish and then have dessert at Better Than Sex. Where the night takes you after that is entirely up to the weather.

Pro Tip: If you don’t want to stay in Key West proper, a good midway point is Hawk’s Cay Resort in Duck Key. You can use it as home base as you drive up and down the keys.

*There are also scuba diving tours at Pennekamp, but be mindful of the risk of getting the bends if you go too soon before/after your flight.

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