Two Days & 11 Can't-Miss Activities for Your First Trip to the Florida Keys

If you’ve never been to the Florida Keys and you’re within a reasonable driving distance (say, most of the South Eastern US) – why on earth not? Besides being the inspiration for this blog, the Keys contain:

The only living coral barrier reef in the United States (and third-largest in the world!)
The easiest-to-access tropical waters in the US
Tropical flora & fauna not found anywhere else in the Continental US
The best place to catch Spiny Lobster
Amazing sportfishing opportunities (if that’s your thing)

And finally, and perhaps most important, the ONLY place not requiring a very long plane ride where the water looks like this:

Seriously, if you have any interest at all in the beach, the water, scuba diving, snorkeling, boating…or just sitting on the beach sipping a mojito – plan a trip to the Keys. And I’m not talking about the standard we-went-as-far-as-Key-Largo trip, which kinda doesn’t count unless you’re the most casual of cheesy tourists. The Keys are split up into three general areas – the Upper Keys, Middle Keys, and Lower Keys. Key West, at the tail end, is probably the most famous – but also the furthest from the mainland. Key Largo, closest to the mainland, is only a short drive from Miami – but is also host to the most t-shirt and shell shops in the Keys, and has the most touristy feel. For the best experience in the Keys, we think you have to drive further south than Key Largo, or as far as you have time for. I put together a suggested itinerary more geared to the outdoorsy and adventurous among us than the shoppers and beach-sitters. Because, truly, great shopping can be found in many places – but the parts of the Keys that can’t be duplicated anywhere else are the water and the wildlife. If it were my first time, I would want to allocate at least 2 days, and I would schedule it this way:

Day 1 – Key Largo / Islamorada (Mostly)

On your drive in, hit the Chamber of Commerce Visitor’s Center (it’s hard to miss) and ask anything you’d like to know without worrying about whether they’re trying to sell you something. There are also some neat informational exhibits to check out.
Hit John Pennekamp State Park and visit the Visitor’s Center-slash-Aquarium for a great overview of the local wildlife (particularly underwater!).
Then, hop onboard their Glass Bottom Boat ($24 or less) or Snorkeling Tours ($30 or less) to really see the best of the Keys. If you’re lucky, you’ll hit Molasses Reef, said to be the most populated reef in the world.
If you have time, hit the History of Diving Museum to learn a ton about the history of scuba diving but also about the history of the Keys and how humans interact with the underwater world.
For dinner, decent quality outdoor shopping, and an unforgettable visit with the fish hit Robbie’s in Islamorada. For a few bucks, opt to feed the tarpon out on the dock – but beware the pelicans, who will steal the fish. Also, be warned – people can (and often do) get bitten by over-eager tarpon trying to grab a fish. Try standing back and watching the macho guy next to you get scraped up and bloody…just try not to be that macho guy. On your way out, hit a few of the local vendor stalls for more authentic Keys memorabilia.
For dessert or an after-dinner drink, head to Sunset Grill overlooking the 7-mile bridge (we got engaged here!). With an outdoor pool, outdoor dining, and a great mix of cocktails, this is a must-stop. Wander out on the dock to see if the underwater lights have attracted any interesting fish, and take some time to enjoy the view of the bridge – and the currents!

Day 2 – Marathon / Lower Keys / Key West

In the morning, hop onboard the Marathon Lady for a half-day party boat fishing trip if that’s your style. With three stops for fishing, we’ve had great experiences every time.
As you head south, keep an eye out next to the road for green iguanas sunning themselves on the sidewalk. We’ve occasionally counted hundreds on a drive from Marathon to Key West.
Spend the afternoon further south (about 45 minutes’ drive) at Bahia Honda State Park. This is an award-winner for a reason, and even with campgrounds closed currently due to Hurricane Irma (as of 3/2018), the beach is still gorgeous. So is the view of the bridge.
Visit Blue Hole on Big Pine Key, the only freshwater lake in the Keys and a great wildlife viewing area, including Key Deer and occasional alligators.
Finally, hit Duval Street in Key West for everything that Key West is famous for…bars, shopping, and more bars. While you’re there, visit Mallory Square at sunset; take some cash for interesting local vendors.

To be fair, while writing this article I realized Key West is actually one of my least favorite Keys, mostly because it’s more about late nights and crazy weekends than the amazing outdoor scenery; but also because it’s more crowded and hectic than the other parts of the Keys. For this itinerary, I would stay in Marathon the first night and Key West the second night. Know that you will pay much more to stay in Key West – but it’s worth it occasionally. A word to the wise – there are many so-called “boatels” (house boat motels) in the Keys, and they may seem reasonably priced. We’ve stayed at several and while I’m sure there are good ones, we have not had very positive experiences. Remember that the Keys is generally hot, humid, and buggy; plan accordingly with regards to accommodations. I hope I’ve inspired you to plan some time in the Keys, particularly since Hurricane Irma (September 2017) has set tourism back a bit. I’m a big fan of supporting small, local businesses, particularly while traveling. Still on the fence about including this in your upcoming travel plans? I will leave you with one final thought: