Road Trip Through the Florida Keys

Plan a Road Trip through the Keys

The Overseas Highway (Rt. 1) through the Florida Keys is a one-of-a-kind route to plan a road trip around and one of my all-time favorites. I love being near the water and you couldn’t feel more surrounded the wet stuff than in the Keys. Add water, water, everywhere to the unique laid-back “Conch” flavor of this area and you’ve got a kick-butt road trip route in Florida!

Florida KeysThe Keys are basically islands, and they’re so close together that they can be linked by bridges – so many bridges that if you have a fear of them, don’t plan a road trip through the Keys. One of the things most enjoyable about this road trip is that every area has something to offer. There’s literally no area that’s boring!

If you plan a road trip through the Keys on the Overseas Highway, plan to go during the week or at least avoid the “rush hour” – the weekends, particularly Friday nights (heading out) and Sunday afternoons (heading back) are notorious for a bumper-to-bumper crawl and that’s no way to see the Keys. Riding down this route is wonderful, and you’ll want to savor it with the windows open, wind in your hair, and water sparkling all around you.

Key Largo

Key Largo may look like a big nothing from the road (a lot of old signs and buildings that have seen better days), but don’t be fooled. This area is home to some of the best snorkeling around at John Pennekamp Coral Reef State Park. This undersea park is one of America’s first, and its living coral reefs located in a shallow water filled with abundant marine life (everything from brilliantly colored fish to dolphins and sea turtles) are extremely accessible with the many snorkels, scuba, and glass-bottom boat tour operators in the area.

Key Largo visitors guide
Plan a Road Trip through the Keys – Stop #1: Key Largo

This was one of my favorite days of our road trip through the Keys – we snorkeled all morning and then ate nearby at my favorite Keys restaurant, Calypso’s. Calypso has delicious food, great service and – my favorite – is full of fun fish décor and located on a marina (bring cash, they don’t take anything else). The whole ambiance is “Conch” (pronounced “conk” – what they call people who live on the Keys) to a T.

Plan a road trip that involves a minimum of a day here before moving on. You’ll want to take full advantage of the park and a whole day will allow you to do so. Overnight in one of the many hotels and enjoy the local restaurants and bars (Sharkey’s Pub is a favorite). Read more in our Key Largo Guide


Islamorada actually covers four islands, not just one, and there’s definitely enough for one full day’s worth of activity (not more – we attempted to make this happen and failed miserably). If you like to fish, however, you could easily spend more than one day as this area is known as the sportfishing capital of the world. There are tons of charters available and potential catches include sailfish, tuna, tarpon, bonefish, and mahi-mahi.

Islamorada travel guide
Plan a Road Trip through the Keys – Stop #2: Islamorada

Robbie’s Pier

If you’re traveling with kids or you just have an interest in seeing giant tarpon fish, go to Robbie’s. This small operation is hard to find – it’s just off the road in Lower Matecumbe Key (to the right as you’re driving toward Key West). It’s a small shop and dock where the giant tarpon fish come to be fed. The water is thick with these huge fish and the shop sells bait to feed them. Kids love it (and some adults do, too). If you plan a road trip that includes this sight, visiting it will last you no longer than a half-hour.

Dolphin Research Center

No matter who you’re traveling with, this is the top must-see/do in this area. As you would guess by the name, this place specializes in dolphins and you can walk around and view the various demonstrations (that’s what we did) or get wet and jump in to interact with these friendly mammals. Instructors will teach you how to “shake hands”, kiss, and ride the dolphins (one under each foot). If you just walk around, this will take you no more than two hours, but if you swim with the dolphins, it can take you an entire morning or afternoon. This is just down the road in Marathon.

Seven Mile Bridge

This now-defunct section of road (also in Marathon) was once the longest segmental bridge in the world. Now it runs alongside the functioning bridge and is great for a morning or sunset walk. You’ll get great views of the water. You can fish from this bridge, so if you fish, you could spend more time here. Otherwise, plan on a half-hour.

Jet Ski or Wave Runner or Rent a Boat

You can’t go to the Keys without getting out on the water. My preference is Wave Runners, but you can also rent a boat. A lot of people plan a road trip and envision hitting the beach a lot as they travel through the Keys. The reality is that the Keys are all about the water. The beaches here are so-so – not the powdery beaches you’d expect – more of mud-like sand that’s gooey (and a little stinky). The water, however, is a different story. It’s clear and clean and easy to navigate – no nasty rocks like in New England. People who live in the Florida Keys usually live (or spend most of their time) on their boats, so you’ll be experiencing the Keys like a real Conch! How much time you want to spend doing this is up to you – the more time you spend, the more likely it is you’ll make Islamorada a two-day stop.

Tiki Bar/Party Scene

If you’re looking for a party scene mid-way to Key West, Holiday Isle is the place for you. No, it’s not fancy – it’s an old resort that’s seen better days – but the party-people still flock here in droves and the scene is like Spring Break. The resort’s Tiki Bar is huge and features live music and dancing. A word of warning: whatever you do, don’t rent a jet ski or wave runner here – most everyone renting one is too drunk to operate one and you could be their next casualty. How much time you spend here depends on your need to party. Honestly, I’d recommend saving some of your energy for Key West.

You can stay in either Islamorada or Marathon and have easy access to all these sights and activities. See what I mean about one day? Unless you can plan a road trip that makes a day out of fishing or boating, the things listed above really add up to one long day of fun and then it’s time to move on. We tried to make two days out of it and all I can say is – help! What do we do now? Oh, no, not “Margaritaville” again! Why does this beach smell?

Key West

Ah, yes! Party Central! If you don’t like wild and wacky people and plenty of cocktails to go with them, don’t bother going to Key West. It’s a beautiful town with many charming old inns and B&Bs so, yes, you could go there for a quiet escape…, but why? There are tons of places all over the U.S. to escape to – this is a place to experience. Put on your flip-flops and don’t step on a pop-top, cause it’s time to get down Key West-style!

Hotels On Duval Street in Key West
Plan a Road Trip through the Keys – Stop #3: Key West

What should you do in Key West? First of all, park your car and leave it there. Try to get a hotel near enough to Duval Street to walk there, but far enough away to sleep at night (if you care). There is little in the way of parking in Key West and it gets more impossible to find the closer you get to the hub, so driving will be more of a pain than it’s worth. Plus, you shouldn’t be driving after that third margarita anyway. Read more in our Key West Guide

Party on Duval Street

This mile-long stretch of road is lined with shops, bars, and clubs. We spent whole afternoons just walking from place to place and you can do this for days if your liver can stand it.

Hemingway Home

Visit the great writer’s Key West home and see where some of the greatest books in literature were written. Do not go here if you’re allergic to cats. The place is rampant with them – sixty in total – and they’re not going anywhere as they date back to Hemingway’s time (guess he liked cats…, just a little).

Sunset at Mallory Square Pier

Who knows when this daily ritual started, but it’s like a circus with street performers everywhere, the usual freaks dressed up in full regalia, and drunken tourists stumbling around while the sun sets brilliantly over the water.


Take a day charter to go kayaking, snorkeling or just to watch the sunset without the insane crowd. There are so many to choose from that you won’t have trouble finding one. The best of the best is Danger Charters – a very knowledgeable full-service sail for both snorkeling at nearby reefs and kayaking through the mangroves.


There are tons of great museums in Key West – from Audubon to Pirate museums. Our favorite was the Shipwreck Museum which had fascinating displays and a great video about one treasure hunter’s experience finding the remnants of a shipwreck (and gold and jewelry and other artifacts).

How long should you spend in Key West?

It depends on you – if you spend a lot of time on each of these things and see everything there is to see, you could plan a road trip that includes 3-4 days here (or even longer if you really love to party – some people never leave!).

If you’re planning on creating a soundtrack for your road trip, make sure to include some Jimmy Buffett songs. If there’s a “Keys” sound – Buffett is it! Also, be sure to eat conch fritters and Key Lime Pie if you plan a road trip through the Keys – both are true road foods for the Florida Keys.

Enjoy this fun-filled road trip down one of the most unique and beautiful routes in the U.S. and don’t be afraid to let loose, wind down, and slow down to enjoy a true Keys experience.

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