A Fishing-First Road Trip Through the Florida Keys

Last Updated on March 3, 2026 by Boatsetter Team

There’s only one road into the Florida Keys, and once you’re on it, you’re hooked. 

From the moment you leave Miami and merge onto the Overseas Highway, the mainland fades away and water takes over. For 120 miles, bridges stretch over turquoise waters and open channels, and in many places boats outnumber cars. You could drive it for hours, or you could plan a multi-stop road trip that brings a deeper connection to spring break: fisheries and local haunts, legendary Captains, and dockside meals. 

Explore our fishing-first road trip through the Keys, designed for anglers who want more than just time on the water.  The road trip begins at Miami Beach Marina, where Miami’s energy meets open water. It’s the ideal starting point—close to the city, but already immersed in serious fishing culture.

Stop One: Key Largo

Less than 90 minutes from Miami is the first stop on our road trip — Key Largo. The gateway to the keys, it’s a natural first stop, offering plenty of things to do, from exploring the beautiful nature at John Pennekamp Coral Reef State Park, to boat tours of Everglades National Park. Spend some time in Key Largo before continuing the adventure into the keys.  

Discover unique boats in Key Largo

including blackened, Matecumbe, or jerked. Bring your catch here and they will cook it! Don’t forget to save room for a slice of their award winning key lime pie.

Fishing Charters in Key Largo

No Florida Keys itinerary is completed without a day spent fishing, and nothing beats going out with a local captain and guide. Book in advance to ensure your captain will be ready and waiting for you at the dock. 

A top-rated fishing charter with Captain Timmy will have you cruising out and catching a gorgeous mahi mahi to enjoy for lunch, equipped with all the gear you need to have a great day on the water.  

Fishing Tips for Key Largo

Not sure where to fish in Key Largo? 

Just offshore, iconic reef systems like Molasses Reef and patch reefs near John Pennekamp Coral Reef State Park hold snapper, grouper, and other reef species in beautiful, clear water. 

For deeper water and pelagic action, heading a few miles out can put you on mahi-mahi, tuna, and more around offshore structures like humps and wrecks. 

If you’re fishing from shore or bridges, spots like Adams Cut Bridge and creek mouths offer good chances at snook and snapper with minimal gear. 

Restaurants in Key Largo

Fish House Key Largo

Feeling hungry after your day of fishing? Bring your catch from  your Boatsetter fishing charter to the Fish House in Key Largo. It’s a laid-back seafood institution beloved for serving fresh, locally caught fish that’s filleted on-site and prepared in classic “Keys style.”

 

Stop Two: Islamorada

Less than two hours from Miami is the next stop on the road trip — Islamorada. Spanning 6 islands, this destination is a top pick for fishing and on-water recreation. 

Here you can enjoy a world-class fishing experience. Book a charter with a local captain and cruise out to catch Snapper, Mahi-Mahi, Wahoo, and so much more. Check out the Caloosa Cove Marina for all your fishing and boating needs. 

Fishing Charters in Islamorada

Islamorada offers some excellent backcountry fishing, and no one fishes the flats better than Captain Mike on this fishing charter in Islamorada. Reel in Bonefish, permit, tarpon, snook, redfish, and more on shallow flats in protected waters and wilderness areas.

Fishing Tips for Islamorada

Fishing in Islamorada means choosing your waters wisely: head to the shallow flats inside Florida Bay at sunrise for bonefish and permit, then move oceanside to the edge of the reef for sailfish and mahi when the wind picks up. If you’re targeting tarpon, fish the bridges along the Overseas Highway during moving tides for the best shot at a hookup. 

For reef and wreck fishing, book a local charter that knows the patch reefs off Alligator Reef, where yellowtail snapper and grouper stack up in clear, current-swept water.

Where to Stay in Islamorada

Since it’s about halfway down the Keys, Islamorada is a great stopping point for an overnight trip during a road trip adventure. Here’s a great place to stay if you’re looking for immersion into the incredible island culture this area has to offer. Explore the beautiful nature of the Marjory Stoneman Douglas Wilderness area, getting a further glimpse of the unspoiled beauty of the Everglades. 

La Jolla Resort

La Jolla Resort is a charming waterfront boutique property known for its laid-back, Old Florida vibe. Sitting on a peaceful canal just steps from the beach, it offers cozy apartment-style accommodations, a heated pool, and dockage for boaters exploring the Intracoastal. With its tropical landscaping and walkable location near local shops, restaurants, and fishing spots, it’s a hidden gem for a relaxed South Florida getaway.

Where to Eat & Drink in Islamorada

Midway Cafe

No fishing trip in the Keys is complete without breakfast at Midway Café. It’s unpretentious, reliable, and perfectly positioned for anglers moving through the Upper Keys. Stop in for breakfast to start your day of fishing on your Boatsetter charter on the right foot.

Square Grouper

Square Grouper is more than a restaurant—it’s a meeting point. Located in Islamorada, it’s where fishing days end, stories start, and locals and visitors mix effortlessly. Stop here for lunch for a great seafood selection, wine, and happy hour deals. 

Robbie’s

Robbie’s is iconic for a reason. Between the docks, the fish, and the energy at sunset, it’s one of the most recognizable stops in the Florida Keys. Watch the tarpon feeding off the dock and enjoy some of the best seafood and cocktails in the Keys. 

Islamorada Brewery

A successful day of reeling in catches calls for a celebratory beer at the end of the day. Stop at Islamorada Brewery after you return to the docks. It’s the perfect spot for sampling locally crafted beers in a laid-back island setting. Grab a seat on the patio and enjoy a tasting flight, often accompanied by live music. It’s a great way to take a break from the drive, soak up the Keys vibe, and enjoy a refreshing pint before continuing your adventure.

Stop Three: Marathon

Marathon is a perfect road trip stop in the Florida Keys thanks to its central location, easy access to beautiful beaches, and laid-back island vibe. You can stretch your legs at spots like Sombrero Beach or explore marine life at Florida Keys Aquarium Encounters before continuing the scenic drive down the Overseas Highway.

Fishing Charters in Marathon

In Marathon, do yourself a favor and book a fishing experience with Captain Joel. His fishing charters bring his world-class education and experience to the keys, offering you and your fishing crew a guaranteed successful day on the water. 

Fishing Tips for Marathon

Fishing in Marathon offers the best of both worlds, with productive reef, wreck, and backcountry waters all within a short run. For consistent action, target the patch reefs in the morning for yellowtail snapper using light tackle and chum, then move to deeper wrecks for grouper or mutton snapper as the tide changes. If you prefer flats fishing, work the edges of Florida Bay on a rising tide for tarpon and bonefish, keeping your presentation quiet and natural in the clear water.

 

Stop Four: Key West

Fishing Charters in Key West

Venturing another 2 hours will bring you to Key West, the final stop on any full Florida Keys road trip. For a serious fishing adventure in Key West, you can’t go wrong with a deep sea charter on The Sanctuary. This boat is equipped with an air-conditioned cabin, providing relief on long, hot days out at sea, a special chair and harness that can handle fighting fish up to 130lbs, and top-notch gear including outriggers, bait wells, and a tournament-winning crew. 

Fishing Tips for Key West

At the end of the road in Key West, the real journey begins—out on the water. This legendary stop along the Florida Keys highway is an angler’s playground, where flats shimmer with tailing bonefish and offshore runs can put you face-to-gill with tarpon, mahi-mahi, and grouper. Trailer your boat down or book a local charter, because here you can chase sunrise bites in the backcountry and still make it in for dockside fish tales by sunset. In Key West, the rods stay rigged, and the stories get bigger with every mile marker you pass.

The Takeaway

This Florida Keys road trip isn’t about chasing hotspots—it’s about moving through the islands with intention. 

From Miami to the Lower Keys, this is fishing as it should be: rooted in place, built by community, and always ready for the next cast.

Book your fishing adventure on Boatsetter and plan the perfect spring break road trip.