Fishing Adventure in the Florida Keys: Exploring Nature, Scenic Hotels, and Rich History

My dad and I don’t speak every day. He lives on the East Coast, and I live on the West. We’re lucky if we see each other once every few months. However, four years ago, we started a tradition: taking one father-daughter fishing trip a year.

We call it a fishing trip, anyway, and we do always spend one day with our lines in the water. Sometimes it’s a highlight, like when we caught enough salmon in Alaska to keep our family stocked with frozen meals for a year. Other times, it’s just a small part of the experience, like when we went fly-fishing in Montana and caught and released one trout each before calling it a day and enjoying a picnic on a beautiful lakefront homestead.

Either way, our fishing trips are not really just about catching fish — they’re about catching up and making new memories together. In Montana, we rode horses through wildflower-dotted backcountry, explored the natural wonders of Yellowstone National Park, and went searching for grizzly bears. Consequently, in Alaska, we took a float plane over Misty Fjords and kayaked with humpback whales.

For our third trip, we set our sights on the beautiful Florida Keys — yes, for the legendary sport fishing — but also for the laid-back beach vibes, fresh seafood, and endless activities out in those crystal-clear waters. Moreover, I was eager to witness my dad handling his first-ever jet ski.

Here’s how to plan your own “fishing trip” to South Florida’s tropical archipelago, where the fish are world-famous, but there’s so much more to write home about.

Renting a Car

While Key West does have a commercial airport, your best bet at getting a direct flight is to travel to Miami International Airport and drive south. You’ll be in Key Largo in about an hour and a half, depending on traffic. You’ll need a car for the rest of your trip anyway, and once you’re in the Keys, the scenic drive is one of the best parts.

As someone who prefers to avoid car rental agencies whenever possible, I opted to use Turo, a car-sharing app touted as the “Airbnb of cars.” Turo makes it easy to search for different types of cars within a specific budget and includes in-app insurance and local pick-up/drop-off options. Moreover, within 30 minutes of landing, I had picked up a white Camaro convertible in Miami Beach and was ready, top down and Beach Boys blasting, for my dad’s arrival.

Flight Tip

Fly into Miami International Airport (MIA) and rent a convertible using car-sharing app Turo for a scenic drive south through the Florida Keys.

Hotels

Although the Keys are one big island chain in paradise, each has its own distinct personality. We wanted to explore them all. I had already visited the adults-only, all-inclusive Bungalows Key Largo, which I highly recommend for a romantic getaway or girls’ trip. Therefore, after a stop at the Key Largo Conch House for lunch, we continued south to Islamorada, the spot for nature trails, state parks, bird watching, and, most of all, fishing.

Cheeca Lodge & Spa

Cheeca Lodge sits on a pristine stretch of white-sand beach in Islamorada, and its private casitas might be the best crash pad for an adult family vacation in all of the Keys. We had a two-bedroom oceanfront casita with butler service and deeply considered flying the rest of the family down and moving in. When we weren’t at the Tiki Bar or riding our bikes around the stunning property, we had plenty of room to spread out and relax. Cheeca Lodge also has tennis courts, a golf course, three restaurants (don’t miss Atlantic’s Edge), a fishing pier, and three pools.

Isla Bella Beach Resort

A trip to the Keys should be leisurely. A nice, slow way to do it is to spend the night at a few different places along the way. Isla Bella Beach Resort is in Marathon, about halfway down the chain, perched on one mile of sandy shoreline. We stayed in a two-bedroom, two-bathroom guestroom with an oceanview balcony and enjoyed sitting by firepit tables on the beach with a cocktail each evening before dining on fresh seafood at Mahina, an open-air restaurant with a Hawaiian feel. The resort has five pools, a marina with water sports, and an on-site marketplace.

Fishing Charters

Islamorada is the “Sport Fishing Capital of the World,” and it’s also the spot for nature trails, state parks, and bird watching. Our fishing boat was the perfect place to take it all in at once, pelicans gliding overhead, egrets walking the mudflats, and bold osprey standing their ground as we whizzed by.

Bamboo Charters

Florida is full of ambitious fishermen, but Matt Bellinger, captain of Bamboo Charters, is one of a kind. His lifelong passion for fishing and more than 30-year love affair with the Florida Keys is revealed through his deep knowledge of and respect for marine biology and the local environment. As comfortable with professional sport fishermen as he is with a family who’s never been out on the water, a tour with Bellinger is a valuable lesson in angling — but it’s also a lesson in biodiversity, sustainability, and Keys culture. Therefore, he even moonlights as a local radio star. Bellinger took us out on the Florida Bay, where you can catch tarpon, snook, redfish, snapper, and more with views of Everglades National Park. At the end, he cleaned and filleted it all, ready to take to The Hungry Tarpon restaurant, where they’d cook our catch.

Restaurants

Seafood is not a large part of my dad’s day-to-day diet, but he enjoyed plenty of it on this trip — a true testament to the quality of fresh fish found throughout the Keys’ eateries. From casual dockside dives to upscale, island-style restaurants, there are plenty of places to find fresh fish, even if you don’t catch your own.

Key Largo Conch House

Our first stop upon arriving in the Keys, family-run Key Largo Conch House, swears by fresh local produce and seafood, served in a homey setting amid lush tropical gardens. Grab a seat on the porch and order some tacos — if you can decide between the mahi, snapper, lionfish, hogfish, lobster, and cracked conch. (In my opinion, you can never go wrong with the mahi.)

Chef Michael’s Islamorada

For a nice night out in Islamorada, Chef Michael’s is the place to be. Chef Michael Ledwith takes “dock-to-dish” seafood preparation seriously, but his prime steaks and roast duck are just as delicious. A local favorite is the hogfish “Juliette,” seared with shrimp, scallops, chardonnay butter, and toasted almonds.

The Hungry Tarpon

Islamorada is one of the rare places in the world where a highway view is desirable, and The Hungry Tarpon is set on a dock in just the right position. Tourists will be lining up to feed the gaggle of tarpon that hovers around its perimeter, but BYOF (that’s bring your own fish) and treat yourself to a cold beer while the chef cooks your fresh catch for you — you’re on vacation, after all.

Half Shell Raw Bar

A slice of old Key West that hasn’t lost its touch, Half Shell Raw Bar is part dive bar, part waterfront oyster house. The chilled peel-and-eat shrimp are an ode to its beginnings as a shrimp warehouse before opening as a restaurant in 1972. Head in for happy hour (seven days a week), and then take a seat at a picnic table and watch the fishermen bring in their daily catch. It should go without saying it’s worth saving room for the key lime pie.

Activities

Fishing may be one of its most popular pastimes, but there are plenty of ways to enjoy the Keys, from outdoor thrills and nature preserves to museums and pieces of living history.

Snorkel or Dive at John Pennekamp Coral Reef State Park

The first underwater preserve in the U.S., John Pennekamp Coral Reef State Park is a must-visit for snorkelers and divers — but you can also explore it by glass-bottom boat, kayak, or paddle board. Combined with its neighbor, the Florida Keys National Marine Sanctuary, it includes almost 200 nautical square miles of coral reefs (the only remaining living reef in the U.S.), mangrove swamps, and ocean.

Bike the Old Seven Mile Bridge to Pigeon Key

We took our bikes from Isla Bella Beach Resort just across the road to the “Old 7,” the former centerpiece of Henry Flagler’s Overseas Railroad. The bridge we all drive today was eventually built beside it, and it was repurposed as a walking and cycling path and fishing pier. Ride just over two miles, and you’ll end up on Pigeon Key, a tiny island that once housed railroad workers and is now a museum offering daily tours.

Join a Jet-ski Safari

The most thrilling way to see Key West is to circle it — from the Atlantic Ocean to the Gulf of Mexico and back again — on a WaveRunner. Barefoot Billy’s offers guided jet ski tours with planned stops to show you the sights (and, if you’re lucky, the wildlife). Don’t worry. There’s also free time to focus on your need for speed.

Explore Key West’s Vibrant History

Check out the Ernest Hemingway Home and Museum and gain a deeper understanding of how Key West inspired so many of the prolific writer’s greatest works. Browse the Key West Lighthouse and Keeper’s Quarters to get a glimpse of maritime life in the 1800s, when it opened with a rarity: a female keeper. At the Key West Butterfly and Nature Conservatory, meet hundreds of colorful butterflies and birds, and wander among lush tropical plants and waterfalls.