Dock and dine in the Florida Keys

On the Florida Bay in Islamorada, approaching Smuggler’s Cove.
Necee Regis for the boston globe
On the Florida Bay in Islamorada, approaching Smuggler’s Cove.

TAVERNIER — The sun is a bright scorching ball hovering in a flawless cerulean sky. Slathered in SPF 30, Red Sox cap firmly planted on my head, I settle in the aft of a 19-foot Hewes fishing boat docked in Florida Bay.

“You like boats?” says my friend Lee Elman. She mouths the words silently so our host won’t hear.

“Not really,” I mouth back, shaking my head and widening my eyes in nervous anticipation.


To be frank, I’m not much of a boat person. However, I like to think of myself as a good sport — and I love fish tacos. So when Lee’s husband, Ray, hops onboard along with Jim Gilbert, our host, boat owner, fisherman, friend, and guide to five days of docking and dining in Key Largo and Islamorada, I smile my biggest smile.

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The 120-mile-long Florida Keys island chain begins at the southeastern tip of the mainland peninsula, about 22 miles south of Miami International Airport. Linked by the Overseas Highway, US Route 1, the islands arc to the south and west along the Florida Straits, defining one edge of Florida Bay, separating the Gulf of Mexico from the Atlantic Ocean.

Necee Regis for the Boston Globe
Fish tacos and fries at Island Grill.

My plan, orchestrated by Jim, is simple: Eat as many fish tacos and other local specialties as possible by visiting one venue a day during daylight hours, traveling by boat to avoid the busy, traffic-clogged highway to experience dining on the islands in a whole new way.

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“NO WAKE” reads the sign as we approach the dock at Island Grill. A tarpon swims past, clearly visible in the pristine waters of the Atlantic. A circular bar defines one room; in another, dining tables occupy an open-air, sand-in-your-shoes space. A small stage offers nightly entertainment, and outdoor dining is available in the evenings “On the Beach” at the end of the dock.


Our waitress, Sam, takes one look at our caps and correctly guesses where we’re from. “I’m from Methuen,” says Sam, who has lived in the Keys since 1999.

Island Grill is known for seafood nachos, barbeque shrimp, and seafood tacos served fried, grilled, or blackened. We order tacos with regular and sweet potato fries, with one of us choosing a Cuban sandwich. The warm-off-the-grill fish topped with avocado and piquant salsa is a perfect combo.

Necee Regis for the Boston Globe
The marina at Snapper's.

Back onboard, our small vessel zips across the pale green expanse of Florida Bay, its flat and glassy surface interrupted by clumps of mangrove islands. I remove my cap to prevent it from flying away. Behind us, the water churns in our wake; before us, a cloudless sky holds a sense of endless possibilities.

Day two. Dollar bills dangle above the tiki bar at the Hungry Tarpon Restaurant. Nearby, tables nestle beneath tarps and the waxy leaves of lignum vitae trees where red-winged blackbirds chirp. On the sound system, Van Morrison croons “Brown Eyed Girl.”

“What’s nice about this place is that it’s almost always in the shade,” says Jim. “And it’s set up nicely for boats — with ropes to tie up.”


We order grilled ahi tuna and mahimahi fish tacos, along with Key West beer, and watch people on the dock feeding tarpon ($1 per person if you aren’t dining). The ahi tuna tacos win our informal tasting competition, though both have a yummy, smoky flavor.

The restaurant is located at Robbie’s Marina, on the bayside, and one can easily make a day of it with boat rentals (18- to 23-foot power boats, and kayaks), snorkeling center, state park tours, fishing charters, and a funky open-air market with shops selling sunglasses, beachwear, jewelry, art, and more. If your fishing expedition is successful, the restaurant cooks your catch.

Betsy Pontius and family, on vacation from Wellfleet, enjoyed supper they snagged on the fishing vessel Blue Heaven.

“We caught a 50-pound mahimahi,” says Pontius. “The captain cleaned and fileted it at the dock. It was so good — you don’t even need tartar sauce. They also have fabulous crispy fries.”

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Day three dawns picture-perfect. The boat slaps the surface hard as we cross swells created by the wake of larger boats whose passengers smile and wave as they accelerate away. We are cruising to Snapper’s, a restaurant with a tiki bar and deck overlooking a marina and the Atlantic.

The menu offers fresh fish and steaks cooked on a charcoal grill, peel and eat shrimp, housemade sauces, hand-breaded fried food, as well as a “You hook ’em, we cook ’em” policy where they prepare your fresh-caught, cleaned fish fillets. Out along the dock, the Turtle Club features a simpler menu with appetizers, pizzas, and beef and fish sliders. The bar menu features more than 20 frozen drinks and rum specialties including coladas, margaritas, daiquiris and over 15 varieties of beer.

“In Keys vernacular, the old geezers go to the ‘fine dining’ side,” says Jim, pointing to the restaurant. “The younger crowd goes out to the point and hangs at sunset.”

The place is bustling in the late afternoon. Is there traffic on the highway? We don’t know, and we don’t care. We chat with Dr. Mindy Jacobs, of Washington and Jilda Clarke, of Fort Lauderdale, who also arrive by boat.

“The mojitos are very good. They use lots of mint, which is important,” says Clarke.

She also recommends tuna nachos, a trio of seviches (fresh fish, shrimp, and conch), blackened dolphin bites (local mahimahi), and gator bites (fried alligator meat). Our favorite, the tuna nachos, turns out to be crispy fried wonton squares topped with seaweed salad and melt-in-your-mouth chunks of fresh raw tuna tossed with sesame oil.

By our fourth excursion, I am getting the hang of the boating life as we chug through a cut from larger Florida Bay, cruise past houses along Snake Creek, and arrive at Smuggler’s Cove, a combined bar, restaurant, motel, and marina with a casual vibe. I help tie up at the dock across from where fishing charters and eco-tours arrive and depart.

We settle on the outdoor deck, at a table made from a Jack Daniel’s barrel, and peruse the eclectic menu of American, Italian, and Floridian seafood dishes, including conch fritters, crab cakes, and peel and eat shrimp. The Lumineers blare over speakers, “Ho, Hey,” and a band sets up in a corner.

Our waitress, whom we dub Mis-Information, tells us happy hour is over (it isn’t), that we’re not on Windley Key (we are), and forgets to mention that it’s Thirsty Thursday, meaning certain drinks are on sale. No matter. Another waiter explains they make everything from scratch, including sauces and Key lime pie, and they smoke their own meats overnight. After days of gorging on seafood, we opt for a delicious slow-roasted pulled pork sandwich, and a half rack of fall-off-the-bone baby back ribs with tangy barbeque sauce.

With the vacation clock ticking down, we plan two stops on day five, disembarking for lunch at Marker 88, a spiffed-up place on the sheltered bayside where lounge chairs, shaded by lignam vitae trees, line a small private beach, and a truck rents paddleboards and kayaks.

If we crane our necks, we can spy the bumper-to-bumper traffic on Route 1.

“That’s the story of the Keys,” says Ray. “You can’t see this from the road. All this stuff is hidden behind the signs.”

Our waitress, Sarah, who moved from Vermont a year ago, calls everyone “sweetie.” We sample tasty grilled fish sandwiches, sesame seared tuna, and conch chowder. The mixed drinks are weak (possibly a good thing for boating), but we discover Kentucky Bourbon Barrel Ale and would order that again.

We arrive pre-sunset at Morada Bay Beach Cafe, a destination with a colorful Caribbean atmosphere where you can dine at tables scattered along the waterfront with your feet in the sand.

The menu is the most sophisticated of the tour, featuring a raw bar, tapas, salads, entrees, and a creative kid’s menu. Alas, they stop serving fish tacos at 4 p.m., but we are more than happy with ahi tuna tartare with avocado, cucumber, jalapeño, and sesame soy vinaigrette — so happy, in fact, we fight over the last bite — and swoon over a watermelon-feta salad and seviche of local fish served with crispy plantain chips. Entrees include a selection of fresh-caught fish, tempura Florida lobster, honey-chipotle baby back ribs, and more. The bar features tropical rum cocktails (Man Overboard, The Painkiller, Floridita), plus margaritas, martinis, and an extensive list of wine and beer.

Nearby, women in long dresses and heels navigate to their table, and children play with glo-sticks in the dimming light. The band plays the Allman Brothers’ tune “Sweet Melissa,” slowing the tune down to a drowsy, dreamy island beat.

“It’s rare to find a place that can be sophisticated and unpretentious at the same time,” says Ray. “It’s a perfect blend of high-quality food and an ambience that changes as the sun sets, the torches are lit, and you can dance in the sand under moonlight.”

Heading back to port, the blazing orange sun sinks close to the darkening sea in a sky streaked vermilion and violet, smudged with charcoal clouds. The salt-tinged wind whips my hair and I inhale its fresh goodness. Maybe I’m a boat person after all.

Necee Regis can be reached at and