Deck, Dock & Dine – Key Largo’s Top Two to Tie-Up At

Story and photos by DinaRella / Aerial images courtesy of Florida Powerboat Club

Key Largo is a world apart in form and fashion from its part-maddening, part-mystifying big brother, Miami; one radiates vivaciousness and the other vacation-ness. The good news is travelwise the two are a mere 45 minutes apart and any boaters center consoling around the Magic City's waterways seeking out a more relaxed vibe can easily dart down to the divine abode for a day trip, or even better, tack on an extended stay at our second highlighted property offering hotel accommodations and overnight dockage for your water baby.

Adored by all, Key Largo, the northernmost island and longest key named for Cayo Largo, has been captivating hearts and souls of sun seekers and seamen in search of that trophy-sized tarpon long before Bogart and Bacall popularized the paradisiacal destination in the 1948 classic crime flick of the same name (filmed on-set at a Hollyweird film studio). Today scuba divers flock to the self-proclaimed Dive Capital of the World, with one of the largest artificial reefs below the sunken 510' USS Spiegel Grove shipwreck, for under-water fun, while hedonists in their head-turning hulls hightail it to the hot-spots for on-the-water fun.

Increasingly skyrocketing in popularity as a vacation destination, there is no doubt Key Largo is geared toward the masses including the tourist tribes trucking down the police-radar infested, two-lane road in their Midwestern-tagged mini-vans and Mustang convertible rentals looking for a little R&R. Consequently, charging a premium on food, fun and wherever you settle in for your forty winks, has become accepted as the norm. Likewise, the Capital Grille or a Cipriani level of hospitality at dining establishments should not be expected; there is no race and the pace is laid-back – it's the Keys not a mega-metropolis.

A majority of the tropical thatched-roof locales put out a bar-food-meets-the-Keys spread and plasticware frequently accompanies your fresh catch, but feeling the rays (sun not sting) on your face, serenity in your soul, and saltwater splashing up on your flip-flips, at the same time a pair of unperturbed manatees pass by, is far worth the five-star service sacrifice. In this Key Largo edition of Deck, Dock and Dine, our two recommended tie-ups to tie one on at are: Jimmy Johnson's Big Chill at Fisherman's Cove and Gilbert's Resort and Tiki Bar

Jimmy Johnson's Big Chill Restaurant

104000 Overseas Hwy, Key Largo FL 33037


 Life doesn't get much better than chillin' at the Big Chill waterfront restaurant enjoying live music and deck-side edibles (the ones on the menu) and drinkables among a friendly crowd, many on their feet twirling around to the tunes. Another big draw for any boaters identifying as football buffs, is former Dallas Cowboys, Miami Dolphins and University of Miami football coach, Jimmy Johnson. When the trainer and his family decided to settle down in Islamorada, the Big Chill and JJ's Sports Bar blossomed into being. Located on the premises opposite the outdoor area, JJ's spacious, air-conditioned bar plastered full of sports memorabilia and multiple televisions, has become one of the hottest spots in Key Largo to cool off at, and the go-to taproom to catch the latest plays on game days.


For the foodies not so inspired by formations and fumbles, the biggest surprise of all may be finding our it's the Enrico's New York Style Pizza team tossing the dough and perfecting the wood-fired pies. Who would have thought the original Calvano family from the 1960s pizzeria would have brought their passione per la pizza to the Keys following their original southbound shift to Fort Lauderdale?

Winning dishes racking up rave reviews come from menu choices combining the best of both worlds, you know... lobster and pizza/pasta, but my bias might be obvious because in full disclosure, I'm Italian and love seafood. Start by savoring the respectable-sized lumps of juicy shellfish in the lobster lovers pasta and lobster mac and cheese before finishing with the ultimate touchdown – sharing an Italian fisherman's pizza with your party. Order it and you will understand why!

Equally tempting are the oysters Rockefeller and Key lime pie for anyone wanting to lunge right into dessert like me. Vegans can easily make a meal from the side dishes and vegetarians have their salads and shroom burgers, whereas those in need of a meat and potatoes fix can choose a rib eye, burger, pulled pork, nachos or potato skins to jingle off a few.

And for the happy people on a liquid diet, the delish specialty mojito made with fresh mango puree is not only highly recommended, but mimics in color the majestic orange swirls in the sky if enjoying one during a sunset happy hour visit. (I know how important it is to match one's mojito with nature!) In season, weekends and nights are busiest with service ranging from amazing to invisible, so try as the name suggests and take a moment to CHILL. Or do it literally in the water... $25 gets you a plunge in the pool and lessens your bar tab by ten bucks.

Gilbert's Resort and Tiki Bar

107900 Overseas Hwy, Key Largo FL 33037


What comes to mind when I think of Gilbert's Resort and Tiki Bar? It would be "Hakuna Matata," the Swahili ditty from Disney's Lion King meaning there are no worries or troubles. Originally established in 1903 as a fishing camp, Gilbert's is that gathering place you've been looking for your whole life, gifting guests with that free-spirited Caribbean Island feel – and no passport or plane trip required to get there. Moreover, due to its northerly location, with a set of Mercury Racing 450s clipped on the center console transom, arriving to Miler Marker 107 by water is often quicker than attempting to cross Miami's traffic-ridden SR 826 or Ives Dairy Road on any given, unmovable afternoon.

Overlooking Blackwater Sound, docking along the promenade at Gilbert's is plentiful and gawking at the nautical nirvana of non-stop speedsters parading past is an added perk. Don't be shocked if a few surprise Atlantic bottlenose dolphins (the same species as "Flipper") try to sneak by too. But wait, unwinding from the daily grind at Gilbert's gets even better, if you're so inclined stretch out your Key Largo stay and wake up in paradise by booking one of the resort's waterfront rooms.

Once docked and off the aft, for food thrills fill your pastel-painted picnic table or bar-top with a bucket of chilled brewskis and basket of crunchy coconut shrimp or crispy wings before moving on to more fishy delights like the fresh tuna nachos or other local favorites like stone crabs or hogfish. For the anti-seafood eaters in your party, an assortment of soups, salads, chicken and burger bites lie ahead, as does a variety of side orders and desserts.

But the best part of all are the "adult juice" options, Gilbert's openly invites you to suck on a boobie or two... and for good reason. In support of fighting breast cancer, Gilbert's donates $1 for every boobie cocktail (composed of four different liquors)  sold to Making Strides Against Breast Cancer – as of February 2021, over $45,000 has been raised!


Not much beats nursing a boobie or two, but a stimulating saltwater swim or an hour to grab some golden-rays could be tempting. Lay-down loungers in the beach area are free for all on a first-come first-serve basis, as well, an entrance-fee free swimming pool next to the tiki bar awaits anyone who's not a fan of digging their feet in the sand. No matter where you hang, at the bar, on the beach or on your boat deck at the dock, live bands pump out the loud jams all the days long, dropping everything from classic rock to pop and reggae depending on bookings.

And if you're looking for more than Bob Marley and Bob Seger sing-a-longs and a sweet sunset to keep you amused, Gilbert's is known for packing in the horsepower, hosting the Florida Powerboat Club's poker run lunches and weekend supercar rallies stocking the parking lot with four-wheeled exotics. And not to leave out the two-wheeled family – heaps of Harleys and rice-burners come screaming down daily and even have their own specially designated area to drop their kickstands. Lastly for the ladies not so hooked on horsepower, a pop-up kiosk of beach-ware, cowboy hats and hand-crafted accessories at the entrance makes grabbing a few gifts for loved ones or oneself, as easy as pie... Key lime of course!

Scroll to top