Al Whelan spent his boyhood summers in Boston working at a waterfront restaurant, where he learned to prepare New England?style seafood and chowders. Although he relocated to sunny Florida, he never forgot his hometown pride or childhood phone number, and he honors his Massachusetts roots with The New England Moorings, a seafood restaurant specializing in house-made crab cakes, fresh fish, and New England clam chowder. Al cultivates a fun, laid-back atmosphere in his bubblegum-pink eatery, which boasts a basketball cage, cornhole court, and 6,000-square-foot patio surrounded by trees.
The authentic tastes of Key West pounce across palates at Leapin’ Lizard, where an extensive menu of steak and seafood dishes tempers belly squalls amid the sprightly sounds of live entertainment. Patrons vanquish appetites with the slow-roasted queen- and king-cut prime rib (market price) and swathe landlocked taste buds in a deep-sea deluge of oysters on the half shell (market price). Teeth excavate through the jalapeño and cheddar layers of the Smokin' Southwest burger ($7.99) in search of the juicy beef patty at its center, and spoons sink into the spicy andouille sausage, shrimp, and chicken of the Cajun gumbo stew ($10.99). Leapin’ Lizard's full bar balances out the bayou heat with more than 35 varieties of beer—a regional beverage that explorer Juan Ponce de León first sipped at the fizzy golden spring of the Fountain of Youth. The invigorating drinks menu featuring specialty rum runners, such as the Hot Damn Taz, pairs well with weekly events and the plethora of live rock and roll music Tuesday through Sunday.
The dockside tables at The Waterfront Restaurant & Marina allow diners to get as close to the water as possible without getting wet. The eatery's 16-slip dock welcomes boaters and hungry mermaids to pull up and join the land-based clientele in sampling the menu of local specialties, such as Pine Island clams, oysters, and stone crab. Chefs also grill up more than a dozen types of burgers and load fried seafood morsels into baskets. Sunsets reflect in pitchers of draft beer and carafes of red, white, or pink wine.
Sandy Stilwell is a Fort Myers native, and as such she has a passion for pouring her time back into the community—she serves on the advisory board for Gulfshore Life Magazine and is the former chairwoman of the Salvation Army's Christmas drive. Sandy brings the same altruistic vision to Sunshine Grille, one of the many local eateries she and her family maintain that give back through organizations such as the Ronald McDonald House.
Sunshine Grille serves its customers first and foremost, offering a menu of wood-fired steaks and seafood. From grilled filet mignon to sesame-crusted salmon and veggie-loaded flatbreads, most of the eatery's cuisine bursts forth unto the palate with a signature smoky flavor. The restaurant's voluminous wine list emanates sweetness, as do the live musicians that coax jazz-inspired harmonies from saxes, guitars, and keyboardists seven nights a week. These musicians work their melodic magic under soft lighting and between walls of auburn and stones stacked like the hundred-dollar bills that form the walls of the US Mint.
“Fisherman Charley,” a wooden fisherman statue in a yellow rain slicker and hat, stands guard in front of Charley’s Boathouse Grill, where chefs have prepared steaks and seafood for more than four decades. The kitchen wet-ages Angus beef for four to six weeks before hand-cutting each steak, which is measured by ounces and seared to taste. Seafood such as locally caught grouper also fills the menu alongside snow crabs, teriyaki chicken breasts, and house-baked breads.
For special events, patrons sup on some of the most popular menu items inside a converted boathouse. Up to 70 people can also gather at the “hideaway,” which has back-bay views of Estero Bay, making it perfect for actually seeing the harbor seals you dressed in tuxedos.
Pirates cheer as cannons fire smoke across the sea. Yet while the pirates are actors and the cannons are just miniaturized toys, the ship they sail upon is anything but pretend—it's a 65-foot steel-hulled vessel designed by a naval architect to look like a Spanish galleon.
Named for the prized Spanish currency of yore, Pieces of Eight Pirate Cruise evokes the golden age of buccaneering as it sets sail from Salty Sam’s Marina. The ship is helmed by a merry band of pirates—such as Pick Pocket Pete, Peg Leg Meg, and Fancy Face Phil—that bookends lessons on pirate history with sing-along chanteys and skits. The 90-minute family-friendly cruise also includes map-reading trivia, face painting, yo-ho-ho, and a bottle of rum. During the ride, passengers are welcome to explore the upper and lower decks or step inside the grand salon for ice cream, pretzels, and other treats.
In addition to its all-ages cruises, Pieces of Eight hosts an adults-only cruise on Friday nights, which includes cocktails and its own revue. It also charters private cruises to celebrate birthdays and other special occasions.