During Keewaydin’s soft opening in downtown Naples, restaurateur Grant Phelan experienced a surreal moment, marking a pinnacle in his family’s dining legacy that began in 1997 with the launch of their first Pinchers Crab Shack. Reflecting on the journey from starting at 19 to standing at 47, Phelan expressed his excitement at being in what he considers the prime location in Southwest Florida. Keewaydin’s on Fifth officially debuted on January 5, taking over the space previously occupied by Yabba Island Grill at 711 Fifth Ave. S., adjacent to The Naples Players’ Sugden Community Theatre. Recalling Yabba’s prominence 25 or 26 years ago, Phelan emphasized the new spot’s appeal, situated near Sugden Plaza on Fifth Avenue, describing it as a dream come true.
Naples-based Phelan Family Brands, known for operating various establishments such as Pinchers, Deep Lagoon Seafood, and Texas Tony’s Rib & Brewhouse, has expanded its portfolio by adding Keewaydin’s flagship. This acquisition comes as part of their diverse collection, which includes CJ’s on the Bay, Phuzzy’s Boat Shack, Two Fillets, and The Bay House, a North Naples establishment acquired three years ago. Last summer, Phelan also obtained Yabba in a four-restaurant deal, including two Chops City Grill locations and Pazzo Cucina Italiana, from the retired veteran restaurateur Skip Quillen and his Naples-based Culinary Concepts restaurant group.
Keewaydin’s, the newest addition to Phelan’s ventures, is named after a popular barrier island off the coast of Naples, reflecting a personal connection for Phelan. Recounting his 30 years in the area, Phelan describes Keewaydin as a symbol of a vibrant, laid-back atmosphere with breathtaking sunsets—an embodiment of the unique charm and allure of Naples. He expressed a desire to capture these elements in the dining experience, emphasizing the goal of creating an island atmosphere, even though a boat is not a prerequisite to enjoy the new Keewaydin’s restaurant.
“We completely transformed the entire establishment,” remarked Phelan. “The bar, flooring, tiles, surfaces, and kitchen equipment underwent a complete overhaul. While preserving the essence of Yabba’s, particularly its indoor-outdoor concept, we introduced new materials to give the restaurant a fresh and vibrant look.”
Although the raised seating area and outdoor dining space were retained, Phelan redesigned the interior, taking advantage of the temporary closure since early July. Reflecting on the outcome, he expressed, “The results surpassed my expectations in every aspect. Yabba always had a solid foundation, and I’m thrilled with the tropical, upscale casual ambiance we’ve crafted over the past six months. The beautiful lighting, fixtures, colors, and overall design seamlessly align with the spirit of Keewaydin’s and the essence of Naples, Florida.”
Highlighting his family’s deep roots in Naples, Phelan’s latest project serves as a homage to the distinctive charm of this area.
He expressed enthusiasm about the local family-owned restaurant, highlighting its uniqueness on Fifth Avenue. The goal is to showcase Naples to both residents and visitors, emphasizing the distinctiveness of the city. The dinner menu at Keewaydin boasts a raw bar, appetizers, soups, salads, and a variety of entrees, including tuna tataki, mojo chicken, macadamia-encrusted sea bass, braised short rib, oven-roasted pork tenderloin, the signature smash cheeseburger, and an array of grilled fish and steaks. According to Phelan, these dishes are innovative creations, with standout options like Oysters Motoyaki and Red Curry Mussels. He particularly recommended the pan-seared black grouper and highlighted the seared diver scallops as a signature favorite. The restaurant sources its fresh seafood from Island Crab Co., a fish market co-owned by Phelan Family Brands in St. James City. Phelan emphasized the commitment to freshness, stating that they obtain seafood locally whenever possible to ensure quality in their offerings.
The restaurant offers a selection of wines by the glass and bottle, beer, mocktails, and craft cocktails with names inspired by local landmarks, including the Ten Thousand Island Tiki, Port Royal Spritz, 5th Avenue Manhattan, The Gordon Martini, and Marco Island Margarita. The lunch menu and service at Keewaydin’s are set to launch on January 25.
In 2024, Phelan Family Brands is set to make headlines with the opening of another Deep Lagoon in Waterside, located in Lakewood Ranch. Additionally, there are ongoing considerations for a couple of acquisitions.
Phelan maintains a reserved stance when questioned about the potential expansion of Keewaydin’s brand to other locations. “Currently, I’m fully occupied with managing this establishment and the other restaurants on Fifth, especially with the upcoming season,” he remarked. “Our primary focus is on refining the Keewaydin’s brand, and as for potential growth elsewhere, well, that remains uncertain for now.”
