On the first night of Keewaydin’s soft opening in downtown Naples, Southwest Florida restaurateur Grant Phelan had goosebumps in what was a surreal moment, a pinnacle in his family’s dining dynasty that started in 1997 with the opening of their first Pinchers Crab Shack. 

“When I was 19 and we started this to where I am now at 47 and being able to stand here, in my opinion, in the best location in all of Southwest Florida, it’s a dream come true,” Phelan said. 

Keewaydin’s on Fifth officially opened for dinner Jan. 5 to replace the longtime Yabba Island Grill at 711 Fifth Ave. S., next to The Naples Players’ Sugden Community Theatre. 

“I remember when Yabba opened 25, 26 years ago and it was the place to be, and I think it’s the best location in all of Southwest Florida. It has Sugden Plaza right next to it and it’s right on Fifth Avenue and it’s a beautiful spot to be.” 

Naples-based Phelan Family Brands, which operates multiple locations of Pinchers, Deep Lagoon Seafood and Texas Tony’s Rib & Brewhouse, adds the Keewaydin’s flagship to its portfolio that also includes one-offs CJ’s on the Bay, Phuzzy’s Boat Shack, Two Fillets and The Bay House, a North Naples icon purchased three years ago. Phelan acquired Yabba last summer in a four-restaurant deal with two Chops City Grill locations and Pazzo Cucina Italiana from veteran restaurateur Skip Quillen, who retired his Naples-based Culinary Concepts restaurant group. 

Keewaydin’s, of course, pays homage to a popular barrier island off the coast of Naples that clearly has personal meaning for Phelan. 

“In the 30 years I’ve lived here, Keewaydin always was an image in my mind and spirit of a really good, fun, laid-back, relaxed atmosphere with incredible sunsets,” he said. “And it envisioned everything to me that Naples is and all the special parts of Naples of why we live here and we’re so lucky to get to be here, and I wanted to put that out in the food and drink for people.” 

While a boat is not necessary to see the new Keewaydin’s restaurant, the idea was to create an island atmosphere.  

“We reimagined the entire space,” Phelan said. “We redid the bar. We redid all the flooring, tile and surfaces and kitchen equipment. We tried to save the good of Yabba’s, which was the inside-outside part, but then brought in all new materials and things to help make the restaurant really pop.” 

Phelan kept the raised seating area and the outdoor dining space but revamped the venue’s interior design since the space was temporarily shuttered since early July. 

“It exceeded my expectations on every level,” Phelan said. “Yabba has always had phenomenal bones and I love the interior space that we’ve created in the last six months—super tropical, upscale casual, beautiful lighting and fixtures. I love the colors and the way it plays into Keewaydin’s and what Naples, Florida, is all about.” 

Stressing his family’s Naples roots, Phelan’s latest creation is a tribute to this unique area. 

“This is a local family-owned restaurant that Fifth Avenue doesn’t have much of,” he said. “We’re just so excited to bring this restaurant to Naples as true Neapolitans to show all of Naples and all the wonderful visitors that come here every year what Naples is supposed to be, and what’s unique about Naples and I tried to reflect all of that in this restaurant.” 

Keewaydin’s dinner menu features a raw bar, appetizers, soups, salads and entrees, such as tuna tataki, mojo chicken, macadamia encrusted sea bass, braised short rib, oven-roasted pork tenderloin, the signature smash cheeseburger and a variety of fish and steaks off the grill. 

“These are all brand new, unique creations,” Phelan said. “The Oysters Motoyaki are super good, the Red Curry Mussels. I really like the pan-seared black grouper. Seared diver scallops are a signature favorite.” 

The fresh seafood is supplied by Island Crab Co., a wholesale/retail fish market in St. James City that Phelan Family Brands co-owns. 

“The seafood comes in from Island Crab if we can get it fresh here,” Phelan said. “We’re getting it fresh and bringing it into the restaurant.” 

The restaurant has wine by the glass and bottle, beer, mocktails and craft cocktails with names derived from local landmarks, such as Ten Thousand Island Tiki, Port Royal Spritz, 5th Avenue Manhattan, The Gordon Martini and Marco Island Margarita. Keewaydin’s lunch menu and service will launch Jan. 25. 

Keewaydin’s won’t be the only restaurant to make news for Phelan Family Brands in 2024. 

“We have another Deep Lagoon opening up in Waterside up in Lakewood Ranch,” Phelan said. “And then we have a couple of acquisitions that we are currently eyeing at the time.” 

Phelan remains noncommittal, though, when asked about the possibility of growing Keewaydin’s brand elsewhere. 

“Right now, I have my hands full with this and the other restaurants on Fifth and we’re getting into season,” he said. “We want to perfect the Keewaydin’s brand and, possibly, who knows?”