Ashley Gerry, co-chair of the 2027 Naples Winter Wine Festival, shares three Naples restaurants she enjoys with her husband, Adam, and their two children.
Dining drives a significant part of the economy in Southwest Florida, where the hospitality sector is one of the region's most dynamic and vital industries. As restaurants open, close and reinvent themselves from season to season, the dining scene reflects broader patterns of growth, risk and community sentiment.
In this recurring feature, Gulfshore Business asks a local business or civic leader to name three restaurants that keep them coming back, offering a glimpse into the eateries shaping how and where Southwest Florida conducts business — and builds community.
Ashley Gerry, who will serve as co-chair of the Naples Winter Wine Festival for the second consecutive year in 2027, sees the dining scene as a key part of Naples' giving community. She shares three favorites she visits often with her husband, Adam, and their two children.
Le Colonial's shaking beef is among the signature dishes recommended by Ashley Gerry. She says the restaurant's French-Vietnamese cuisine and elegant atmosphere make it one of her favorite dining destinations in Naples.
Le Colonial
Le Colonial is a feast for the senses, with a gorgeous interior that instantly transports you, making you feel as though you’ve stepped somewhere far beyond downtown Naples. Its French-Vietnamese menu offers a refreshing departure from the usual, bringing a unique and sophisticated flavor to the local dining scene. Start with Cha Gio-crispy shrimp and pork roll, followed by Bo Luc Lac-shaking beef for an entree.
457 Fifth Ave. S., Naples
The cheese soufflé is among the signature dishes served during Champagne Brunch at Sails in downtown Naples. Ashley Gerry recommends the restaurant for its elegant atmosphere, attentive service and beautifully presented cuisine.
Sails
Sails’ Champagne Brunch offers an atmosphere of understated elegance paired with impeccable service, creating an experience that feels refined and effortlessly welcoming. Each dish is a work of art: delicate, beautifully presented and executed to perfection. Favorites include the cheese souffle or crab and avocado, with an entree of lasagna and the fish du jour, enjoyed with a beautiful Champagne or a white Burgundy.
301 Fifth Ave. S., Naples
Barbatella's short rib ravioli is one of Ashley Gerry's favorite menu items. She says the Third Street South restaurant's outdoor setting and family-friendly atmosphere make it a favorite for dining with her husband and two children.
Barbatella
Barbatella is a favorite to dine with the kids. Set outdoors by a fountain underneath the lit trees, with a warm and inviting charm, it’s the perfect spot for easy and memorable evenings together as a family. The manager, Mario, loves to take the kids inside to pick out their gelato for dessert. Try the baked eggplant or the artichoke Caesar salad to start, followed by Capricciosa pizza or the short rib ravioli.
1290 Third St. S., Naples
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