Naples's Fall Dining Is Already Set. Waterside's Next Restaurants Are Still Behind the Barricade.

The former Brio Italian Grille space at Waterside Shops is walled off. Brio held that address for almost 20 years. Inside, contractors are turning 7,617 square feet into Buck & Rider, a seafood restaurant from Scottsdale. When Waterside Shops announced it in April, the target was late 2026. Naples Press now reports the target as early 2027.

That slip shapes Naples's fall. The restaurants you can book this October are the ones that opened between April and early summer, and they are already open. The larger names that Waterside's announcements made sound imminent belong to winter and beyond. The open rooms also differ in scale, and the scale decides which part of the day each one covers.

Four Rooms, Four Sizes

Heyday belongs in a different category from the other three. Chef Kayla Pfeiffer opened Bicyclette Cookshop in North Naples in 2023, and the James Beard Foundation named her a semifinalist for its Emerging Chef award in 2025. Gulfshore Life's preview said Heyday would open April 27 and would run Southwest Florida's first chef residency program. The opening residents were Jorge Pabon, former executive chef at Michelin-starred Estela in New York, and Isaac Villaverde of Panama City's La Tapa Del Coco. Their stays ran through June. Ryan Lay of Palace Pub & Wine Bar built the beverage list around small producers and a dedicated vermouth program. Check Heyday's current residency calendar directly, because the dates above are from the spring preview.

The Size of the Room Decides the Hour

Put the openings side by side and they hardly overlap on a clock.

Tiny Kitchen is a lunch stop. Alejo and Sam, the couple behind it, spent years as CDL Empanadas at the Third Street Farmers Market and on a trolley before getting their first storefront. Florida Weekly's July review lists hours of Monday through Saturday, 10 a.m. to 6 p.m., subject to change. The kitchen makes its own dough and most of its cheeses. Business Debut reports the beef comes from Jimmy P's, the mushrooms from Care to Grow Mushrooms, and much of the produce from Mondragón Farms. The opening plan called for about 10 empanadas a day, choripán on a baguette with chimichurri, and a Caesar salad made entirely in house. It has a turntable where guests can play records. With only 21 seats, the lunch hour decides whether you get a table.

Annie's covers the widest stretch. The hotel's first building opened May 15, and Naples Press describes a room that starts with espresso and house-made pastries and moves to a more refined but approachable American menu by evening. The restaurant is open to people who aren't staying at the hotel. The room has large murals by local artist Janine Wesselmann, a central piano and a gilded ceiling detail. Olde Naples Hotel sits between Third Street South and Gordon Drive, one block from the beach. The property is part of Opal Collection, which also runs the Edgewater Beach Hotel and The Capri Inn in Naples.

Eddie V's covers the night. Gulfshore Business lists dinner service from 4 to 9 p.m. Sunday through Thursday and 4 to 10 p.m. Friday and Saturday. Happy hour in the V Lounge runs 4 to 6:30 p.m. daily, with live music trios starting at 6 p.m. on Sundays and at 6:30 p.m. the rest of the week. Reservations are recommended but not required, and valet is available. Darden, which also owns The Capital Grille, describes Eddie V's as the more contemporary and seafood-forward of its two Naples restaurants, with live jazz and a high-energy lounge. The Capital Grille has been in North Naples since 2008 and is styled as a stately, private-club chophouse. Darden built Eddie V's on the steel frame of the former Bank of America Private Bank building on the southwest corner of Waterside Shops.

Line those hours up and a full day of new openings works out like this:

1. Espresso and a pastry at Annie's, which opens for the morning.
2. Empanadas and a record of your choice at Tiny Kitchen before its 6 p.m. close.
3. A drink at the V Lounge during happy hour, then dinner at Eddie V's.
4. Heyday Cookshop, once you have confirmed its current hours and residency calendar.

Annie's, Tiny Kitchen and Eddie V's occupy different parts of the clock, and Heyday is the one to confirm.

What Slid, and What Might Still Move

Waterside's April 28 announcement grouped three arrivals together: Eddie V's, Buck & Rider and RH by Restoration Hardware. Only Eddie V's has opened. On Buck & Rider, founder Adam Strecker said in Waterside Shops' announcement that he was looking forward to opening "just before the end of the year," and Gulfshore Business had it at November 2026. That is the target that has since moved to early 2027. Strecker, who founded Hi Noon Hospitality, helped launch BrickTop's at Waterside in 2006, the same year Brio opened, and Buck & Rider will be the brand's first location outside the Southwest.

RH is the other open question. Naples Press describes a nearly 30,000-square-foot RH campus on the former Nordstrom footprint, with galleries connected by landscaped walkways to a central restaurant in a glass atrium. RH "hopes" to open near the end of this year, according to that reporting, and there is no confirmed date.

Waterside's fall list is retail. Dior has opened a standalone boutique after moving out of its space inside Saks Fifth Avenue. Vuori is targeting a 4,000-square-foot store this fall, next to a new 8,500-square-foot Anthropologie in the space Ann Taylor vacated. Piranesi is opening a fine jewelry store across from Dior, and Peter Millar is taking the former White House Black Market unit.

Where That Leaves the Fall Calendar

Three things follow for anyone planning October and November evenings around Naples.

The dinner list for the next several weeks is short and known. Eddie V's covers the evenings, Annie's covers the widest hours, Tiny Kitchen closes at 6 p.m., and Heyday's current hours are worth confirming directly. Sizzle Dining, the prix-fixe promotion at Naples-area restaurants, runs through September 30, so that window closes tomorrow.

Buck & Rider belongs on a winter or spring calendar. If you hear it described as a fall opening, that description predates the move to early 2027.

The RH restaurant has only a hoped-for date, so it is worth checking again in December before making plans around it.

Owners near Third Street South or the Waterside Shops corridor who are watching these openings and wondering what they mean for a rental or a sale can talk it through with Uptown Property Services. Search Homes to see what's on the market nearby.