For most of the last decade, the drive from the Airport-Pulling gate to Waterside Shops has been a routine you could set your watch by. Saks, Hermès, a pass through Bricktop's, home by seven. That routine is being rewritten in real time. Between April and December of this year, the 29-acre open-air center at 5415 Tamiami Trail North is absorbing the biggest tenant change since The Forbes Company bought it two decades ago, and the parts you have not seen yet are larger than the parts you have.
If you live inside Grey Oaks or Estuary, this is not a mall story. It is a story about which reservation you can still walk into on a Thursday, which parking lot fills first in January, and which brands you no longer have to fly to Miami to buy in person.
What's Already Open
Eddie V's Prime Seafood opened June 7 on the southwest corner of the property, on the outparcel that used to be a US Bank branch at Seagate Drive and Myra Janco Daniels Boulevard. It is the first Darden fine-dining concept at that tier to land anywhere in Southwest Florida, and the layout is not small: a 361-seat room with a main hall, a stage-equipped V Lounge running live music trios nightly, a hidden speakeasy, and two private dining rooms. The wine list runs past 300 selections, which lands squarely in the same conversation Grey Oaks members already have with the club's own program.
Inside the mall, Christian Dior has moved out of its old shop-within-Saks and taken a standalone boutique in the former Williams Sonoma footprint. Brunello Cucinelli is building out the adjacent space. Peter Millar took the former White House Black Market unit and is now selling its sportswear and golf apparel a short cart ride from three of Grey Oaks' fifteen holes. Tumi added a luggage shop, The Beaufort Bonnet Co. brought its children's line, and Sephora finished a full renovation in August.
The summer perk worth knowing about if you have out-of-town guests visiting before season: a beverage cart called The Squeeze is handing out complimentary lemonade Fridays and Saturdays during peak hours through August.
What's Landing Between Now and Year-End
The three openings still ahead are the ones that will reshape how the north end of Naples eats.
- Buck & Rider. Targeting late 2026 in the former Brio Italian Grille footprint at 5505 Tamiami Trail North. Brio closed April 12 after twenty years, and its parent company's second Chapter 11 in five years cleared the lease. Buck & Rider is a Hi Noon Hospitality concept out of Arizona, and Naples is its first location outside that state. Open kitchen, expansive raw bar, indoor-outdoor seating.
- RH Naples. Late 2026, on the 29,382-square-foot former Nordstrom pad at the northwest corner. Six skylit galleries connect through landscaped courtyards to a 174-seat restaurant sitting under an elongated glass atrium, with a wine bar attached. The construction permit was issued August 7, 2025.
- Piranesi. A 781-square-foot fine jewelry unit opening this fall directly across from Dior, in the space Gulf Coast International Properties vacated.
- Vuori. The California performance-apparel brand opens this fall next to Sephora.
- Anthropologie. Relocating to a larger inline footprint, opening this fall.
- Omega. Moving in late 2026 or early 2027 to a 1,848-square-foot unit near Santa Fe Café. Its current 2,519-square-foot space becomes Van Cleef & Arpels.
Look at that list the way a Grey Oaks member would read a new club roster. Peter Millar and Vuori are two of the most-worn labels on any Florida practice range. Piranesi, Van Cleef, and Omega deepen a jewelry corridor that already runs Tiffany and Hermès. Buck & Rider and Eddie V's are not overlap concepts — one is a raw bar built around flown-in fish, the other is a wine-forward chophouse.
The pattern is the interesting part. As reported in Gulf Shore Business and in Tim Aten's coverage for Naples Press, the Forbes Company's ~$100 million reinvestment is not filling vacancies with equivalents. Nordstrom, Barnes & Noble, and Brio each left because their national formats broke down, not because Waterside pushed them out. What is going in their place are concepts that have historically required a drive to Fort Lauderdale, Tampa, or the West Coast to find. That is the sentence to underline.
Waterside is not being refreshed. It is being replaced, one anchor at a time, with formats residents used to travel to see.
Why This Matters More From Grey Oaks Than From Anywhere Else
Grey Oaks sits closer to Waterside than any other private golf community of comparable scale in Collier County. From the Airport-Pulling gate, the drive is under ten minutes outside of high-season traffic. That geography has a consequence most residents already know intuitively and are about to feel more sharply.
When Eddie V's, Buck & Rider, and the RH restaurant are all open on the same fall night, three sit-down destinations at the same address will be pulling reservation attention that currently spreads across Tamiami Trail North and Fifth Avenue South. The reservation math on the northern end of town resets. Friday-night waits at Bricktop's and California Pizza Kitchen, already the two most-walked-into rooms on the property, will change. The question of where you can still book a same-week table three nights before season starts will get harder to answer.
There is a narrow window to get ahead of that, and it closes when the fall openings light up.
The Summer That Is Rewarding the People Who Stayed
Fifth Avenue and Third Street South are running their off-season pricing right now, and the specific rooms doing it are worth naming.
- Chops City Grill. 25% off entrees and steaks through summer, which is the sharpest discount that steakhouse has run in recent memory.
- Bistro 821. Summer prix fixe menus with multi-course options at reduced price points.
- Ocean Prime. Recurring lounge happy-hour pricing on cocktails and small plates.
Third Street generally opens up in a different way. Rooms that require weeks of lead time in January have walk-in tables in July and August. This is when to try the places you were shut out of last season.
For newer independents worth working into rotation before the fall wave hits: Heyday Cookshop opened in April at 4691 Tamiami Trail North at Neapolitan Way, from Chef Kayla Pfeifer, a James Beard Emerging Chef semifinalist and Food Network Chopped champion. It is her second Naples room after Bicyclette Cookshop. Tiny Kitchen at 524 Park Street runs Argentinian street food out of a 680-square-foot space near Fifth Avenue South. Annie's Bistro inside the new Olde Naples Hotel at 200 Broad Street South is open to non-hotel guests and runs from morning café through evening bistro. Claypot Turkish Restaurant at 4910 Tamiami Trail North, Unit 310, does everything in scratch-made clay pots.
There is also a quiet category of same-address changes worth flagging because the door looks familiar and the kitchen is not. Zen Asian BBQ in North Naples is now Papa Joe's Trattoria under the same owner. Señor Tequila's at Marquesa Plaza became Tequilas Mexican Bar & Grill under new ownership. Ambrosi & Sons moved from East Naples to the Shoppes at Vanderbilt. If any of those were in your rotation, treat them as new restaurants.
One Weekend Worth Bookmarking
Artis-Naples' summer programming at Mercato runs chamber music, jazz, and the Festival of Great Organ Music through July and August. Rock the Block at Mercato lands August 20, 2026, with live music, drinks, and family programming in the middle of the promenade. Mercato is ten minutes north of the Estuary gate, and it is exactly the kind of low-lift Wednesday evening that gets harder to grab once season starts.
Pair it with dinner at Violi, the Greek room that replaced Bravo in the plaza last year, and you have used the summer for what summer here is actually for.
What the Grey Oaks Address Buys You This Fall
Three fine-dining rooms opening on one property, twenty months of first-to-market Southwest Florida launches at Waterside, and a corridor of jewelry and apparel brands that used to require a plane ticket. All of it sits inside ten minutes of the gate. Whether that argues for holding, upgrading, or listing depends on what the property is and what it was bought for. The reinvestment across Seagate Drive raises the floor under everything within a short cart-and-car radius, and the residents who are paying attention right now will be the ones who use the summer instead of watching the fall.
If you are thinking about what the shift at Waterside means for a Grey Oaks address you own, or one you are considering, Taylor Stewart reads this market from the inside and is happy to talk through it. Get your free home valuation to see where your property sits before season resets the numbers.
