Walk out the door of a Gulf Shore Boulevard address in The Moorings this September and turn south. Within roughly a mile you pass fresh construction fencing at 801 Gulf Shore, a beachfront restaurant awning that has been dark since 2022, and the first pours of a foundation at the old Executive Club site. Turn north instead and the shoulder-season crowd at The Village Shops on Venetian Bay is thinner than it will be in ninety days. For a neighborhood that usually treats fall as a slow inhale before winter, the calendar this year reads differently.
The reason is coincidence more than plan. Three of the largest capital projects in central Naples are hitting public milestones inside the same three-month window, and all three sit inside a resident's normal walking, biking, or short-drive radius. The practical takeaway for anyone who lives here: the routes and reservations that defined last year's shoulder season are worth rewriting.
The South End: HB's Comes Back and The Wager Arrives
The most visible change sits at the southern edge of the neighborhood's daily orbit. Naples Beach Club, A Four Seasons Resort opened in November 2025 on the site of the historic Naples Beach Hotel & Golf Club at 801 Gulf Shore Boulevard North, and the reopening did what long-time residents cared about most: it brought back the two rooms that had been community gathering places for decades.
When HB's and the Sunset Bar opened to the public on November 17, more than 200 people crowded the beachfront deck. For the first time since the old hotel closed, they could return to the Gulf-facing stretch where generations had gathered as the light changed. If you tried HB's in the first months and found it in flux, the fall calendar matters: the restaurant will be closed throughout August 2026 for exciting updates, with a newly enhanced HB's welcoming guests back in September. That timing lines up almost exactly with the moment Moorings residents typically re-emerge from summer.
Sunset Bar has stayed open through the changes and is worth building a Friday into. Live music runs at Sunset Bar every Friday, Saturday, and Sunday starting at 6:00 pm through the summer, and every evening at golden hour, a ceremonial conch shell blowing marks the transition from day to night. A useful piece of local knowledge for residents who assume the resort is walled off from the neighborhood: The Merchant Room, HB's, and Sunset Bar are all open to the public. Valet parking is $15 with restaurant validation. The beach is publicly accessible.
The bigger fall addition is the fifth venue. A fifth venue, The Wager sports gastropub with bowling, opens in Q3 2026. The scope is more ambitious than the "sports pub" label suggests. The Wager is a lively yet refined sports-centric gastropub pairing elevated pub fare with an impressive selection of draught beer. Entertainment options include Four Seasons' first regulation four-lane bowling alley, a professional putting green and a thoughtfully curated game room. Alongside it, The Picture House is a 22-seat state-of-the-art theatre showing first-run movies. For a neighborhood whose evening options have historically been dinner, a drive to Mercato, or home, a bowling alley and a first-run cinema inside walking distance is a genuine shift.
One more fall milestone at the south end sits on the golf side of the property. The golf course designed by Tom Fazio, The Gardens, is scheduled to open fall 2026. The redesigned Tom Fazio 18-hole course, spanning 100 acres, is scheduled to debut in 2026 with new hitting bays, comfort stations and a clubhouse overlooking Old Florida–style landscaping. The course sits on land that includes more than 104 acres placed into permanent conservation easement, carving out a significant buffer of green space in one of Southwest Florida's fastest-growing communities. The near-term implication for residents is quieter: the tree line at the south end of the neighborhood is now locked in.
Inside The Moorings: The 3300 Gulf Shore Groundbreaking
The change closest to home for many residents is happening inside the neighborhood itself. A groundbreaking celebration was held Jan. 29 for 3300 Gulf Shore, a luxury waterfront residential community planned at 3300 Gulf Shore Blvd., between the Gulf and Doctor's Bay. The eight-story development by Florida-based Kolter Urban will feature 51 condominiums, a private 16-slip marina and high-end amenities at the former Executive Club site in the Moorings.
Two numbers deserve a beat. Fifty-one residences on a full beachfront-to-bay parcel is a low-density plan for a site of this size, and a sixteen-slip private marina is a genuinely rare amenity even in a neighborhood defined by dockage. The eight-story development will feature 51 expansive condominiums with two to five bedrooms, a private 16-slip marina and many other high-end amenities at the former Executive Club site in the Moorings. For residents living on the boulevard immediately north or south, the fall calendar will now include construction staging where the old Executive Club sat idle for years. For residents thinking about where the neighborhood's next benchmark price gets set, this is the project to watch.
The North End: Venetian Village Before the Season Turns
Head the other direction and the pace is different but the shoulder-season window is real. Fall at the Village Shops on Venetian Bay is quieter than most residents give it credit for. The Village Shops on Venetian Bay is an elegant, waterfront shopping and dining destination located on the northern edge of the community, featuring upscale boutiques and fine-dining restaurants like MiraMare Ristorante and Bayside Seafood Grill & Bar. A short reminder of what's actually within a resident's walking or short-driving radius on the north end:
- The Village Pub, a Naples neighborhood tradition since 1995, on Venetian Bay
- MiraMare Ristorante, described by the property as the Italian anchor, serving classic and contemporary dishes including homemade pasta, risotto, seafood, and wood-fired pizzas
- M Waterfront Grille, which offers contemporary American cuisine with a Florida-fusion accent and an award-winning Sunday brunch, positioned as an independently owned and managed restaurant a short distance from Artis—Naples
- Bayside Seafood Grill & Bar and T-Michaels Steak & Lobster, both with water-facing tables that book first when December's parade calendar opens
- Park Shore Marina at the Village Shops, offering cruising and fishing boat rentals from its location at the Village Shops on Venetian Bay, with bareboat charters also available
The reservation math is the useful part. In September and October, water-facing tables are available on walk-in at times that would be impossible from January through April. The Village on Venetian Bay is the site of the annual Naples boat festival parade every December, and the water-facing tables at Bayside, T-Michaels, and MiraMare that overlook the parade route are the first to go. If you host family in December, the fall shoulder is when to lock those tables down.
Cultural programming on the north side is also worth pinning. Artis—Naples summer programming from July through August 2026 features a variety of live music events, including chamber music, jazz concerts, and the Festival of Great Organ Music. Programming continues into the fall as the season ramps.
A Resident's Fall Calendar
The individual updates matter less than how they stack against a normal Moorings shoulder season. Here is the same information as a working calendar rather than a news list:
| Window | What's new inside your walking or short-drive radius |
|---|---|
| Now through late August | Sunset Bar open with weekend live music; HB's closed for updates; Venetian Village on walk-in schedule; 3300 Gulf Shore in early foundation work |
| September | HB's reopens after its August refresh; The Merchant Room reservation window loosens before season |
| Q3 (late summer into early fall) | The Wager debuts with four-lane bowling; The Picture House cinema opens |
| Fall 2026 | The Gardens by Tom Fazio opens for play; 104 acres of adjacent land now in permanent conservation easement |
| November onward | Venetian Village reservations begin to tighten; December parade tables at Bayside, T-Michaels, and MiraMare start to fill |
The pattern is legible once you lay it out. A resident who has been eating at home more than they meant to has a genuinely new set of options this fall, most of them on foot or a short drive, and each of them tied to a specific opening date rather than a vague "coming soon."
The Through Line
The Moorings has always sold a version of itself that sounds contradictory on paper. Living in The Moorings offers a rare blend of understated luxury and everyday coastal ease. Nestled between US-41 and the Gulf, this prestigious Naples neighborhood is beloved for its peaceful streets lined with a mix of original Old Florida ranch homes and modern estate residences. Many properties enjoy direct Gulf access via private docks on Moorings Bay, while others are just a short stroll or golf cart ride from the sand. Quiet and central at the same time is the neighborhood's real product.
Fall 2026 is the year that product gets richer without getting louder. The two anchors at either end, Naples Beach Club and Venetian Village, are both adding capacity and programming that residents can access on foot. The one large new-build inside the neighborhood is capped at 51 units on a full beachfront-to-bay parcel. And the largest piece of land in a resident's sightline just got locked into conservation for good. The neighborhood's shoulder-season rhythm is worth relearning this year, because by the time season arrives, the walking radius will be doing more work than it did last winter.
Work With Kim
For residents thinking about how these openings, groundbreakings and new addresses reshape long-term value in The Moorings, The Kim Price Group offers a private, senior-led perspective grounded in three decades of central-Naples transactions. Work With Kim — Request a Private Consultation.
