For years, the shorthand for eating on Longboat Key ran along a single axis of price. Casual at the north end, dressy at the south, with a handful of anchors in between that never seemed to change. That shorthand is expiring. The island's two dining bookends are both in motion right now, and the everyday stretch in between is quietly filling in with places built for people who actually live here.
Here is where the map stands in August 2026.
The North End: Whitney's Files to Grow
The most concrete change is at 6960 Gulf of Mexico Drive, the site of Whitney's Restaurant on the northern tip of the key. On July 22, 2026, the Business Observer reported that the owners had filed a zoning map amendment with the town's Planning and Zoning Department to demolish the former office building next door and extend the restaurant's footprint. The application describes an outdoor deck under a slatted canopy, room for 200 diners, and a 1,370 square foot addition covering a commissary kitchen, cooler and storage space, and restrooms.
That is a large number for the Village. For context, Whitney's was itself the redevelopment of a shuttered gas station a few years ago. The application language leans hard on the idea that the expansion should preserve what it calls the relaxed and informal character of the Village. Read the filing carefully and it is a bet on outdoor volume, not on white tablecloths.
A useful way to read this: the north end is choosing to double down on shoulder-season dining capacity, the kind of seating that only makes sense if you believe residents and repeat visitors will keep the deck full through the off months.
Nothing about the project changes anything in the next few weeks. The value of the news to residents is knowing that the north-end approach is now a lit runway, not a rumor.
The South End: Portofino Goes Dark Until October
At the other end of the island, the Longboat Key Club Moorings is running its own construction schedule. Portofino Ristorante & Bar, the Northern Italian room that looks out over the marina, closed on May 30, 2026 for renovations and is scheduled to reopen September 30, 2026 according to the resort's own dining page. That leaves the marina without its usual dinner anchor for four months.
The resort's other restaurants have absorbed the traffic. The Tavern & Whiskey Bar shifted to a dinner-only, seven-nights-a-week schedule for June and July. Spike 'n Tees keeps its poolside golf-course rhythm. Banyan Poolside Lounge handles the light lunch and sunset cocktail. Worth remembering for anyone planning to bring a guest: the Longboat Key Club's restaurants are not open to the public, only to resort guests and members. If your out-of-town family wants Portofino when it reopens, the reservation still has to go through a room or a membership.
The St. Regis, One Full Summer In
The resort that reset the south end is the St. Regis Longboat Key, which sat on the former Colony Beach & Tennis Resort footprint at 1620 Gulf of Mexico Drive and opened to the public on August 16, 2024. The developer, Chuck Whittall of Unicorp National Development, marked the day as being fourteen years to the day since The Colony closed. The property carries 168 hotel rooms, 69 condo units, a four-acre saltwater lagoon, and seven food and beverage outlets.
The question residents actually ask is which of those outlets they can walk into without a room key. The answer, one year in, is most of them.
| Venue | Concept | Public access |
|---|---|---|
| The St. Regis Bar | Piano lobby bar, cocktails, afternoon tea | Yes |
| CW Prime | Signature steakhouse with a tableside spirit room | Yes |
| Riva | Coastal Italian, pasta and seafood | Yes |
| Aura | Open-air pool grill, Latin American | Yes |
| Monkey Bar | Tiki drinks and light bites on the beach, named for The Colony's original | Yes |
| Café Caroline | All-day coffee and casual bites | Yes |
| Oshen | Rooftop lounge, Japanese-Peruvian small plates | Hotel guests only |
The Monkey Bar detail matters locally. The original was the informal heart of the old Colony, and reviving the name was the property's most visible acknowledgment that it inherited a place, not an empty lot. Residents who remember the first version have a reason to walk over and judge the second one.
The Middle Stretch Is Where the Locals Actually Sit Down
Between the resort bookends is where daily dining lives, and this is the layer that has quietly reshaped itself.
Guppy's Good Times opened at 5610 Gulf of Mexico Drive in October 2024. It is a transplant of a Conshohocken, Pennsylvania original, and owner Robin Gupta went to unusual lengths to import the actual ingredients rather than approximate them. The Philly cheesesteaks use Liscio's rolls trucked in from New Jersey. The signature Conshi Crush cocktail was engineered as a bar centerpiece. Gupta told the Your Observer newsroom that the pitch was neighborhood sports bar, eight televisions, and a crowd whose origins are, in his phrasing, from everywhere else. That reads as a very Longboat Key thesis, and it is a category the island did not really have before.
Lo' Key Island Grille sits directly next door at 5620 Gulf of Mexico Drive, Suite 2. Fresh seafood, wings, burgers, retractable screens on the patio, and a 4 to 9 pm daily rhythm with all-day happy hour on Sundays. Together the two addresses have turned that small commercial pocket into an unofficial second Village.
Euphemia Haye at 5540 Gulf of Mexico Drive is the counterweight. It opened in 1975, was purchased by Chef Raymond and D'Arcy Arpke in 1980, and has run under their kitchen for 45 years. The Haye Loft dessert room upstairs remains the after-dinner room on the island. It is the piece of the middle stretch that does not move, and its stability is what lets the newer arrivals experiment.
Add Chart House on the bay side and Dry Dock Waterfront Grill on the pass, and you have a mid-island lineup that reads more like a small town's main street than an island footnote.
One Practical Wrinkle for August
If you are driving to any of the north-end places over the next few weeks, plan for interruptions. The Town of Longboat Key started a water main replacement project in Country Club Shores HOAs 1 through 3 on July 6, 2026, using pipe bursting rather than open-cut trenching. That reduces surface disruption, but Gulf of Mexico Drive around Country Club Shores is still worth checking before dinner reservations. Details on scope and phasing sit on the town's site at longboatkey.org.
The Shape of the Map, Now
Read across the whole island, three things are true this summer that were not true two summers ago.
- The two ends of the key are competing at scale, not just at price. The north end is building outdoor volume. The south end has installed a resort with seven kitchens.
- The island now has a real everyday tier. Guppy's, Lo' Key, and the endurance of Euphemia Haye add up to a middle stretch you can rotate through in a normal week without feeling like you are visiting the same three rooms.
- The old assumption that Longboat Key dining is either resort-controlled or a short list of legacy holdouts is out of date. There are more independent doors open now than there were before the last construction cycle began.
None of this is a small change for daily life on the island. Where you park, what shoulder-season nights look like, whether you can host visiting family without a resort reservation, and how far up or down Gulf of Mexico Drive you tend to drive on a Tuesday all shift with the map. The next data point to watch is whether the Whitney's application clears zoning on the timeline the owners have asked for. If it does, the north end will be running at a scale it has not seen in decades, right as Portofino reopens on the south end. That is a Longboat Key evening you have not been able to plan before.
If you are thinking about what this evolving dining and lifestyle picture means for your own place on Longboat Key, or you know someone considering a move within the island, Tonna Gruber and the Let's Move team follow these shifts in real time. Let Us Guide You Home.
