For years, the honest answer to "what's open on the Key in July?" was a shorter list than anyone wanted to admit. That answer has changed. Between a new luxury resort with seven dining rooms, a handful of independent openings along Gulf of Mexico Drive, and a summer events calendar that now runs on its own current, the island's off-season has quietly become one of the more interesting times to actually live here. The trade-off is that a few longtime favorites are dark for renovation at the same moment. Knowing which is which is the whole point of this post.
When the Club Goes Quiet, the Island Doesn't
The most useful piece of local intelligence for July and August is a closure. Portofino Ristorante and Bar, the Northern Italian room overlooking the Marina at Longboat Key Club Moorings, is closed temporarily from May 30 to September 30, 2026, for renovations. If Portofino was a monthly ritual for you, that ritual is on pause until fall. The Resort's other venues remain in rotation for members and guests, including The Tavern's farm-to-table menu that changes with the seasons and Spike 'n Tees, the open-air spot overlooking the Links on Longboat course where the kitchen runs from freshly squeezed juice at tee time to a light lunch and a cocktail at the bar.
For anyone whose summer routine leaned on the Club side of the island, this is the year to explore mid-key and north-end options that have opened in the last twenty-four months.
The Gulf of Mexico Drive Newcomers
The mid-island stretch has quietly assembled a new roster worth knowing by name and address.
Guppy's Longboat Key, 5610 Gulf of Mexico Drive. The original Guppy's Good Times is a Conshohocken-based restaurant in the suburbs of Philadelphia that celebrated 19 years of business this September. Owner Robin Gupta brought the concept south with intent. The menu ranges from cheesesteaks and burgers to tacos, minus the sushi from the Philly original because there wasn't enough space. He tracked down local vendors for the same brands he uses up north, including Liscio's rolls, so the cheesesteak is the real thing.
Lo' Key Island Grille, 5620 Gulf of Mexico Drive #2. Open 4 pm to 9 pm every day, with daily happy hour and all day on Sunday. The patio is built for the shoulder seasons: retractable screens for shade, fans to keep things cool, and heaters for chilly nights.
Ventura's Italian Kitchen and Wine Bar, 6814 Gulf of Mexico Drive. The Longboat original spawned a second Manatee County location on the mainland at 4805 Cortez Road W. in Bradenton, which tells you something about how the concept is landing. Ventura's also caters the pizza for the neighborhood's summer shopping nights, which is a fair proxy for how integrated it has become.
Each of these three sits within a two-mile radius. On a Tuesday in August, that is now a legitimate dinner-and-a-nightcap loop without leaving the Key.
Seven Concepts, One Property
The St. Regis Longboat Key, which opened at 1620 Gulf of Mexico Drive on the former Colony Beach and Tennis Resort site, changed the summer math on this island more than any single business has in a decade. Designed by SB Architects, Hirsch Bedner Associates, and Dutch East Design, the 18-acre resort is the only St. Regis to open in the U.S. this year.
The dining lineup is worth memorizing, because most of it is open to the public and not just to hotel guests:
- CW Prime, described in the Residences materials as a signature chef-driven steak and seafood restaurant.
- Riva, coastal Italian, which participated in the 2026 Taste of the Keys with meatballs and a menu focused on cuisine from Northern Italy and the Adriatic Coast.
- Aura, an open-air pool grill leaning Latin American.
- Oshen, a rooftop lounge with a Japanese-Peruvian menu, guest-facing rather than public.
- Caroline's, the all-day cafƩ.
- The Spirit Room, a private cocktail speakeasy.
- The St. Regis Bar, the lobby room with a mural by Floridian artist William Savarese.
Then there is the Monkey Bar, which is more legacy than launch.
The legacy of The Colony wouldn't be possible without the famous Monkey Bar, which has come back to life in the St. Regis Longboat Key. The bar is right on the beach and features a modern twist on Tiki cocktails. It also serves up light bites, like the Murf and Surf Dog, an homage to The Colony's Murf Klauber and the Murf Dog. The St. Regis version of the hot dog is topped with lumps of lobster meat.
For residents who remember the original Monkey Bar, the reboot is either sacrilege or a small miracle depending on the afternoon. Either way, the bar is open daily and closes at sunset, which makes it a workable pre-dinner detour rather than an evening in itself.
The resort's Fourth of July programming this year gives a sense of the ambition. The Great Lawn hosted an elevated oceanfront barbecue from 7 to 10 pm on July 4 with chef-led stations, live entertainment, and family-friendly experiences. Expect similar treatments around Labor Day and the holidays.
Where the Island Gathers on Weeknights
The most locally revealing evening of the summer so far did not involve a resort at all. The Summer Night Out event welcomed back Longboat Key locals and summertime visitors with shopping, good food, and bubbles on June 18. Heather Rippy, owner of Driftwood Beach Home and Garden, and Design2000 Salon co-owner Irina LaRose brought back their seasonal Summer Night Out, a monthly chance for businesses in Whitney Plaza to connect with residents and visitors during the slower summer season.
The new twist this year was inside the shops themselves. Rippy and LaRose added a chance to meet the local artists and merchants who sell their work at Driftwood Beach and Design2000. At Design2000, Tryla Brown Larson showcased her Herb Methodology booth, where she offers natural remedies and teas inspired by her grandmother's knowledge of the medicinal properties plants have to offer.
Whitney Plaza is one of those quiet anchors that residents pass a hundred times a season without stopping. The monthly cadence of Summer Night Out is a good excuse to change that habit.
The Fourth That Just Happened, and What's Still on the Calendar
If you missed it, this year's Freedom Fest was not an ordinary one. After being rained out last year, the town came back big with its parade, butterfly release, and park rededication. The celebration marked the United States' 250th anniversary and included the rededication of Bicentennial Park. Commissioner Steve Branham delivered a speech for the rededication, and Public Works Director Charlie Mopps unveiled the new plaque celebrating the country's history at Bicentennial Park. The plaques are worth a walk-over the next time you are near Bay Isles Road.
What is still on deck for the season:
- Sarasota Music Archive's Wednesday Jazz Happy Hour summer series kicked off with Johnnie Barker and Friends, who bring jazz, soul, and rhythmic groove to downtown Sarasota. A short bridge drive and a solid weeknight.
- Summer Circus Spectacular at the Historic Asolo Theatre. The Ringling and the Circus Arts Conservatory produce the annual show, with ringmaster Ashley Vargas presiding over clowning, juggling, hand balancing, aerial arts, and duo roller skating. Runs through Aug. 8.
- Shared Light: Lynn Goldsmith at Marie Selby Botanical Gardens. The photography exhibition is on display indoors and outside through Sept. 13.
Save the date for one more piece of Longboat-specific programming worth marking. The 15th Taste of the Keys was held Feb. 26 at the Longboat Key Club Harbourside Ballroom, with proceeds supporting the garden club's scholarship and rebuilding programs. The 2027 edition will be along soon enough, and the roster of participating restaurants keeps expanding. This year's newcomers included Lo' Key Island Grille, Flambo, and Ringside at Cirque St. Armands Beachside.
Slow Mornings Still Belong to the Parks
The counter-argument to a busier summer is that the quieter places matter more, not less. Two are worth the routine.
Quick Point Nature Reserve sits at the south end of the Key and reads as a bay-facing counterweight to the Gulf-side beach walks most residents default to. Joan M. Durante Community Park, mid-island, is the practical answer for a morning with a dog, a book, or out-of-town family who need a low-key hour. Both are the kind of places where a resident notices what has changed in a season more than a visitor ever will.
For the birders among you, Sarasota Audubon's Fly Wild Bird-a-thon sends teams of two into the county for a day of birding, spotting as many species as they can while raising funds to support conservation, education, and exploration. Registration runs through their site.
A Working Summer Itinerary, Not a Best-Of List
The through-line here is not that Longboat Key has more to do than it used to, though it does. It is that the island's summer texture has shifted. A resident's calendar between Memorial Day and Labor Day can now include a resort dinner at CW Prime or Riva, a Whitney Plaza evening at Driftwood Beach and Design2000, a cheesesteak at Guppy's, a Tavern lunch when the Club side is otherwise dark, and a Wednesday jazz set across the bridge. That is a fuller ledger than the island offered five years ago, and it means the season no longer runs on out-of-town rhythm alone.
If you are thinking about how this shift affects the way properties here are lived in, marketed, or valued, the team at Roger Pettingell tracks these currents closely and is always available for a considered conversation. Contact us when the timing is right.
