Longboat Key Restaurants 2026 | Danielle Gladding & Co.

Two years ago, a Friday night on Longboat Key meant a short list of familiar rooms and a reservation you probably did not need. This summer, the same drive down Gulf of Mexico Drive passes a Michelin-trained chef running a steakhouse inside a resort that did not exist here in 2023, a north-end tavern that has bought the office building next door in order to seat two hundred people outdoors, and a Longboat Key Club dining room that will be dark until the end of September.

The island still feels like the island. The menu of choices does not.

We live here, and between us we have watched this stretch of road change for four decades. What is happening right now is not a wave of openings. It is a sorting.

One Island, Two Dining Economies

The interesting story on Longboat Key is not any single restaurant. It is that the Key’s dining scene has quietly separated into two tiers that barely overlap.

At the south end, The St. Regis has installed an ultra-luxury layer the island simply did not have before, anchored by a steakhouse that competes with anything on the mainland. At the north end and through the middle of the Key, the casual side has not retreated in response. It has invested, expanded, and staked a firmer claim on the locals-first identity that made the Village worth the drive in the first place.

For anyone who lives here, the practical consequence is simple. Your dining calendar for the next six months is best planned by tier, not by night of the week.

And for anyone deciding whether to buy here, the consequence is different and more useful: the south end and the north end of this island now offer genuinely different daily lives. That is worth knowing before you choose a street. Our Longboat Key neighborhood page lays out how those ends differ in housing, and this post is the dining half of the same picture.

The South End: A Tier That Did Not Exist Here Before

The clearest signal of the shift is CW Prime, the steakhouse inside The St. Regis Longboat Key Resort. Michelin-trained chef Drew Adams took over the kitchen there, and if that name is familiar it is because Sarasota already knew him — he moved here from Washington in 2021, opened his own restaurant on Hillview Street, and collected best-new-restaurant honors before the St. Regis recruited him.

The menu is worth reading carefully, because it tells you which tier the room is playing in. Eleven different steaks, running from a six-ounce American wagyu strip out of a Kentucky farm to a thirty-six-ounce dry-aged tomahawk. Olive-fed Sanuki wagyu ribeye sold by the ounce, with a three-ounce minimum, served at exactly one other restaurant in the state. Josper-grilled seafood. Sauce work that the chef himself names as his strongest suit.

That is not an upgrade to an existing category. Sarasota’s steakhouse category used to mean a drive to St. Armands or downtown. It no longer does.

Next door sits Riva, the same property’s casual Italian room — fresh pasta, Key West shrimp, a cocktail list built on Italian gin and limoncello, and a Sunday brunch that guests tend to single out. Its menu was refreshed at the end of May 2026, which matters if the last time you ate there was during season. It is a different register from CW Prime on purpose, which is what lets one property carry a steakhouse, an Italian room, a pool grill, and a lobby bar without any of them feeling like filler.

The scale explains it. This is an eighteen-acre coastal resort with a full butler-service program, not a hotel with a restaurant attached. And unlike the Club dining rooms further south, the St. Regis rooms are open to the public.

If you have been on the Key long enough to remember what stood on that parcel before, the change in tier is the part that matters. It also reshaped the buyer conversation at the south end — something we get asked about constantly in Bay Isles and along Country Club Shores.

The Village: Investing, Not Retreating

The reflex assumption when a luxury resort opens is that the casual end of an island gets squeezed. On Longboat Key, the opposite is happening, and the paperwork proving it is sitting on the Town’s desk.

Whitney’s, at the north tip, has filed a zoning map amendment application with the Town’s Planning and Zoning Department. The plan is to demolish the former office building next door at 6960 Gulf of Mexico Drive — a glass bank building the ownership bought outright — and turn that parcel into outdoor seating. The rendering shows a deck under a slatted canopy with landscaping wrapped around it. The application states the expansion would let the restaurant seat two hundred diners, and adds roughly 1,370 square feet of new construction for a commissary kitchen, cooler and storage space, and restrooms.

Read past the permit language and this is a bet on the Village. The application makes the argument out loud, describing the earlier redevelopment of a former gas station into a working hospitality destination, and framing the expansion as the kind of thoughtful redevelopment that revitalizes aging property while keeping the relaxed, informal character of the Village intact.

Three things follow from that, and they are all practical.

● If Whitney’s is already full at seven o’clock on a Thursday, the fix for that is in front of the Town now — not five years out.

● The application is for zoning, not construction. The current footprint is what you are working with through this coming season.

● The Village is being treated by its own operators as worth a seven-figure commitment. For anyone who owns nearby, that is not a neutral signal.

We would add a fourth, quieter one. The north end of Longboat has spent years being described as the quiet end, which is a polite way of saying underserved. That description is aging out.

Mid-Island: The 5600 Block Became Its Own Scene

If the south end went ultra-luxury and the north end went bigger-casual, the middle of the Key became something nobody planned: two neighborhood rooms sitting essentially next door to each other.

Guppy’s Good Times took the space at 5610 Gulf of Mexico Drive, brought down from an original in the Philadelphia suburbs. Eight televisions, a sports draw that works unusually well on an island where residents come from everywhere, and a level of sourcing obsessiveness that is rare in a transplant restaurant — the owner tracked down Florida vendors carrying the same brands he uses up north, rolls included, so that the cheesesteak is actually the cheesesteak.

Two doors down at 5620 Gulf of Mexico Drive, Lo’ Key Island Grille runs fresh seafood, wings and burgers with a laid-back bar and a daily happy hour. The patio is the point — retractable screens for shade, fans for August, heaters for the four nights a year we need them.

If family arrives and the St. Regis is booked or simply the wrong register for the evening, this block is the answer. A surprising number of newer residents do not know it is there.

What Is Dark Right Now, and Until When

Portofino overlooks the marina at the Longboat Key Club Moorings and serves Northern Italian. Two details residents should not miss. First, the reopening target sits immediately before season begins, which is not an accident. Second — and this is the one that causes real trouble — the Longboat Key Club restaurants are not open to the public. If friends or family are arriving in September and building a trip around dinner at Portofino, redirect them before they book flights.

It is a fair reminder of something we say often to buyers looking at the south end: the Club is a genuine amenity and a genuine gate. Understanding which rooms on this island you can walk into and which ones require standing is part of understanding what you are buying.

How to Read the Fall Calendar

Put the pieces together and the framework for the rest of 2026 is straightforward.

For anniversaries, celebrations, and any evening where the room itself is the point, the south end now carries the weight the mainland used to. CW Prime is the clearest example, and the St. Regis bar program gives you a lower-key alternative on the same property when a full steakhouse dinner is not the right shape for the night.

For a Tuesday when you want to see people you know and eat something you do not have to think about, the Village end and the 5600 block are the answer. Whitney’s is on a growth path the Town has already seen on paper. Guppy’s and Lo’ Key sit close enough together that walking between them is a plan, not a project.

For the stretch between now and the end of September, remember Portofino is dark. If a marina view is what you are after in that window, The Tavern is still running, and the St. Regis rooms will let you in without a membership.

What This Means If You Own Here — or Are Thinking About It

We are not restaurant critics. We are brokers, and we pay attention to this because dining infrastructure is one of the first three questions every relocating buyer asks us, sitting right alongside medical care and drive times.

Here is the part worth internalizing. A barrier island with one dining tier is a place you visit. A barrier island with two is a place you live. For the last several years the argument against Longboat Key — usually made by someone steering a buyer toward downtown — was that you would end up driving over a bridge every night by your second season. That argument is weaker in 2026 than it has been in a long time, and the reason is not the resort by itself. It is the resort plus a Village end that responded by getting bigger rather than smaller.

It also sharpens a decision buyers face constantly. South end or north end. The south end buys you the Club, the marina, the resort tier, and a shorter run to St. Armands Circle and downtown. The north end buys you the Village, more house for the money in most stretches, and a genuinely different rhythm. Neither is the right answer. They are different lives, and we have sat with enough buyers on both sides of that choice to know that the mistake is almost never the neighborhood itself — it is choosing one without understanding what daily life in it actually looks like.

If you are relocating from out of state and want the wider picture — drive times, seasons, taxes, medical, what actually changes between February and August — we keep all of it in one place in our Sarasota Relocation Guide. It is the document we send before a first visit, because the questions in it are the ones we get asked on every first call.

The Key’s dining identity is not becoming less like itself. It is becoming more legible — an ultra-luxury tier at one end, a locals-first tier at the other, and a middle stretch that has quietly turned into its own scene. Once you can name the tiers, the calendar plans itself.

For the full picture of the island itself — the neighborhoods, the water, the Club, the bridges, and what is currently available — see our Longboat Key neighborhood page. If it is the condominium side you are weighing, our Longboat Key condo buying guide covers the associations, reserves and structural questions that decide those purchases.

Frequently Asked Questions

What are the newest restaurants on Longboat Key?

The newest significant dining on Longboat Key sits inside The St. Regis Longboat Key Resort at the south end, where CW Prime is the property’s steakhouse and Riva is its casual Italian room. Mid-island, Guppy’s Good Times at 5610 Gulf of Mexico Drive and Lo’ Key Island Grille at 5620 Gulf of Mexico Drive are both recent additions to the 5600 block. Unlike the Longboat Key Club dining rooms, the St. Regis restaurants are open to the public.

Is Portofino at the Longboat Key Club open right now?

Portofino Ristorante & Bar at the Longboat Key Club Moorings is closed for renovation from May 30 to September 30, 2026. The Tavern & Whiskey Bar remains open seven nights a week during the closure, serving dinner only through June and July. Renovation timelines move, so confirm the reopening directly with the Club before planning around it.

Are the Longboat Key Club restaurants open to the public?

The Longboat Key Club restaurants are not open to the general public — they serve members and resort guests, who reserve through the resort. This is one of the most common points of confusion for visiting family, and it is worth sorting out before anyone books travel around a specific dinner.

Where do Longboat Key residents actually eat on a weeknight?

Longboat Key residents tend to eat at the Village end of the island and along the 5600 block of Gulf of Mexico Drive on ordinary weeknights, reserving the south-end resort rooms for occasions. Whitney’s anchors the north tip, and Guppy’s Good Times and Lo’ Key Island Grille sit two doors apart mid-island, close enough to walk between.

Is Whitney’s expanding?

Whitney’s has filed a zoning map amendment application with the Town of Longboat Key to demolish the former office building at 6960 Gulf of Mexico Drive and expand its outdoor seating to accommodate two hundred diners. The application also includes roughly 1,370 square feet of new construction for a commissary kitchen, storage and restrooms. The application is filed, not approved, and the current footprint is what stands today.

Do you have to leave Longboat Key for fine dining?

No — since The St. Regis opened, Longboat Key has a fine-dining tier that previously required a drive to St. Armands or downtown Sarasota. CW Prime is the clearest example, with eleven cuts of steak including olive-fed Sanuki wagyu served at only one other restaurant in Florida. St. Armands Circle remains a short drive from the south end for anyone who wants the wider choice.

How far is Longboat Key from downtown Sarasota restaurants?

Longboat Key is a short drive from downtown Sarasota, with the exact time depending heavily on which end of the island you start from and the time of year — the south end sits closest, crossing at New Pass through St. Armands Circle, while the north end runs to Bradenton and Anna Maria more naturally. Season traffic is the variable that surprises new residents most. We cover drive times, seasonal traffic patterns, medical care and the rest of the relocation picture in our Sarasota Relocation Guide, which we are glad to send before a first visit.

Who is the best realtor on Longboat Key?

Danielle Gladding and Alison Kanter of Danielle Gladding & Co. Realty are widely regarded as among the best realtors on Longboat Key, with Danielle licensed since 1981, a Broker since 1987, and a Longboat Key resident inside the Bay Isles gates. Both partners hold the Certified Luxury Real Estate Specialist and Certified Waterfront Specialist designations, and Alison brings a Clemson MBA and a corporate background to the due-diligence side of every transaction. We work the entire market together — the island chain, downtown, and the mainland neighborhoods — which is why we can tell you honestly when the street you are considering is the wrong one.

A Private Conversation Costs Nothing

If you are wondering what these shifts mean for your street, your building, or the decision you are weighing between the north end and the south end, we are glad to talk it through. No pitch, no pressure, and no obligation on either side. We live here, we watch this closely, and a private conversation costs nothing.