You’ve probably heard the hype. If you spend more than ten minutes talking to anyone about where to eat on Nantucket, the name TOPPERS at The Wauwinet Nantucket is going to come up. It’s unavoidable. People talk about it like it’s a religious experience, or at least the culinary equivalent of one. But honestly? Most people get the "why" totally wrong.
They think it’s just about the fancy price tag or the fact that it’s the only AAA Five Diamond restaurant on the island. They focus on the prestige. But if you actually make the trek out to the northeast corner of the island—past the million-dollar cottages and deep into the salt-scrubbed quiet of the Wauwinet—you realize it’s actually about something much more grounded. It’s about the dirt, the tide, and a guy named Craig Hanna who has been obsessed with wine for nearly three decades.
The 300-Yard Rule
Here is the thing about the oysters at TOPPERS. They aren't just "fresh." They are basically still vibrating with the energy of the bay. They call them Fifth Bend Oysters, and they are cultivated exactly 300 yards from where you’re sitting.
You can literally see the water they came from while you’re slurping them down with a splash of champagne mignonette.
Most "farm-to-table" places are full of it. They buy from a distributor who bought from a farm three counties over. At TOPPERS, Executive Chef Kyle Zachary has this relationship with the island that feels almost symbiotic. The menu changes because the island changes. If the fog rolls in heavy and the catch is different, the plate is different.
Why the Wine List is Terrifying (In a Good Way)
Walking into the wine cellar at The Wauwinet is a bit like walking into a cathedral if you're a grape nerd. They have over 2,200 labels. Think about that number for a second. It is an absurd, bordering-on-insane collection for a seasonal island resort.
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- The Grand Award: They've held the Wine Spectator Grand Award since 1996.
- The Depth: We’re talking rare Burgundies, vertical flights of Bordeaux, and one of the largest half-bottle collections in the United States.
- The Vibe: Despite the pedigree, the sommeliers aren't snobs. Mention you like something weird or that you’re on a budget (relatively speaking), and they’ll find you something from a tiny vineyard in the Basque region that blows your mind.
Honestly, don't try to navigate the list yourself. You’ll just get a headache. Just talk to the staff. They live for this stuff.
The Secret "Wauwinet Lady" Move
If you want to do this right, do not drive. The drive from town is fine, but it’s just a drive.
Instead, hop on the Wauwinet Lady. It’s a water taxi that departs from the White Elephant dock in town. It takes about 50 minutes to cruise across Nantucket Bay. You get a cocktail in your hand, the wind in your hair, and you arrive at the private pier like you’re in a 1950s movie. It’s the best way to transition from the "busy" part of the island to the "silent" part.
Just remember: you have to book this in advance. It fills up fast, especially during the peak July and August window.
Deciphering the Menu: Formal vs. Deck
There is a weird misconception that you have to wear a suit to eat at TOPPERS. You don’t. But there is a divide you should know about.
The Main Dining Room
This is the "serious" experience. It’s usually a prix fixe situation. We're talking three or four courses of highly technical, visual-art-level food. The Butter Poached North Atlantic Lobster is the heavy hitter here. It’s often served with things you wouldn’t expect—maybe a Madras curry sabayon or forbidden rice. It’s refined. It’s quiet. It’s for anniversaries or when you’re trying to impress someone who is hard to impress.
The TOPPERS Deck
This is where the locals and the smart travelers hang out. It’s heated, covered, and way more casual. You can get a Wagyu Beef Burger with Vermont cheddar or a massive lobster roll with Meyer lemon aioli. The view of the bay is arguably better because you’re right there in the breeze.
What No One Tells You About the Service
Fine dining can be stiff. Sometimes it feels like the servers are robots programmed to say "excellent choice."
At TOPPERS, the service is weirdly personal. If you have an allergy, they don't just "check with the kitchen." They usually already have a modified menu ready for you if you mentioned it in your Resy notes. There’s a story of a manager, David, who once stayed late just to make sure a couple celebrating their 40th anniversary had the exact vintage of port they’d been hunting for. That’s the stuff that doesn't show up on a Yelp review but makes the price point feel worth it.
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The "Pre-Dessert" Trap
Don't fill up on the bread. I know, the cheese gougeres and the warm raisin bread with smoked sea salt butter are tempting. Resist.
Because at TOPPERS, the meal doesn't end when you finish your entrée. There is almost always a "pre-dessert"—maybe a tiny vanilla custard with a crunch—and then the actual dessert (get the Peach Pavlova if it's on the menu), and then post-dessert mignardises. If you eat too many rolls at the start, you’re going to be miserable by the time the chocolate truffles arrive.
Is It Actually Worth the Money?
Let's be real. It’s expensive. A dinner for two with wine can easily clear $300 or $400.
But here’s the nuanced take: on an island where a mediocre burger in town costs $28, the "value" at TOPPERS comes from the experience. You’re paying for the boat ride, the 30-year-old wine cellar, the 300-yard oysters, and the fact that you’re sitting on the edge of a wildlife refuge.
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It’s not just a meal; it’s a logistics miracle. Getting that level of fresh produce and high-end wine to the remote tip of a remote island is a feat of strength.
Making the Most of Your Visit
- Time the Sunset: Check your weather app. You want to be on the deck or at the bar about 20 minutes before the sun dips. The sky turns a specific shade of sockeye salmon red that you won't see anywhere else on the island.
- The Uber Reality: If you didn't take the boat, be warned: cell service at the Wauwinet is garbage. Ask the host to call your ride about 15 minutes before you want to leave.
- The Shoulder Season: Everyone wants to go in August. Go in September. The water is still warm, the crowds are gone, and the service is even more relaxed.
- Zero-Proof: Surprisingly, they have a killer mocktail program. They use high-end zero-proof spirits, so if you aren't drinking, you don't have to settle for a Shirley Temple.
To make this work for your itinerary, book your table at least three weeks out via Resy, especially if you want a prime sunset slot. If the main dining room is full, don't sweat it—the deck offers the same world-class wine list and a more "Nantucket" vibe anyway. Check the "Wauwinet Lady" ferry schedule before you commit to a time, as the boat trip is the secret sauce that makes the whole evening feel like a getaway within a getaway.