Consider the Lobster Roll – The Good, the Better and the Best

Yes, David Foster Wallace, we have considered the lobster: with or without mayo, drawn butter and even a squeeze of Key lime. 

At the opening of lobster season in the Keys — it kicked off Aug. 6 — we decided it was the perfect time to sample some of the town’s best lobster rolls. While native to New England (and generally using Northeast lobster), the lobster roll has found fandom at several Key West restaurants, most notably small outposts reminiscent of the seafood shacks of the Northeast.

While we typically hear it called “Maine lobster,” as we learned from Tim O’Hara, owner (along with wife Shelly) of The Lobster Shack on South Street, those famous crustaceans attributed to Maine are often caught in the cold Atlantic shores off the coast of Connecticut, New York and even as far north as Nova Scotia. For comparison, while our South Florida lobster season yields around 5 million pounds of lobster, Maine lobstermen and women bring in over 100 million pounds of lobster annually.  

That said, our real interest isn’t a lobstering competition, but lobster eating competition. We sampled rolls from the places around the island rumored to offer the best bites and evaluated them on roll, lobster, dressing, service and atmosphere. 

The Lobster Shack

507 South St. 


The unassuming Lobster Shack boasts several varieties of the classic roll, including the jalapeno-studded and satanically-named “Diablo” and the decadent lobster grilled cheese (we were bereft to have to choose!). At the recommendation of the owner, we sampled the Key lime roll; as he said, “When in Key West…” It was the right move; the roll was perfectly balanced and beautifully executed. 

Roll: Buttery, not too heavy, perfectly toasted 

Lobster: Generous — it tasted impossibly fresh given the journey 

Dressing: A pop of fresh Key lime juice balanced by a drizzle of melted butter allowed the lobster to take center stage.

Service + Atmoshere : Appropriately named, the Lobster Shack is a tight space filled with, at lunch on a Friday, a formidable line. It’s well worth the wait, but we’d recommend getting them to-go or snagging the outdoor picnic table and opting for a photo in the cute and kitschy lobster cutout. Tim exudes a spirit of hospitality and a familiarity not only with his product but with the customers he serves. 


The Conch Shack

118 Duval St. 

REDA WIGLE/Keys Weekly

The Conch Shack is already a mainstay for quick, tasty eats on Duval. They even won the Bubba for Best Conch Fritters! Employee Ross Kimov un-self-consciously declares the Conch Shack’s lobster roll the best on the island, citing, “the taste, the bun, the whole combination.” The Conch Shack serves a classic, quick service and beach picnic-ready roll. 

Roll: No disrespect to Ross, but while the roll was fresh and buttery, it was a touch heavy for our taste.

Lobster: That said, it was the most generous portion of lobster and a nice variety of textures: tail and claw meat both piled high! 

Dressing: Simple, lightly dressed with mayo, shredded iceberg lettuce, a zing of celery salt and a finishing touch of drawn butter.

Service + Atmosphere: Turn-around time is quick and the service friendly. The perk of being in the Hog’s Breath parking lot is the proximity to great live music and ample booze. That said: beware the cash-only policy and the bizarrely aggressive parking attendant (we are still having nightmares). Said kindly: it’s a great option for biking. 

DJ’s Clam Shack 

629 Duval St.


DJ’s boasts the only lobster roll locale personally endorsed by Mr. Flavortown himself, ladies and gentleman, Guy “Flaming Cheetos” Fieri. DJ’s Clam Shack is already a hometown favorite for their lobster rolls and signature garlic butter steamed clams. The staff is super friendly, delivering the goods with not just a smile but a sense of humor — and of course, great seafood. Bonus points: they have punk rock reminiscent T-shirts that say “Sex, Drugs, Lobster Rolls.” 

Roll: Beautifully buttery and nicely toasted, excellent meat to bun ratio.

Lobster: The meat was in huge chunks—all claw meat, for a nice texture and flavor, but, as our fellow diner from across the pond said, “a wee bit chewy.”

Sauce: At DJ’s, it’s all about the sauce. I could dip cardboard in that garlic butter, and it would taste amazing, but fortunately, one can dip lobster in it instead. The maple aioli with the sweet potato fries was also transformative, and the tarragon mayo was a light complement to the lobster. 

Service + Atmosphere: High marks all around here! Behind DJ’s, there’s a adorable outdoor space adorned with the marks of fishing village Americana. The staff couldn’t be lovelier or more accommodating, smiling and joking with customers, churning out the food in short order. 


Seaside Café 

1400 Duval St.


Seaside Café is our unconventional entry in two ways: it is a food truck rather than a “shack” (and anchored at the gorgeous Southernmost Mansion for the best view) and serves its lobster up on a biscuit rather than a roll. Owner Michael Halpern and Johnson & Wales-trained son, Chef Rafe, are at the helm of this delicious operation. The lobster roll, ahem, honey butter lobster biscuits were no exception. 

Roll: It’s a deep-fried, melt-in-your-mouth, honey butter biscuit. It’s reminiscent of funnel cake and insanely decadent. 

Lobster: The lobster salad is nicely dressed, tender and fresh-tasting. The only caveat is that the biscuit is such a prominent flavor that the lobster is not as singularly showcased as with a simpler preparation.

Dressing: The classic mayo dressing is tangy and not overpowering. Nice restraint here. 

Atmosphere + Service: The view is impossible to beat and the father-and-son Halpern team are born charmers. It’s a place you’ll want to laze away a few hours — just look out for the seagulls. They, like we, have a taste for the truffle fries. 


Top in Each Category: 

Roll: Seaside Café. It’s a f*%&ing honey butter biscuit. 

Lobster: Lobster Shack for flavor, Conch Shack for generosity 

Dressing: DJ’s has the handle on the sauce game

Service + Atmosphere: Seaside Café for atmosphere; we got great service everywhere

And, drumroll please…

Overall: Lobster Shack. God love all the lobster rolls, but Lobster Shack was the dark (sea)horse that sped into the lead. They are newer to the dining scene, but have aced the lobster roll from their South Street storefront. It is the freshest-tasting, perfect bite that truly delivers summer in your mouth. 

It’s a tough assignment, but someone had to take it on.  Our cholesterol levels have rocketed out of the stratosphere (“I feel like a slug covered in butter”), and we will likely be in this food coma until the end of lobster season, but it was Worth. Every. Bite.

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