The Wofford Guide to Nantucket
A few notes from The Woffords on where to eat, where to have a drink, what to do if you get here early, and where to shop.
If You Only Have a Day
Short on time between sessions? Here's the condensed version:
Where to Eat
Casual Bites
My favorite sandwiches on the island. A mercantile and bakery on Centre Street known for its sourdough — try the Kevin Sandwich or one of the breakfast sandwiches. Small spot, so it can look picked-over by afternoon; go early.
The best burgers on the island, and — surprisingly — genuinely great sushi too, upstairs in the Cisco Kitchen & Bar. A Nantucket institution since 1972, housed in an 1840s whaling bar. Reservations recommended.
The ice cream hotspot on Broad Street, with lines out the door all summer long. Homemade ice cream in a warm waffle cone is the move — cash only.
My favorite coffee on the island, and the food is great too. Breakfast and lunch on Main Street, with a Middle Eastern/Persian-leaning menu — great breakfast sandwiches, superfood lattes, and cold-pressed juices.
On the island for over 50 years and known for their oversized sandwiches on housemade bread, plus the famous chocolate chip and oatmeal raisin cookies. Set back in the trees on Cliff Road with picnic tables outside — a great grab-and-go before the beach.
Elevated Dining
Small, cozy, and BYOB, with a genuinely famous brunch. At dinner, my favorites are the pastas, caesar salad, and tuna tartare with scallion pancakes — ask for extra pancakes, you'll want them. Sit at the bar for the most fun.
Out in Sconset, in a rose-covered cottage with a beautiful garden — the vibes are spectacular, especially if you can sit outside. Food is fair rather than a highlight, but the burger is solid. Worth the trip for the setting alone.
Elevated, oyster- and seafood-forward, and just as popular as Nautilus. Right on the water at the entrance to the Boat Basin, so the harbor views do a lot of the work. If there's no table, take the wait as an excuse to wander and grab a glass of rosé — people line up before opening and they'll usually find you a seat. Lunch here is a treat too, especially on a nice day.
Classic French bistro that's been on Broad Street since 1976. Sit downstairs in the café for something casual, or upstairs for a more refined night out.
Hands-down one of the best restaurants on the island. Small, shareable plates with a pan-Asian bent — think crab fried rice, scallion pancakes, whole roasted Peking duck. Reservations are genuinely tough to land, but don't let that stop you — call or walk in, and they can usually find you a seat at the bar (first come, starting around 5:30).
A cozy upstairs bistro with candlelit rooms — New England by way of France and Italy. Excellent pastas (the black truffle bucatini is a standout) and well-executed entrees across the board.
Still very good. Asian-inspired seafood in a lively, colorful room — the salt & pepper wok-fried lobster is the dish to order.
A longtime favorite of ours — great for dinner, and just as great for a drink before or after. Global, farm-to-table small plates in a cozy 19th-century house, perfect for sharing a lot of dishes across the table. Our go-to order at the bar is the spicy daiquiri.
Classic, old-school Nantucket, set below street level in an 1831 whaling captain's mansion. Quiet, refined, American/French menu. A favorite among our friend group, and the food holds up.
Nantucket's original harbor-side fine-dining icon, right on the water at Harbor Square. A seasonal institution since 1976 (celebrating 50 years this season), with refined, locally-sourced seafood and genuine hospitality. Reservations recommended — this is the classy sibling to the more casual Straight Wharf Fish next door.
One of my absolute favorites. Fresh seafood, great salads, always-good specials, plus a fish market if you want to grab something to cook yourself. A bit more casual than Nautilus or Cru — walk-in or online waitlist only, no reservations. Fair warning: I could eat here every night this week and be perfectly happy.
Another Sconset favorite, up on the bluff overlooking the Atlantic. Food is fair, but the chicken milanese is genuinely great, and the setting can't be beat. Stick around after dinner for the piano bar — everyone sings along with Jamie. Ask for Salvatore on the wine list; he's the sommelier here in summer and works at Bice in Palm Beach the rest of the year — tell him we say hi. Come here for a fun night out.
At The Wauwinet, about nine miles out. Pricey, but it's the island's only AAA Five-Diamond restaurant and the sunset views over Nantucket Bay are worth every penny. You can drive or take the Wauwinet Lady boat over — makes a nice afternoon of it.
Things to Do
Nantucket's iconic brewery — live music, food trucks, outdoor games, and craft beer in a big outdoor setting. We'll be there together Tuesday night for the welcome party, but it's worth a return visit anytime.
Go on a Beach Adventure
For something off the beaten path, head to Madequecham on the south shore: a wide, quiet stretch reached by a long dirt road, with no lifeguards or facilities, so it stays genuinely uncrowded even in August. Radar Beach, near Tom Nevers, is another under-the-radar (no pun intended) local pick if you want to keep exploring.
Hiking
Nantucket has thousands of acres of protected conservation land criss-crossed with trails. Self-guided highlights include the Middle Moors ("Serengeti"), Sanford Farm, Head of the Plains, and Ram Pasture — see the Land Bank's trail list for the full map. For something guided, Nantucket Walkabout runs 2-hour naturalist-led hikes ($65–80/person) across spots like Gardner Farm, Sankaty Bluff, Shawkemo Hills, Smith's Point, and the Coskata-Coatue Wildlife Refuge.
Nantucket's only public 18-hole course, a links-style layout about a mile from the ocean and three miles from town. More polished and championship-caliber than Skinner's, with a full clubhouse, driving range, and restaurant on site.
Play Golf at Sconset Golf Course
A fun, historic 9-hole course out in Sconset, first opened in the 1890s and now the oldest course still active on the island. Locals call it "Skinner's." Public, walkable, and a nice change of pace from the more manicured Miacomet.
Young's Bicycle Shop, a family-owned institution on Broad Street since 1931, is the easiest way to get around downtown and beyond. Paved bike paths lead out to Sconset, Cisco, and the south shore beaches — a great way to see more of the island at your own pace.
For the history buffs, two good options. The NHA's Historic Downtown Tour runs Monday–Saturday at 10:45am with a Museum Guide, covering the rise and fall of the whaling industry and the growth of tourism. The Nantucket Preservation Trust runs two others: "A Walk Down Main Street" (Tuesdays at 3pm, meets at 11 Centre Street) and a 'Sconset Tour (Thursdays at 3pm, meets at 1 New Street, Siasconset) — both $20/person, registration required. Handy timing: the Main Street tour runs Tuesday, and the 'Sconset tour runs right through Thursday the 24th.
Visit Coatue
A wild, undeveloped barrier beach across the harbor from town, part of the Coskata-Coatue Wildlife Refuge. Rather than renting a Jeep and airing down your own tires, take the Trustees' guided tour — a safari-style, over-sand vehicle ride (about 2 hours, $75/person) departing from the Wauwinet Gatehouse, running Thursday–Monday at 10am and 2pm in season. You'll pass salt marshes and barrier beach out to Great Point Lighthouse, with a good chance of spotting seals, osprey, and other shorebirds along the way.
Where to Shop
We'd recommend wandering town and popping into shops that pique your interest, as there are so many of them! The ones below are just a few of the classics. One fun fact worth sharing: Nantucket has a "formula business" bylaw that bans chains with 10+ locations from downtown, so almost everything you'll walk into is a genuinely unique, one-off store. You will see a few (somewhat contentious) exceptions, though — Ralph Lauren, Veronica Beard, Staud, and Vineyard Vines, to name a few.
On India Street since 1974, and billed as "the shop meant for the person who has everything." Scrimshaw, 14k gold jewelry, lightship-cane woven bangles, and genuine leather goods — wallets, belts, weekend bags. A good stop for a real gift.
The spot for Nantucket lightship baskets — the woven baskets and "friendship purses," often with a carved ivory or scrimshaw lid, that originated with the island's old lightship crews. On Main Street since 1948, and still handmade by local artisans; a genuine collector's item and a classic Nantucket souvenir, though not a cheap one.
The iconic Nantucket shop for everyone, on Main Street since 1945. Home of Nantucket Reds — the faded red canvas pants made famous by JFK and immortalized in The Official Preppy Handbook.
Where to Relax
A Nantucket wellness sanctuary since 2009, at 6 W Creek Rd. Great craniosacral therapy and alternative healing — massage, functional medicine, bodywork, all in one calm space.
Ocean Day Spa, right in the hotel. Some of the best deep tissue massages I've had.
Late Night
Nantucket's iconic dive bar and live music venue, on Dave Street. Live bands most nights all summer, pool, darts, dancing — expect a raucous, no-pretense crowd.
A vintage 19th-century railroad car turned piano bar on Main Street. Everyone ends up singing along by the end of the night — get there early to snag a spot near the piano.
Already one of our dinner favorites, but the bar scene here is just as good late — right on the water, always a crowd.
A cozy, no-reservations boutique wine bar on Broad Street. Low lighting, well-chosen wine list — a much quieter alternative if you actually want to talk.
Our go-to for a nightcap too — the spicy daiquiri at the bar is the move.
Lobster Roll Taste-Off
Nantucket takes its lobster rolls seriously enough that a local magazine tracks prices island-wide every year. If you want to turn lunch into a game, grab a group, order all six below, and argue about which one wins — genuinely different styles, not six versions of the same thing.
A consistent favorite in Nantucket Current's reader polls. Fish market and food truck combo on Hummock Pond Road, with a lovely garden setting — big chunks of lightly-dressed lobster on a toasted potato roll.
A BBQ joint has no business having the island's most talked-about lobster roll, but here we are — currently ranked #1 on Tripadvisor. Big chunks of lobster in lemon aioli on toasted brioche, harbor views from 20 Straight Wharf. ($38)
The splurge. Choice of hot lemon butter or cold lemon mayo, brioche bun, pickled onion, right on the water. ($50)
Worth it for the setting alone — toes in the sand, sunset views, an island classic since 1958 on Cliffside Beach. ($48)
The no-nonsense classic. Family-owned since 1974 on Washington Street, straightforward New England style. ($45)
Proof you don't need to spend a fortune. Hot or cold, takeout only — grab it on your way to the beach or the ferry. ($35)