Just 30 miles off Cape Cod, Nantucket is the definition of a dreamy New England summer. Think sunny beach days, bike rides down quiet roads, lobster rolls on repeat, and evenings that stretch out over cocktails by the water. With its cobblestone streets and weathered shingle houses, the island feels like it was plucked straight out of a postcard.
Back in the late 1600s, whales were discovered offshore, and by the 1700s Nantucket was basically the epicenter of the whaling world. Between 1750 and 1840, the island was booming — the oil from whales was as valuable then as actual oil is today. Wild fact: some of America’s very first billionaires made their fortunes here through whaling! When that industry fizzled out in the 1880s, Nantucket reinvented itself as a seaside escape — and let’s be real, it’s been luring visitors with its natural beauty and laid-back luxury ever since.
If you’re heading to Nantucket for the first time, there are a few non-negotiables: grab a drink at Cisco Brewery, (the energy there is unmatched), hop on a bike and cruise around, spend at least one full day at the beach, and eat as much as humanly possible. Lunch at Fresh is a solid move, or swing by Bartlett’s Farm for a picnic spread. You have to stop at The Juice Bar for an ice cream cone piled high — it’s a rite of passage. For dinner, you can’t go wrong with Cru, (lobster rolls + waterfront cocktails), The Proprietors Bar & Table, (creative and cozy), Millie’s (casual and fun), or Sister Ship (elevated but laid-back). Honestly, the food scene on this tiny island is shockingly good.
What makes Nantucket extra special is the vibe. The whole town comes alive in the warmer months: boutique shopping, strolls past rose-covered cottages, oysters and champagne on the water, beach walks at sunset. It’s equal parts charming and chic.
If you’re planning a trip, summer is prime time — Memorial Day through Labor Day is when the island is buzzing, with July and August hovering around a perfect 76°. That said, May and September are insider favorites: you still get the beautiful weather without the big crowds.
Getting there is easier than it sounds. Nantucket has its own airport (Delta, JetBlue, and United all fly in, along with local Cape Air). If you’re coming from Cape Cod, you can hop on a ferry — the regular one takes just over two hours, or you can zip across on the high-speed ferry in about an hour. Pro tip: sit outside with a drink, because the ride itself feels like part of the vacation.
To Eat:
- *Bartlett’s Farm– Nantucket’s oldest family-run farm. Perfect spot to bike out to (about 20 minutes from town) and grab a sandwich for lunch. You’ll find fresh veggies, flowers, and groceries too.
- Millie’s Restaurant – Super laid-back, Baja-style seafood. Think fish tacos, quesadillas, and don’t miss the queso. Great for a casual hang.
- *Cru – Right on the water and always buzzing. Their lobster roll is a must, and you’ve got to try a “Cru-comber” cocktail while you’re there.
- *Bar Yoshi One of my absolute favorite meals on the island. Tiny, unfussy Japanese spot with killer sushi. Order the veggie spring rolls, beef yakitori, and Wagyu bao buns—you won’t regret it.
- *The Hub – Local coffee shop where you can grab a pastry in the morning and poke around their Nantucket-y gift shop.
- Provisions – This is the spot for a sandwich on Nantucket. Their “Turkey Terrific” (thanksgiving dinner on a sandwich) is legendary, but honestly everything on the menu hits. Perfect to grab before the beach or pack for the ferry.
- Straight Warf – More elevated seafood, perfect for a nice dinner. Grab a seat on the porch by the water if you can.
- Fresh – Craft sandwiches that are perfect to take with you to the beach. Easy and delicious.
- Nantucket Meat & Fish Market – Family-owned gourmet market with prime meat, fresh seafood, and solid prepared food. Pro tip: grab their bagels in the morning.
- Lemon Press – Bright, buzzy spot for smoothies, cocktails, and fresh plates. Their breakfast burrito is ridiculously good.
- *The Proprietors Bar & Table – One of my go-to dinner spots. Relaxed but creative. The hummus and fried broccoli are game-changers.
- Something Neutral – Super casual, picnic-table vibes with hearty sandwiches and chocolate chip cookies you need to try.
- *167 Raw – Probably my favorite lobster roll on the island (I like mine cold!). Grab one from the truck at 167 Raw Fish Market, then head to their garden with a beer—it’s right next to Cisco Brewery.
- Galley Beach – Beachside restaurant with a chic vibe. Amazing cocktails, great food, and you can hang at the beach bar/lounge before or after.
- Nautilus – A fun, rustic-modern spot for inventive small plates and cocktails with an Asian twist. Perfect for sharing.
- Lola 41 – Always lively. The menu is all over the map (in a good way)—sushi, burgers, cocktails… it’s a scene.
- Born & Bread – Great bakery and café for breakfast or lunch. Their breads and pastries are worth it. Get a breakfast sandiwch or their Candied B.L.T – and grab a sourdough loaf for the return home!
- Sister Ship – Really cool vibe. Elevated cocktails, Mediterranean-inspired seafood dishes, and an airy café feel during the day.
- Ventuno – Cozy, upscale Italian spot with incredible pastas. Feels a little more tucked away and special.
- Or, The Whale – Chic but relaxed. Perfect for brunch or dinner—lots of shareable plates and great drinks on the patio.
To Drink:
- The Chicken Box – A right of passage in Nantucket. This dive bar is.. Unpretentious roadhouse with regular concerts (jazz, blues, rock), plus pool, ping pong & darts.
- Cisco Brewery – Rustic brewery for live music, tastings & tours along with 3 bars serving craft beer, wine & drinks.
- Slip 14 – Homey indoor-outdoor New American spot for fish-focused fare & creative cocktails with water views.
- The Gazebo – have to get their famous Mudslide drink here!
- O Bar – Owned by Bar Yoshi, this classy cocktail bar is perfect for an after-dinner drink!
- The Club Car – California-inspired fare in a restaurant attached to a retrofitted railway car that’s a lively piano bar.
Coffee & Sweets:
- The Juice Bar – Crowds flock to this unassuming depot for homemade ice cream & waffle cones plus healthy juice.
- Handlebar Café – Relaxed neighborhood cafe serving java & nibbles in a cozy space with armchairs & a back patio.
To Shop:
- Bodega – Home goods & interiors
- Atlantic – Curated home goods
- Vineyard Vines – Men’s & women’s apparel
- Faherty – Men’s & women’s apparel
- Peter England Nantucket
- Centre Point – Home Goods & interiors
- Dawn – Men’s & women’s apparel
- 12 Trees Nantucket – Home goods & interiors
- Anderson’s – home goods
- Nomad – Boho-chic inspired home goods and linens
- Murray’s Toggery Shop – Men & women’s apparel
To Do:
- Rent a boat with Barton & Gray
- Go sailing!
- Rent bikes and ride to the beach!
- Hang at Cliffside Beach Club
- Visit Moors End Farm
- Bike to Bartlett’s Farm for lunch
- Hit up the beaches:
- Surfside Beach– This is one of the most popular beaches on Nantucket. Very family friendly though the surf can get heavy at times.
- Cisco’s Beach
- Steps Beach
- Children’s Beach
- Check out the historic Whaling Museum
- See the Sankaty Head Lighthouse
- Catch a movie at Dreamland Theater
- Have some sunset beers at Cisco Brewery
To Stay:
- The White Elephant – Quintessential coastal New England mansions with wooden shutters, salty air coming off the water, and beachfront lobster rolls are the essence of White Elephant Nantucket. The iconic hotel on Nantucket Island has a heated outdoor pool and is close to the town of Nantucket and the Brant Point Lighthouse.
- Greydon House – A former sea captain’s house right off the wharf in town, Greydon House is where classic style meets historic environs. Of all hotels on Nantucket, they’re the only one with 20 unique rooms by Roman and Williams (Ace Hotel New York and The Standard, High Line).
- Faraway Nantucket – Faraway opened in the heart of downtown during the summer of 2021, just steps from cafes, restaurants, and shops. Though it’s not situated on the beach, the 62-room property reminds guests that they are, indeed, on an island, from the coastal-inspired rooms to the Mediterranean, seafood-centric menu offerings at their restaurant, Sister Ship.
Have you ventured to Cape Cod or Nantucket for a proper New England summer? It’s not the easiest place to get to, but it’s so worth the trip! A very “New England” debate I had while on Nantucket: are you a “hot” or “cold” lobster roller kinda person? Let me know! 😀
Stay Risky,
– John
* via Travel & Leisure
