Nantucket Strolls & Lobster Rolls: Where Great Food Meets Great Music

After stepping off the ferry and breathing in the crisp, salty air of Nantucket, it’s time to ease into island life. Whether you’re staying in a charming boutique inn or a cozy seaside cottage, check in, freshen up and get ready to explore. The best way to start your Nantucket adventure is with a visit to Cru, a stylish waterfront spot perfect for unwinding after your journey. Grab a seat on the patio and indulge in a round of oysters and cocktails. As you sip and savor, watch the boats sway gently in the harbor, setting the tone for a relaxed and indulgent island getaway.

Once you've had your fill, take a leisurely stroll through the historic streets of downtown. Cobblestone paths lead past charming boutiques, art galleries and classic New England architecture. Stop by Murray’s Toggery Shop for a peek at the island’s signature Nantucket Reds or browse the shelves at Mitchell’s Book Corner for a beach read to enjoy later. As the sun begins to dip, make your way toward Brant Point Lighthouse for golden-hour views, where the soft light casts a magical glow over the harbor.

For dinner, start your night at The Nautilus, a lively spot known for its inventive, shareable plates and expertly crafted cocktails. The menu is inspired by bold flavors, blending global influences with the freshest island ingredients. If you’re in the mood for something more casual, Sayle’s Seafood offers some of the best lobster rolls on the island, perfect for taking to the beach for a sunset picnic. After dinner, head over to The Club Car. This is a Nantucket institution that offers both an incredible dining experience and one of the best nightlife spots on the island. Whether you opt for a dessert cocktail or a nightcap, stay for the legendary piano bar, which kicks off at 9 pm. The intimate setting, with its spirited singalongs creates an unforgettable atmosphere that perfectly captures the magic of Nantucket after dark.

Wake up to the crisp ocean air and start your morning with a scenic bike ride or a leisurely stroll along the Sconset Bluff Walk. You'll find winding paths leading past rose-covered cottages and breathtaking views of the Atlantic. The peaceful sound of waves crashing below and the charm of this hidden coastal trail make for a perfect start to the day. When hunger calls, head over to The Sand Bar at Jetties Beach for a laid-back lunch by the water. With its casual, toes-in-the-sand vibe, this spot is perfect for unwinding with friends over a basket of fried clams, a lobster roll or a refreshing frozen cocktail. The ocean breeze, paired with the sight of boats bobbing just offshore, makes for an effortless afternoon. After lunch, stretch out on the sand, dip your feet in the water and soak up the Nantucket sun before heading back to your hotel for a quick freshen-up.

As the evening approaches, make your way to Bar Yoshi. This cozy yet stylish restaurant is perfect for a light but flavorful dinner after a day at the beach. From sushi rolls to poke bowls, the menu is filled with shareable bites that highlight the island’s freshest catches. The outdoor seating provides a serene atmosphere, making it the perfect place to sip on sake or a crisp glass of Sauvignon Blanc as the sun begins to set.

No trip to Nantucket is complete without a stop at The Juice Bar, the island’s most famous ice cream shop, now a viral sensation thanks to TikTok. Whether you go for a homemade waffle cone, a scoop of their rich, creamy flavors or a towering sundae, it’s a must-visit for a sweet end to the night. But if you’re not quite ready to call it a night, head over to The Gaslight, where live music and craft cocktails keep the island's energy going. With an ever-changing lineup of talented musicians, it’s the perfect place to dance, sip and let the night carry you away — making for yet another unforgettable Nantucket experience.

For a dose of Nantucket’s rich maritime history, start your day with a visit to the Whaling Museum. It is an essential stop for anyone wanting to understand the island’s storied past. Housed in a former candle factory, the museum offers a fascinating glimpse into Nantucket’s whaling industry, which once made the island one of the wealthiest in the world. Walk beneath the impressive skeleton of a real sperm whale, explore artifacts from the whaling era and learn about the daring voyages that shaped Nantucket’s identity. The rooftop deck also provides stunning harbor views, making it a great spot to take in the island’s beauty while reflecting on its history.

After stepping back in time, take a leisurely stroll through the surrounding historic district, where 18th- and 19th-century homes with widow’s walks and sea-weathered shingles transport you to a different era. Stop for a coffee at Handlebar Café or a pastry at Born & Bread, then continue wandering the charming streets lined with historic markers, boutique shops and art galleries. The area around Main Street is perfect for getting lost in Nantucket’s timeless charm, where every corner holds a bit of history and character.

With a morning of history and exploration behind you, it’s time to shift into island mode. Head to Cisco Brewers for a laid-back afternoon filled with live music, craft drinks and great food from the rotating food trucks. Whether you’re sipping a Whale’s Tale Pale Ale, a refreshing rosé from Nantucket Vineyard or a house-made cocktail, the brewery’s lively, open-air setting is the perfect way to round out the day before heading back into town for dinner and nightlife.

After soaking in the energy at Cisco, head to dinner at The Brotherhood of Thieves, a classic Nantucket tavern with a cozy, old-world feel. Enjoy a hearty meal in the dimly lit, pirate-themed dining room, or opt for a seat on the patio if the weather is right.

After dinner, venture downstairs to the whiskey bar, where a curated selection of rare and specialty whiskeys makes for a fun post-dinner experience. If you’re still in the mood for more music and a lively crowd, end the night at The Chicken Box, Nantucket’s iconic live music venue. With its dive-bar energy, packed dance floor and fantastic bands, it’s the perfect spot to let loose, sing along and dance the night away — wrapping up a quintessentially Nantucket day.