Nantucket Revisited: A Weekend to Remember

This Cafe Life
Aug 7
4 min read

Updated: 5 days ago

The first time I visited Nantucket, I saw it through the eyes of a third-generation islander - someone who knew its rhythms, its rituals, and the stories told behind weathered shingles and hydrangea-lined paths. I was introduced to more than just postcard-worthy views; I was welcomed into her family, and into the quiet beauty of a place that feels both timeless and alive. Summers were spent waiting on tables, scalloping and swimming out from Coatue.

Recently, I returned. This time with fresh eyes and a slower pace - and it reminded me exactly why this tiny island leaves such a big impression. Whether it’s your first visit or your fifteenth, Nantucket has a way of settling into your memory. Here’s how to spend a weekend enjoying the best it has to offer.

Getting to Nantucket

The Steamship Authority leaves from Woods Hole on the Cape and fortunately they have high speed ferries that can accommodate your car, bikes and gear. We flew out of Providence when we could. There are direct flights from NYC and Boston. Either way, you'll have to book your reservations in advance. Flying may be affected by inclement weather - keep that in mind when making your choices.

Best Places to Stay

If you're not staying with friends or family, consider:

The White Elephant – Harborfront luxury, central location.
The Nantucket Hotel & Resort – Classic Island hospitality.
Greydon House – Boutique style meets historic charm.
Brass Lantern Inn – Quaint and walkable.
VRBO rentals – A great option for families or longer stays.

Favorite Restaurants

The Proprietors Bar & Table - Hand's Down Favorite. Globally inspired plates. It’s inventive, relaxed.
Straight Wharf Restaurant - Harbor views and the island’s best oysters, solid, unpretentious seafood.
Brant Point Grill - Perfect for groups and sunset dinners. Located at the White Elephant.
Cru - Chic harbor front dining with a standout raw bar and one of the best wine lists on the island.
Brotherhood of Thieves - A cozy, historic pub, hearty fare, great burgers - perfect after a beach day.
The Rose & Crown - Family-friendly by day, live music and karaoke by night. A casual crowd-pleaser.

What to See & Do

Sankaty Head Light - On the eastern edge near Sconset, this red-and-white striped lighthouse is iconic. Ride your bike out early for a stunning sunrise over the cliffs.
Whaling Museum - Housed in a former candle factory, this beautifully restored museum tells the story of Nantucket’s whaling past. The 46-foot sperm whale skeleton is just the beginning.
Brant Point Light - Steps from the ferry, this petite lighthouse is both your welcome and farewell. Toss a penny into the harbor on your way out - tradition says it ensures your return.
Cecelia Joyce & Seward Johnson Gallery - A vibrant space for local artists and visiting exhibits, right in the heart of town.

Local Shops & Boutiques

Murray’s Toggery Shop – Home of Nantucket Reds and so much more.
Nantucket Lightship Baskets – Timeless, handcrafted, and heirloom-worthy.
Respoke – Espadrilles made from vintage scarves? Yes, please.
Nantucket Looms – One-of-a-kind weavings and home goods in a dreamy Main Street setting.
Mitchell’s Book Corner – The best place for a beach read.

Nantucket Beaches the Locals Love

Ladies Beach – Moderate surf and mellow vibes. Grab a picnic from Bartlett’s Farm.
Gunrack – Surfer favorite.
Nonantum Road Beach – Quiet and tucked away.
Fisherman’s Beach – Popular with locals casting lines.
Western Avenue Beach – Secluded and scenic.
Steps Beach – Arguably the island’s best views and a perfect sunset spot.

Seasonal Events Worth Catching

If your trip lines up with these events, consider yourself lucky:

Daffodil Festival – A spring tradition full of color and cheer.
Nantucket Food & Wine Festival – For culinary travelers.
Nantucket Film Festival – Showcasing indie and big-name talent alike.

Some places change. Others deepen. Nantucket is one of the few that manages both - and that’s what makes revisiting it so special. From local legends to new discoveries, every trip offers something just a little different… but the magic? That stays the same.

Exploring New England

Planning a trip to New England? Whether you’re chasing the perfect lobster roll, wandering cobblestone streets, or soaking up ocean views, this collection of travel guides covers the region’s most inviting destinations. From the creative pulse of Providence to the windswept beauty of Nantucket and the rugged Maine shoreline, you’ll find the best places to stay, dine, and explore - in every season.

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