Slow mornings. Long bike rides. Iced coffee from somewhere on Main Street. A late lunch with a glass of rosé at a harbor-side table. An afternoon nap. Cocktails on a hotel porch as the boats come in. Dinner that runs long because the conversation is good. Cashmere on the walk home. The kind of weekend that resets you for the entire summer.

You do not over-plan Nantucket. You hold a few key reservations, you book your bikes, you let the rest of it unfold.

A few logistics worth knowing.

Memorial Day weekend on Nantucket sells out months in advance. The best hotels go first — book six to nine months ahead if you can. Restaurants like Cru, The Chanticleer, Topper’s, and Lola 41 take reservations the moment the window opens. Put them on your calendar and book the second they release.

You do not need a car. In fact, you actively do not want one. The island is small, parking is a nightmare, and ferries with cars book out a year in advance. Bikes, taxis, and your hotel shuttle will get you everywhere you need to go.

The weather in late May is dreamy but unpredictable — pack layers. The harbor breeze in the evening is real, and a good cashmere sweater earns its place in your bag.

Getting There

There are three ways onto the island. The Hy-Line High-Speed Ferry from Hyannis gets you there in one hour. The Steamship Authority takes a little over two hours but feels more nostalgic — sit out on the top deck either way for the arrival into the harbor, because that first glimpse of Brant Point Lighthouse is the moment your trip really begins. Direct flights into Nantucket Memorial Airport (ACK) run on JetBlue, Delta, American, and United from major Northeast hubs. The splurge option is Tradewind Aviation’s semi-private service from Westchester (HPN) — and on Memorial Day weekend, it is worth every penny.

The White Elephant — The iconic Nantucket hotel and the one I would book first. Right on the harbor, classic East Coast elegance, the porch alone is worth the trip. If this is your first time on the island, this is where you stay.

The Wauwinet — The romantic splurge. About a thirty-minute drive from town and tucked between the harbor and the ocean, it is quieter, more secluded, and the most beautiful place on the island for a couple. Topper’s restaurant on property is a destination in itself.

Greydon House — For the design-forward traveler. Beautifully renovated, sits right in the middle of town, and the rooms feel like a magazine spread. A great choice for a girls trip.

The Nantucket Hotel — The best option for families. Pool, kid-friendly programming, walkable to everything, and still completely charming.

Cru — The Nantucket lunch. Right on Straight Wharf, oysters, lobster rolls, towers of seafood, and rosé that flows like water. The most photographed lunch on the island for a reason. Book it the moment reservations open.

The Chanticleer — In Sconset, surrounded by climbing roses and a garden that genuinely takes your breath away. Lunch under the wisteria here is one of the great experiences on the island.

Topper’s at The Wauwinet — Refined, romantic, special-occasion dinner. Take the complimentary launch from town for the full experience.

Lola 41 — The lively, late-night dinner. Sushi, energy, a great bar. The place to land when you want a fun night.

Straight Wharf — Classic Nantucket fine dining. White tablecloths, harbor views, beautifully done.

Sister Ship — Buzzy, modern, design-y, fantastic cocktails. Newer to the scene and worth a stop.

Millie’s — Casual and beachy out in Madaket. The sunset from the deck is unmatched and the margaritas are exactly what you want after a beach day.

Black-Eyed Susan’s — The breakfast spot. Cash only, no reservations, lines around the block — and worth every minute.

The Juice Bar — A non-negotiable. Get the homemade ice cream in a fresh waffle cone at least once. Twice if you can.

Murray’s Toggery Shop — Home of the original Nantucket Reds. You cannot leave the island without something from here.

Nantucket Looms — Hand-loomed throws, beautifully made home goods, the kind of pieces that become heirlooms.

Jessica Hicks Jewelry — Delicate, elevated, the perfect island piece.

Erica Wilson — Classic Nantucket needlepoint and beautifully made gifts.

Milly & Grace — Curated women’s clothing with a coastal sensibility.

Lemon Press — Cute boutique mixing in great resort wear.

Mitchell’s Book Corner — One of the great independent bookstores in the country. Pick up a beach read for the weekend.

Stephanie’s of Nantucket — Resort wear and easy summer pieces.

Force 5 Watersports — For the boat day basics — coverups, hats, totes.

Rent bikes for the entire trip. Young’s Bicycle Shop on Steamboat Wharf is the move. The island is built for biking and you will get everywhere faster than you would in a car.

Bike to Sconset. The path runs about seven miles each way, mostly flat, and the village at the end is the most photogenic spot on the island. Walk Bluff Walk along the cliffs, photograph the rose-covered cottages, have lunch at Sconset Café or under the wisteria at The Chanticleer, and bike back. A perfect day.

Spend a morning at Steps Beach or Jetties Beach. Steps is the prettier one and a little more secluded. Jetties is the family beach with the calm water and the easier walk.

Book a charter on the harbor. Endeavor Sailing offers two-hour sails on a classic schooner that take you out past Brant Point Lighthouse and into the bay. The most romantic two hours of the trip.

Memorial Day Parade and Ceremony at Children’s Beach. This is the heart of the weekend. The parade runs through downtown on Monday morning and ends with a ceremony on the beach. Genuinely moving, very small-town America, and exactly what Memorial Day on Nantucket is about.

Visit the Whaling Museum. Twenty minutes is all you need but it grounds you in why Nantucket is Nantucket — and the rooftop view of the harbor at the end is worth the ticket alone.

Do an afternoon at Topper’s at The Wauwinet even if you are not staying there. Lunch on the lawn, a drink afterward, the launch ride back into town. One of the great Nantucket afternoons.

Watch the sunset from Madaket Beach. Bring a bottle of wine, a blanket, and your husband or your girlfriends. The west-facing beach gives you the best sunset on the island. End the night at Millie’s just up the road.

Wander. Walk the cobblestones of Main Street. Stop into every gallery and bookstore. Get the ice cream. Sit on a bench by the harbor. Some of the best moments on Nantucket are the ones you do not plan.

Pack layers and lean into the Nantucket aesthetic. White denim is practically a uniform on the island. A navy blazer for dinner. White button-downs and linen pants. A few pieces of Nantucket Reds (or salmon-pink chinos as a stand-in). A great cashmere sweater for the harbor breeze at night. White sneakers for the cobblestones — no heels, ever. A straw tote and a panama hat. A swimsuit even if you do not plan to swim, for the spa or the pool. A light rain jacket because Memorial Day weekend can throw one rainy afternoon at you. Comfortable shorts and dresses for biking.

xx, J.