The simplest, most enjoyable experiences usually have you feeling boundless. Driving around with the top down and the music blasting. A breathtaking split-second drop from the diving board. But departing a dock on a ferry bound for a perfect little island with the wind in your hair has got to be one of our favorites. Leaving mainland USA yet not straying too far from home is one of those limitless journeys that have you feeling free. Luckily, we have the best spot in mind for your next vacation, and its Nantucket, MA. We’ll even rent or sell it to you, too, as we have a William Raveis office located in the center of town on Oak Street.
30 miles south of Cape Cod, Nantucket is a designated National Historic Landmark Districk, surviving architecturally and environmentally as an example of a late-18th and early-19th century New England seaport town. In its earliest years, Nantucket promoted the whaling industry but today it supports thriving tourism, offering sailing, surfing, several beaches and quaint shops and restaurants. Because of its heritage, Nantucket is also a historians dream with hundreds of landmarked sites, shipwreck tales and original families still living there.
While riding the fast ferry, Hyline or Steamship, from Hyannis, call ahead to make a Friday lunch reservation at Cru. With a visually stunning waterfront setting, this restaurant on Straight Wharf is a hotspot for oysters, lobster rolls and cocktails by the harbor. This season they’ll be serving their own signature Rosé wine, matching perfectly with the pink summertime sunsets. Lunch will conveniently leave you at exact check-in time for your rental with Windwalker William Raveis, so rent a bike or Jeep from Young’s and head over to your casa for the weekend.
Afterwards, we suggest getting some beach time in at one of Nantucket’s ten best. Depending on where you are staying there are several options, but our favorites (with local nicknames included) are “Steps” (Jetties Beach), great for kids and close to town or “Ladies” (Cisco Beach), home of the island’s best surf school.
End the night with a scenic drive west to more secluded Madaket Beach. Home to the island’s strongest waves, you won’t be coming here to swim. Your best bet is to order tacos or quesadillas from Millie’s and picnic on the beach to watch the legendary sunset.
Sleep soundly all night with the windows open to welcome that seaside breeze and wake up to a healthy breakfast at Fog Island Café. Some of the best service on island is found here, and you will be in and out in no time after one of their pesto egg scrambles with side of black beans. After jump-starting your morning, pack up the Jeep with snacks and meals-to-go from Bartlett Farms and drive out to Great Point. A beach permit, available at the entrance, and four-wheel drive are required for the trip but this pristine beach and a visit to the Great Point Lighthouse is worth it. The lighthouse sits on the end of a seven-mile strip of sand overlooking the gap between Nantucket and Monomoy Island. Spend the day swimming, exploring the lighthouse and soaking up the island sun.
A whole day at the beach deserves some retail therapy, so post Great Point, head back to civilization on Main Street. Our favorite shops in and around downtown Nantucket are the Blue Beetle, CJ Laing, Milly & Grace and Nantucket Looms. An absolute afternoon essential in ACK (the island’s airport code and popular nickname) is a trip to Cisco Brewers, where you can imbibe in a Nantucket brewed beer, wine or cocktail while listening to local live music. Get the Figawi Wowie, a blueberry vodka lemonade or a Cisco Grey Lady Ale and be sure to check out their food trucks from local restaurants Roamin Pizza, 167 Rawbar & the Lobster Trap.
Fancy it up on your last night at Straight Wharf. Be sure to call ahead for reservations so you don’t miss out on some of the island’s always fresh and always delicious food. Get the bluefish pate, a Nantucket hors d’oeuvres staple & the clambake for your main. Head to the Straight Wharf Bar after for dancing and music.
By Sunday morning, you’ll be feeling like a local, so lazily make your way to the Handlebar Café, to caffeinate and re-charge for the trip home. We think that the Nantucket red sweatshirts are probably the only souvenir item of clothing that is cool to wear, so get a few of those in town before you leave. We suggest grabbing one of the delicious mason jar salads to-go from Corner Table, part of Nantucket’s Culinary Center, and taking a stroll out to the Brant Point Lighthouse to watch some of the majestic sailboats in the harbor. As one of those oldest (and most haunted) islands in America, we hope Nantucket has cast its spell on you. On the ferry home, mentally plan out your next trip!