With no Wal-Mart, no Wendy’s, and no way off the island after 10:00 p.m. (unless you have your own boat), Nantucket may seem sort of strange to the uninitiated. There aren’t any stoplights, in most places you can drive on the beach (with a proper permit). And the downtown streets are “paved” with cobblestones and lined with independently owned boutiques.
For men, there is no shopping experience quite like the iconic Murray’s Toggery Shop (home of the original Nantucket Reds). Meanwhile, women have lots of curated boutiques to discover, including Milly & Grace for the best hostess gifts, Blue Beetle for Nantucket bangles, and The Lovely for a dress you’ll want to wear that very night.
When it comes to food, world-class dining abounds around every corner. Be sure to get a LoLa burger at LoLa 41, the wok-fried lobster at The Pearl, house-made pasta at Ventuno, and the clambake at Straight Wharf.
JETTIES
If you’ve got kids, then Jetties Beach just outside town is your go-to spot. It’s the perfect beach for wee ones, and is also home to new hotspot Sandbar at Jetties Beach, which serves up family-friendly fare at its finest. Enjoy a big glass of frosé with your feet in the sand as your children run around on the beach in front of you. This restaurant is just as good for a morning mimosa as it is for a sunset cocktail. And take note, every August, the island’s biggest fundraiser—Boston Pops on Nantucket, which raises hundreds of thousands of dollars for the island’s hospital—takes place on Jetties Beach. This year’s special musical guest is The Beach Boys!
MIACOMET GOLF CLUB
For those who want to switch up the sandy shores for greener pastures, the 18-hole course at Miacomet Golf Club is a Nantucket gem. This award-winning public golf course is meticulously maintained and has a classic clubhouse that doubles as a great place to get a turkey club and a cold draft of locally brewed Whale’s Tale Pale Ale by Cisco. Just beyond the course is Miacomet Pond, which leads straight out to a liberating beach for those (ahem!) looking to get rid of some tan lines.
SURFSIDE
Nantucket is a biking haven, and the bike path leading out to Surfside Beach is the best route for cyclists searching for an extra workout before beach time. Along the path out to the south shore, there are three great spots for quick dining. Enjoy homemade chocolate croissants and a great latte at the new 45 Surfside Bakery & Cafe. Get your lunch at Yummy, which specializes in fresh smoothies and has a killer burger. And after you make it all the way to Surfside Beach, you’ll find the Surfside Beach Shack, the island’s only grab-and-go beach-front spot with some great healthy options on the menu.
CISCO BEACH
Beach. Bartlett’s. Brewery. Not necessarily in that order, but those are the three B’s you’ll really get to know if you head out to this popular spot on the island. Cisco Beach is beloved for its surf-worthy waves, while Bartlett’s Farm is ideal for the juiciest tomatoes, lush florals, and a vast selection of pre-made food perfect for a beach picnic.
Cisco Brewers is one of the coolest places on the island to sip and savor some Cisco brews, Triple Eight Distillery spirits, and Nantucket Vineyard wines. It has live music daily, food trucks and a raw bar set up all summer long, and there’s no way you can leave without purchasing a T-shirt. The logos and super soft material will have you rocking it as your travel outfit and a constant reminder of this happy place.
SCONSET
The village of Sconset (which has its own zip code and is really the only other “town” on Nantucket) is literally something out of a storybook. From 300-year-old rose-covered cottages to Gatsby-esque homes on the bluff to the Instagram-worthy Front Street, this seaside destination is a timeless treasure. Make sure you take a drive out on Baxter Road and marvel at the classic ocean homes (with some of the best names!) and get your photo in front of Sankaty lighthouse—truly my favorite place on the island. If you’re searching for an old-school dining spot that will tickle your floral fancy, be sure to brunch at The Chanticleer in their rose garden.
WAUWINET
Want to really get away from it all? A trip out to Wauwinet is just what the doctor ordered. Let the air out of your Jeep’s tires and experience acres of carefully preserved conservation land as you gear up for the ultimate beach drive. It takes about 40 minutes over sand to reach Great Point Lighthouse, where often the only other beach companions you will find are a plethora of seals along the shore. On your drive back, stop at The Wauwinet hotel and take a step back in time. Savor it with a Painkiller (the drink), a delish lobster roll, and relax on one of their comfy lounge chairs as you watch the sun set over the ocean on the lawn (where, bonus, no phones are allowed).
MADAKET
When I say Madaket, you say sunset. Madaket! Sunset! Madaket! Sunset! This quaint fishing village on the west end of the island is home to the most delightful dusk moments and also to Madaket Millie’s, an awesome Tex-Mex spot for margaritas, tacos, fresh salads, and the infamous Madaket Mystery. Millie’s casual ambiance and adjacent market create an ideal setting for kicking back with family and friends on island time.
My favorite beach is also found along the Madaket shores, but alas I cannot say where. With 82 miles of coastline, Nantucket has an amazing amount of pristine beaches, but islanders tend to keep that one sneaky, secret preferred beach to themselves. Now have fun and go find your own.
NANTUCKET BOAT BASIN
Nantucket is all about the ocean, and the view from the Nantucket Boat Basin offers a truly spectacular perspective on island life. It’s a safe haven for those looking to dock before dining and drinking onshore at restaurants like Slip 14 and CRU, so be sure to stroll by during peak season to see some of the world’s most prestigious yachts. It’s a true visual feast. And if you want to take your maritime adventure to new heights, no one knows the harbor luxury scene quite like Nantucket Mermaids. This nautical concierge cultivates your yachting experience, from fully crewed boats to catered sunset cruises to week-long excursions on the water.