Contributed By Julie Palo Hayes

Images via Kayla Douglas

The preppy sister to Martha’s Vineyard, Nantucket is a summer spot beloved by New Englanders for its innumerable charms.

A more relaxed pace of life on ACK sweeps over its guests from the moment they arrive, almost as if this compact island operates on its own time zone. Unsurprisingly, those who return year after year know some secrets to what make this place so special; and we were lucky enough to crack some of the local code thanks to Julie Palo Hayes, a SmartFlyer travel advisor who splits her time between Boston and Nantucket.

Getting There

Located just 30-miles off of Cape Cod, this vibrant summer destination can be reached via flight or ferry. Julie shares, “Flying is fast and convenient both from Boston and New York City, but when the fog for which the ‘Grey Lady’ is known rolls in, expect delays. That being said, taking the ferry is more reliable. For travelers in the tri-state, there is a seasonal ferry (from May to September) operated by Seastreak departing on Fridays. From Boston, I recommend driving to Hyannis (MA) and taking the 1-hour express ferry on Steamship or Hyline.”

Beach, Please

Even when town is bursting at the seams during high season, you can find a spot on the beach alone…

One of the best things about the island is that there really are beaches that suit so many different tastes. Julie puts it best, “The endless supply of beautiful beaches on the island is one of its charms; plus, they are all public. Even when town is bursting at the seams during high season, you can find a spot on the beach alone…it just depends on what you’re feeling that day! Cisco is your spot to watch the surfers. Or, try for yourself with the help of instructors situated right on the beach to give lessons. Steps Beach is walking distance from town and a great spot for mellow waves. For more off-the-grid vibes, check out Radar Beach. You need a vehicle to get there, which is half the fun.”

Getting Around, The Local Way

Speaking of needing a car, the authentic way to see the Nantucket is to rent a jeep (with a beach permit) and go off-roading! This way, you can visit the farthest corners on the island, like Great Point where you’ll discover miles of uninhabited beaches and have the chance to observe the seals and wildlife. Take a picnic and soak up the serenity. Or, if you’re only visiting for a weekend and want to stay more central to your hotel, it’s all about hopping on a bike. Some properties will offer them, or, Young’s Bicycle Shop is a great spot to rent so you can take advantage of the bike paths around the island.

Shopping

A mecca for all the preppy prints and island-chic pieces you could ever want, the Grey Lady makes shopping a breeze. Everything is easily accessible and walking distance in town, with trendy brands often doing summer pop-ups. Julie shares, “New this year, there are two lifestyle shops, Nomad and the well-known Gwyneth outpost, Goop. But, don’t miss staples like Perch, Gypsy, Milly & Grace, CJ Laing, and Erica Wilson. Also, make a point to check out the small shops all along Old South Wharf where you can discover some great finds like Remy Creations and Skinny Dip.”

Dining, dining + more dining…

Brekkie, brekkie

Black-Eyed Susans: Go early and put your name in, or, bring the paper while you wait at this local favorite. Whether diners are in the mood for some classic buttermilk pancakes or  huevos rancheros, it’s all right here.

Lemon Press: This bohemian oasis on Main Street is ideal for grab-and-go options in the morning. Chef Ivan Ceceña offers acai bowls, avocado toast, smoothies before flipping the menu (and space) to a more internationally-inspired dishes in the evening.

Downyflake: Did someone say fresh donuts? The only trick is, they often run out by 10am, so make sure you get here early to snag one!

Handlebar Cafe: This spot is beloved by many for morning coffee runs thanks to owners Courtney and Jason Bridges, who’ve built a community around their welcoming staff.

Lunch Hot Spots

Sandbar at Jetties Beach: Ideal for families, everyone is happy at this spot where parents can soak up the water views while kids play in the sand. There’s a wonderfully fresh raw bar, delicious burgers and sandwiches on the menu.

Juice Bar: Rarely will you find a Nantucket guide that doesn’t mention this ice cream institution (and with good reason). You can’t walk by without being lured in by the smell of homemade waffle cones being made – which are often motivation enough to wait on the perpetually long line. You can’t go wrong with any of their flavors!

Dinner Res, Please.

Proprietors: This is a great spot for tapas, tasty cocktails and a cool, distinctly New England vibe. The small plates are perfect for sharing amongst a more adventurous party.

The Pearl: Book the Chef’s Table for a small group out on the patio at this upscale restaurant. Enjoy private cocktails on their porch! Just don’t forget to order the famous salt and pepper wok-fried lobster. It’s to die for.

Cru: An island institution, this spot is always buzzing. Sit and watch the yachts pass by as you enjoy a seafood tower.

Before + After Din Drinks

Cisco Brewers: End the afternoon at Cisco for a microbrew and live entertainment. This is the watering hole for the island, so you’re likely to meet some friendly locals. Just be sure to come before dinner, they close at 7pm!

Galley Beach: This is one of the best spots on the island for pre-dinner sunset cocktails with your toes in the sand.

Chicken Box: When looking for late night fun, live music and good vibes, this is your go-to.

Where to Stay

When staying in town, you have access to fantastic restaurants, boutique shops and you’ll be walking distance to a few beaches.

With only one downtown – comparative to the Vineyard’s six – you are either in town or out of town while on Nantucket, it’s that simple. Julie elaborates, “When staying in town, you have access to fantastic restaurants, boutique shops and you’ll be walking distance to a few beaches. Home rentals are also popular and while your travel advisor can assist in securing one, be mindful that most of the top-notch properties are booked by January; so, advance planning is crucial. In terms of hotels, there are a lot of nuances to consider which is what I help my clients break down based on their style of travel.”

The Nantucket Hotel & Resort

Located in the heart of downtown, this family-focused property has been #Nantucketing since 1891. Think: low-key luxury with Kids Club, game room, two pools and a big gym. It really is both a playground for adults and children alike.

White Elephant

Wonderfully tailored for a wide range of guests’ needs, there are several accommodation options under this brand’s umbrella, including the Hotel, Cottage and Residences and Inn. And we’ve broken it all down below so you don’t have to.

White Elephant Hotel
Positioned on the shore with a lovely sandy area made for the kiddos, we love this spot for its location and quintessential Nantucket-style décor. With 66 guestrooms featuring a range of views, the Harborview Suite is a real standout thanks to its outdoor balcony and working fireplace.

White Elephant Cottages
A one-minute walk from the hotel, these standalone cottages are great for groups of families or friends. The vibe is more residential with coastal-style furnishings and kitchens complete with pantry. For the ultimate preppy aesthetic, the “Lily Cottage” designed by Lily Pulitzer charms guests with a blue and white color scheme, Pratesi linens and custom artwork.

White Elephant Residences + Inn
Offering the most modern styling on Nantucket, accommodations here include one, two- and three-bedroom residences (sans water views). It’s common for families to return to the residences rather annually for week or so rather than renting a house. Guests love that there’s a pool on-site!

Lark Hotels

For a more boutique feel, there are a couple options under the management of Lark Hotels that offer historic, yet contemporary approaches to ACK. At the top of Main Street, 76 Main welcomes guests with its nautical vibes and cozy courtyard. Alternatively, 21 Broad is a bit newer to the scene and feels playful with its colorful décor, modern amenities and outdoor deck for happy hour. Oh, and did we talk about the freshly baked cookies?

The Wauwinet

This Relais & Châteaux property is situated about 15-minutes from town, allowing it to feel like another world away from action. Rooms were recently renovated and have modern touches while staying true to the island vibe. Best suited for couples, it also retains an element of formality. Fun fact: their Michelin-starred restaurant is the only place on island that requires a coat and tie for dinner! To see what else the island has to offer, the complimentary shuttle or boat ride to explore town are wonderful options.

Odds + Ends

With Julie’s insider tips, you’re sure to be armed with all the knowledge you need to make the most of your stay on ACK. The only thing left to decide is when to go! Her advice? “Nantucket hosts a great Film Festival during the month of June. This is an ideal time to hit the island before it gets too crowded! For perspective, there are about 10k year-round residents, but, during July and August the population swells to over 50k people. But, no matter when you come, leave the heels at home and stick with platforms or flats given cobblestone streets and laid-back atmosphere.”