Nantucket VIP Guide — Insiders Tell You the Real Island Hotspots: The Best Restaurants, Hotels and Hidden Haunts

Nantucket Island might be diminutive in scale, only 14 miles long, but it looms large on the itineraries of sophisticated travelers, including a handful of Texans who call the gray lady home for the summer. We surveyed several of those seasonal expats from the Lone Star for a guide to the best of everything on tiny Nantucket.

Summer is top tourist season for the island but those with the flexibility to linger favor September and October. As Franci Neely says, “The water is still warm and the skies have a clarity I’ve never seen anywhere else in the world.”

Where To Stay: Houstonian Phoebe Tudor, who chairs Nantucket by Design in August, has her eye on the new, as of last October, Greydon House, which spreads through several renovated buildings and is decorated by red hot designers Roman and Williams (Hotel Emma in San Antonio). The White Elephant, within walking distance of downtown, has since the 1920s been the blue blood’s favorite, particularly the suites and small cottages.

The Nantucket Hotel & Resort; historic Jared Coffin House; and The Wauwinet, a favorite of honeymooners for its stunning isolation, continue to win visitor praise. For those seeking a more quiet experience, the experts recommend taking a house in the Madequecham Beach area. Nantucket Island Resorts represents many of the top properties.

Where to Eat: Le Languedoc (downstairs or at the bar); Company of the Cauldron, which has just been purchased by Joseph Keller, Thomas Keller’s brother; and Galley Beach restaurant and bar boasting tables literally on the sand and amazing sunset views. Toppers at The Wauwinet, on the far eastern tip of the island, is the island’s most elegant restaurant with fine cuisine and service and one of the best wine lists in the country.

For more casual dining, try the Fog Island Cafe in town for breakfast as well as Downy Flake Donuts. Summer lunch in the garden at Chanticleer in Sconset is highly recommended. Try Madaket Millie’s on the west end for a unique and delicious mashup of Mexican food with local produce and fish and Maine lobster (and live music on Sunday nights) or Cru Restaurant at the end of Straight Wharf for the best view of all the gorgeous boats docked in the marina, along with a great oyster bar.

Tudor offers these insights: “For the kids and all candy lovers, there is an awesome ‘secret’ candy room in the back of Force Five Watersports, totally unmarked, no signs anywhere. Someone has to tell you or you’d never find it. They carry all kinds of retro candy brands that we may not have seen since we were kids.  Aunt Leah’s Fudge, is another can’t miss, on the side of Straight Wharf.

Adventures: With a minimum of five bike rental shops and miles of scenic bike paths across the island, bicycling is “the logical way to see Nantucket Island” since 1931, according to Young’s Bicycle Shop.

If the weather is right, not to be missed is spending a day at Great Point, one of the three light houses and an idyllic nature preserve.  If you’re up for deep sea fishing Albacore Fishing Charters is recommended. And don’t forget the romantic sunset sails. Teens like the south shore beaches with big waves and surfing lessons, youngsters fare better in the gentler surf and warmer water on north shore beaches, including Jetties Beach, which has a welcoming snack bar.

No need to forgo your yoga routine while in Nantucket. Classes are offered at the Yoga Room, and local fave Bettina Broer offers private lessons as well as early morning classes outdoors at the Children’s Beach.

Special Events:  The Nantucket Film Festival in June is always a crowd pleaser as is the Nantucket Historical Association’s Nantucket by Design. Also in August, the Boston Pops concert on Jetties Beach complete with fireworks, benefiting the Nantucket Cottage Hospital.

The Fourth of July in Nantucket is old Americana at its best. The morning is full of activities for young and old (pie eating competitions, watermelon eating competitions, and old-fashioned declaration of independence readings) on the cobblestones of Main Street in Nantucket town. At noon the fire engine lets its water hoses loose on those who dare to brave the drenching.

What to wear: Think Tommy Hilfiger and Vineyard Vines. Neely advises, “Simple and casual.  Do not bring high heels. You will break your ankles, women. There are cobblestones in Nantucket!  This is not the place to show off your fanciest jewelry and largest hairdos. You can even go without makeup!” Hats and summer sweaters are a must.

Best shopping:   Barbara Harris Water Jewels; Nantucket Looms for Island collectibles and gorgeous handmade woven throws; Sylvia Antiques; John Rugge Antiques, Atlantic Antiques; Seaman Schepps for classic fashions with a coastal twist; Erica Wilson for just the right casual clothes for the laid-back Nantucket lifestyle.   

Tourist taboos:  Driving fast in large cars. No honking, please. In truth, unless you have disabilities, you don’t need a car on the tiny island where bicycles rule and the Nantucket Regional Transit Authority provides lifts in its jaunty vehicles called The Wave. 

The last word: From Neely:  “Bring some great books. Nantucket is truly a time to chill out. And leave your impatience at home.”