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Planning a trip to Nantucket this summer? Insider Itinerary is an occasional series here at Dandelion Chandelier that shines a light on the best places to see, stay, and dine in some of the hottest travel destinations worldwide. Our far-flung correspondents are sharing their inside tips on how to best experience their chosen cities, especially if you’re visiting for the first time. Consider it your local luxury GPS. In this edition, we share luxury insider tips on the best first trip to Nantucket.

Insider Itinerary

Our far-flung correspondents have previously shared their tips on the ideal itinerary for a first trip to Cape Town, South Africa and Copenhagen, Denmark. Next up? Nantucket.

Because we’re knee-deep in Martha’s Vineyard and have never ventured to its neighboring island off the coast of Cape Cod, we turned to Betsy Morganexecutive-in-residence at LionTree, a media + technology advisory firm. Betsy is a longtime media and startup CEO, having run both The Huffington Post and TheBlaze. Media mogul, financier, Wonder Woman and long-time expert on all things Nantucket — there’s no better person from whom to get the scoop on the best the island has to offer.

insider tips on the best first trip to Nantucket

How long have you had a summer home on Nantucket?

My parents bought our house on Nantucket in the early 90’s.  I first traveled to the island when I was a child.

Why did you choose it? What drew you there?

Nantucket might as well be an anagram for “Family”.  It’s family-family-family on the island.  People come to Nantucket because their parents are here, and then later parents stay because their kids are here.  My husband’s family is five generations deep on Nantucket.

What are the top “must see” sites, or experiences, or activities? What are 1-2 places you’d suggest as good inns or hotels to stay at for a first visit?

We keep a list of “Things to Do and See on Island” for our house guests and friends visiting the island. For island rookies, the highly recommended top 5 activities are a walk along Main Street, a visit to the Whaling Museum, spending time on Jetties Beach, a trip to the South Shore (any beach from Surfside to Cisco), and a visit to Siasconset.

The Nantucket Whaling Museum

Jetties Beach Bar & Restaurant

For those with more time, or second visitors, the “must see” list includes taking in the sunset at Smith Point; Pick-Your-Own Strawberries at Bartlett’s Farm (only in July); Beer in the garden at Cisco Brewers; and a hike through Sanford Farm.

Sunset at Smith Point

While lodging on Nantucket in-season is obscenely expensive, the good news is that all hotels and inns are regularly renovated.  The top-shelf hotels include The White Elephant and Greydon House (in town) and The Wauwinet (out of town).  There are also scores of B+B’s in town that are perfectly nice.

Greydon House

What’s your favorite shop on the island?

The Nantucket Looms on Main Street.  They just celebrated their 50th anniversary.

Nantucket Looms

Favorite beach?

There are North Shore beaches (calm waters) and South Shore beaches (waves).  So many amazing options.  Try Step Beach for the North Shore and Miacomet/Ladies Beach for the South Shore.

Ladies Beach on the South Shore of Nantucket

Favorite restaurant?

Take your pick really.  In the shoulder seasons Le Languedoc Bistro (downstairs!) is a cozy spot with longstanding and friendly waitstaff.  Ditto for Ship’s Inn.  Otherwise you can never go wrong with The Straight Wharf Restaurant for some of the best seafood on the East Coast.

The Straight Wharf Restaurant

Tell us about life during the summer on Nantucket: What do people do, are there big annual events, traditions, or other elements of community life there that a newcomer would find interesting?

The Nantucket Chamber of Commerce has packed the annual calendar with a zillion festivals and events that serve as anchors in the social calendar.  Lots of residents and visitors plan their Nantucket trips around these dates.

There are too many to list, but some of the highlights include the Daffodil Festival (April), Figawi (an annual sailing race across Nantucket Sound from Hyannis to the island every Memorial Day Weekend), Nantucket Film Festival (June), the Boston Pops Concert on Jetties Beach (August), The Nantucket Project (September), the Cranberry Festival (October), and the Christmas Stroll (in early December).

Other visitors plan their trips to avoid these events, so as to avoid the crowds.  Both strategies work.

There are a number of private clubs on island that for some families are the focus of their social lives, but by no means is this the center of life on island.

Activities in the summer tend to focus on the water: beach time, boating, sailing, fishing, etc.  In the shoulder seasons, people migrate towards town and the moors—Nantucket has preserved large amounts of land that make nature walks a must.

What’s new — or relatively new — on the island this summer that people should be sure to check out?

Lemon Press on Main Street (healthy foods and smoothies); Townpool on Main Street (a MUST if you have kids. candy store downstairs, mini golf upstairs, puzzle hunt new every day); Ladybird Lingerie on Centre Street (the women who own the store are amazing); and Nautilus on Cambridge Street (you need to stand in line to get a daily reservation for dinner. and there is a whole mini-industry of entrepreneurial kids who will stand in line for you (for a price)).

The Nautilus

What’s the preferred car on Nantucket? Something fancy? Or something really simple?

Rent a Jeep and make sure to ask the agent for instructions about driving on the beach.  Then drive to Great Point.  You won’t regret it.  Don’t you dare rent a luxury car.

Who would we be surprised to learn has a house on Nantucket?

Mr. Rogers spends summers on Nantucket for many, many years.  I met him on my first trip to the island.

Describe the Nantucket vibe in three words.

Sea, Sand and Sun.  Or better yet: Family, Fun and Fog.   Yes, there can be lots of fog.

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Pamela Thomas-Graham

Pamela Thomas-Graham is the Founder & CEO of Dandelion Chandelier. She serves on the boards of several tech companies, and was previously a senior executive in finance, media and fashion, and a partner at McKinsey & Co.