Stepping off the Hy-Line Ferry from Hyannis, Massachusetts, my visit glimpse at Nantucket was the crowded summer pier. Our ferry, the “fast ferry” is just an hour from Cape Cod, and, important to many starting a getaway to the island, features a full bar in which to get the party started early. Traveling with a number of girlfriends who have all visited “ACK” before, I was the newbie to the former whaling island, now summer playground of New Englanders.

Arriving in Nantucket Town, I was greeted with cobbled streets and gray clapboard buildings, white picket fences and blue hydrangeas spilling out of every patch of green grass. This was a scene out of movies, and I was delighted to see Nantucket was as charming as I hoped it would be.

Where to Stay

Nantucket’s premier resort, and where many festivals, events and fine-dining takes place with waterfront views, is the White Elephant Hotel. Besides its original and commanding presence overlooking Baby Beach and Brant Point Lighthouse, the hotel features 66 guest rooms, lofts and garden cottages. My friends and I were staying in a three-bedroom cottage. Not only did we have a front porch facing the aforementioned hydrangeas and picket fence, but inside we were even more delighted to find what awe felt was like renting a house: bedrooms with enormous, down-filled beds, a large open concept kitchen/dining/living space with high-end fixtures, furnishings and details, and light and airy bathrooms.

Staying in the hotel or the cottages means walking about three blocks from the ferry, and thusly means you’re three blocks from all of the shops and restaurants. Of course, you can also eat with a waterfront view at the hotel’s outstanding Brant Point Grill, which rests along the Harborside Lawn, a perfect place to enjoy sunset cocktails with a picture-perfect backdrop.

Just around the corner from White Elephant is the Nantucket Inn. The new hotel restored a former aging property to bring about a year-round property with one- to four-bedroom suites, as well as its own cottages with kitchenettes. While it doesn’t have the esteemed name of the White Elephant, this newcomer’s decor and setting is right on par, but also goes above and beyond with its amenities.

Consider the free kids’ programs, free shuttles to ferries and restaurants, and free bicycles to take for a spin around the island, the Nantucket Inn is more family-friendly and gives you a bigger bang for your buck. Its restaurant, Breeze, emulates as Caribbean vibe, including a friendly staff from the Caribbean that lends the restaurant an island feel versus the White Elephant’s slightly more stuffy environment. Still, you won’t go wrong with either property.

Where to Play

If you’re visiting an island, of course the beach is going to be on your mind. Nantucket is not like a Florida island, where the beach runs parallel with all activities, attractions and hotels. Instead, while Nantucket is only 14 miles long and 5 miles wide at its widest expanse, Nantucket gives off a feel of a much more space. There are no high rises. There is not a mile-long stretch of miniature golf and tacky T-shirt shops. Boutiques here are high-end preppy: Lilly Pulitzer, Vineyard Vines, Ralph Lauren.

Its numerous beaches are hidden behind dunes and tucked away in the island’s nooks and crannies. The most popular beaches are Jetties Beach on the North Shore, Surfside Beach on the South Shore, and Sconsett Beach for those staying on the more remote East Shore. During our visit, we visited Steps Beach at night, when in late July and early August, is blue with the light of bioluminescence of harmless jellyfish. You can wade in the waters and be surrounded by blue light under the twinkle of stars in Nantucket’s near pitch-black sky.

Nantucket’s allure is that you can do exactly what generations before you did during a summer vacation: Stroll Nantucket Town to shop, dine on fresh seafood at both seafood shacks and high-end restaurants led by popular Boston and New York chefs, bike along sand-strewn bike paths, relax on the beach, and, maybe, just maybe, if you feel like Getty rowdy at the end of day, heading to “the Box” for lively entertainment.

When asking my Uber driver to take me to the Chicken Box (it’s full name), he asked if I really wanted to go, being it was a bit “sketchy.” Upon arrival, I could see the Box wasn’t like the rest of the island. This was the dive bar-slash-live entertainment venue where your shoes will stick to the floor and many 20-somethings will rush the stage for a local band as if they were truly rock stars known around the globe. It’s also one of the only places open late on the island, so it is the place to party, and not within walking distance — you will need a cab/Uber.

A visit to the Whaling Museum should be a mandate for an first-time visitor to the island. The small museum is big in history, taking you through the island’s beginnings as a whaling island. On this island were the whalers who encountered a whale so great and evil, Herman Melville was inspired to write “Moby Dick” after learning of the tale, which is available to read in “Heart of the Sea.” (Don’t bother with the recent film; it is not as detailed and filled with OMG moments as the book.) You’ll easily enjoy the museum in an hour, but leave with a better understanding about the island and its year-round residents.

Where to Eat

Half the people on the ferry arriving in Nantucket Town head straight to the Gazebo at Harbor Square, luggage in hand. Knowing rooms may not be ready before 4 p.m., new arrivals reconnect with old friends, new friends and island residents at this buzzing hotspot, which is literally a gazebo bar and restaurant. Bring your luggage, grab a seat (if you can find one) and dive right in for your first Nantucket experience.

Away from Nantucket Town, in its own little corner of the island, is the relatively new Cisco Brewery. Besides offering great local ales, such as the Whale’s Tale Pale Ale, it features a very large outdoor patio with games, live music, food trucks and the best sunset views.

If you’re looking to sample the cuisine by top chefs, you’ll want to visit Greydon House. An intimate hotel of just 20 rooms in Nantucket Town, its restaurants is led by Michelin-star chef Marcus Ware. Take a break from lobster rolls and simple scampi here, where you’ll find more exotic choices, a Mexican night and a beautiful brunch.

About

I am an experienced and award-winning editor and writer with 20 years working in travel media. Not only have I served as editor-in-chief of a TripAdvisor website for nearly a decade, my writing has been published in travel magazines and online, and I have been quoted as a travel expert online, in print, on radio and on television.

I have spent my life moving around the U.S. — the Midwest, Florida, Atlanta, Boston and now Northeast — and growing up, my history-loving father tried to show me every detail of American history through day trips and weekenders. Without realizing it, he set up the kindling for my eventual wanderlust. After finding a $240 round-trip flight to London, I got my first passport, hopped a flight, and was forever in love with traveling outside of the country. London ignited my wanderlust and ever since, I travel as often as I can. If I’m not traveling by plane, I’m in a car, exploring my town, county, state… I never stop moving.

My favorite thing about the work I do is helping others plan their perfect vacations, which is why I founded Anywhere World Travel, a travel concierge company. I’m not a travel agent; I am an experienced traveler who can save you time by using my knowledge and background to help you plan your trip. Visit Anywhere World Travel for more information.

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