A Week on the All-American Island of Nantucket for My Birthday

Thirty miles off the coast of Massachusetts, surrounded by the brilliant blue waters of the Atlantic Ocean, lies the dream summer destination – the island of Nantucket. When visitors hear about this island, nicknamed the Grey Lady, images of the Kennedys, oceanfront clambakes, antique sailboats, and American flags come to mind. Nantucket perfectly captures the elegance and nostalgia of an All-American summer and, as a Nantucket wedding photographer, it has become my absolute favorite getaway in the country.

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We recently spent a week on the island celebrating my birthday, and the trip truly could not have been more perfect. We’re already planning our next trip back and I’m excited to share all of my favorite places and experience with you. Scroll down for my full Nantucket travel guide.

Nantucket Town: I could write an entire blog post about this topic alone – Nantucket town is beautiful, historic, and offers some of the best dining and shopping in New England. I’d recommend heading out on foot and ambling down the beautiful tree-lined roads (Orange Street, Ray’s Court, and Fair Street are three of my favorites) to admire the stunning architecture and pocket gardens.

Old North Wharf: Originally built in 1770, the Old North Wharf is dotted with picturesque fishing cottages that were converted to artists’ studios, summer cottages, and “picnic houses” in the early 20th century.

Stop & Smell the Flowers: The flowers of Nantucket are truly in a league of their own. Thanks to its coastal climate, excellent drainage, and mild temperatures, plants on the island seem to explode into a riot of flowers. June is rose season while July is all about the hydrangeas. To see both, I’d recommend visiting between the first and second week of July.

Brant Point: This picturesque Nantucket neighborhood is home to the much photographed Brant Point Lighthouse that offers views of the glorious Nantucket Harbor, as well as a lovely beach that is just a few minutes walk or bike ride from town.

Endeavor Sailing: A trip to Nantucket isn’t complete without seeing the island from the water, and there is no better way to do this than by taking a trip on the beautiful Endeavor sailboat. Captain James Genthner, licensed by the United States Coast Guard, has over 35 years of experience sailing the pristine waters of Nantucket and makes the experience truly unforgettable.

Great Point Drive: For a completely unique Nantucket experience, rent a Jeep Wrangler (we love to get them from Youngs), buy a beach pass, pickup sandwiches from Something Natural, deflate the air in your tires, and drive to the Coskata-Coatue Wildlife Refuge. The road will eventually turn into a sandy path that winds through picturesque ponds and through seagrass onto one of the most pristine beaches that you will have ever seen. Open the windows, turn on the music, and enjoy the incredible feeling of driving on the beach alongside the endless Atlantic ocean. The road ends at the Great Point Lighthouse and features an infinite amount of wonderful swimming destinations. This is truly one of my all-time favorite travel experiences and is an absolute Nantucket must!

Cliff Beach: Across from Cliff Road and dotted with elegant oceanfront estates, Cliff Beach overlooks the Nantucket Sound – meaning the waters are slightly warmer and perfect for children.

Ladies Beach: This off-the-beaten-path beach on the southern shores of Nantucket is a local favorite that features excellent body surfing and boogie boarding and is a great place to escape the crowds during the peak summer months of July and August.

Bike Rental: Renting a bike on Nantucket is a must – the island is incredibly bike friendly with ample paved paths and slow speed limits. Nantucket Bike Shop and Youngs are both wonderful businesses that make it easy to rent beautiful bikes.

Steps Beach: The picture-perfect Steps Beach offers protected shores with gentle waves washing onto the sandy beach, and gray-shingled mansions dotting the surrounding sand dunes.

‘Sconset Bluff Walk: No matter where you are staying on the island, a day trip to the charming hamlet of Siasconset (nicknamed ‘Sconset) is an absolute must. There, pickup some sandwiches from Claudette’s and brownies from the Sconset Market before beginning your stroll on the ‘Sconset Bluff Walk. This path, considered by many to be the most scenic on all of Nantucket, ambles along the bluff by small fishing cottages covered in roses and epic seaside estates to Sankaty Head Lighthouse.

Cisco Beach: For the perfect day trip, hop onto your bike and head down the Cisco bike path to Cisco Beach. En route, make a pit stop at Bartlett’s Farm and pickup a gourmet beach picnic spread (my favorite items include the lobster roll, caprese sandwich, and grilled corn salad). Located on the southern shore of Nantucket, Cisco Beach features some of the biggest waves on the island, thus making it a favorite for surfers. After you’ve worked up an appetite, bike to the beloved Cisco Brewery and enjoy their amazing IPA’s along with freshly shucked oysters and live music.

Madaket Beach: Located on the western shore of Nantucket, Madaket Beach is the perfect place to watch the sun set. After, grab a casual but delicious dinner at Millie’s – an island staple named after the beloved Madaket Millie.

Galley Beach: A place to see and be seen, this oceanfront restaurant offers the perfect location to enjoy champagne and oysters while watching the sun set with your toes in the sand.

Brant Point Grill: Located inside of the luxurious White Elephant hotel, this waterfront restaurant is a favorite of mine for a decadent Sunday brunch that features decadent cocktails and exceptional seafood.

Toppers at the Wauwinet: This elegant restaurant showcases seasonally-inspired New England cuisine with an emphasis on local produce and seafood. The locally harvested Retsyo Oysters on the half shell are  a must – they are cultivated just 300 yards away. In peak summer months, the hotel offers a complimentary ride to and from town on their beautiful boat, and shuttle service the rest of the year. Pro tip: Arrive to the hotel early and enjoy a cocktail (or two) on the picturesque lawn overlooking the Nantucket Bay.

Chanticleer: Originally opened as a small tea house at the turn of the century, the Chanticleer is the most romantic restaurant on Nantucket. Located in the charming hamlet of ‘Sconset, this restaurant features dining spaces in a beautiful rose garden as well as in several quaint dining rooms. With an incredible menu and fantastic service, the Chanticleer is always one of my top recommendations for a special night out.

Greydon House: We opted to stay in the newly opened Greydon House, located in a historic Colonial home, this über-styish boutique hotel was designed by Roman and Williams and features beautiful decor, fantastic service, and an incredible location in the center of town. If you’re looking for more of a retreat experience, the White Elephant and Wauwinet are two of my other favorite Nantucket hotels.

Photos by Nantucket Wedding Photographer Molly Carr


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After pursuing my degree in fashion, I began my career as a travel photographer, exploring the world one country at a time and telling the stories of the people, places, art, and ideas that moved me. But, it was when I photographed my first destination wedding that I truly found my life’s calling.

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