WHAT TO DO
Nantucket is an island located 30 miles south by ferry from Cape Cod within the state of Massachusetts. It probably takes its name from the Wampanoag word natocke which means ‘far away island’. Nantucket Island’s original Native American inhabitants, the Wampanoag people, lived undisturbed until 1641 when the island was deeded by the English (the authorities in control of all land from the coast of Maine to New York) to Thomas Mayhew – a merchant from Watertown, Massachusetts and the neighboring island of Martha’s Vineyard. The island’s settlement by the English did not begin in earnest until 1659, when Mayhew sold his interest to a group of investors, led by Tristram Coffin. In 1966, the Town of Nantucket was designated a National Historic Landmark for being the finest surviving architectural example of a late 18th and early 19th century New England seaport town. Today, Nantucket is a popular tourist destination and summer colony. Due to tourists and seasonal residents, the population of the island increases to at least 50000 during the summer months. With plenty of dune backed beaches, cobblestoned streets, historical buildings, great restaurants and a fascinating whaling past, ACK is a traveler’s dream.
Start your adventure in the heart of the downtown historic district at the Nantucket Whaling Museum, located at 13 Broad Street. One of the island’s highlights, this captivating museum occupies an 1847 spermaceti (whale oil) candle factory and the excellent exhibits relive Nantucket’s 19th century heyday as the whaling center of the world. There’s an informative documentary on the island, incredible scrimshaw exhibits (engravings and carvings done by sailors on ivory, whalebone or baleen) and a 46 foot sperm whale skeleton rising above it all. Be sure to head to the rooftop deck for lovely views of Nantucket Town. Nearby at 1 India Street is the Nantucket Atheneum. More than just the public library, this stately Greek Revival building is a sight in itself. The second floor Great Hall has hosted such notables as Ralph Waldo Emerson and abolitionist Frederick Douglass. Found at 62 Centre Street is the First Congregational Church. Everyone comes to this church, which traces its roots to the early 1700s, for the commanding view from the top of the steeple – it’s well worth the 94 step climb. Built in 1686, the Jethro Coffin House is the town’s oldest building still on its original foundation. It’s in a traditional ‘salt box’ style, with south facing windows to catch the winter sun and a long, sloping roof to protect the home from harsh north winds. It is located at 16 Sunset Hill, a half mile northwest of the town center via W Chester Street. Note: admission to the Jethro Coffin House is included in the ticket price for the Nantucket Whaling Museum or can be purchased as part of a package that includes admission to the rest of Nantucket Town’s historic houses and sites.
New England has many magnificent lighthouses and there are 2 on Nantucket that are not to be missed. The first is Brant Point Light, found just outside the town center on Easton Street. Welcoming ferries and yachts into Nantucket Harbor, this lighthouse was established in 1746 and is still in operation. It’s quite tiny (only 26 feet), but extremely photogenic – it’s well worth the short stroll from town. The second is Sankaty Head Light, found on Baxter Road near the quaint village of Siasconset. Although this village is barely seven miles from town, it thinks of itself as worlds apart. Nantucket Town may seem uncrowded and unhurried compared with the rest of mainland America, but Siasconset (aka Sconset) takes it to another level. About one mile north of the village, the 1850 Sankaty Head Light stands photogenically, in its new position on a bluff since 2007, having been relocated due to erosion. It is still operating. Note: a couple of times a year, the lighthouse is open for visitors and offers free tours to the top.
Back in Nantucket Town at 96 Main Street is the Hadwen House. A walk through the Nantucket Historical Association’s Hadwen House, a Greek Revival home built in 1845 by a whaling merchant, provides testimony to just how lucrative the whaling industry was in its heyday. The house also hosts rotating exhibits on various topics relating to Nantucket’s history. To see where drunken sailors used to spend the night, visit the Old Gaol at 15 Vestal Street. This 1805 jail served Nantucket for 125 years. It was constructed using massive oak timbers with iron bolts running the length of the walls. Today it’s under the helm of the Nantucket Historical Association. Not far away at 50 Prospect Street is the Old Mill. It is America’s oldest working windmill (built in 1746), as your guide will demonstrate by grinding corn (weather conditions permitting). Note: the mill is also managed by the Nantucket Historical Association and you can visit, along with the other sites previously discussed, with a ticket to the Nantucket Whaling Museum or a historic homes and sites pass. The Nantucket Lightship Basket Museum is located at 49 Union Street. What the lighthouse is to the New England coast, the lightship was to the sea – essentially a floating lighthouse to warn of dangerous shoals or sandbars below. Sailors would stay aboard the lightships for weeks on end, and to combat boredom they created beautiful, intricate baskets that have become emblems of Nantucket. This small museum highlights these craftspeople and their products.
Nantucket is famous for its pristine beaches – I would like to share some of my favorites. Jetties Beach, one mile northwest of town via N Beach Street, is the best all round beach close to town. It is well equipped with changing rooms, and a summertime bar and restaurant. You’ll find some of the most consistently surfable waves at Cisco Beach, at the end of Hummock Pond Road. The onsite Nantucket Island Surf School can handle everything you’ll need for hitting the tasty waves. Surfside Beach, three miles from Nantucket Town at the end of Surfside Road, is a top draw with the hip crowd. It has full facilities, including a snack shack and a moderate to heavy surf that can make for good bodysurfing. Lastly, there is Sconset Beach, located at the eastern most tip of the island – take a short walk from ‘downtown’ Siasconset to this pleasant spot. The east facing beach gets pounded by the open Atlantic Ocean, which has eroded much of the long, narrow beach in recent years. In fact (previously mentioned), the erosion has been so severe that not long ago the Sankaty Head Light, on the north side of the village, was moved inland to prevent it from tumbling over a 90 foot cliff.

WHERE TO EAT
Nantucket has several great places to eat and enjoy a drink or two. Start your day at Corner Table, located at 22 Federal Street. A real local gathering place, this sweet cafe has great coffee, a cabinet full of high quality eats to have here or take away, daily soups and sandwiches, a sofa or two, and a sustainable, community minded ethos. Black Eyed Susan’s can be found at 10 India Street. It’s hard to find anyone who doesn’t adore this petite, long running, gourmet place. For breakfast, try the sourdough French toast topped with cinnamon pecans and orange butter – c’est tres bon. Note: the restaurant is cash only. You can get your organic juice and almond milk latte fix at Lemon Press, a stylish cafe at 41 Main Street. The menu of sandwiches, wraps and bowls combines unique ingredients to create tasty, health conscious meals. Go with the Holy Kale bagel sandwich made with jalapeno whipped feta and garlic sauteed kale. If you’re in the mood for diner chow, head to Downyflake at 18 Sparks Avenue. This family owned spot is a popular stop on the island for tasty and unpretentious grub on the edge of town that’s known for its all day breakfasts (blueberry pancakes, big omelets) and simple comfort food. Note: it also doubles as a bakery with homemade doughnuts.
Brotherhood of Thieves, located at 23 Broad Street is not to be missed. A longtime favorite of locals, who come for the friendly tavern atmosphere (set off with brick and dark woods) and some of the island’s best burgers. Also yummy is the fish burrito made with local cod, and the broiled Nantucket scallops. The craft beers on tap, some island brewed, go down easy at this classic sailor’s pub. Note: try to score a table in the downstairs section, which retains the historic tavern atmosphere. For the island’s best fried clams, cheapest lobster dinners and other seafood treats, head to Sayle’s Seafood at 99 Washington Street on the south side of town. Note: it’s all takeout at this fish market and clam shack, but there’s outdoor seating where you can enjoy your feast. Lola 41 can be found at 15 S Beach Street. This hip joint is named after Nantucket’s latitude, and the menu borrows from others along that parallel – including Spain, Italy and Japan. The bistro menu has plates large and small (shrimp tempura, gnocchi Bolognese, kung pao chicken), and the sushi menu is creative and delicious. The Japanese influence looms largest on the drink menu, where you’ll find a few Japanese beers, an extensive menu of sake, and cocktails like the Con Cu Bine (cucumber vodka, sake, passionfruit and lychee) and the Tokyo Drift (Suntory whisky, housemade sour mix, passionfruit puree and St Germain). Another popular place is The Nautilus, located at 12 Cambridge Street. In a sea of seafood restaurants, this spot offers a tantalizing alternative with its menu of global minded (but decidedly Asian focused) dishes. It offers hearty mains, such as thick and satisfying dandan noodles, as well as a bevy of fun small plates like scallion pancakes and harissa spiced lamb chops. Note: they also do some killer cocktails – do try the Tequila Mockingbird (tequila, roasted grapefruit, chilis and rosemary) and the Kermit The Frog (vodka, pineapple, lime and ginger).
For some afternoon delight, make your way to The Juice Bar at 12 Broad Street. There is so much goodness to choose from at this treasured ice cream shop near Steamship Wharf. A green menu on the front door lists all the flavors for homemade ice cream, frozen yogurt and fresh juices. More than 50 homemade ice cream flavors are available each day, like peppermint stick, the green monster and local blackberry. Get there in the late afternoon for a warm waffle cone with a scoop of your favorite flavor – I destroyed the green monster (mint ice cream with cookie dough). Not far away on the harbor is Cru. Found at 1 Straight Wharf, this stylish hot spot, right on the water offers expansive raw bar options and cooked seafood fare. This is the place for perfectly shucked oysters, chilled white wine and top notch views. Nearby at 6 Harbor Square is the Straight Wharf Restaurant. The best place for fresh caught seafood served with a harbor view is the deck of this popular restaurant featuring New American cuisine. Start with iced oysters with lemon granita, then move on to the restaurant’s very own clambake: buttered lobster, sweet corn, chorizo, potatoes and littleneck clams. Note: be sure to save room for dessert, the walnut pie brownie (Cape Cod cranberries, maple brown butter ice cream and kumquat) is divine.
For dinner, head to The Proprietors at 9 India Street in Nantucket Town. Creative, globally inspired cooking and fine cocktails are all the rage at this restaurant and bar that proudly flaunts local farm to table fare. Your eyes may be bigger than your belly when reading the small plates focused menu: the housemade charcuterie is a solid choice, as are kimchi pancakes, roasted bone marrow and hamachi crudo. The cocktail menu shines with concoctions like a barrel aged white Negroni, and a house bottled gin and tonic made with toasted rice and green tea infused Japanese gin. The beer and wine selections are equally impressive. Note: the restaurant does a superb Sunday brunch. Next door at 5 India Street is the excellent Company of the Cauldron. A splendid choice for a romantic dinner, this intimate restaurant has attentive service and top rated food. It offers only reserved seating times and four course prix fixe dinners, with the likes of rosemary skewered shrimp followed by beef tournedos. As chef Joseph Keller (brother of renowned chef Thomas Keller) concentrates his magic on just one menu each evening, it’s done to perfection. Note: book well in advance. Located out in Siasconset at 9 New Street is Chanticleer Restaurant & Gardens. Eating here is a fully realized dining experience. This lovely restaurant is set in a whimsical garden setting and chef Jeff Worster’s menu of New England inspired seasonal cuisine is superb, featuring everything from roasted Vermont chicken to an upscale take on an old school patty melt. Reservations are highly recommended. Note: call ahead in May, June and October as the restaurant’s hours might vary. Also in Siasconset, at 8 Main Street is Sconset Cafe. This place is a village institution for its laid back style as much as for its delish crab cakes. Pick up a bottle of wine at the store next door and enjoy it with your meal. Note: the restaurant is byob and reservations are recommended.
End your evening on Nantucket with a drink or two. Gazebo can be found at 4 Harbor Square. There’s lots of action at this bustling open air bar right on the wharf. You can keep one eye on who’s getting off the ferry and the other on your adult beverage. Close by at 1 Main Street is The Club Car. This longtime ACK institution underwent a complete revamp in 2017 when it reopened under new ownership. Set apart from the retro dining room, the marble topped bar runs the length of the historic train car that gives the place its name. Like the space, the cocktail menu is funky and playful, with unique takes on classics like the Negroni (pink gin, sweet vermouth and strawberry infused Campari served in a pour it yourself bottle), the Paloma (containing two tequilas and grapefruit three ways), and the Pina Colada (clarified, with a bit of German amaro). Note: the famous piano is still there, and as the bar fills up, patrons will inevitably start singing along. Up the road at 38 Main Street is Or the Whale. Named after the subtitle of Moby Dick (author Herman Melville is said to have based his classic novel on the tale of the ill fated Nantucket whaleship Essex), this recent opening has a solid cocktail menu featuring classics like the Old Fashioned and Negroni done right, as well as a carefully curated selection of wines by the glass. If it’s a nice evening, opt for a seat on the spacious back patio. Oran Mor is located at 2 S Beach Street. Perched above an art gallery and an antique shop, this spot is quintessential Nantucket with its homey, nautical decor. The intimate round bar looks like something out of a captain’s cabin, embellished with maritime quotes and illustrations. It may not look like a spot for trendy drinks, but the menu is creative and modern with a perfect mix of spirit forward cocktails and more tropical, refreshing libations. Finally, no trip to Nantucket is complete without visiting Cisco Brewers, located a few miles outside the town center at 5 Bartlett Farm Road. It feels less like a conventional brewery and more like an outdoor festival – with multiple bars, tents and food vendors daily. Note: a shuttle van makes the trip from 23 Federal Street in town every twenty minutes.

WHERE TO STAY
Nantucket offers a number of places to call home during your stay and there are 2 that I especially enjoyed. Both are in prime locations and provide exceptional service, modern amenities and comfort. The first is the White Elephant, located at 50 Easton Street. Built as a collection of cottages in the 1920s, this upscale hotel overlooking Nantucket Harbor is a short walk from Brant Point Light and the ferry terminal. The refined rooms offer flat screen TVs and free WiFi, plus private patios with harbor views. Upgraded quarters add separate living rooms with sofabeds. Amenities include beach and ferry shuttle service, morning coffee and pastries, and evening wine and cheese socials in a polished library. The Brant Point Grill eatery has harbor views, and there’s also a spa on site.
A second option is Greydon House, located at 17 Broad Street in the town center. Set in a converted 1850s home, this elegant boutique hotel is adjacent to the Nantucket Whaling Museum and not far from the Atheneum. Chic, individually styled rooms feature flat screen TVs, complimentary WiFi, Bose Bluetooth speakers and designer toiletries. Upgrades add living rooms. Other perks include morning coffee on the house, and the posh Italian restaurant Via Mare.
Nantucket has an abundance of charm, history, beaches and fine dining. It treated me well and I look forward to returning.