Nantucket, Massachusetts | Island Day Trip
Take it slow on Nantucket, look around, and savor the island’s flavor.
MORNING: Nantucket is one of the most bike-friendly islands in New England, and you can access the entire span on pedal power alone. Of course, a bike isn’t mandatory. You can make a day of walking around Nantucket Town and then take a taxi to Siasconset or Madaket. But going by bike lets you really feel the island.
Your first decision is the ferry. The Steamship Authority‘s Fast Ferry boats depart at 8:00 a.m. and will have you to the island in an hour. Hy-Line Cruises also runs a fast boat; 6:30 a.m. is the early one, with another at 9:10. Both sail out of Hyannis Harbor, and you’ll pay for parking. Alternatively, if you’re willing to spend 20 more minutes onboard, you can park for free on Freedom Cruise Line‘s boat out of Saquatucket Harbor in Harwich Port (leaves at 8:00 a.m.).
You’ll arrive at Nantucket Harbor, conveniently sited in the heart of town. If you haven’t brought your own bike, head over to Cook’s Cycle Shop on nearby South Beach Street, where rentals are considerably less expensive than those on Steamboat Wharf. You can also rent mopeds or Jeeps, if that’s more your speed.
However you choose to explore, you’ll need energy, so start your day at Black-Eyed Susan’s, where locals line up for Pennsylvania Dutch cakes and sourdough French toast. After breakfast, it’s a 10-minute walk over to the lighthouse on Brant Point at the end of Easton Street to wave at the ships coming and going. If you have small children in tow, Children’s Beach is another popular gathering place for young island families for its calm waters, playground, and picnic areas. Also near town: Jetties Beach off Hulbert Avenue has tennis courts, a snack bar, a bar, bathrooms, and a gift shop.
If you’re not up for the beach, head to town and learn about the island’s boom-bust-boom economy at the Whaling Museum (see “Memory Etched in Tooth and Bone,” this issue’s “Local Treasure,”). Pay a few dollars more for your ticket and you’ll also gain access to several historic properties, including the 1686 Oldest House and the 1746 Old Mill (the oldest functioning mill in the country). The Nantucket Historical Association, which manages these sites, also offers walking tours in town. History buffs will also want to visit the old African Meeting House, once the central gathering spot for the African American community of the 19th and early 20th centuries.
Shoppers will have a field day in town, though prepare for sticker shock if you’re not a member of the .05 percent. Murray’s Toggery, the closest thing to a department store, has more-reasonable prices and all the Nantucket Red pants you’ll ever need. Erica Wilson and In the Pink nail the island-socialite look. John Rugge Antiques Shop outfits the beach house of your dreams. And Nantucket Bookworks is the Platonic ideal of a small-town bookstore, with a well-curated selection and lots of cozy nooks.
Stop for lunch at CRU, a newish place at the very end of Straight Wharf, where open windows catch island breezes and the seafood is fresh and sophisticated, as are the wines (see “Best of New England,”, for more on CRU’s oyster bar). For inexpensive local flavor, you can’t beat the fish sandwich at Easy Street Cantina. Satisfy your sweet tooth at Petticoat Row Bakery (folks there make a mean whoopie pie).
AFTERNOON: The journey is the destination. It may be a cliche, but it’s entirely true on Nantucket. The island is crisscrossed by bike paths that keep you safely off the main roads and amid stunning scenery. To take in the full sweep of meadows, bogs, ponds, and ocean vistas, ride Polpis Road to the tiny fishing village of Siasconset, which feels like a trip to a simpler, quainter time. (Tip: Look for the ‘Sconset Bluff Walk, which begins at Front Street, and takes you past stunning estates with gorgeous views.)
Alternatively, ride southwest out to Madaket for a beach afternoon followed by a spectacular sunset. On your way there, take a detour south to enjoy the tour at Cisco Brewery and its adjacent distillery and winery. Expect samples and bring your own snacks.
EVENING: Head back to town for dinner so that you don’t fret about making the ferry. iis just steps from the harbor, with a menu of pristine fish. (Tip: The food in the barroom is fantastic and less expensive.) A few blocks away, American Seasons takes a culinary tour of America that will renew your love of country. And families will appreciate the something-for-everyone menu at The Boarding House.
And thus ends your day in paradise. Last ferry leaves at 10:00 p.m. (on Hy-Line). Bon voyage!