Winter Weekend on Nantucket

There are countless reasons to plan a winter weekend on Nantucket – the winter season is the perfect time to fully unplug, enjoy the snow-covered streets, stroll the island’s empty yet stunning beaches and pay a visit to the many businesses open year-round. With daily flights on Cape Air and ferries running from/to Hyannis multiple times a day, the island is easily accessible yet peacefully quiet and exceptionally affordable.
Hotel Pippa’s Winter Wonderland Offer entices guests to linger on the island for a few days and enjoy some much-needed relaxation after the holiday season. For those who want to partake in local activities, visiting Bartlett’s Farm, Nantucket’s largest and oldest family-owned farm, for its exceptional on-site market full of seasonal fruits and vegetables. Nantucket’s very own Cisco Brewers is open year-round, offering beer and spirits tastings, live music in a relaxed environment.
If you feel like further venturing outside, guided driving tours are available to discover the island’s famed lighthouses, windmill and beaches. Head out to Cisco Beach for a stroll – we strongly recommend spending time at Cisco Beach (or the island’s other beaches) after a snowfall, as the paths resemble a white carpet and the landscape is absolutely stunning.
Sankaty Lighthouse is always picture-perfect and warrants a stop in nearby Siasconset (or as the locals call it ‘Sconset), one of the most charming places on island with beautiful cottages, large mansions and winding roads. No trip to ACK is complete without a visit to the Brant Point Lighthouse, one of the four Nantucket attractions on the National Register of Historic Places. Admire the stunning panoramic views and beautiful private homes from the top of Steps Beach and take a walk on the empty beach (if the temperatures allow) to find shells.
As you make your way downtown, enjoy a walk through the inviting cobblestone streets of Nantucket and explore Main Street through the quaint yet stylish shops that remain open year-round. Before heading back inside, we recommend stopping by The Hub of Nantucket for some delectable sweets and pastries.
You can also scour Mitchell’s Book Corner and Nantucket Bookworks for books to read up in your warm, comfortable room at Hotel Pippa. If the Whaling Museum (around the corner from Hotel Pippa) is open, check out the latest exhibit to learn more about Nantucket’s rich history.
After cozying up inside with a good book, cup of tea or warm cocoa by the fireplace, you can take full advantage of the delicious restaurants open year-round on island. In the heart of downtown, the Dreamland Theatre offers movies, plays or shows/concerts for a healthy dose of entertainment.
While most events are scheduled during the summer season, a highlight of the off-season programming is the Elin Hilderbrand weekend, when the best-selling author visits Nantucket, the backdrop for many of the locations and sites used in her books. The festivities typically include a private island tour with Elin, book signing and reading, and many more events.
Winter will be over before we know it – now is the time to explore Nantucket during the off-season and revel in the natural beauty of the island without the crowds. We look forward to welcoming you!