Winter is the perfect time to plan a romantic getaway to Nantucket. The island is an ideal and idyllic escape for couples or partners looking to relax and spend some quality time with one another for Valentine’s Day and beyond.

Nantucket is the ultimate destination to fully unplug, enjoy the cobblestone 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 is the perfect home base for those looking to linger on the island for a few days and enjoy some much-needed relaxation. There are also countless local activities to explore during the off-season: visiting Bartlett’s Farm, Nantucket’s largest and oldest family-owned farm, for its exceptional on-site vegetable and fruit market, or spending time at Nantucket’s very own Cisco Brewers to listen to live music and taste the latest seasonal brews.

For the most adventurous couples, driving tours are available to discover the island’s famed lighthouses, windmill and beaches. Head out to Cisco Beach for a stroll after a snowfall as the paths resemble a white carpet and the landscape is absolutely stunning. Visit 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 romantic stroll through the inviting cobblestone streets of Nantucket and explore Main Street through the quaint yet stylish shops that remain open year-round. You can scour Mitchell’s Book Corner and Nantucket Bookworks for books to read up in your warm, comfortable suite at Hotel Pippa. Cozy up by the windows with a good book, cup of tea or warm cocoa. If you want another dose of culture but prefer to stay inside, the Dreamland Theatre offers movies, plays or shows/concerts year-round.

For those looking to plan a getaway when winter transitions into spring, it is never too early to book your stay at Hotel Pippa for Daffodil Weekend. By reserving now, guests will secure the best rooms and rates for this true Nantucket tradition – a weekend full of festivities, complete with art shows, an antique car parade and community tailgate picnic.

Don’t wait, book your romantic getaway to Hotel Pippa now!

Nantucket is the perfect Christmas shopping destination. You can find selections of fine art and great books, world-class wines or fantastic jewelry at the shops downtown. You can also browse some of the best gifts from New England designers and support local businesses while finding the best presents for your family and friends. All just a short walk away from Hotel Pippa!

Main Street and the downtown area glow with some of the most beautiful holiday décor. Hundreds of decorated seven-foot Christmas trees line downtown streets and are illuminated throughout the season. The massive 20-foot tree at the top of Main Street is decorated by a local artist and watches over locals and visitors running their seasonal errands during the busy Christmas season.

The Nantucket Whaling Museum, steps away from Hotel Pippa, is transformed into a sumptuous winter wonderland by the Nantucket Historical Association. We highly recommend checking out their Annual Festival of Trees, showcasing more than 80 Christmas trees designed and adorned with unique decorations – a must-visit for those on island during the holidays.

Throughout the season, you can also enjoy the island’s environment through nature walks, eat your way through the island’s best restaurants and explore the miles and miles of trails open all year, perfect for long reinvigorating walks.

Our seasonal favorites also include Cisco Brewery, where you can enjoy live music and seasonal brews, or The Pierce Gallery which features a large collection of art, including original works from Norman Rockwell and Gertrude Fiske.

From the enormous wreath on Brant Point Lighthouse, to the cozy, small town feel of Main Street, Nantucket during the holidays is an atmospheric treat to behold! Join us this holiday season and retreat to Hotel Pippa for an exciting season getaway!

Steps away from the hustle and bustle of downtown Nantucket, Hotel Pippa offers a comfortable reprieve to travelers and locals looking to make the most of the last autumn weekends and enjoy the many activities keeping Nantucket residents and visitors busy during the off-season. They can join family scalloping season, giving them a glimpse of the seasonal harvests that make Nantucket unique and special. At low tide, they can join locals raking and catching this local delicacy.

For those planning to be on island for Thanksgiving, they can join the annual Turkey Plunge, another seasonal tradition that is not to be missed. Hundreds of residents gather and sprint into the freezing cold ocean on Thanksgiving, a unique moment in the morning of the special holiday aimed at raising money for the Weezie Library for Children.

Back at Hotel Pippa, the front desk team can assist with reservations in anticipation of the Thanksgiving weekend. Countless restaurants on island offer Thanksgiving dinner but reservations are recommended. Menus blend local produce, freshly fished seafood and high-quality meat with traditional Thanksgiving dishes, promising a memorable dinner in a cozy environment.

The day after Thanksgiving also marks the start of the holiday season, a magical time on the island. Nantucket Noël kicks off with the much-anticipated Christmas Tree Lighting & Caroling ceremony. Locals and visitors alike gather on Main Street and anxiously wait for the Town Crier to start the traditional countdown. All of a sudden, 100 Christmas trees magically illuminate the central cobblestone thoroughfare, bathing islanders in a blaze of colored lights. Traditional holiday carols resonate through the streets, led by talented local a cappella groups. The event kicks off a busy holiday season full of festivities and activities, giving visitors and locals alike reasons to come back over and over again before the year wraps up.

Hotel Pippa still has availability for Thanksgiving so don’t wait and book your stay with us soon!

The perfect way to fully enjoy fall on Nantucket entails seasonal outdoor activities, long walks on the beach and taking in some of the cultural events happening throughout the season. Our best suggestions include art walks to explore the nearby art galleries, roaming through the books on a rainy day at Mitchell’s Book Corner, or attending one of the talks or speaker series hosted by Nantucket’s various cultural institutions.

Another key fall event is Nantucket’s annual Halloween Parade, which starts at 4:30pm on October 31. The parade makes its way down Main Street, just a 3-minute walk from the hotel! If you want to pick up a costume, stop by Dan’s Pharmacy, and if you have an adventurous eye, pop into Island Treasures, a trendy consignment store that will have just the unique costume piece you’re looking for. For those who want to explore the spooky side of Nantucket, we recommend Notorious Nantucket, an 80-minute ghost walking tour in the heart of the island, as well as the ORIGINAL Nantucket Ghost Walk, a 90-minute tour of Nantucket’s most haunted destinations at night. Hear the tales of the whaling era from the tour’s original guide and embrace the eerie history of the island.

For those looking to make the most of outdoor activities, they can participate in nature walks – the best way to explore the vibrant eco-system of the island – or birding field trips to find the 120 bird species that call Nantucket home. Active travelers can also mingle with the locals through yoga classes, group runs and bike rides.

These are just a few events that are taking place on the island this fall. For the ultimate relaxing getaway, we encourage you to book a midweek stay and enjoy a 20% discount on our seasonal rates. Use code FALL20 for a 20% discount on midweek stays – this offer is valid for stays booked between October 10, 2019 and November 30, 2019. For guests with pre-existing reservations at Hotel Pippa, the 20% discount can apply to any additional nights booked during the previously mentioned booking period.

Don’t wait – we cannot wait to be the host of your perfect autumn retreat!

After Labor Day, the on-island population shrinks to a fraction of what it is during summertime, the water is still warm enough for a dip at any time of day, and the breeze picks up just enough to offer enjoyable days at the beach or walking through town. Hotel stays are more affordable and dinner reservations are easier to secure. Traffic has subsided, making it easier for everyone to take a leisurely bike (or car) ride to Great Point to watch the seals. We also recommend taking a stroll on the ‘Sconset Bluff Walk to take in the stunning scenery, pick up late summer/fall vegetables and fruits at Bartlett’s Farm for an impromptu picnic, or browse books and gifts at the island’s stores on cobblestoned Main Street.

The months of September and October are also full of festivals and events for foodies, art enthusiasts and curious visitors. The Nantucket Project (Sept 19-22) gathers a group of bright and curious people to explore ideas and share stories about what truly matters. The four-day event features marquee presenters, change makers, artists and more – all in a beautiful and inspiring location. The festival is the perfect excuse for a quick Nantucket jaunt for those seeking engaging conversation, enlightening dinners, evening socials, and island-wide morning activities.

The Nantucket Arts Festival (October 4-13) showcases the breadth of talent cultivated by island artists during this one-week celebration. Literary talent and heritage are honored with readings by authors at the Atheneum and local bookstores. For those who prefer to take in diverse shows, the local stages feature performances by theater groups and musicians, and the visual arts are well represented everywhere you turn during this weeklong celebration on Nantucket.

Culinary explorations abound during Nantucket’s Fall Restaurant Week (Sept 30-Oct 6) as diners can take advantage of delicious prix-fixe menus at the island’s most coveted dining establishments. Visitors and locals alike can discover island favorites, seasonal dishes and fresh seafood. With high season behind them, Chefs tend to use the late summer/early fall to experiment with new ingredients and different preparations, providing creative and innovative dishes for curious diners. At Hotel Pippa, guests can delight in Chefs Jeff and Nina Bachinsky Gimmel’s seasonal menu, which includes Crab and Bartlett Corn Risotto and Local Tomato Toast with Whipped Ricotta and Tomato Vinaigrette.

There is no shortage of reasons to visit Nantucket in the fall, including a 20% discount on midweek stays during the months of September and October (use code DINING for a midweek stay during Restaurant Week and ARTS for a midweek stay during the Nantucket Arts Festival). Don’t wait, contact our front desk team to book your Nantucket getaway!