A Romantic Winter Getaway

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!

Holiday Season on Nantucket

The holiday season is special anywhere – but it’s particularly beautiful on Nantucket. While the few weeks between Thanksgiving and Christmas can be stressful, there is no better time to escape to Hotel Pippa for a cozy stay and holiday shopping jaunt. The seasonal celebrations and festive atmosphere are the perfect occasion to create memories that will last a lifetime… and get a head start on holiday shopping in a merry environment.
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!

Pre-Holiday Season on Nantucket

With Thanksgiving approaching, the festive spirit of the holiday season is upon us, ushering in a new atmosphere on Nantucket. The first signs of winter are starting to show around the cobblestone-paved Main Street, and fall decorations adorn the beautiful shingle style homes and residences on the island. As locals and visitors start planning for Thanksgiving, Hotel Pippa is getting ready to kick off the holiday season and welcome guests to retreat in its cozy quarters as the brisk fall air gets cooler and cooler.
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!

Reasons to Visit Nantucket This Fall

As the leaves start changing and the brisk autumn breeze starts to make its way to the island, Nantucket becomes the perfect retreat for anyone looking to relax and escape to cozy New England. There is still plenty to do on the island – so pack a few sweaters and a light jacket and come enjoy a side of Nantucket that few people get to see!
TThe 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!

Fall on Nantucket

While it is starting to feel like summer is coming to an end, there is so much to look forward to on Nantucket. Fall might well be the best time to plan a getaway to the island, especially for those who are a bit crowd-averse.
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!

The Best Way to Summer on Nantucket: Midweek Stays & Exploring The Island’s Best Beaches

It’s officially peak season on Nantucket, which means the island is bustling with visitors and weekenders coming from all corners of the Northeast and beyond. We at Hotel Pippa love the vibrant atmosphere of summer on Nantucket, walking the busy Main Street or seeing guests enjoy the island’s many stunning beaches and dreamy sunsets.
If you haven’t made plans to escape to Nantucket this season, we wanted to let you in on a little secret: the best way to summer on the island (and to avoid the crowds) is to plan a midweek getaway here. You will find that Nantucket is as exciting as ever on weekdays (and weeknights!) but plane fares and hotel rates are more affordable, and the crowds thin out during the week.
The other secret we like to share with our guests is an exhaustive list of our favorite beaches. The island boasts 82 miles of picture-perfect, freely-accessible, and highly-acclaimed beaches. The team at Hotel Pippa can outfit guests with towels and beach chairs for a relaxing day at the beach; water games and sunscreen for the family; or snacks and a bottle of wine for a picnic by the ocean. Here are some of our favorite spots we recommend exploring this summer:

Steps Beach

The water is usually calm and a bit warmer on the Nantucket Sound side of the island. Steps Beach is off Cliff Road about two miles from town, sandwiched between Dionis and Jetties, and is not on most people’s radar. As you approach its signature set of stairs leading down, enjoy the view of harbor and the sound. Steps Beach offers protected shores with gentle waves washing onto the sandy beach, and gray-shingled mansions dotting the surrounding sand dunes.

Jetties Beach

The most popular spot on the calm North Shore, Jetties Beach is where locals and visitors mingle. Sandbar at Jetties Beach offers the quintessential beachfront experience – a low-key atmosphere paired with a view of Nantucket Sound. The Jetties Sailing Center, a nonprofit that promotes access to watersports on the island, offers sailboat rentals and lessons for those looking to venture out on the water.

Cisco Beach

After a big storm, experienced surfers on the island rush to Cisco Beach – this spot has a loyal following and is popular with young adults and surfers. It’s also home to Nantucket’s best surf school and visitors can rent surfboards, wetsuits, and stand-up paddleboards. On your way home, be sure to visit local brewery Cisco Brewers and try some of the select beers they brew onsite, which can only be found at the brewery.

‘Sconset Beach

No trip to Sconset Beach is complete without a refueling stop at the Sconset Market to pick up the shop’s famous brownies. The enchanting bluff walk leads to the beautiful and peaceful beach where you can see seals swimming close to the shore. A hidden gem, the beach is never extremely crowded and lends itself perfectly to a romantic walk at sunset.

Great Point

The pristine beach and Great Point Lighthouse (also known as Nantucket Lighthouse) make the long journey to the area worthwhile. The lighthouse sits on the end of a seven-mile strip of sand overlooking Nantucket Sound and Coatue. Here you will find windswept dunes, waving marsh grasses, miles of golden sand, and clear blue waves. Great Point is home to the island’s best fishing, which means you will find a crowd of passionate fishermen and plenty of bluefish (you can sometimes spot harbor seals fighting over them!). The only condition to experience this dreamy setting: four-wheel drive and a beach permit are required.

Brant Point Beach

Technically a swimming beach, Brant Point is much more suited for sitting and watching the harbor traffic. A scenic viewpoint that features Brant Point Lighthouse, the second oldest lighthouse in the US, this spot is ideal to go wave goodbye to friends and family departing the island. One of the most photographed spots on Nantucket, it is also a special favorite for wedding photos. You can also stumble upon an actual ceremony taking place at Brant Point Beach, making it a locals’ favorite for people watching!
So pack up your towel and sunscreen – we hope to see you at the beach or at Hotel Pippa this summer!
Book your stay at Hotel Pippa

It’s Festival Season on Nantucket

As if you needed more reasons to plan a getaway to Nantucket, the summer season is packed with festivals that are not to be missed. Throughout the month of June and July, the island bustles with multi-day events that celebrate food, arts and entertainment, wellness, nature and local traditions. So grab your friends and family members, book your stay at Hotel Pippa and check out this exhaustive list of our favorite festivals:

Nantucket Book Festival (June 14-16)

Avid readers and book lovers can celebrate the pleasures of this intimate pursuit during a multi-day event that features private readings, talks, panel discussions, book fairs and book signings, as well as parties celebrating the literary pastime. You will find local and national authors mingling with Nantucket residents, visitors and families throughout the festival. Most events are free and located in the heart of downtown Nantucket.

Nantucket Film Festival (June 19-24)

A celebration of independent filmmaking, the Nantucket Film Festival gathers some of Hollywood’s biggest actors and directors as well as rising stars of the industry. Now in its 24th year, the festival honors the art of screenwriting and has become one of the premier destination film festivals in the world. Visitors flock from all over to experience screenings, signature programs, and standout hospitality with the beautiful sandy beaches and shingled cottages of Nantucket serving as the most perfect backdrop.

Nantucket Yoga Festival (July 12-14)

Yoga instructors and wellness experts come together to celebrate the impact of yoga on a healthy lifestyle. The festival is full of workshops and classes, discussions and collaborations taking place in the ideal setting of Bartlett’s Ocean View Farm. The weekend event is a true celebration of conscious living, the independent spirit and creative collaboration, with a contagious spirit of positivity.

Nantucket Comedy Festival (July 11-13)

An annual event that brings top comedians to Nantucket, the festival also serves as the major fundraiser for Stand Up & Learn™, an island-based, year-round comedy education program serving Nantucket’s children. You can do good while partaking in world-class laughs for four straight days, headlined by Don Gavin.

Nantucket Garden Festival (July 16-18)

A staple of festival season, the Nantucket Garden Festival highlights the beautiful gardens of Nantucket, with a focus on conservation, sustainability, and education. Attend the opening night soirée, join workshops, tour gardens, and enjoy local blooms as part of Nantucket’s three-day garden party. 

Nantucket Atheneum Dance Festival (July 22-27)

The Nantucket Atheneum Dance Festival brings the best of ballet – dancers, musicians and choreographers – to the island for performances in an intimate venue, the Nantucket Atheneum. This year marks the 12th year of the event, featuring world class stars from the New York City Ballet, LA Dance Project, Miami City Ballet, and Pacific Northwest Ballet. The festival includes free programs for all ages and culminates with two evening performances that are not to be missed.
For those looking for reasons to return to the island in the off-season, Nantucket boasts additional festivals during the fall, continuously enriching locals and visitors’ time on the island.
Whichever festival you plan to attend, book your stay at Hotel Pippa and enjoy the hotel’s convenient location, steps from the heart of downtown.

Memorial Day on Nantucket

Are you ready to kick off the summer season this upcoming Memorial Day Weekend? We, at Hotel Pippa, are excited for the months to come and thrilled to welcome guests for high season on Nantucket. We still have a few rooms available for the holiday weekend – three days of sailing races, strolls on the beach, on-island explorations, delicious local meals, and fun activities.
There are many on-island traditions on Memorial Day Weekend – seasonal visitors make their way to the island among thousands of sailors hailing from all over the country for the Figawi race. The historic cobblestone streets of Nantucket are vibrant with locals and travelers taking advantage of the mild weather, bustling shops and countless events.
Explore the island’s gray-shingled cottages, manicured gardens and blooming hydrangeas by taking a bike ride through the island’s villages and visit Cisco Brewery for beer and wine tastings and local live music.
On Saturday, get up early to watch the Skippers and boat owners prepare their boats, gather their crews, and head out to the start line. Beginning around 8 am, the parade of sailboats head out of Lewis Bay, pass by Kalmus Beach, and gather off the Hyannis Port jetty. The pursuit regatta officially starts at 10 am and finishes at the entrance of Nantucket Harbor, with a parade into Nantucket Boat Basin. Standing on the beach at Brant Point Light is a great spot to watch all the action.
On Sunday, walk the docks at Nantucket Boat Basin and watch the local high school teams from across the Cape and Islands compete in the annual regatta called the Figawi invitational. On your way back to downtown Nantucket, stop for a delicious ice cream at The Juice Bar and collect local souvenirs at the shops. On Monday, the Memorial Day Parade passes through Main Street, an occasion to honor local and visiting military veterans.
Throughout the weekend, enjoy New England cuisine and eclectic foods are Nantucket’s restaurants – most of them reopen for the summer season on Memorial Day weekend and offer the freshest seafood and local produce. We highly recommend making reservations in anticipation of your visit, and our front desk team can assist once on-site as well.
As high season approaches, Memorial Day weekend on Nantucket is the perfect time to reconnect with family and friends, enjoy the island’s beautiful beaches and perfect summer vibes.

Spring on Nantucket

After a long New England winter, there is no better spring escape than a trip to Nantucket. A getaway to the charming island that Hotel Pippa calls home guarantees an idyllic break from daily life, blissful temperatures, festive events, and affordable rates.
As Nantucket brightens up, visitors can enjoy a relaxing stroll on the beach or fun explorations through the historic cobblestone streets, gray-shingled cottages, blooming hydrangeas and winding dirt roads leading to the beach. It’s time to take advantage of all the fun outdoor activities, events and festivals offered on island, pre-summer rush.
Pack up a few layers and hop on the high-speed ferries or one of the many direct flights into Nantucket to make the most of your trip. With Daffodil Weekend around the corner (April 26-28), nature enthusiasts can reserve their stay at Hotel Pippa and enjoy the ‘Sconset tailgating picnic, a highlight of the annual flower festival on Nantucket. The weekend festivities also include art shows, tours, a classic car parade, exhibitions, contests, lectures, and the annual Nantucket Daffodil Flower Show.
Before kicking off the summer season over Memorial Day Weekend, Nantucket will welcome the Wine & Food Festival, a prime occasion to pay a delicious visit to the island (May 15-19). Started when the first vintners arrived on the island, it now draws over 3,000 attendees for this annual spring fête and boasts a continually growing family of vintners, wineries, renowned chefs and restaurants. Today, the NWF marks the awakening of the island when restaurants, galleries, activities and tours open for the season, and celebrates Nantucket as a culinary destination.
If you prefer a more low-key weekend getaway to Nantucket, book your stay at Hotel Pippa and plan a bike rental to ride through the winding roads of the island, stopping at Bartlett’s Farm or Cisco Brewers. Reserve ample time to browse the book trove that is Mitchell’s Book Corner or Murray’s Toggery Shop for a selection of Nantucket reds. Dive into the island’s history at the Nantucket Whaling Museum and marvel at the mix of Colonial, Federal, Greek Revival, and Victorian homes in the local historic district. Make sure you save one evening for a sunset walk on one Nantucket’s many public beaches. End your night discovering local art at the galleries adorning Centre Street, across from Hotel Pippa.
We can’t recommend a spring visit enough – it’s the perfect time to experience Nantucket without the summer crowds and you can connect with our front desk team to inquire about special rates and seasonal offers. Don’t wait, book your getaway now! Don’t wait, book your reservations getaway now!

Daffodil Weekend

A true Nantucket tradition, the 45th Annual Chamber Daffodil Festival will take place throughout the island April 26-28, 2019. Now is the time to book your stay at Hotel Pippa, located steps from downtown Nantucket and all the excitement of the flower festival.
Daffodil Weekend started as a simple affair in the 1970s, when islanders would show off their classic cars and take part in a community tailgate picnic in Siasconset. Decades later, the festival is a celebration of springtime awakening where islanders and visitors gather to enjoy the blooming flora, warmer weather and vibrant atmosphere around town.
Organized by the Nantucket Island Chamber of Commerce, this weekend of festivities includes art shows, tours, parades, exhibitions, contests, lectures, and the annual Nantucket Daffodil Flower Show. Locals and guests alike are encouraged to enter the different categories of the show, which always takes place at Bartlett’s Ocean View Farm.

(photo credit: Roberta White)

A highlight of the weekend is the famous ‘Sconset Tailgate Picnic that follows the Antique Car Parade. The team at Hotel Pippa can source a locally-inspired picnic basket for those who wish to join the festival-goers and see the elaborate picnic displays and all-around fun first-hand.
Other weekend events include a Daffy Hat Contest, a Children’s Parade featuring decorated bikes, strollers, wagons, and other self-propelled vehicles, a window decorating contest, the famous Sconset Tailgate Picnic, a Family Picnic at Children’s Beach, and more! The Pine Woods Morris Dancers often perform throughout the day at various locations. There are activities for all ages, and faithful festival-goers dress up for the occasion and participate enthusiastically.

(photo credit: Roberta White)

We always recommend our guests allocate some time for a stroll on the beach and for a drive around the island to see the blooming flowers and stunning gardens. Our front desk team can also arrange dining experiences around town, so everyone can taste the bounty of fresh seafood and spring vegetables and fruits featured on the menus around the island.

(photo credit: Roberta White)

Guest rooms are still available for Daffodil Weekend and we look forward to celebrating spring awakening with you! Call our front desk now to book your reservations before the weekend sells out.
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