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.

In the years that followed, the event started drawing large crowds and quickly gained a robust reputation nationally and internationally, becoming a not-to-be-missed holiday shopping event. Now, more than four decades later, Nantucket’s Christmas Stroll is still held the first weekend of December every year. The event is part of the Chamber of Commerce’s “Nantucket Noel,” and preparations begin just before Thanksgiving.

The day after Thanksgiving, hundreds of decorated seven-foot Christmas trees line downtown streets and are illuminated during a public ceremony with caroling at dusk. A local artist is chosen to adorn the huge 20-foot tree at the top of Main Street, a tree that “magically” talks to all who visit it during Christmas Stroll Saturday, on December 1.

That same day, carolers in costume sing familiar holiday tunes at various downtown locations. Main Street is vibrant throughout the weekend, with craft shows, live performances, special dinners at island restaurants, tours, exhibitions and more. Midday on Stroll Saturday, the Nantucket Town Crier will ring in the 45th Annual Christmas Stroll and will lead everyone to the wharves to meet Santa, who arrives via Coast Guard Cutter. Santa will walk down the wharf, and then ride to the Jared Coffin House downtown to meet with children.

Starting on November 30, the Nantucket Whaling Museum, steps away from Hotel Pippa, will be transformed into a sumptuous winter wonderland by the Nantucket Historical Association. Their Annual Festival of Trees showcases more than 80 Christmas trees designed and adorned with unique decorations – a must-visit for those on island during Stroll Weekend or during the holidays.

There is so much to see and do during Stroll Weekend – the Hotel Pippa team is available to schedule dinner reservations and recommend the best activities to make the most of the weekend. Island restaurants pull out all the stops during the special weekend, creating scrumptious feasts and delicious prix-fixe menus.

It’s Thanksgiving Day, and you are ready to tackle the day and create lifelong memories with your closest friends and family. Start your day with some well-deserved me time and a strong cup of organic coffee from Petticoat Row Bakery, a downtown bake shop that is open year-round and offers freshly homemade delectable sweets and artisan breads. Steps away from Hotel Pippa, it also offers scrumptious breakfast sandwiches on freshly baked biscuits.

Grab a pair of sneakers and head to the Thanksgiving 5k race, organized every year by the Nantucket Triathlon Club. It never hurts to get a quick run in before sitting down for Thanksgiving dinner with the family. The race typically meanders around Brand Point and up to the Cliff, offering stunning views along the way.

Next, you can choose to join an annual Nantucket tradition – the Cold Turkey Plunge at Children’s Beach. The most adventurous islanders plunge into 20-, 30-, and sometimes 40-degree water without a wetsuit. The event benefits a local charity and is always a lot of fun!

After a warm shower, head over to the Nantucket Fish & Meat Market to get a feel for the town’s energy as families stock up for their Thanksgiving Feast. We would recommend also visiting Bartlett Farm for produce and Annye’s for the most divine prepared sides and dishes.

If you’d like to contribute to the menu, you can try your hand at scalloping and bring some Nantucket scallops back home to serve as delicious locally-sourced appetizers. Sauteed Nantucket Bay scallops are a true delicacy and can be easily and quickly prepared while the rest of the kitchen handles the turkey, stuffing and more.

If the weather allows, take a bike ride out to Cisco Brewers and indulge in their tasty spiked cider to warm up. You can also stock up on their seasonal brews, Nantucket Vineyard wines or vodka, gin or whiskey from Triple Eight Distillery. You can also join the public tour before heading back, a short but very informative tour that covers the operating procedures and methods of a functional winery, brewery and distillery.

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 front desk team at Hotel Pippa can assist with reservations in anticipation of the Thanksgiving weekend.

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.

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.

Located on the South shore of the island and home to the Shack snack bar and Taco Truck, this beach is perfect for anyone looking for an easily accessible beach with food, ice cream and facilities, perfect for sunbathing or swimming in the waves. This is one of the few South Shore beaches that has a Wave Shuttle bus that can drop you right off and bring you back into town.

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.

The site of the original harbor, Water Tower Beach is known for its calm, almost lake-like character where locals like to go shelling.

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.

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

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.

On the far western end of the Island, Madaket Beach is home to the island’s strongest waves. Even the most adventurous beachgoers will recommend setting up a picnic on the notably soft sand and taking in the incredible sunset. Smiths Point also located in Madaket is the most westerly point of the island. Thos beautiful sanctuary is off the beaten path and is only accessible through permitted four-wheel drive cars.

About 3 miles out of town is Dionis, which enjoys the gentle sound surf and steep, picturesque bluffs. It’s a great spot for swimming, picnicking, and shelling. The dunes provide shelter from the summer’s typical southwesterly winds. The beach also boasts stunning views of Nantucket Sound.

One of the most remote beaches on island, Eel Point Beach is Nantucket’s finest sea shelling spot and one of our preferred areas to catch the sunset. Located on the western end of the North Shore, it has a lot of sea grass, which explains why you will spot many eels. Due to its remoteness, visitors will need four-wheel drive transportation to get to Eel Point.

An ideal beach for families, Quidnet Beach is a short walk over the dunes and offers beautiful views of Sankaty Head Light. Sesachacha Pond is also a good spot for kayaking and sailing. The fine, soft sand provides great shelling opportunities.

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!

A haven for calm and warm waters, Pocomo Point is an excellent spot to windsurf or launch a kayaking adventure. It is also a great beach for small children.

Low Beach is between ‘Sconset and Tom Nevers around 8 miles outside of Town on the South Shore of the island. This long stretch of beach is scarcely crowded and perfect for those seeking privacy and beautiful views of the water. Make sure you pack accordingly and bring enough food and drinks for the day as the remoteness of this beach does not lend itself well to making a trip back into ‘Sconset.