Nantucket, known for its pastel shorts, boat shoes, and summer breezes, may not seem like an obvious winter destination. But in December, this island undergoes a stunning transformation into a winter wonderland. The first weekend of December, in particular, is when Nantucket truly shines, and this celebration is known as the Christmas Stroll, or simply “Stroll” to the locals. If you’re considering a winter getaway, let us share with you why December is the perfect time to visit Nantucket.

The Enchanting Nantucket Christmas Stroll
The Nantucket Christmas Stroll is a beloved tradition that has been cherished for decades. During this festive weekend, the island comes alive with holiday cheer. As your ferry approaches Nantucket, you’ll be greeted by the Brant Point Lighthouse, adorned with an oversized wreath, setting the tone for what’s to come. Once you step foot on the island, you’ll find picturesque cobblestoned Main Street transformed into a charming Christmas scene. A large Christmas tree at the center of the town adds to the enchantment, and there are dozens more lining the streets, each exquisitely decorated by a nearby shop. Victorian-era carolers serenade passersby, creating an enchanting atmosphere. Out in the harbor, you’ll even spot a miniature Christmas tree bobbing on a dinghy. And in true Nantucket style, Santa Claus arrives on a Coast Guard vessel, leading a festive parade through town.
Exploring the Winter Wonderland
Nantucket’s streets become even more picturesque, adorned with Christmas trees and holiday lights. The cobblestoned Main Street, in particular, takes on a whole new level of charm. As you stroll through town, you’ll find yourself immersed in the holiday spirit. What sets this experience apart is that there’s no need for a strict itinerary; simply enjoy the season at your own pace. Nantucket in December offers a sense of wonder and nostalgia that’s truly magical.

Unique Shopping and Dining Experiences
One of the highlights of the Christmas Stroll is the fantastic shopping opportunities it presents. Many local shops stay open late, offering a delightful array of unique gifts and treats. Whether you’re seeking charming souvenirs or one-of-a-kind presents, Nantucket’s boutiques and stores have you covered. Additionally, Nantucket’s dining scene gets into the festive spirit, offering holiday-themed culinary experiences. Don’t forget to savor some mulled wine at noon, adding an extra layer of warmth to your Stroll experience.
Festive Activities for All Ages
While the Christmas Stroll is perfect for families with kids, it also caters to adults looking for a more sophisticated celebration. Children can enjoy activities like cookie decorating and special tours, while Santa’s Village Marketplace offers a delightful selection of food, crafts, and beverages. However, adults can partake in the fun as well, embracing the opportunity to dress in theme, whether it’s festive, tacky, or whimsical.

The History of the Christmas Stroll
The Nantucket Christmas Stroll has deep roots in the island’s history. It began over 40 years ago as a way to keep locals from leaving the island to do their holiday shopping on the mainland. The first Stroll was a single afternoon of festivities, with shops enticing customers with hot cider and Christmas cookies. Over the years, it has evolved into a destination event, drawing visitors and reuniting summer residents on the island. This rich history adds to the charm and significance of the Stroll.
Beyond the Christmas Stroll
- Santa’s Arrival: Santa arrives in Nantucket by boat with the assistance of the Coast Guard. The Town Crier leads the way to welcome Santa and Mrs. Claus, who then visit the Jared Coffin House library to meet with children. This is a magical experience for families.
- Festival of Trees: The Nantucket Whaling Museum hosts the Festival of Trees, featuring over 80 uniquely decorated Christmas trees designed by local businesses, artists, and organizations. It’s a visual delight and adds to the holiday spirit.
- Yuletide Fair: The Nantucket Lighthouse School’s Yuletide Fair is a beloved community event featuring handcrafted holiday items, gifts, a bake shop, and craft activities for children. It’s a great place to find unique holiday treasures.
- Holiday Performances: Nantucket offers holiday-themed theatrical performances, including “A Sherlock Carol” and “Madeline’s Christmas,” providing entertainment and festive cheer.
- Red Ticket Drawing: To encourage local shopping, businesses participate in the Holiday Red Ticket Program, giving customers a chance to win cash prizes. The drawing takes place on December 24th, adding an element of excitement to holiday shopping.
- Tree Lighting Ceremony: The holiday season officially begins with the Tree Lighting Ceremony on Main Street, where over 150 trees are illuminated in a beautiful display of lights and accompanied by musical performances.
- Brunch with Santa: Families can enjoy a delicious brunch with Santa at The Nantucket Hotel & Resort, making it a memorable experience for children during the holiday season.

Planning Your Nantucket Holiday Getaway
If you’re ready to experience the enchantment of Nantucket during December, now is the time to plan your trip. The Nantucket Christmas Stroll Weekend takes place in early December, with a full schedule of island traditions, culinary delights, and festive activities. To add an extra touch of magic to your stay, consider booking accommodations at “3 Gulls & A Buoy – A Seafarer’s Escape,” our luxury family vacation rental on Nantucket. It’s the perfect place to unwind and create cherished holiday memories.

Embrace the Magic of Nantucket This December
December is indeed the perfect time to visit Nantucket, where you’ll discover a winter wonderland filled with holiday charm and nostalgia. Nantucket offers a holiday experience unlike any other, whether you’re enamored with the enchanting Christmas Stroll, the picturesque streets, the distinctive shopping and dining, or the island’s rich history. Join us in experiencing the magic of Nantucket during the most wonderful time of the year. Book your stay today at “3 Gulls & A Buoy – A Seafarer’s Escape” and make this December unforgettable.