New York Holiday Season Tour: 5th Ave to Rockefeller Plaza

Experience the joy of the Holiday Season in New York City
From US$272 privately
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Tour Details
2 hours
Product Type
  • Rockefeller Center
  • The Plaza Hotel
  • St Patrick's Cathedral
  • 5th Avenue
  • Winter Village At Bryant Park
Photos & Highlights
  • Learn about the city's treasured Holiday Traditions as we stroll through Holiday Markets and window displays in Mid Town
  • Led by a local historian or architect
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Tour Description
Many of the world’s most beloved Holiday traditions began in New York City. Santa Claus rings in the most wonderful time of year at the Annual Macy’s Thanksgiving Day Parade, Bryant Park is transformed into a Winter Wonderland, and 5th Avenue becomes a whirlwind of window displays and Holiday Markets. 

Our tour explores these modern traditions as well as their origin stories. We’ll trace the footsteps of the Rockefeller, Vanderbilt, and Carnegie families who transformed midtown during New York’s Gilded Age.

Please note that although there is extensive decor up after Black Friday weekend, the tree lights often don't go up until the first Wednesday of December.

Itinerary Details

Millions flood to New York City during the coldest time of the year to experience the magic of the holiday season! Known for having one of the biggest Christmas trees in the world, New York is also the birthsite of many well-known holiday traditions. Clement Clarke Moore’s quintessential Christmas tale, “The Night Before Christmas was written from his home in Chelsea. Thomas Nast, a cartoonist, created the popular image of Santa published in the January 3, 1863 edition of Harper’s Weekly. Sleigh rides were the primary mode of transportation around the wintery streets of the city in the early 19th century. 

However, beyond these holiday traditions in New York, it’s the twinkling lights and window displays portrayed through some of the most historical and architecturally pleasing buildings on the world’s most expensive retail street that captivates viewers from all over the world. Together we’ll travel back in time and through the modern world of Christmas as we learn about the famed architects and their styles that built the skyline of Manhattan. 

Beginning at The Plaza Hotel, we discuss the development of estates and mansions along 5th Avenue, when the area was mostly farming land. As we stroll past the famous 5th Avenue window decorations we uncover the dynastic industry families that made 5th Avenue one of the most luxurious streets in the world. We'll view the masterful window displays at Bergdorf Goodman, Tiffany's, and Cartier, along with others. We'll also visit long-time homes of the Rockefeller family, as well as Saint Patrick's Cathedral. The tour will conclude near Rockefeller Plaza, which is home to the longest-standing municipal Christmas tradition in the city. Depending on the group's interests, we may also explore the Bryant Park Winter Village.
What if it snows? 
In New York, we experience all climates. This tour will run in the rain, snow, and unfavorably cold weather. Dress appropriately as the tour is spent walking about 1.5 miles outside.

How will we navigate through the crowds?

The holiday season is one of the busiest times of the year in Mid-town Manhattan. Please be mindful as you're navigating sidewalks and street crossings with your Context Expert.

Can we take pictures at Rockefeller Center?
Our experts are not photographers. We will have access to a great view of the Christmas tree and window displays as we walk past them where clients can capture photos themselves, but we will avoid crowds by not stopping under the Christmas Tree.

Are there snacks included?
We can stop for a bathroom break and coffee/hot chocolate at your own expense if needed along the way.

Can I learn more about New York City's history before my trip?
Yes! Context offers several online learning seminars about American culture and history, available here. 
Where You'll Start
(5.0) 2 Reviews

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Very personalised , Debra was very knowledgable , we even sang down 42nd St , would highly recommend