- Category
- Architecture, Holidays with Context
- Duration
- 2 hours
- Location
- New York
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
Beginning at The Plaza Hotel, we discuss the development of estate 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, 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 Villiage.
FAQ
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 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.

Francesco was born in Sicily and grew up in New York. He graduated with a Master's degree in Architecture and worked professionally in that field for his entire career. When he retired, Frank started leading tours of his city as a way to share New York with visitors from all over the world. When leading tours of the history, architecture and food scene of NYC, Frank is introducing visitors, or new friends, to this intriguing city, revealing its hidden and sometimes forgotten past, in order to better understand its present. A true “Cicerone”, storytelling is at the center of Frank’s tours and he introduces visitors to the characters from New York’s rich history, from his Sicilian grandmother to Emily Roebling, a little know contributor to the construction of the Brooklyn Bridge. Frank’s passion for all things New York shines through on his tours all over Manhattan.

Ethan Angelica has been working in the arts and culture sector as a tour guide, experience designer, consultant and programmer for nearly two decades. He is the founder of Angelica & Associates, LLC, an audience-building project focused on crafting unique experiences in museums and culture spaces to encourage new attendees. He has created tours of museums, cities and cultural site on every continent except Africa and Antarctica, and worked with organizations as diverse as the National Park Service, the Central Park Zoo, SFMOMA, The National Museums of Norway, California Academy of Sciences, Chicago Cultural Alliance and Te Papa Tongarewa in New Zealand. A seasoned storyteller, Ethan loves to dig for the little-known backstories and unique personal histories that make spaces and places come to life. When he's not leading a tour or designing a new program, Ethan can be found sipping craft beer, strolling his home neighborhood of DUMBO and teaching the Audience Development course as a part of Baruch College's Arts Administration MA program.

Becky studied urban history as an undergraduate at the University of Pennsylvania and for her master’s at the University of Leicester, UK, researching nineteenth-century city planning and its social implications. In New York, she co-wrote a history of liquor distilling in the city and discovered musty secrets for guides in Time Out. A freelance writer, she primarily covers travel for publications like New York magazine, Travel + Leisure, and the Washington Post. The coolest place she’s been in the city: behind the clock above Grand Central Terminal.
Reviews can only be left by Context customers after they have completed a tour. For more information about our reviews, please see our FAQ.