Check Availability
from US$ 80.10 per person
  • Adult (13+)
    - +
  • Child (5-12)
    - +

Exploring Old New York: A Theatrical Ramble Through Downtown NYC + Sightseeing Cruise + One World Observatory

Activity Schedule

  • When does it run?


  • Duration

    4.5 hours (approx.)

  • Start time

    9:30 am & 11 am

  • Meeting Point

    Park up at the north east corner of Broadway and 2 Wall Street (just opposite from the famed Trinity Church - you can’t miss it) 20 minutes before your tour is due to start and wait for the drama to commence.

  • Ending Point

Key Highlights

  • Turn back time: A ramble through old New York from the 1700s to the present day, led by three period actors
  • See (and snap): Downtown sites like the New York Stock Exchange, Castle Clinton, the 9/11 Memorial site, South Street Seaport, the Charging Bull and lots more
  • Dig a little deeper: Gain fascinating insight into the life and times of New Yorkers, then and now
  • Try something different: A fun, customisable experience to suit every travellers’ whims and fancies - this isn’t your average walking tour
  • Soak up breathtaking views of the New York City from the top of One World Observatory
  • Take a sightseeing cruise and sail past New York's top attractions


What if we told you there’s a different kind of walking tour out there - one that involves the freedom to drop off and rejoin as you please, and a handful of ostentatious period costumes. Intrigued? You’re right to be - this walking tour is the very first of its kind in the Big Apple. Led by three period actors, this group tour through Downtown Manhattan embarks on a kind of theatrical retelling, focusing on the historical events, sites and people that made the city what it is today.

The tour is broken up into three hour-long slots. Each slot is run by an actor-guide, and each actor-guide represents (and tells of) a key era in NYC’s history. Spanning the days of New Amsterdam all the way to contemporary times, this tour passes through Downtown’s major landmarks - places like Wall Street, the Charging Bull, and the 9/11 Memorial pools - as well as some lesser known gems too. A nice little extra feature of this tour are the break points. At two spots throughout the tour, travellers are able to opt out of the tour for a while, explore the area on their own or have a bite, and pick up where they left off on the next tour of the day. Nice touch hey? For those who love history but are bored of the same old thing, this is a winner. 

PS. Fancy a cheeky upgrade? This experience also comes a One World Observatory ticket and a Liberty sightseeing cruise. 

About your guide 

City Ramblers NYC has burst onto the New York travel scene with a set of experiences that go far beyond the average walking tour. If you’re into theatrics and history told with a bit of flair, you’ll love these tours. 

Here’s the plan… 

Meet an aristocrat or a street urchin from the 1700s just opposite Trinity Church. (Yes, we know how this sounds). Underneath all that period dress is your first guide of the day: a storytelling actor with the task of taking you and the group all the way back to 18th century America. In this first leg, you’ll learn about colonised New Amsterdam, the first incarnation of Wall Street and the great fire, told from the perspective of someone who lived it (not actually, but you get the gist). 

You’ll finish up the first leg of the tour down by the pier. If you want to have a break and explore the area further, you’re welcome to pick up the next tour along - just meet the next group in the same spot (your guide can let you know exactly what time to do so). Otherwise, you’ll continue on with your second blast-from-the-past actor-guide. Next, you’ll discover the South Street Seaport. Though plush these days, the area was once a working trading port, full of dockers, sailors and, on occasion, pirates. In this hour, you’ll check out bars where Thomas Edison, Butch Cassidy and Theodore Roosevelt had a few tipples and some architectural gems like the Century 21 Department store, City Hall Park and the Woolworth building too. 

After the hour, you’ll have reached another break point by the One World Trade Center, and the same option to venture off applies. The last section of the tour fast-forwards to the early noughties, specifically to the events surrounding 9/11. With your final actor-guide, you’ll spend some time at 9/11 Memorial Grounds and discover some of the new projects and architecture designed to both commemorate and revitalise the area. Then, the group will make their way to Castle Clinton, stopping by iconic Downtown attractions like the Cunard Building, the Charging Bull and “Fearless Girl” statues and Battery Park. The tour finishes by Castle Clinton, where the picture-perfect Statue of Liberty towers in the distance.


  • Theatrical walking tour
  • Three actor-storyteller guides
  • Audio headsets (so you don’t miss a thing)
  • Flexible tour experience (hop on and off when it suits you)
  • One World Observatory
  • Sightseeing Cruise


  • Transfers (we’ll see you there)
  • Tips (get that warm, fuzzy feeling)

Please note

The confirmation voucher includes City Rambler NYC’s contact details. They’re a nice bunch, and will happily answer any logistical questions you may have. Please give the City Rambler NYC team a call at least 24 hours before the tour’s due to kick off to reconfirm the final details.

So there’s no last minute rush, aim to arrive at the meeting spot 15-20 minutes before the tour starts. 

This tour takes place outside, so be sure to dress appropriately for the weather, and opt for comfortable shoes. The tour will run rain or shine. 

City Ramblers NYC doesn’t give refunds for any cancellations, however you can reschedule your tour up to 48 hours before your scheduled departure. 

One of the cool things about this tour is that it’s customisable. Think of it as kinda like a hop-on, hop-off bus experience, but for walking tours. The walk-on/walk-off points include South Street Seaport – Pier 15 (tours passing through at 10:30 am and 12 pm) and the Oculus, One World Trade Observatory (tours passing through at 11:30 am and 1 pm). This may be too specific to include in terms of future-proofing. 

This tour is often on the move and each participant will be provided with an audio headset.

travel inspiration from guidebook

  • New York – Best of the Best
    New York – Best of the Best

    Do get caught between the moon and New York City The post New York – Best of the Best appeared first on The Guidebook - isango!.

  • Touring New York on a Budget:  A Guide to an Affordable N.Y. Trip
    Touring New York on a Budget: A Guide to an Affordable N.Y. Trip

    Experience New York on the cheap!

  • Traditional Ways To Celebrate Christmas In America:  A Retrospective
    Traditional Ways To Celebrate Christmas In America: A Retrospective

    'Tis the Season To Be Jolly