‘Discover New York’ vacation package

1st Stop – Historic Lower Manhattan / Financial District

The suggested start time for your tour is between 9 am and 10 am. 

Your tour begins in Lower Manhattan where we’ll explore some of the forgotten history that relate to the beginnings of our nation. The Financial District is the most historic part of New York, back when it was called New Amsterdam.

We’ll walk you through the streets as they were laid out by the Dutch over 350 years ago. You’ll learn some incredible history related to the Revolutionary War and the founding of our nation and see the site where George Washington was sworn in as our first president. 

Take a picture in front of the Charging Bull sculpture and take a walk around the City’s first public park, Bowling Green. There are many secrets hidden in plain site in this part of Manhattan. Your guide will share with you the moving stories of New York’s early history and how it affects NYC to this day.

The Financial District is also a favorite site for movie producers! John Wick, Hitch and Batman were all filmed here (among many others). 

Down at the southern tip of Manhattan in Battery Park we’ll catch a glimpse of the Statue of Liberty and explore the colorful history of our country’s first immigration station, Castle Clinton.

2nd Stop – Trinity Churchyard, St. Paul’s Chapel and City Hall Park 

Nearby, we’ll take a walk through the cemetery at Trinity Church.

After paying our respects to one of our founding fathers, Alexander Hamilton, we’ll take a much closer look at a mysterious tombstone of an early Freemason. Using a special cipher, your guide will show you how to decode the secret message engraved on it. 

Just up Broadway from Trinity Church we’ll see St. Paul’s Chapel where Washington went to pray after he was inaugurated. St. Paul’s also played an important role during the rescue efforts of 9/11. But it’s what’s in the churchyard that will truly mystify you! An obelisk with a mysterious set of coordinates engraved on it stands in the cemetery. You guide will explain to you this first of three obelisks we will see on our tour today and its relation to the Freemasons. 

Across from St. Paul’s Chapel is City Hall Park. Surrounded by some of the most beautiful buildings in the City, this park has a few secrets to share. Adjacent to City Hall also happens to be the site of one of the most scandalous construction projects in the history of the New York City, the Tweed Courthouse!

3rd Stop – South Street Seaport 

Once the heart of New York’s shipping empire South Street Seaport tells an interesting story. You’ll find out just how and why New York became the largest and wealthiest city in America.

Walk the cobblestone streets with your guide and learn some of the secrets of this quaint historic district. These streets are filled with the memory of the rough and tumble sailors and ruffians who once inhabited them. Their ghosts whisper to you of a time when this area was far different from the tourist attraction it is today. Uncover the real South Street Seaport, as it was over a 150 years ago. 

At the entrance to the Seaport you’ll also see the Titanic Memorial Lighthouse, placed here in 1913. 

4th Stop – DUMBO Brooklyn 

Next stop, Brooklyn… oh how sweet it is! We’ll take a ride over the Brooklyn Bridge and spend some time exploring the historic waterfront neighborhood of DUMBO. Get your camera ready to take advantage of the postcard-perfect views we’ll show you of the Manhattan skyline. 

5th Stop – Brooklyn Heights 

The next neighborhood over from DUMBO is the Brooklyn Heights, the first area in the U.S. to be designated an historic district. You’ll see some incredible architecture and stroll the quiet, tree-lined streets. Brooklyn Heights looks like it fell out of a Norman Rockwell painting. 

We’ll take you down to the Brooklyn Promenade where several movies were filmed and take in, once again, more amazing views of the iconic Manhattan skyline.

6th Stop – Cortlandt Alley & Doyers Street/Bloody Angle (Chinatown)

Next, you’ll head back into Manhattan across the Manhattan Bridge. You’ll take a trip to old Chinatown to a street that was once so dangerous it was nicknamed Bloody Angle. Your guide will share with you the story of the Chinese gangs that once roamed these streets. We’ll discover an old repurposed tunnel that once was used as an escape route.

If you’ve never seen Gangs of New York we highly recommend watching it before your trip. Your guide will show you the streets depicted in the movie, which were a part of the most notorious slum in America: the Five Points. Hear the stories of the real gangs of New York: the Dead Rabbits, Bowery Boys, Plug Uglies and others. 

After this we’ll take you over to another hidden alley that looks more sinister than it actually is. Loved by movie producers Cortlandt Alley has been used for scenes in Batman, Crocodile Dundee, and Men In Black. 

7th Stop – Greenwich Village

One of the most charming and picturesque neighborhoods in New York, we’ll show you some of the lesser known aspects of this part of town. 

Hidden courtyards, mafia hangouts, the narrowest house in New York, an old elm tree used for public hangings… let’s just say Greenwich Village has more secrets than anyone would ever imagine.

Nearby, we’ll take a stroll along The High Line, NYC’s most unique public park. From this vantage point you’ll catch a glimpse of the Hudson River as your guide points out the pier where the Titanic survivors first arrived after being rescued. 

Next, your guide will take you off the beaten path to discover and uncover the Village’s fascinating history, its cultural significance and many landmarks. And while you’re here, you’ll have some authentic NYC-style pizza at one of the most popular spots for locals! 

8th Stop – Flatiron Building/Madison Square/Worth Monument

From Greenwich Village it’s a short ride to Madison Square where we will see 3 buildings recognizable in the Manhattan skyline: the Empire State Building, the gold pyramid-topped New York Life Insurance Building and the Metropolitan Life Tower. 

But it’s what’s across the street that will capture your attention. The Flatiron Building, built in 1902, was Midtown Manhattan’s 1st skyscraper. Its unusual triangular shape created quite the frenzy after it was completed. Hear the story of one of NYC’s most interesting buildings. 

Across from the Flatiron Building stands our 2nd obelisk: the Worth Monument. General Worth – who Fort Forth Texas is named after – is buried here. But this obelisk has an interesting relationship to the previous obelisk we saw and the final obelisk we will see later. 

From this spot your guide will show you a vintage video from the early 1900s. You’ll see horse & carriages and NYC as it was at the turn-of-the-century, from the exact spot you are standing! You’ll feel like a time traveler! 

Just up the road is perhaps the most important block in America related to the history of American popular music: Tin Pan Alley. People walk by this block every day without realizing the critical role it played in the evolution of today’s music industry. Learn some interesting facts and trivia here and walk away with a newfound appreciation of this forgotten street in Manhattan.

9th Stop – Secrets of Herald Square & Times Square 

As the song says: Give my regards to Broadway… remember me to Herald Square. Tell all the gang at 42nd Street that I will soon be there. Herald Square was once the center of Manhattan’s theater and entertainment district before Times Square. 

There’s more than meets the eye at two of Manhattan’s busiest and most popular squares. You’ll take a walk with your guide and explore some of the quirks and little-known facts about Herald Square. There’s more to it than just Macy’s! 

Watch a vintage video from the early 1900s of Herald Square, when trollies, horse & carriages and ladies with big hats and long dresses once lived. 

Just 10 blocks uptown and we come to the Crossroads of the World, Times Square. You may be dazzled by all the huge electronic billboards. But what will really get your attention are the many remnants still here from Broadway’s golden era of the 1920s and earlier. Discover some of these hidden gems with your guide on a walk through one of the most famous intersections in the world.

10th Stop – Grand Central Terminal

Inside arguably the most famous train terminal in the world are so many fun and interesting secrets. When you see the inside of Grand Central Terminal you may never want to leave. This is truly one of the most beautiful interior spaces you’ll ever see. 

You may remember Grand Central from movies like Alfred Hitchcock’s North By Northwest or Madagascar. But there’s more than meets the eye. 

Walk through this landmark building with your guide and uncover its secrets. For example, did you know the zodiac painted on the ceiling is backwards? Or that there are tennis courts on the roof? You’ll explore this landmark with your guide and discover some exciting history and interesting facts. 

11th Stop – Secret cellar at the 21 Club

Just a couple blocks east of Times Square,  52nd Street between 5th and 7th Avenues, was known as the Speakeasy Belt due to the literally dozens of speakeasies located on these 2 blocks.

Grab your fedora and take a trip back in time with your guide – back to the roaring 20’s and early 1930s. The only remaining former speakeasy left on 52nd Street is the famous 21 Club restaurant, a legendary dining, party, and see-and-be-seen spot for New Yorkers of the time and for generations to come.

A hundred years later and the 21 Club is still going strong. Boy, if these walls could talk. There’s a lot more to the 21 Club then an expensive dinner and cocktail. Find out why writer Ernest Hemingway was almost killed by mobster Legs Diamond. Go into the basement and discover the hidden room where politicians and New Yorkers alike would drink and party during prohibition!

12th Stop – Roosevelt Island Tram

Moving along over to the far east side of Manhattan we find one of New York City’s most unexpected tourist experiences: a tram that takes you 250 feet above the city for the price of a subway fare. This is the Roosevelt Island Tram. 

Running alongside the tram is the Queensboro Bridge. Many movies have been filmed on the Queensboro Bridge, also called the 59th Street Bridge… a song’s even been written about it: Paul Simon’s 59th Street Bridge song (Feeling Groovy). You may also remember the bridge from the television show Taxi and the movies Spiderman, Anger Management and The Great Gatsby with Leonardo di Caprio. 

We’ll take a ride on the tram and get close-up views of the often-overlooked yet beautiful Queensboro Bridge. This is guaranteed to be one of the highlights of your tour!

13th Stop – Central Park, Cleopatra’s Needle & the secret of the 3 obelisks

Next, we head on over to Central Park. Hidden behind the Metropolitan Museum of Art, in a mysterious location is the 3rd and final obelisk we’ve been talking about.

It’s called Cleopatra’s Needle and it’s a 224-ton, 3,000 year old monument brought in from Alexandria, Egypt. Learn about the massive effort it took to get this obelisk to its current location, and why it is placed where it is. 

Your guide will reveal to you the mystery of the 3 obelisks here at Cleopatra’s Needle.