City Itinerary: New York, NY

“Dear New York this is a love letter / To you and how you brought us together / We can’t say enough about all you do / ‘Cause in the city we’re ourselves and electric too / Brooklyn, Bronx, Queens and Staten / From the Battery to the top of Manhattan / Asian, Middle-Eastern and Latin / Black, White, New York you make it happen” — An Open Letter to NYC by the Beastie Boys

I ❤ NYC. I fell in love with the city on my first visit in 2009 and since then I’ve been back two additional times. I was planning on visiting again next month, however lack of money and time resulted in this trip idea having to be scrapped. So instead I decided to dedicate my first Itinerary Tuesday to The Big Apple.

NYC can be difficult to cover in just a few days given the number of boroughs, museums, events, landmarks, etc. that it has to offer. I’m going to do my best to outline an itinerary of what you can do in three days (think of it as a long-weekend vacation), but by all means if you have more time to spend here, this city sure as hell deserves it. New York can also be a bit expensive, so everything I’m going to suggest is either free or easy on a traveller with a budget.

I’m warning you now — when it comes to New York, and life in general, I can be a bit ambitious. I’m a fan of walking Manhattan, so I’ve outlined walking tours of some of my favourite areas. Despite my many trips to the city, I’ve yet to hit up a museum or a gallery (my Art History minor is feeling very neglected these days), so I decided to leave those out of my suggestions. My itineraries will hopefully provide a primer of what you can see in New York on foot and on the cheap.

One thing I would suggest picking up before you do anything else on your first day is an unlimited 7-day Metro card from any subway station (and some convenience stores). It costs about $30 but is well worth it, especially if you get tired of walking everywhere. If you’re only going to be in NYC for a few days, surprise a local by paying it forward and offering them your pass so they can enjoy the remaining time on it.

In light of Hurricane Sandy which ravaged the city in October, I realize that this post may not be the most appropriately timed. However, New York City deserves some loving, so feel free to use these suggestions in the spring or summer, or whenever you may get a chance to visit.

Day 1:

One thing you must do when you’re in New York is see the great Statue of Liberty. If you have some extra funds, I’d suggest you take the ferry that goes to Liberty Island and spend some time staring up her robes from her base. However, if you’d like the chance to see her and not spend any money in the process, catch the free Staten Island Ferry from Whitehall Terminal. The best subway line to take would be the 4/5 to Bowling Green and walk south (you can also take the 1 to Rector Street and walk from there). The ferry runs about every thirty minutes and takes about the same time to complete the route (one-way). Once you get to the terminal on Staten Island, get off the ferry and walk around to the boarding area for your return trip to Manhattan.

After your ferry ride is complete, walk north on West Street to see Battery Park and Ground Zero. Grab a coffee, sit at the site and take a moment to reflect. From here continue walking north on West until you hit Warren Street and turn right. Continue along Warren to Church Street and hang a left. Behind the wrought iron fencing is St. Paul’s Chapel. Completed in 1766, the chapel is a Natural Historic Landmark and the longest continually used building in New York. It contains George Washington’s original pew and more recently acted as a place of refuge and rest for recovery workers during the aftermath of 9/11. Make sure to go inside to check out the memorials (you might want to bring tissue with you if you get emotional).

From St. Paul’s head back south down Church Street until you hit Fulton Street and turn left. Continue walking until you find yourself at the South Street Seaport. Walk around, check out the shops and museum, and grab a snack to refuel (also stock up on water). The next part will take some time to complete, but you’ll be sure to work up an appetite for the greatest coal brick oven pizza outside of Naples — Grimaldi’s in Brooklyn!

But first, you must walk across the Brooklyn Bridge to get there. Walk back west along Fulton to Nassau Street and turn right. Walk a few blocks north to City Hall and you’ll see the pedestrian access to the bridge.

The 6.4km walk across the Brooklyn Bridge is easy but can take anywhere between 1-3 hours to complete, depending on your pace. However, crossing this bridge puts you in quite a unique situation — it’s one of the few places where a plane can fly over a pedestrian who’s walking over a car that is driving above a boat that is above a subway. Picture that and remember it during your walk across the East River.

Once you get to the Brooklyn end of the bridge, there will be a stairway down to street level at Prospect Street. Head west along Prospect to Cadman Plaza West (Old Fulton Street), turn right and continue walking for about five minutes until you reach Grimaldi’s (on your right at Front and Cadman).

One thing I love about Grimaldi’s is that they use San Marzano tomatoes — the only tomatoes that can be used for true Neapolitan pizzas in Naples, the birthplace of pizza. Anyone who follows their lead and uses the only tomatoes designated as authentic are good in my books. Grimaldi’s also won a Food Wars challenge for best pizza in New York.

I go to Grimaldi’s every time I’m in New York. You can only order by the pie, not the slice, so make sure you bring someone to share this amazing pizza with. My suggestion is the classic margherita with extra basil.

After you waddle out of Grimaldi’s you can take the subway back into Manhattan, enjoying a quick fifteen minute stroll through Brooklyn to get to the 4/5 subway station at Borough Hall (when you exit the pizzeria turn left and follow Cadman Plaza West until you see the sign for the subway — it’s just after Montague Street after Cadman become Court Street).

Take the 4/5 into Manhattan and get off at Canal Street. You are now in the heart of Chinatown. Wander around for a bit then head north (either via Center Street, Center Market Place or Mulberry Street) into Little Italy and Nolita (which stands for “North Of Little Italy). From here I’ll take you to a great bakery, Sugar Sweet Sunshine Bakery.

From wherever you are in Little Italy or Lolita, head east to Bowery Street and turn left. Walk a few blocks north on Bowery and look for Delancy Street — turn right. Continue walking until you hit Essex Street, turn left and walk one block north to Rivington Street. The bakery will be on your right at #126. Seating is quite limited inside, but if you have a chance take a few minutes to enjoy your cupcake here (and maybe a coffee) while you take in the ambiance of this cute bakery.

After Sugar Sweet Sunshine, get back to Bowery via Delancy, walking north along Bowery to West 4th Street. Turn left and walk until you see Washington Square Park. Visit the arch, sit, people watch, let all that food digest and enjoy whatever street performers might be present (the last time I was there, there was a man playing a baby grand piano as well as a few dudes doing an impromptu acrobatic show).

If you’re still hungry after all this walking I’d suggest you visit Katz’s Delicatessen in the Lower East Side. You’ll have to backtrack a bit to get there (it’s not far from the bakery), but it will be worth it. This deli was the location of Sally’s famous fake orgasm in When Harry Met Sally (“I’ll have what she’s having!”). To get to the deli from Washington Square Park take West 4th back to Bowery, turn right and continue walking until you reach East Houston Street. Turn left and walk for about two and a half blocks. Katz’s will be at the corner of East Houston and Ludlow Street.

From Katz’s you’ll probably want to go back to wherever you’re staying as you’ve done a lot of walking today. Using your handy Metro card and this map you can figure out how to get home.

Day 2:

The starting point for today will be Greenwhich Village — a place where writers such as Mark Twain, Edgar Allan Poe, E. E. Cummings, Dylan Thomas, Allen Ginsberg, Jack Kerouac and William Burroughs were inspired by their surroundings. The best way to enjoy Greenwhich is to simply wander its streets. Defying the typical grid pattern found in the rest of the city, the streets here take up their own system, having been laid out before the grid method even existed in New York. Grab some breakfast, wander and enjoy the tree-lined streets and townhouses.

After Greenwhich make your way north to Chelsea by walking up Eighth Avenue. At West 23rd Street and Eighth, turn right and stop in front of  the Hotel Chelsea. This historic property, a designated New York City landmark, has seen its share of notorious residents — Bob Dylan, Virgil Thomson, Charles Bukowski, Janis Joplin, Leonard Cohen, Patti Smith, Iggy Pop…just to name a few. It was also where Sid Vicious of the Sex Pistols killed his girlfriend, Nancy, and where Arthur C. Clarke wrote 2001: A Space Odyssey. Steeped in history, this place deserves being the subject of a picture or two. It’s been closed for renovations since 2011, so unfortunately you won’t be able to go inside, but it’s still a must-see for this neighbourhood.

Continue east along West 23rd until you reach Seventh Avenue. From here you have the option of either hopping on the 1 subway going north, or walking eleven blocks to West 34th Street. At West 34th and Seventh is the iconic Macy’s store. Browse around if you like, or simply snap a shot of its famous facade. After Macy’s walk a few more blocks east along W. 34th until Fifth Avenue and you’ll find yourself in front of the Empire State Building. Ticket costs vary ($25 to go up to the Main Deck on the 86th floor; $42 for both the Main Deck and the Top Deck, the highest observation deck in the city), so depending on your budget you can either appreciate the building from the outside or take the elevator up for a view of the city.

From the Empire go north up Fifth Avenue through the neighbourhood of Murray Hill and grab a shot of yourself with the lions outside of the New York Public Library, at the corner of Fifth and West 42nd Street. Turn right onto West 42nd and after a block or two you’ll see Grand Central Station on your left. Give yourself some time inside and don’t forget to look up while you’re in there.

Head back out to West 42nd and walk one more block east to Lexington Avenue. Here you can see the Chrylser Building, which at one point held the record for World’s Tallest Building until the Empire surpassed it in 1931. Turn left onto Lexington and walk north for eight blocks until you reach East 50th Street. Turn left.

Here is the Waldorf-Astoria Hotel — the first hotel to offer room service. Swanky. Now look to your right. Here stands St. Bartholomew’s Church, aka the church that Angelina Jolie blows the floor out of in Salt. From this corner continue walking a few more blocks west to Fifth Avenue and you’ll find yourself in front of St. Patrick’s Cathedral, begun in 1858.

An example of Gothic architecture, this cathedral is sure to wow — it has the ability to fit 2200 people inside and it’s Pietà sculpture is three times larger than Michelangelo’s famed Pietà in St. Peter’s Basilica, Vatican City (okay, so maybe my Art History minor has come to some use then). Wander around for a bit inside, enjoying the stained glass windows and the solitude from the busy streets.

From St. Patrick’s continue west along East 50th and on your left will be the Rockefeller Center and the GE Building. Visit the Top of the Rock for another observation experience, or simply stay at street-level and admire the Art Deco frieze above the entrance to the GE Building, which depicts Wisdom and includes the quote “Wisdom and Knowledge shall be the stability of thy times”.

On the northwest corner of this same intersection you’ll find Radio City Music Hall. If you go in December make sure to check out the Rockettes and the Radio City Christmas Spectacular. Continue along East 50th to Seventh Avenue and turn left. Brace yourself for Times Square. Try to time this for the evening in order to get the most out of the lights.

You’ve done a lot of walking today. You have one more day ahead of you so get back to your room and enjoy some well-deserved sleep.

Day 3:

Your final day will begin with an awesome and affordable breakfast Sylvia’s Restaurant in Harlem. The self-proclaimed “Queen of Soul Food”, Sylvia opened her doors back in 1962. Here you can get two eggs with home fries for only $3.95. To get here take the 2/3 subway and get off at 125th Street. Walk north on Lenox Avenue for about a block and a half and Sylvia’s will be on your right.

After breakfast, walk about a block east along West 125th to see the Apollo Theatre, one of the oldest and most famous music venues in the United States. The Apollo is where Ella Fitzgerald had her first show in 1934, and it also helped start the careers of Billie Holiday, James Brown, Diana Ross & The Supremes, Gladys Knight & the Pips, The Jackson 5, Patti LaBelle, Marvin Gaye, Luther Vandross, Stevie Wonder, Aretha Franklin, Ben E. King, Mariah Carey, The Isley Brothers, and Lauryn Hill.

From the Apollo continue walking east on 125th until you hit Lexington Avenue. Jump on the 4/5/6 subway and head south to 86th Street. Get up to street level, continue south on Lexington to 82nd Street and turn right. A few blocks ahead of you on the border of Central Park stands The Metropolitan Museum of Art. Go inside if you’d like and take a look around, but be sure not to miss a photo-op sitting on its grand stairway in front.

Walk north from the Met along Fifth Avenue until you reach 86th Street Transverse Road. This will take you right into Central Park and to the Jacqueline Onassis Reservoir, the site of many jogging scenes in many movies. Take 86th back until you reach East Drive and turn right. Along this road you’ll pass The Loeb Boathouse. Once you reach Terrace Drive turn right, stopping at Strawberry Fields to pay tribute to the late John Lennon at his memorial. Exit the park at West 72nd Street and in front of you is The Dakota, the building where Lennon lived and was fatally shot outside of in 1980.

From the Dakota continue along West 72nd until Broadway where you’ll be stopping for lunch at Gray’s Papaya, the famous hot dog restaurant where you can get their Recession Special of two hot dogs and a drink for under $5. Gray’s has been a staple of New York pop culture for years, appearing in Nick and Norah’s Infinite Playlist, You’ve Got Mail, How I Met Your Mother, Sex and the City, The Back-Up Plan and even Glee.

After your lunch, walk back east on West 72nd until you reach Eighth Avenue. Turn right and walk south until you reach Columbus Circle at West 59th Street (Central Park South) and turn left, following the southern border of the park. In just three blocks you’ll be reaching one of the best places on earth — FAO Schwartz. Celebrating their 150th anniversary this year, FAO has been in the business of providing toys to many generations of New Yorker’s. It was also here that Tom Hanks played the huge piano in Big (I’d provide a clip of the movie but apparently they have all been taken off of YouTube, so here is a video of some FAO staff showcasing Heart and Soul and Chopsticks).

And that’s it! These are some of my favourite things to do in New York, so I hope you enjoy them as well. Like Grimaldi’s, I also regularly visit Sugar Sweet Sunshine and FAO whenever I’m there (I’m a creature of habit, what can I say), so make sure to check these out if you’re in Manhattan (or Brooklyn).

I hope you have enjoyed this first posting for Itinerary Tuesday. I’d like to end it now with an announcement…

Starting next Tuesday I’ll be providing itineraries for international cities thanks to some help from my friends at Rough Guides! If you’re going abroad and enjoy travel guides like I do (I had to get a separate bookshelf just for my travel-related works, most of which are guides from past trips), then be sure to check them out. They’re available at major bookstores as well as online (check out the Canadian page here, or visit

Thanks Rough Guides and thanks to you for reading!


One thought on “City Itinerary: New York, NY

  1. Pingback: New York, You Make It Happen |

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