New York City – an itinerary for 5 days/4 nights

New York is America’s most recognizable city and world-class in every sense. No matter what your personal feelings about the city—and opinions tend to run strong—it’s a city that everyone should see at least once.

The itinerary below is based on a vacation I took there last week after an inordinate amount of research and planning. Hopefully, someone else will also find it useful. This itinerary was prepared for adults traveling without kids. (Not to say that kids wouldn’t enjoy a lot of it, but you’d have to scale it back quite a bit I think.) It was also prepared with the goal of saving money wherever possible without missing out on a unique New York experience.

I apologize in advance for the length of this post. It’s not very friendly to the Twitter generation.

What you’ll need

I’m not going to write out a detailed packing list here. Anyone can pack given personal preference and common sense. But I will recommend two things. First, bring a very good pair of walking shoes. If you follow this itinerary, you’ll be doing a lot of walking and your feet will feel it. Second, I recommend this Streetwise laminated folding map of Manhattan. It will be your guide to getting to all the locations listed below and includes subway routes. Streetwise also offers a mini subway map, but I didn’t find it very useful.

How to get there and where to stay.

Most anyone reading this on the Internet already knows the basic travel websites to search for airfare and hotels: Expedia, Travelocity and Kayak, etc. I also recommend Voyij, a search website that aggregates information from other travel website, and Travel Zoo, which runs specials and last minute bargains. Keep in mind that if traveling by air, you will be arriving at one of three New York-area airports: LaGuardia (LGA), JFK International (JFK) or Newark, New Jersey (EWR).

I recommend finding a hotel somewhere near Midtown Manhattan just because it’s central to most of the sights. Of course, Midtown hotels can be expensive, but there are deals to be had. I also recommend checking with the Bedbug Registry before you finalize your reservations. Some New York hotels have a notorious problem with bed bugs.

How you’ll be getting around

The first thing you want to do when you arrive in New York is to get a metro pass, your ticket to unlimited subway and bus rides. Forget taxis, they are too expensive for this budget-minded itinerary. New York subways are safe, clean and reliable. (Subway stations aren’t always clean, but they are safe and have character. And taking in the smells of the NYC subways is a part of the experience.) Almost everyone in New York takes the subways, and the subways take you almost anywhere you’ll want to go. A seven-day unlimited ride Metro Card costs $27 dollars. The kiosks in the subway station take credit cards and cash.

Manhattan is fairly easy to navigate, with your folding Streetwise map in hand. The island has a rough grid, with avenues running north-south and streets running east-west. (Broadway angles across the island, cutting diagonally across avenues.) The blocks are rectangular; it takes a lot longer to get from avenue to avenue than it does from street to street. When figuring out whether to hoof it or take the subway, keep in mind that 20 streets equals 1 mile.

DAY ONE: Arrive in New York City and Have a Look Around

Check into your hotel. Find the nearest subway stop and commit it to memory. Figure out which trains run through that station and where the nearest hubs are for transfers. Buy your Metro card, then take your first ride down to Madison Square Park at the intersection of 5th Avenue, 23rd Street and Broadway. Madison Square Park is a very scenic little park in an older section of Manhattan. On the southwest corner of the park is the Flat Iron Building (left), one of New York’s most photogenic buildings, rivaled only by the Empire State and the Chrysler. Inside the park is the trendy fast-food spot the Shake Shack, where Manhattanites wait in line for top-quality burgers, fries and custard shakes. Get some food and eat it in the park. You are hungry, after all, since airlines don’t feed anyone anything these days. Hopefully you’re not so hungry that you can’t stand the wait—that line can be daunting.

Next, stroll down Fifth Avenue and look at the storefronts. Enjoy the view of the Empire State. Take a right turn when you get to 29th Street and see The Little Church Around the Corner. As the story goes, in 1870, Joseph Jefferson was trying to arrange a funeral for a friend, the actor George Holland at one of New York’s stuffier cathedrals when the pastor there told him to try the little church around the corner “they do that sort of thing.” The name stuck.

When you get tired or bored of walking, hop on the subway and ride to Rockefeller Center (6th Avenue around 50th Street). Walk around the center and look at the sculptures and fantastic art deco architecture, then get tickets to the “Top of the Rock,” the observation deck on top of Rockefeller Center’s tallest tower. (Tip: there are always men near the ticket booth passing out $2 off coupons. Plan ahead and you can Google a $3 off coupon.) The Top of the Rock is both cheaper, though still a bit pricey, and more convenient than the Empire State. It also arguably has better views, with views of the Empire State and Central Park. (Unfortunately, the view of the Chrysler Building is partially obstructed. You can’t have it all, I guess.) From the observation deck, sit and enjoy the view as well as exceptional people watching and watch the lights come out in the city below. Off in the distance, squint and you can see the Statue of Liberty.

Once you’ve had your fill of the city, head back to the subway and ride to Union Square on 14th and Park Avenue. This park is very lively at night. Walk just south down Park Avenue to Max Brenner Chocolate Bar, a chocolate-themed restaurant for dinner (optional) and desert (required). When we visited, the service was spotty. The kitchen took forever to prepare our desserts, and both of our dessert orders were slightly off, but what we did get was delicious, so it’s hard to complain too much.

DAY TWO: Hike through and around New York, then take in a Broadway show

Wake up and make your way to Times Square. At 200 W. 44th Street, just east of 7th Avenue, buy a bagel and schmear at Times Square Bagels, then take it to the plaza and find a place to sit and eat your New York breakfast while you look at the giant signs and people watch.

When breakfast is over, hop on the subway and ride to the station at 81st Street and 8th Avenue, near the Museum of Natural History. This will be your starting point for a stroll through Central Park. From the 81st Street entrance, head east into the park to the Belvedere Castle, up on a hill overlooking the Delacorte Theater. This quirky little building is a neat landmark. From there, make your way through the Ramble, a wild area in the park that will almost make you forget entirely that you’re in a major metropolis. Move generally south and southeast until you come to the Loeb Boathouse on the eastern side of The Lake. If you time it just right, you’ll arrive at the Boathouse at 10:00 am, just as rowboat rentals begin. Rent a boat and row through the Bow Bridge (left) to the western half of the Lake where the best views of Central Park can be had. Return the boat and walk over to Bethesda Terrace and Fountain, on the south end of the Lake. Walk down the tree-covered Mall to the south, then cut west to the Strawberry Fields memorial adjacent to the 72nd Street subway station, and near the spot where John Lennon was shot and killed.

Ride the subway to the Port Authority subway station, then head east on 42nd Street toward the Hudson and Pier 83. You’ll pass by a hot dog restaurant as well as several street vendors. Now might be a good time to have a New York hot dog and/or a pretzel. At Pier 83 you can purchase tickets for the Circle Line boat tour around Manhattan. Though it’s a touristy thing to do, I recommend the boat tour because it’s a good way to see all five boroughs from the water and to get a sense of the geography of the city. The tour guides are also pretty informative. (Tip: If you buy a Entertainment Book before you leave, there’s a buy-one-get-one coupon for the Circle Line tour that will save you up to $37 dollars. There are also BOGO coupons for several other museums and attractions.) The Circle Line boat tour also provides nice views of Ellis Island, the Statue of Liberty and the Brooklyn Bridge, among other sights. If you want to go for the super-cheap option, take the Staten Island Ferry from the South Ferry dock in lower Manhattan. It’s free and offers nice views of lady Liberty.

After the boat tour, you may want to wander Times Square before seeing a Broadway show that evening, but avoid eating there. The food near Times Square is mostly overpriced chain restaurants filled with tourists. When you get hungry, head west to 9th Avenue and pick from one of the many ethnic restaurants in Hell’s Kitchen. (A couple of recommendations: Empanada Mama’s and Pam Real Thai.) Times Square is flashy and bright and worth seeing, but it does get old quickly. Definitely see the three-story Toys R’ Us store with an indoor ferris wheel. Unfortunately, most of the stores are just flashier versions of stores you would find in your typical American mall. But it’s still fun to wander around and look at the lights.

A few words about the Broadway shows. Everyone knows that you can get discount tickets at the TKTS booth in Times Square based on shows that haven’t sold out that day’s performance. The downside is that you have to wait in line and are at the mercy of random availability. It’s a better bet to go ahead and purchase your tickets ahead of time, and websites like Broadway Box and Theater Mania offer some of the same discounts that you could get at TKTS, with advanced seating and no waiting in line.

It’s also worth researching which shows are good. Look for recent Tony Award winning productions and avoid the long-running shows that may be on their third or forth cast change and may have gotten stale. Also be aware that some shows might cancel before you get there if they aren’t as successful as hoped. (For example, the SpiderMan musical—with music by U2—set to open this fall is purportedly in trouble and may have the plug pulled.)

After your show, head back over to Hell’s Kitchen to Kyotofu, a cool little desert restaurant where most of the treats are tofu-based, and all of them are delicious. It’s the kind of restaurant you might only find in New York, so just try it. You’ll like it. Order different desserts to share or split the three-course prix fixe dessert selection.

DAY THREE: Herald Square, the Village and Chelsea

Grab breakfast somewhere (why not have another bagel? It’s really true that the bagels aren’t as good anywhere else.) and then head down to Herald Square (roughly 34th St. and 6th Avenue) for shopping, window or otherwise. Macy’s is a bit overrated, in my opinion, but it’s the flagship store. Check out H&M, a store selling European fashion on the cheap. Wander around and window shop.

Around lunch time, take the subway to the East Village, catching a transfer to L subway train and get off at 1st Avenue and 14th Street. Walk a few blocks south and eat lunch at one of the Momofuku restaurants: Momofuku Noodle Bar or Momofuku Ssam. These restaurants were created by the iconoclastic New York chef David Chang. The former specializes in perfectly prepared ramen noodle dishes, the latter serves what’s been referred to as “Asian burritos.” Both restaurants are small, casual and moderately priced and neither takes reservations. (A typical noodle bowl at the Noodle Bar will run about $14 and is very satisfying.) Chang does have a more upscale restaurant, Momofuku Ko, that takes reservations six days in advance and offers a six-course tasting menu, but get your reservations early because it only seats 12. You’ll also need directions because it’s nearly impossible to find. Momofuku’s food is very flavorful and Chang is widely recognized by food critics and other chefs as being something of a culinary genius. There is also a dessert bar called Momofuku Milk Bar that serves something called crack pie (really) that is reportedly addictive.

After lunch, get back on the L train, but head west to begin your tour of Greenwich Village. I printed a walking tour from the New York times and found it worked well. If your early enough you can have dinner from the famous dosa cart in Washington Square. Another cheap and tasty option is to get falafels from Mamoun’s a few blocks down Macdougal Street (only $2.50 per falafel. The humus is the same price and also tasty.) Or, if you want to go more upscale, try Po, Mario Batali’s Italian restaurant in Greenwich Village. Wander into the shops on Bleeker Street; for my time and money, it’s the most interesting place to shop in the city. Have a mediocre cupcake at the Magnolia Bakery just to say that you did (but don’t expect much).

If you have time, go see the newly opened park at the High Line in the meatpacking district. (I didn’t see it, but wish I had. The two avenue walk to and from the nearest subway station seemed daunting at the time.)

For the evening’s entertainment, head over to Chelsea to catch a show at the Upright Citizen’s Brigade Theater. The UCB relocated from Chicago and brought “long-form” improv with them. UCB alum include Amy Poeler and writers for 30 Rock, Conan O’Brian and Letterman. Shows are scheduled almost every night and are cheap and fun. Check the calendar on the UCB’s website then email in your reservations. The theaters they use are tiny so you may not get in without a reservation and without arriving a half-hour early.

DAY FOUR: The Museums

I highly recommend that you start your day in The Cloisters, one of New York’s best and least-visited museums on the northern tip of Manhattan. Perhaps because it’s so far away from the usual tourist spots, The Cloisters doesn’t get much traffic. Frankly, that’s a good thing. This Met outpost is set in Fort Tryon Park on a lush green hill overlooking the Hudson River. The building itself incorporates pieces of five different medieval monasteries and the building houses a very impressive collection of medieval art, presented in context among Gothic and Romanesque architecture and tranquil gardens. Despite being clear on the other side of Harlem and Washington Heights, it’s really only about a twenty-minute subway ride away from Midtown. Get off the subway and you can either take a quick bus ride right to the museum’s entrance or take a ten-minute walk through the park. Entrance into The Cloisters (recommended donation $20) also gets you into the Metropolitan Museum.

When you are done with your visit to The Cloisters, take the subway to 52nd Street and Lexington Avenue where you will have lunch at Le Relais de Venise, a French restaurant that serves exclusively “steak frites,” i.e., steak and fries. There are five such restaurants worldwide (Paris, Barcelona, two in London and this one in New York). Service is very straight forward: tell your server how you want your steak prepared (blue, rare, medium or done) and what you want to drink. She’ll bring you sliced, tender steak with a tangy gravy sauce and perfectly cooked fries. Clean your plate and she’ll bring you a second helping. The set menu, sans drink, will cost you $24 per person, but it’s good food and a good experience. The dessert menu is varied and tempting, so order dessert also.

After eating at Le Relais de Venise, take the subway north to Central Park East and the Metropolitan Museum. The Met is way too much museum for one day, but too amazing to skip altogether, so you’ll have to pick what you want to see. One could spend a week in the Met and not see everything. The Egyptian exhibit is very popular. My favorite was the European painting exhibits where it’s room after room of Monet, Van Gogh, Manet, Degas, Cezanne, etc. It’s overwhelming, but in a good way. Central Park West around the Met is also known as “museum mile.” You may also want to check out the Guggenheim or the Whitney. There’s more museum than there are hours on this itinerary.

Once you’ve seen medieval art (The Cloisters) and classical art (The Met), it’s time to venture over to the MoMA for your dose of modern art. (TIP: If museum day falls on a Friday, the MoMA is free after 4:00 pm. You’ll have to stand in line to get in and the museum will be crowded, but you’ll save $20 per person.) Take the elevator to the top floor (special exhibits) and work your way down one floor at a time, watching as the art gets more experimental and absurd. Take in your fill of Liechtenstein, Warhol, Rothko and Mondrian. Ask yourself, “is this art?” and watch other people asking themselves the same thing.

On the southeast corner of 53rd Street and 6th Avenue the line for a certain food cart starts forming at 6:30 even though the food doesn’t get served until after 7:30. Once the halal cart (unofficially known as “Chicken and Rice”) starts serving, the line moves quickly. The cart is open all night long and the line never goes away. Six dollars buys you a plate with rice and grilled chicken or gyro meat, and a little bit of pita bread, served with a tangy white sauce and a very spicy red sauce. One plate is enough to feed two hungry adults if you care to share. It’s kind of a communal New York experience to stand in line and then eat your food on a nearby bench.

You’ll have time after dinner to walk around the city. If you feet are tired (and they will be), you might want to take the subway down to the Angelika Film Center just a block east of Houston and Broadway. Or you could stroll around SoHo (south of Houston Street), then wander over to Little Italy for a cannoli and some gelato.

DAY FIVE: Architecture and pizza.

In the morning, head over to Grand Central Station. This famous train station in the heart of Midtown still serves travelers. The Beaux-Arts architecture is both amazing and iconic. If you’re a fan of old movies, Grand Central is a must. From Grand Central, walk up to Saint Patrick’s Cathedral, an amazing Gothic cathedral just a block away from Rockefeller Center. Walk past the shrines to various saints and take in the Cathedral’s dark and reverent atmosphere. After leaving Saint Patrick’s you may want to walk up to the FAO Schwartz flagship store on 58th Street and 5th Avenue. The store has been upstaged by the Toys R’ Us on Times Square, and also inexplicably got rid of their iconic singing clock, so it’s not what it once was. The Plaza Hotel across the street is also worth seeing. Take the subway over to Bryant Park and walk through the main branch of the New York City Public Library, another amazing Beaux-Arte building. Take the elevator to the top floor and covet the main reading room, wishing that your library at home was as nice. Be sure to go to the children’s reading room in the basement where, inconspicuously enclosed in a glass case you’ll see the original Winnie the Pooh, Piglet, Eeyore, Kanga and Tigger that inspired A.A. Milne.

By this point, you’re going to be hungry. Take the subway (the 6 train) to the Spring Street station, then head a couple blocks east to Lombardi’s, the oldest pizzeria in the United States. You may have to wait to get a table, and the service isn’t always speedy either, but the coal-oven fired, thin crust Neapolitan pizza is quintessential New York pizza.

Finish your souvenir shopping and pick up your luggage at the hotel—you have a plan to catch.

A few words about this itinerary: I purposely left off a few things. There are no sporting events, for example. I would have been more tempted to see a game at the old Yankee Stadium, but I’m not a Yankees fan (or a Mets fan) anyway. If baseball’s your thing, you’ll have to find a way to squeeze it in. I didn’t visit the Statute of Liberty or the Empire State and made do with the views from the Circle Line and Rockefeller Center, respectively. I also didn’t get to some Manhattan neighborhoods (e.g., Harlem, the Financial District, Tribeca) at all. If I had more time, I would have enjoyed exploring Brooklyn. Ground Zero shows up on a lot of travel guides as a “must-see” destination, but my understanding is that in its present state, it’s simply a construction site.

If you’ve made it this far, feel free to critique this itinerary and offer your own suggestions of what to see, do or eat in New York City.