Originally post ed Jan 2019 and updated July 2020
I have lived through many life stages in Manhattan and have experienced the glories of this city in all its forms. I moved here more than 20 years ago when I was in my 20’s and single. At that time, I spent a fair amount of time in bars, at dance clubs and on the volleyball court. Later, when I got married, my husband and I practically made a job out of eating our way through ALL of the Manhattan restaurants. Then, with small children, my goals shifted a bit once again. We spent many long days playground hopping our way around town. Now, my children are teens, and we are experiencing yet another side of the many facets of this 13-mile long island.
I guess what I’m trying to say is we know our way around NYC a bit! With all of these experience in mind, I have attempted to put together a few comprehensive itineraries for both the tourist in our great city and for the resident on a staycation. If you are new to NYC start with our beginners guide. If you are a pro – start here.
A Sample NYC Itinerary for the Experienced New Yorker
This 5 day guide to NYC for the pro is intended for the person who has already strolled down 42nd Street and been to the top of the Empire State Building. Even as resident New Yorkers, one of the benefits of living here is all of the access to culture and fun activities. This 5 day guide to NYC for the pro is good for the person who lives here and is having guests for a few days. Or, for the person coming to NY for the 3rd or 4th time that hasn’t really quite gotten all the sights under their belt. It’s good for the NY resident who just woke up on a Saturday morning and wanted a little change in their life.
Our recommendations are meant to be enjoyed in sections, as they geographically make sense. Each day is meant to cover an area of Manhattan that you may not yet have fully explored. Restaurant recommendations are intended to be “middle of the road” places that are popular with the locals. Want more NYC? Also see our guides to the different neighborhoods of Brooklyn. We have covered Prospect Park, Williamsburg, DUMBO, Greenpoint, Fort Greene and Bushwick.
Day 1: Scavenger Hunt Day
If you have read my blog before you know I love a Scavenger Hunt. It’s as great way of digging a little deeper into the Big Apple. As resident New Yorkers, we have been doing them for years and we always learn something new. I love Watson Adventures or Pogo Events. Watson Adventures offers neighborhood hunts, museum hunts and the very popular Murder at the Met hunt. Most of their hunts are on Saturdays and should be booked at least a few days in advance.
Pogo Events offers themed hunts like the Game of Thrones Scavenger Hunt, the Dog Friendly Scavenger Hunt, and an Amazing 90’s Scavenger Hunt. Their hunts fall on different days of the week, as they are frequently affiliated with a theme or a holiday. Also, sometimes they offer prizes. Combine the 3-4 hour hunt with a meal in whatever neighborhood you end up in. You will have filled the better part of a day with fun facts and good food.
Day 2: Ferry to DUMBO (Photo Op Day!)
Start your day with a little help from NYC’s rapidly improving ferry service. Taking the ferry allows you to see the iconic NYC skyline from the Hudson River as well as the Statue of Liberty. The ferry goes a few different places but we recommend a ride to a super cool part of Brooklyn – DUMBO. For just $2.75 each way, you can leave from Wall Streets Pier 11 (see map of route on left) and be in DUMBO in under 15 minutes.
Once you hop off in Brooklyn, see my DUMBO highlights tour here for food and shopping recommendations. You can spend the better part of a day in Dumbo or in the nearby Brooklyn Bridge Park. Whatever you do, make sure you have your camera ready! Sitting between the Brooklyn and Manhattan bridges, with spectacular views of downtown NYC, this neighborhood has the best photo ops in all of New York. Tip: Try not to go on a weekend where the crowds will be at their worst. After braving the crowds in DUMBO, hoof it back to the island on foot over the Brooklyn Bridge. If you time your Brooklyn Bridge crossing with the sunset, even better.
Eat at:
The pedestrian path of the Brooklyn Bridge will let you off right in the financial district. Just a few blocks away, Da Claudio at 21 Ann Street for a wonderful Italian meal courtesy of the Marini family. Or take the short walk across the narrowest part of the island to one of Tribeca’s many great restaurants. We like Tiny’s at 135 West Broadway for excellent everything, Max Restaurant at 181 Duane Street for good home cooked Italian, or Gunbae Tribeca at 67 Murray St. for Korean BBQ and Karaoke.
Day 3: Explore Harlem – The Double Decker Bus Tour
Start your day on 8th Ave and 42nd at the Double Decker Bus Tours for the less popular tour of uptown and Harlem. If you are an NYC pro, this tour will surely entertain you. It covers less popular spots such as Lincoln Center, Grants Tomb, parts of Colombia University, Apollo Theater and Central Park. You can hop on and off at will, but here are my recommended stops:
- At 110th Street in Morningside Heights, hop off at the Cathedral of St. John the Divine the cathedral of the Episcopal diocese of NY. If you happen to be there for the First Sunday in October, don’t miss the Blessing of the Animals where all creatures great and small arrive to be blessed. Prior years have included alpacas, cows, geese, and even a camel! However, if you are not lucky enough to be there early October, definitely explore the Ten Secrets of St. John the Divine here.
- After getting back on the bus, continue up to 125th street at the Apollo Theater. Wednesday nights at 7:30 is Amateur Night at the Apollo and a great way to spend an evening, especially with teens. Just two blocks away, you can have a meal in one of the Harlem greats, Red Rooster, Sylvia’s Place, or Harlem Shake all within a 3 block radius.
- Take the bus back downtown along Museum Mile and consider stopping in one of the many great museums along the way. If you aren’t an NYC beginner you have probably been to the Met. Try some of the less obvious but equally good spots include the Museum of the City of New York, The Jewish Museum, The Guggenheim, or the Frick. Museums are generally open until 9pm on the first Friday of the month and close around 6pm on other days. Check hours for each museum individually.
Shop at:
For fun gift shopping before heading home, hop off the bus around 80th street and head over to Madison Ave. Our favorite is E.A.T. Gifts at Madison and 80th. You are sure to find something fun and quirky for every age!
Day 4 – Lower East Side to Upper East Side
Lower East Side
- During the rise of industrial America, more than 70% of all immigrants in the US came through New York City. Start your day on the Lower East Side with a tour through the Tenement Museum to learn more about this time in history. The museum also offers tickets for a good neighborhood walking tour if you don’t want to go it alone. If you do prefer exploring without a tour group, hit the following highlights on your own.
- Trade culture and knowledge for some good old fashioned fun. Just two blocks away are two great spots you shouldn’t miss. First, Economy Candy on Rivington is the kind of old fashioned candy shop you dream about. Then, Two Bits Arcade on Essex is a great place give kids a break from all that walking.
- Around the block, on Allen St., check out the Bluestockings Bookstore and Activist Center. You will be treated with a comprehensive education on feminism, activism, and LGBTQ rights.
- Getting hungry? Hit one of my favorite spots. Russ & Daughters at 127 Orchard St. for bagels and schmear. The famous Katz’s Deli at 205 E. Houston for pastrami sandwiches as big as your head. Or, Vanessa’s Dumpling House at 118A Eldridge St. for some of the best dumplings you’ll ever have.
- If you haven’t had your fill of art on this trip yet, pop into the never crowded New Museum on the Bowery. Manhattan’s only dedicated contemporary art museum can be seen in an hour and is worth it for the building itself.
Upper East Side
- In the afternoon head uptown to enjoy a little relaxation in one of NYC’s little known great parks, Carl Shurz Park. Hop on the nearby F train at 2nd Ave and switch to the Q train at 34th St. Take the Q train to 86th street and wander over the the east river. Carl Shurz Park is at 86th and East End Ave. A stroll along the river allows for some great views that you may not have yet appreciated. For one, the Roosevelt Island lighthouse (did you know there was one?), or the Robert F. Kennedy bridge (formerly the Triboro Bridge). Also, Randall’s Island, and the official residence of the mayor – Gracie Mansion.
- Consider a Broadway show to top off your day. You can purchase last minute tickets for many great shows on Todaytix.com . Better to download the app on your phone and buy tix right from the park.
Day 5 – Discover Washington Heights
Today we explore the hilly, northern tip of Manhattan known for it’s beautifully preserved pre-war buildings, and good Dominican food.
Fort Tryon
- Take the A train to 190th Street for a morning in Fort Tryon Park and the Cloisters. Landscaped to look like a grand country estate, Fort Tryon park has 67 acres of gorgeous gardens, rolling hills and stone archways. Walk along Margaret Corbin Drive in the park to The Cloisters a Manhattan must-see. A castle built from the stones of French cloisters, this gorgeous building hosts the Met’s collection of European architecture, sculpture and decorative arts. Don’t miss the unicorn tapestries. On your way out of the park, rest your legs at the New Leaf Cafe for beautiful terraced views of the park.
The Little Red Lighthouse
- After your park visit, gear up for a 35 min walk down to Fort Washington Park. Here you will pay homage to NYC’s best kept secret The Little Red Lighthouse. If you have kids with you, grab a favorite of our house, the The Little Red Lighthouse and the Great Grey Bridge. To get there, walk south from 190th street and west to the Henry Hudson Parkway. Cross over the parkway and follow the path to the Hudson River Greenway. A 10 minute walk on the winding downhill path and you will realize why this place is such a secret. The Hudson River Greenway runs along the river all the way down to Battery Park. Depending on how much time is left in your day, you could spend hours here.
- Note a few complications. Access points to and from the park are only at 181, 168, 155, 145 and 125 streets. So if you start walking south, make sure you are committed and make sure you enter the park at one of the above streets. Also, food options are limited. There are a few kiosks around but not really until you get further south. There is a restroom a little south of the lighthouse near the tennis courts.