3 Questions to Answer Before Planning Your NYC Vacation

The decision is made- You Are NYC Bound! 4 Days and 3 nights in the city that never sleeps. New York City is the most amazing city in the world. There are endless things to do, see, experience, eat, and be wowed by. So now to the planning.

Spoiler alert: it can be overwhelming. Hundreds of websites await to provide advice, to take your money, and to tell you exactly how you should spend your precious hours in the city that never sleeps.

Having helped dozens of people plan their trips to NYC, I now always start with the same 3 questions. How you answer each one will influence the rest of your planning.

#1: Subway or Taxis

NYC has an amazing public transportation system, but it is not for everyone. For some, it seems to confusing or risky (there are some interesting characters at times). For others, it seems like an adventure and more of the “real NY” experience.

The reason I ask this question is less about $$ and more about time. Using the subway will save you time in the majority of scenarios. It can also save you money as hotels in Queens, Brooklyn, and Harlem are cheaper than Manhattan.

Tips for the Taxi crowd--NYC is the epicenter for car services like @Uber, @Lyft, and @Gett. If you are new user, then you can get free credit for signing up. PRO TIP: I can send you a link that will get you credit. After taking a ride, you can give credit to someone else in your group. This will give you more credit and then they can credit another group member!

Tips for the Subway crowd--The subway runs 24 HR/day, but service does slow in frequency after 11pm. You should definitely buy the 7 Day Unlimited card for $32, as it will save you money. PRO TIP: the Google Maps App has options for public transit, walking, and biking in NYC. Use the app when trying to figure out how to navigate the city.

#2: Shoe string budget or the entire piggy bank

Fact- NYC is expensive. Fact- you can have a good time on a budget. Your budget will drive your planning. You can spend less by booking a hotel outside the city, packing snacks, and walking rather than paying for transit. Yet, each of things will also cost you valuable time.

Some of the best things in NYC are free (IE: Central Park, the Brooklyn Bridge, the Metropolitan Museum of Art, and the SI Ferry for views of the Statue of Liberty). On the flip side, some of the best in NYC definitely cost money (IE: Broadway shows, incredibly restaurants, Top of the Rock, and visiting the Statue of Liberty or Ellis Island).

My advice: strike a balance. You don’t to miss out on great food, fantastic shows, and top notch historical attractions. You also don’t want to stay in New Jersey or Yonkers. A return trip to NYC costs money as well. So ensure you have the budget to do all that you want prior to booking.  

#3: Times Square or the Real NYC

Having lived in New York for so many years, I have a definite bias when it comes to this question. Times Square is amazing to visit, but it is not really NYC. It is Disney World located in the middle of Manhattan. You definitely need to check it out…but only for a day. Get tickets to a Broadway show, see the lights at night, grab a drink at sunset in the View Restaurant, and soak in the energy of thousands of tourists.

Other than that, I don’t have advice for those wanting to hang out in Times Square. The food is terrible and overpriced. It is super crowded with people that have no sense of direction or awareness of others. The hotels are crazy expensive for a very small room.

My advice: dedicate one day/evening to Times Square and give the rest of your time to the best NYC has to offer. Take in the tourist attractions, walk the Brooklyn Bridge, eat in small restaurants located down an interesting side alley in the West Village, hang out in art museums on the Upper East Side, catch a Yankee/Mets game, hunker down in a dive bar in the East Village, score an amazing brunch in the Lower East Side, and try as many pizza joints as possible.

Once you have answered these 3 key questions, then you are ready to plan your trip! Remember- you can’t go wrong. Adventure, great food, and interesting people await around every corner.