I spend a lot of time in the city, and I've learned a lot about traveling around and getting the most out of my visits, so here's some advice for you!
1. What should you book ahead? Obviously your hotel. Especially in the city book ahead. Do you have to book far ahead? No, just ahead. And make sure you find a place that suits your trip and mode of travel. And, always book ahead for special events; sports, concerts, etc. Just like you would if you went to an event as such locally wherever you live.
Other than that, it all depends. Time of year, day of the week, whether it's a holiday or not, is it a school break? All questions to ask when doing regular activities in the city. If it's a random Wednesday in March, you can probably walk into just about anything and get a ticket. Know the high times. Tall buildings, anything World Trade Center, small museums, immersive art, bus and boat tours, and so on. If you want to go up to The Edge at Hudson Yards, you probably won't need to book in advance unless it's a very busy day. However, if you want to do the city climb, book that in advance. Rockefeller Center you can probably walk in and go to The Top of the Rock, but the studio tour is normally booked. Look it up. Know how it works in advance. Governor's Island is a park, but it has a spa and glamping. You can always catch the ferry, but book activities in advance.
Also, most restaurants you can walk right in most of the time and not worry about a reservation. However, if you want to go to a particular high end restaurant, book ahead. If you want to do afternoon tea and the Russian Tea Room, book in advance. If you want to eat at the Rainbow Room, book far in advance. If you want to try some great food in Chinatown or Little Italy, Hell's Kitchen or Koreatown; you'll most likely find great food without a reservation. It all depends on how fancy you wish to be.
2. What not to book. Parks are public and free. I can't advocate this enough. You really get the sense of a neighborhood's personality when you visit a park. New York City has some of the most amazing parks anywhere. Central Park alone will keep you busy for days most of the year. However, Pier 17 and Pier 57 both have rooftop parks, which is something everyone should see. There's Little Island Park, which is truly unique. Most of the waterfront along the rivers is parks. Battery Park, Domino Park, the Elevated Acre, Prospect Park, Madison Square Park, Columbus Square Park, Flushing Meadows Park, Governor's Island. They are all amazing, so go and see.
So many times, we think that places will be full and they just aren't. I have many places that I go that should be crowded, but most of the time aren't. I love the New York Botanical Gardens. They always have something going on and it's always beautiful. I've never found an unmanageable crowd there. It's great. Roosevelt Island is another great spot. Quiet, beautiful, easy to get around and plenty to see. You can also ride the tram over for the view. Food is good. It's all good with a free red bus to get around on.
I love to walk those bridges. All of them but the Verrazzano Narrows Bridge are walkable. The views are always second to none, and the experience is really educational and fantastic. They are a mode of public transportation and it's free. You get some exercise too.
Getting around can be an activity. It's how my YouTube Channel started. Some trains are underground, some are raised with a view. Some pop up out of the ground like a roller coaster. Some of the stations have entertainment. There's one with an underground market. They have mosaics to look at and art displays in some of them. There's a restaurant at Herald Square. Michelin Star. Don't overlook the entertainment value of your mode of transportation. Like I said, there's an aerial tram at Roosevelt Island. Take a ride on a NYC Ferry or the Staten Island Ferry. Transportation can be fun.
My point is, remember to go with the flow. When you stop by to see one thing, you might discover 5 more things you find interesting. Don't plan too much. Take time to smell the coffee. It's everywhere.
3. When to go and when not to go. This one is for planning folks. New York has plenty of activities and seasons. They have more seasons than the rest of us do. They have the usual four. They also have baseball season, hockey season, basketball season, football season, US Open season, Christmas season, cherry blossom season, ice skating season, election season, several playoff seasons, concert season, fashion week season, fleet week, 4th of July, and vacation season. That's a lot of seasons, and they each effect the prices and availability both hotels and activities. I don't fly to New York, but I'm guessing it effects that too.
New York is one of the busiest cities on Earth. Built on pure capitalism, events and holidays are almost always happening. And, if that doesn't get you, then Valentine's Day, St. Patrick's Day or the weekend might make the difference between a nice trip and an unaffordable nightmare. Check ahead before booking that flight or hotel. And, don't drive in the city. Can't stress that enough. Parking is expensive and impossible. There's a congestion charge south of the park and bridge tolls. Traffic is crazy. One way streets are one of the biggest deterrents I've ever encountered. Don't drive and always check ahead for a holiday or special occasion.
Recently, I went to Chinatown on a random Tuesday and it was Lunar New Year. Rookie mistake, and I should have known better. The more random the day, the easier your trip and your bank account will be. I almost always visit the city on a weekday. Trains run regularly as do the subways, buses and ferries. It makes life easier.
The only exception to that rule is early in the week and primarily Mondays. Check ahead. A lot of museums and other attractions are closed on Mondays.
