Your New York City trip

Starts Here!

I can help you plan a short layover, a long vacation and everything in between.

New York City has so much to offer, but for many travelers it feels overwhelming and they need help coming up with a plan. You can hire me to plan your trip or you might use the resources here to do your own planning. Either way, you have to start somewhere. This page addresses the questions I get asked most often as people begin their NYC travel planning process.

I recommend that you start here:

When to Start Planning

The ideal time to begin planning your trip to NYC trip is 8 to 10 weeks ahead of your desired travel dates. This will allow you to have a greater selection of flights and hotel rooms available, which will likely also translate to better prices. It will also give you the best selection of events, show times, restaurant reservations, etc.

As your travel date approaches fewer rooms will be available, the best seats at shows purchased and the most popular reservation windows already booked. In fact, some shows and restaurants are so popular that if you don’t secure seats right when they become available they fill up quickly. That being the case, if you have your heart set on dining at a particular restaurant or attending a specific show, do some research to know when seats become available. It is common for reservation windows to open 2 weeks, 21 days, or 30 days in advance (every restaurant is different) and when they do, you need to jump on it!

For example, on a recent trip to NYC I wanted pre-theater dinner reservations at PEAK in Hudson Yards. Their reservation window opens 21-days in advance and so I set a reminder and an alarm on my phone for 9 a.m. the day the reservation book opened to secure my table. Just 30 minutes later, all the dinner reservations for that date were completely taken. Do your research and plan accordingly.

Last minute trips

If you get the opportunity to go to NYC on short notice (I've planned trips with a 36 hour notice!) you can still put together a great trip. You just need to be flexible, both with your budget and your preferences. Because NYC is such an enormous city, there are plenty of amazing restaurants, things to do, and quality places to stay. If you’re planning a trip on short notice, you may not get your first choice, but there will be plenty of other good options.

NOTE: If you hire me to create a custom itinerary for you, please note that I cannot guarantee itineraries less than two weeks prior to your travel date.

The Best Time to Go

Each season has its advantages, when visiting New York City. The winter is by far the most economical time to visit. If you want to maximize your budget, I recommend a winter trip. Yes, it will be cold, but how much is it worth to you? You have the potential of saving hundreds of dollars on your hotel, airfare and on theater tickets. As an added bonus, crowds are greatly reduced so you will spend less time standing in lines.

The spring and fall are the most desirable times to visit NYC. Temperatures are mild and though there could be some rain, there is also plenty of sunshine making it a lovely time to walk neighborhoods and enjoy the many parks. In my opinion, the two best months to visit NYC are May and October, just prior to and after the peak summer travel season.


Honestly, summer is my least favorite time to be in New York City. Not only are you contending with an influx of people, but it can get hot and uncomfortably humid. That said, for many people-especially for families-summertime is the only time available to take a vacation. Undoubtedly, summer is the most vibrant time to visit the city. It offers the most opportunity for outdoor and adventure activities. In addition, the days are longer, giving you a chance to squeeze even more into your trip.

Where to Stay

If it is your first trip to the city I recommend staying in Manhattan. It has the most popular landmarks and sightseeing and because of that, it will reduce the amount of time you spend on the subway or in a car getting around. I like to maximize my time in the city and staying in Manhattan is one of the best ways to do that.

Finding a hotel in or around Midtown, between 14th and 59th streets is most convenient. Although many clients stay in Times Square and the Theater District with no complaints, I recommend slightly quieter neighborhoods like Chelsea, The Flatiron District and even a bit more north in Lincoln Square. The reality is you’re not coming to New York City to sit in your hotel room but having a safe, quiet, and comfortable place to rest after a long day of exploring will vastly improve your experience.

Keep in mind, if you stay in an area far south like the Financial District or more north on the Upper East or West Sides, you’re not likely to swing back by your hotel mid-day to grab a coat or change your shoes. You’ll want to take what you need for the day with you since going back and forth will significantly cut into your time sightseeing. I frequently stay in Chelsea, bordering the Flatiron, and it is perfect. Being just one block from a subway stop enables me to come back to my room during the day to drop off packages, grab a jacket and use the restroom. For seasoned NYC visitors, I absolutely recommend venturing out a bit (prices are often times better) but for a first time visit a location in Midtown is ideal.

Determining Your Budget

If budget is a strong consideration for you when planning a trip (which it is for most people), I recommend determining your budget before you start planning. A trip to New York City can be expensive, but it doesn’t have to be. I’ve planned many trips to the city on a shoestring budget.

When creating a budget keep these things in mind:

Airline Tickets

Airline tickets and lodging will be most affordable if you purchase them well in advance when there is a greater selection available. They will also be much less expensive in the winter months. January through early March. I’ve flown from the West Coast to the East Coast, round trip for less than $250 and split the cost of an apartment with a friend for less than $100 per night (my share). These trips were all in January through early March.


Apartments (through Sonder and Airbnb) can be a cost-effective way to travel since you can prepare your daily coffee, an occasional meal or bring takeout back to the apartment (saving on tax, tip and expensive beverage charges).


Transportation will be the cheapest (and often is the most efficient) if you rely mostly on walking and taking the subway. Each subway trip is only $2.90!

The occasional Uber or Lyft ride can add up quickly, however, they are more cost effective if you’re sharing them with another person in your travel party. Nothing beats the convenience of being picked up at your doorstep and being dropped off at the doorstep of your destination.


Food is another primary budget item to consider when traveling to NYC. You can find meals in the $10-$15 range (grocery store, coffee shops, bakeries, street food, fast-casual dining) all the way up to fine dining in the $200-$400 dollar per person range. This is all a matter of personal preference but if you’re on a tighter budget you can still enjoy the flavors of the city. I especially recommend checking out one of the many food trucks, grabbling a slice of pizza (less than $5) or a NY bagel + spread (less than $8).


I have a million tips and ideas on how to see the city on a budget. There are so many no-cost and low-cost things to do that you truly can fill your days seeing the city without spending much money at all. Here are some of my favorite things to do, for free, in the city: The High Line, Central Park, New York Public Library, Grand Central Terminal, Governor's Island, and the 9/11 Memorial. And don’t forget, my very favorite thing to do in New York City, wandering it’s many diverse neighborhoods!


Hire a NYC travel expert to help you plan!

If you're going to New York City for the first time, or for the first time in a long time, it is helpful to work with an NYC travel expert. I will help you navigate the logistics of timing, budget, and travel party dynamics while incorporating your unique needs and interests. Reach out! Let's plan your trip together.