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New York City tends to be a popular traveling destination during the holiday season. Whether you’re trying to get to the Big Apple to see the Macy’s Thanksgiving Parade in November or to do some shopping and take in the big lights during December, NYC is a great place to spend some of your down time during the colder months of the year. That being said, you do have a few obstacles that could turn a fun trip into a frustrating one. You have the threat of snow, you have the extremely cold weather, the large crowds … just these three things could be enough to convince you to stay home and take in the city that never sleeps from the comfort of your couch at home. We’ve got a few tips that could help improve your NYC trip.

1. Know when to book your flight.

When’s the best time to book that flight? In a general you, for domestic flights, try to book three months in advance. For international travelers, book a month and a half  to five months in advance. Sure, you could find a ticket outside of that window of time but airfare experts at sites like or estimate that you can add $5 a day to your ticket price for every day you don’t book if you’re traveling domestically. Plan accordingly! No need to spend half of your travel budget on that ticket.

Not big on planes? Consider taking a train into the city if you live close enough. The fares are going to be a fraction of what a plane ticket is but keep in mind it’ll likely take longer for you to reach your destination. It’s scenic, you’ll have fewer baggage fees to deal with and potentially more leg room than you’ll have on a plane. If you’re not big on sitting for long periods of time, Amtrak may not be for you.

2. Choose your hotel wisely.

When I travel, the hotel is just as important as getting the airfare worked out. The good news is that the city is packed full of hotels for you to choose from. Staying in a hotel far away from the subway or transportation line could make your trip a pain, especially in colder months when you may not be up for a lot of walking. We suggest staying close to Times Square. Two hotels we’ve stayed in that we’d recommend is Yotel ( or The Out NYC ( which are in the Hell’s Kitchen district but steps away from the Port Authority Bus Terminal.

Staying in this area will give you easy access to the subway lines, you’ll be closer to airport shuttles and you won’t be too far away from major tourist attractions and areas of interest.

Bar 54 at Hyatt Centric Times Square overlooking Freedom Tower

3. Plan ahead for transportation.

Ok, what do you think about when you think of NYC? Yes, those yellow taxis. That’s fine but taxi fare can add up. Think about how you’re going to get around before you even arrive in the city. Book car service or do what we do and buy a ticket for the NYC Airporter shuttle which has routes from both JFK and LaGuardia. Fares for the Airporter shuttle are competitive and far more affordable than what you’ll pay for a taxi to and from the city, especially if you factor in traffic and any weather issues. You can purchase your tickets ahead of time from

Once you’re in the city, do as the natives do and take the subway! Listen. We know, you’ve heard horror stories about the subway from friends, family and on television shows but this is the easiest and most affordable way of getting around. Purchase a week pass if you plan on being in the city over 4 days. Buy a simple day pass and load up $10 or so dollars each time if you only plan on being there a few days. Save your cash for taxis for those occasions when you’re traveling with friends or are far away from a subway route.

4. Pack for the season.

From November through March, New York can be a bit cold. Even that’s putting it mildly. Factoring in frigid temperatures and snow or sleet, you may hit the city to find yourself unprepared and thus miserable. So, waterproof boots are a necessity, as is a heavy coat, a good pair of gloves, a scarf and maybe even a hat. These things will protect you from the elements and also help keep you from looking silly walking around the city unprepared.

5. Plan a season-appropriate itinerary.

New York City is different in each season. What you could get away with in the spring or summer isn’t going to work well in the colder months. For the colder months, you may want to plan to spend more time indoors. Hit up the museums, do a tour of some of the top eating places in the city, hit up all the stores. Of course if you’re in the city, why not see a Broadway play? Get a discount on some of the top shows by purchasing your tickets from the TKTS ticket booth (

The Chelsea Market and vendors in Union Square and around Bryant Park are all worth checking out. If you’re into beer, perhaps taking a tour of Brooklyn Brewery is your thing. The list of things to do indoors is limitless but the key is to do your research ahead of arriving and plan out your days by hitting up places that are close together or near the same subway route.

6. Cash or credit?

A great tip we’ve heard is to pack $100 in cash for each day you plan on being in the city. Yes, you can use your card at many vendors and stores but in NYC, cash is king. There are bars where you can only use cash, there are some vendors that will only accept cash. Plus, cash often makes things easier when traveling and helps you stick a to budget. Not to sound like your mother but never flash your money in public, especially in the city during the holiday time. Find a safe location in a store or away from crowds to remove or deal with your money rather than pulling it out in front of everyone at once.

Also, be sure to check our Bar 54 in Times Square!

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