First Winter Holidays – Things I Wish I Knew


No worries, I am not going all Game of Thrones on you, but it’s a fact that the winter season is fast approaching in several countries.

Winter Holidays is usually a term for people looking for warm destinations to get away from the winter in their country. However, as you know, many people also venture in countries during the winter season.

If you’re from the Caribbean, like me, or from another tropical region/country, you’re pretty much accustomed to 25-31 degree Celsius (77-88 Farenheit) temperatures and rainy days. Also,  unless you’re fortunate enough to not live in cyclone/typhoon prone regions, then you are not affected by strong winds.  

By the way, the Caribbean still needs our help to recover from this year’s devastating Hurricane Season (Click here to see how you could help.)

Ok. Back to the topic at hand!

I thought I would compile a few things I wish I knew before heading to my 1st Winter Holiday. New York City gave me a memorable introduction to Winter.

Hopefully, this post would give some insight to those who are about to embark on their first holidays during the winter season.

Please don’t make the same mistakes and Good Luck 🙂


Your Body Might Not Like Winter!

So here I was thinking: Winter Clothes, CHECK; Winter Accessories, CHECK; Winter Shoes, CHECK. Sprinkle that with lots of Positive Vibes. Yes, I am good to go. Let’s Do This!

Here I come New York! Maybe 3-4 days to get accustomed to the temperatures. Then, New York would be mine! Or so I thought!

Oh how I was wrong!! My Caribbean fingers took 2 weeks (out of 3) to be “just ok” with these winter temperatures. Sadly, both pairs of winter gloves I wore — at the same time— didn’t seem to be enough. My little nose, oh well, the poor thing had a hard time the first week . And I, for once,  wished I still had my long dreadlocks, just for extra warmth.

Although I knew I don’t even like air-conditioning, I took on this trip with positive thinking in my pocket. Not so easy, it turned out!

Wait, am I missing wearing my short pants by hour 48!  All these Layers of clothes, say what!!

My advice: Leave your country with a positive spirit, but expect your body to handle things at its own pace. It’s highly likely that your body lets you down or disappoints during your trip!

Manhattan, New York
Bryant Park's Winter Village, New York
Winter Village at Bryant Park

Winter Breeze Is No Joke!

I’m sure you’ve seen funny movie scenes where someone would attempt to cross the streets and ends up being slapped around and pushed back by strong winds, making the crossing quite lengthy, or painful/funny to watch.

Well, this same scene happened to me while trying to cross a street in the vicinity of the Rego Shopping Center, in Queens. I wouldn’t want to know what my faith would have been if I had not just had lunch at that mall!! Ppphheeww!!

Did I say that I didn’t find my crossing incident very funny?!

It was actually such an irritating event that I cancelled my touristy plans for the rest of the afternoon and simply took the subway, back to the apartment. Yup, I’ve since regretted doing so, especially since I was stuck home the following day due to heavy snowfall! If I only knew!! Hhmm…Bummer!!

Here’s another example of how the wind blew away my plans (pun intended). A night, we went strolling through the streets of Manhattan. Once we arrived at the 9/11 Memorial Park, the strong wind there wasn’t friendly, to say the least. We didn’t stick around for long, as a result! Brrr!!! 

My suggestions here:

  • Be mindful that good weather conditions to be in “Tourist Mode” are not guaranteed throughout your stay. 
  • Do not let small things/inconveniences spoil your mood.
  • Make the most of each day.
9/11 Memorial Park, New York
9/11 Memorial Park
Grand Central Terminal, New York
Grand Central Terminal

Tourist Mode's Minimum Homework

Oh yea, this vacation taught me to never go on holidays without reading up about tourist attractions/activities that I would want to check out BEFORE the actual trip!

Not doing your homework prior to your holidays leaves room for disappointments and wasted time.

Aaahhh, The Statue Liberty! A rather “painful” experience if you ask me!

So as you know, going to the Statue of Liberty means being seaside, right?

So add strong winds to low temperatures (-7C/ 19 F) and…. Voila! You get a long queue of people looking like they’re all going to Hell! Don’t like my teaspoon of drama? Well, sorry but it’s the truth!

Ever watched 100 people looking like they’re freezing to death, to the point that you wonder which one would drop first? Well, I am glad for you if you haven’t. That sight isn’t pretty!

It really didn’t matter what anyone wore that day. No one seemed comfortable! Standing for 1-2 hours before getting onto that boat to see the Big Lady was a painful and slow procession! I’ve never been so happy to see a (Security Check) building in my life!! Aaawww, it was oh so warm and nice in there…!

Signs - Statue of Liberty


My advice:

  • Buy your ticket online. You’ll save a lot of time as you won’t need to queue as much. By the way, I saw the sign “The Crown is closed today”. Just when my “frozen” heart was wondering how much more it could take! Bummer! Please buy your ticket weeks prior to your trip as the crown access is limited and sells out quickly. So online ticket = perks, time savers.  
  • It’s best to schedule a morning visit. Certain things are not accessible in the afternoon. I also arrived too late to buy food at the cafe on Liberty Island. I recommend packing some snacks and sandwiches. Food options on the ferry are also limited.

This piece of advice also applies to many other monuments/tourist attractions.

Statue of Liberty, New York

Time Square BallDrop: a Freezing Venture

The BallDrop!!! Everybody knows about that New Year’s Eve Annual Event where millions of people gather on Time Square and surrounding streets to welcome the New Year. You know, the one where they release a 12,000 lbs sparkling ball at 11.59 pm on 31st December, from the top of the One Time Square building, while screaming a countdown to midnight.

I was told that it was only possible to secure a close spot on Times Square by going there from 3pm on that day.

However, both family members (also tourists) weren’t feeling well and got rather “disturbed” by how low temperatures were that morning. Indeed, we saw a woman being interviewed  on Tv at 9am from Times Square. She seemed skeptical about whether she could weather the cold (pun intended) until the start of the festivities (8pm).

Well needless to say that plans to attend this much sought-after event fell apart upon seeing that interview!  

Therefore, like millions of people did that night in the US and worldwide, we watched the Ball drop on TV, along with 2 more family members! The only difference with some TV viewers was that the fireworks from Times Square shook our apartment (located in Astoria, Queens). Did we come out to watch them? Nope, just not in the mood to put on coats and what not!! Lol!

My advice to you:

  • If you want to be in the vicinity of Time Square, during the festivities, you can choose from a variety of parties at nearby hotels or restaurants ($70-$500). It will be warmer there! A $900+ budget will allow you to see the actual ball drop live from certain nearby hotels.
  • With a $200+ budget, you could buy a Time Square BallDrop Pass to access several parties that night throughout Time Square.
  • If you want to party in the vicinity of Time Square, in the streets, then  get a group of friends/family members (minimum of 5 persons). You can then have your own lil thing going on before, during and after the show. It would also be easier to maintain your spot by taking turns for bathroom breaks. Good vibes and Love are essential ingredients to a recipe strong enough to endure these temperatures. Just secure your spot from early.


Brooklyn Bridge, New York
Manhattan, New York

1 Winter Trip might not be enough

Don’t give me wrong, Traveling is awesome. However, just like everything in Life, things don’t always go the way we would want them to.

Did I cancel a few adventures because my body didn’t feel up to it? Yes, many times!

Would I have seen more of New York if it weren’t winter time? Definitely!

Will I travel again during winter? Yes. I can’t miss out on what the world has to offer just because of winter (Iceland… huh hmm… I see you!)

Ideally, getting involved in activities that would warm my blood, would be the cherry on top, now wouldn’t it. Snowboarding Snow-kitting maybe? You know, fun stuff!

My last advice:

  • It might take you more than one trip to conquer Winter temperatures.
  • Be with loved ones during your first Winter Holidays. It would more than make up for the discomfort you might experience in these temperatures. Love and Laughter were what made my trip so Special, despite the many disappointments.

Astoria, you were great and oh so yummy!! New York, I’ll be back!!


Let me know in the comment if you’ve ever travelled in a season that didn’t make you feel comfortable and put a damper on your trip. Come on, I know I am not the only one out there!

Apollo Theatre, Harlem, New York
Apollo Theatre
Apple Store on 5th Avenue, New York

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12 Replies to “First Winter Holidays – Things I Wish I Knew”

  1. I love winter, to the extent that I moved from Italy to Sweden and I am at my happiest when the snow comes and stays. I had the pleasure to visit NYC both in the summer and in the winter, and I would absolutely go back in the winter! It felt so magical, with all the lights and decorations, and, well… the snow was pretty 😀
    Still, as much as I love winter, I did have a few occasions when I really froze my ass off in NYC. I will never forget a particularly windy day when I was out the whole day and I thought I’d lose the tip of my nose. And one night I went out with a friend of my cousin, it was not supposed to be a date but it felt very awkward… anyway. He took me to Jersey City to take some photos of the NY skyline at night and the air was so cold I couldn’t stop crying. Well, I wasn’t crying, tears were just coming out of my eyes because of the cold, and my cheeks were also cold so I could barely feel them, and at some point he asks me why I am crying… I wanted to bury myself XD Oh well, I’ve got a fun story to tell 😀

  2. Oh, your poor thing! I can only imagine what it must have been like experiencing winter for the first time as a tourist! Ugh! I’m from Denmark, and worked with tourists for many years there, and I always adviced them not to come during the winter time, haha. However, if you really are to visit in winter, I think your tips are great pieces of advice! Thanks for sharing!

  3. Getting the tickets for tourists tractions ahead of time can save hours. Also, I have also encountered unexpected weather in New York and at least it’s not difficult to find a clothing store.

  4. I’m from Canada so I totally know cold, we spent some time in NYC in January this year and it was soooo cold! We had a blast though! We were actually there with some friends who live in Bermuda so they weren’t coping as well either! haha

    1. I’m rather comforted by the fact that you found it cold in January too, despite you being accustomed with Winter! Ahahah! I feel it for your Bermudian friends 🙂 that was so me! send my regards!

  5. Having grown up in Wisconsin, USA, I have always known very cold winters. Winter in NYC must have been a shock for you!

    1. Aaahh Sandra!! Your body grew up in those temperatures 🙂 It wasn’t a shock for me since I knew it was winter time, but it is just my body who didn’t adapt as quickly as I had hoped it to! Lol, I’ll try again some other time!

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