How I Planned a New York City Adventure Using my Skype Group Chat!

As a professional travel blogger and full-time traveler, it’s usually me exploring and then giving you all the tips on where the best adventures are. But I decided to turn the tables this time and do all of the things that were suggested to me by everyone who joined my Skype group chats while I was in New York City!

What I loved most about it was that out of all the times I’ve been to New York City, I never saw or did the majority of things that were recommended to me in the group chat! It was awesome to get insights from locals who live there, and people near and far who had visited and found their own little gems in the city.

Spoiler alert: One of those little “gems” came in the form of a helicopter that dangled me out of its open doors over the city!

As a perk to everyone who so graciously offered me their best recommendations in the group chat each morning, I did special behind the scenes Highlights on Skype’s new mobile platform that could only be seen if you were in the group chat! I also ended up doing a super fun meet up for brunch, where the secret location was revealed on the Highlights!

Sound like a fun adventure? Here’s the full details of how it went down!

Each Morning We Did a Skype Group Chat

I had four days in New York City, and each morning started with an hour long group chat on Skype to gather recommendations, tips, and advice. The participants came from a variety of my social media platforms, and as I mentioned, were an awesome mixture of both NYC locals, and visiting fans of the city.

It was really fun to interact with so many people at once, and to be able to connect like minded travelers all in one chat! Plus Skype has a ton of awesome new features that make chats more fun; like video messages, GIFS, and emoticon reactions to comments!

Once I decided what sounded like the awesomest adventures, I made a list, checked it twice, and headed off into the city to tick them all off!

Here Were The Best Recommendations!

1. Take a Helicopter Tour Over New York City

Holy WOW! All I can say is this was the maximum awesome, adrenaline explosion, adventure of a lifetime experience in New York City! Well I can actually say a lot more, that’s how incredible it was so I’ll just go ahead and elaborate.

For starters, you know how New York City can make you feel really small? Well not when you do a helicopter ride! OH. And I didn’t do just any helicopter ride…I opted for the one that has no doors, and harnesses you in so you can dangle out the side of it over the city! They call that the “adventure seat”.

Luckily everyone in my group chat gave me the last minute advice not to wear my “typical clothing” (AKA flowy skirts or pants with shoes that easily come off) because MAN where my legs flying around up there! Mostly by choice as I wiggled my feet out for a “foot selfie” to post on my Skype Highlights!

2. Have a Crazy Milkshake at Black Tap

When someone said that Black Tap was “Every Facebook video and Instagram photo in one spot”, I obviously HAD to go check it out. Needless to say…it did not disappoint! Black Tap is notorious for its massive, creative, “Crazy Milkshakes” that tend to tower over the edge of the glass they’re served in, and include fun ingredients that are more like props that add to the craziness.

For example, I went for the “Bam Bam Milkshake”, appropriately named because it’s Fruity Pebble flavored. But not only is the actual milkshake a liquid dream of your favorite childhood cereal, but the rim is vanilla coated with actual Fruity Pebbles stuck to it, plus a heaping mountain of whipped cream with even more Fruity Pebbles showered on it, and THEN! There’s all these fun surprises in the whipped cream; like a freaking Fruity Pebble rice crispy treat (Mind. Blow. I know.), a strawberry Pop Tart, and of course…a Nerd’s Rope.

I lasted about eight sips before I had to give up and walk it off to the next location. I made sure to warn everyone in the Skype group chat that you should definitely bring friends to share a milkshake with if you go to Black Tap!

3. Go to Hotel Rooftops

So I don’t know if you know this, but New York City is probably the best place in the United States for rooftop views and festivities. Technically I should be biased since I’m based in LA, and I should be super picky since I’ve been to over 70 countries and probable three times as many cities…but hands down, New York City wins in this category.

Luckily my group chat participants had a plethora of suggestions for me to rooftop-hop around the city! I got to quite a few, all with different views and different crowds that were all equally amazing. All of the rooftops that were suggested were local spots, which meant I didn’t have to pay a fortune to go to the observatory decks of places like Top of the Rock, One World Trade Center, or the Empire State Building, which was definitely an added bonus!

First I went to Jimmy at the James Hotel which offered a stunning up-close view of One World Trade Center, as well as panoramic views all the way to the Hudson River. Then I went the rooftop at the new Public Hotel, which is a hip and sceney place, especially during Fashion Week!

Later for a view of Times Square from above, someone suggested the Knickerbocker, so I went there, but since it’s not too high, I set off for a better view. I remembered someone also suggested the new Alor Hotel, so headed up there for a brilliant up close view of the Empire State Building right in front of me! A massive added bonus was that they have a portion of the deck that’s glass that you can walk on (AKA look straight down about fifteen stories)!

4. Eat Pizza at Artichoke Bastille’s

Naturally when going to New York City, you must have the best pizza, right? Well add on having pizza as a main diet and you’ve got one hot topic for a group chat discussion! A lot of people recommended some amazing places in Brooklyn, but since I hadn’t gotten to number six on this list yet, I opted for the number one suggestion in Manhattan: Artichoke Basille’s Pizza.

Out of all the pizza I’ve eaten in my life (which is a lot…not joking, I eat it in almost every country), I finally felt like this was real New York pizza! It’s gooey cheese made power-line-threads from my mouth to the crust like you see in movies, and also like in movies, I ate so much that I could not move for a good half an hour.

Trust me when I say…you probably only need one (giant) piece!

5. Walk the High Line

To be honest, I already knew about the High Line because it’s totally my kind of thing; nature in the city. But since so many people suggested it, and also suggested some areas that made for a great view of the Hudson River (and because I needed to walk off the pizza), I was more than happy to take a stroll down the whole thing!

In my opinion, the High Line is one of the most genius things to have happened to New York City recently. As you know, it’s a “concrete jungle”, so to give everyone a breath of fresh air, a 1.45 mile-long open air walk way was created where an old industrial railroad used to be.

The High Line is above the hustle and bustle of the streets, but eye-level with the many skyscrapers that it weaves through along its route. It has various trees, plants, art instillations, and resting points along the way as well, and some people even sunbathe on its built-in lounge chairs!

6. Learn How to Use the Subway

Another one of the things I really loved about doing the Skype group chat, was asking not only for recommendations for things to see, but advice for getting around in the city as well! As I mentioned, New York can make you feel really small, and also really lost! So small and lost that the subway can seem terrifying! And that’s coming from a girl who mastered the Rail System in Tokyo!

But I’m not going to lie, using the subway in New York City is ten times easier than it sounds, and also ten times cheaper than using a taxi or car service. As instructed by one of my group chat participants; all you have to do is purchase a Metro Pass from one of the kiosks in the subway stations, load up on credits, and catch the right train! Don’t worry, the subway maps are way easier to figure out than they look, and despite what people may say about New Yorkers being unfriendly, I guarantee there will always be someone right behind you to ask where you’re trying to go if you look lost and confused!

7. Have A Meet Up at Frying Pan

For my group chat participants who lived in or around New York, a meet up was a popular suggestion, and there was a unanimous vote to have it at a place called the Frying Pan! Of course, they didn’t know this until the night before when I announced it on my Highlights to keep the suspense building, but everyone showed up right on time for brunch the next day!

Frying Pan is this AWESOME open-air restaurant/bar that’s built on a barge that floats on the Hudson River! There’s even two boats that are tied to it, one of which you can even eat on! The weather was perfect and so were all of the stories from everyone who came!

We had a clothing designer whose office was literally across the street, a travel agent who lived across the bridge in New Jersey, and even one of my biggest fans who came all the way from Washington DC to hang out

8. Go to A Broadway Show

Like most girls, I’m a sucker for a good theater show, and it doesn’t get much better than seeing one on Broadway in New York City! At first I was really worried about the prices of the tickets, but a few of my group chat participants had really good hacks for finding them for cheaper than at the box offices.

Many of them suggested going to the red TKTS booths located in Times Square, that sell discounted tickets the day of shows for the seats that haven’t been filled. The only catch is that sometimes you get your hopes up to go see a show…and there’s no more tickets left…(Happened to me three times).

The best Broadway show I’ve seen so far has been The Book of Mormon, but according to everyone in the group chat, Hamilton and Lion King are must-sees as well!

9. Be Touristy in Times Square

Ok, Ok, we all know Times Square is the opposite of a unique, local New York City experience, but I had to do at least one token touristy thing! Although I’ve been there tons of times, the lights and the energy never get old!

There’s constant crowds around the breakdancers trying to make a buck with their make-shift street performances, and of course, the many (actual) characters trying to get you to pose for a photo.

10. Give a Secret Travel Tip to the Group Chat!

On the last day of my Skype group chat we opened the topic for all travel tips, so I gave a few of my own! Many of the participants were curious to know how I find the best hotel and flight deals, which was the perfect topic since that happens to be my specialty!

I explained how Skyscanner is my go-to for finding the cheapest flights, especially if you want to play “flight-roulette” like I usually do! Usually I use the search tool on their website, but on Skype’s new mobile platform, you can actually use a Skype bot to chat with and get those same awesome results by asking questions in the form of a chat!

All you have to do is type in where you’re leaving from, where you want to go (even if it’s “anywhere”!), and when you want to go, and the bot will chat back to you with travel plans! Try it out!

Wow, well as you can see, I had one incredible weekend in New York City, and an even more incredible experience having the awesome participants in my Skype group chat help me plan what to do! I can’t wait to try this in other cities, and see what kinds of amazing adventures I can get up to!

If you haven’t already done so, be sure to update the Skype app on your mobile device to get all of these awesome new features, and don’t forget to add me; ‘AlyssaOnSkype’!

Disclaimer: This post is in collaboration with Skype, however all experiences are 100% real, and all opinions, content, photos, and opinions are all my own!