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The Solo Traveler Blog

Amanda’s Skyscanner Trip to New York City

New York City, New York, America

Near Madison Square Park with the Empire State Building in the distance

December was the second month for our  Skyscanner Solo and Spontaneous  ”Cheapest Flight to Everywhere”  Contest.

We’ll be looking for our third and final winner next week. Make sure you’re on the Solo Traveler newsletter (sign up on right) to receive details. If you want to know how the contest works in advance read Win Airfare to ???: The Solo and Spontaneous Contest

Our November winner was Rachel of Jaen, Spain. Off she went to Oslo, Norway. Our December winner was Amanda of Ohio. Her trip was to New York City. A huge thank you to Skyscanner and their innovative travel booking engine for making this possible.

Here’s what Amanda had to say about her solo trip to New York City…

When I found out I won this month’s Skyscanner Solo and Spontaneous “Cheapest Flight to Everywhere” contest less than 3 weeks before Christmas, I immediately thought New York City would be the perfect place to take a spontaneous solo trip to get me in the holiday mood. Although it was pretty rainy during my trip, it didn’t dampen my enthusiasm to tour the city. I thought I’d forgo the usual tourist destinations and explore some of the lesser-known parts of the New York.

Theater and Shopping solo in New York City

My first night, I headed to the Upright Citizens Brigade Theater, founded by Amy Poehler and others, to enjoy some improv theater in Chelsea. It was hilarious and only $10! They offer several shows a night and a wide variety of acts. It’s a great place to go when traveling solo.

The next day, it was Christmas shopping central:

I headed to the Chelsea Antique Garage, a parking garage that has lots of vendors set up on Saturday, selling their wares… everything from books to jewelry to home furnishings.

After that, I hopped on the subway and headed to the Brooklyn Flea Market, located in the gorgeous former Williamsburg Savings Bank, to check out more antiques and locally made wares. The venue was gorgeous and there were so many things to see and buy.

I then headed to Soho to check out some fun boutiques

Then I made my way up Fifth Avenue to check out the Christmas window decorations in all the big department stores and see the Rockefeller Christmas tree and ice skating rink. I had a nice dinner that evening away from the bigger tourist spots. It was delicious, and the staff was so friendly.

The Rockefeller Center Christmas tree

New Yorkers are friendly to Solo Travelers

If you’re brave enough to explore some of the lesser-known spots in NYC, you can meet some really great, friendly people. I met so many friendly people at the markets in Chelsea and Brooklyn and got to sample some of the local flavor of the city.

It definitely pays to familiarize yourself with the different neighborhoods and have a plan before you go since NYC is so huge. Also, if you study the subway system before your trip, you can get anywhere in the city very inexpensively. I felt safe in all the neighborhoods I was in, but it’s always good to keep your eyes open and be aware of your surroundings. I found New Yorkers to be really helpful with directions and using the subway while I was there.

NYC is a great place to explore as a solo traveler!

Checking out the handmade goods at the Brooklyn Flea

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  • http://gonytours.com/ Leslie Horning

    I’m glad you chose to come to NYC on your solo trip. What a place! Before moving here, I actually made a solo trip to NYC myself. Other than the fact that I kept getting lost, it was so much fun. There is always something exciting going on in NYC anytime of the year, but especially during the holidays. Glad you had fun!

  • http://www.facebook.com/keeler3 Amanda Keeler

    Ahh, I did the Sex and the City tour a few years ago too. I loved it! If you ever go back, definitely check out the antique garage!

  • http://www.facebook.com/keeler3 Amanda Keeler

    Thanks Greg! I hope my tips come in handy. Have fun traveling!

  • Kandice

    I took my first solo trip to New York and I loved it! I had a wonderful time and I can’t wait to get back there in the next couple of years. I took the Sex and the City tour while I was there and it took me all over Manhattan in only three hours. I wish I had known about the antique garage. I’m glad you had fun!
    travelwithkandice.blogspot.com

  • Greg Galbraith

    Hi Amanda, Congratulations again for winning the contest, and for sharing your story with us! It sounds like you had a great trip and I appreciate the tips you shared regarding getting to know the area you are traveling to before you get there.. I think that will really come in handy when traveling to a new destination for the first time..

About Janice Waugh and Tracey Nesbitt

I'm an author, blogger, speaker and traveler. I became a widow and empty-nester at about the same time. And then, I became Solo Traveler... Here's the full story. >>

Tracey Nesbitt I’m a writer, editor, food and wine fanatic, and traveler. On my very first trip abroad I learned that solo travel was for me. Here's the full story. >>

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