Thanksgiving NYC & Boston 2016 Itinerary

So we have just returned from our week-long Thanksgiving trip to NYC & the Boston-area (thank you School Board!). It was great spending time with both sides of our families in such a whirlwind vacation. Here’s our general itinerary for the trip:


We flew out of Orlando to arrive in NYC around 11 pm, my cousin, Matt, and my two great aunts picked us up and we stayed in his sweet Manhattan studio apartment right by Central Park.



We decided to sleep in a little because all of our late night travel the day before left us exhausted. We spent the day around New York with Matt and his girlfriend, Christina. They were fabulous company and tour guides!

Our first stop was the Brooklyn Brewery. We talked about everything from family to politics, scary I know! 🙂 Ate some street dogs (my fav!) and Brooklyn pizza and just walked around Midtown a bit. Late afternoon we went back to Matt’s place to make some mulled wine and watch Harry Potter. Ended the evening at midnight in Time’s Square.



My family is very close-knit, which is something I absolutely adore. So my aunt and uncle, two-great aunts, and my grandmother all came to Matt’s apartment for some bagels. Let me tell you, a tiny studio apartment got even smaller!

We met up with my Tio Carlos at a bar and proceeded to explore Midtown together. Will, my Tio Tom, and I went to MOMA while my uncle, aunt, and cousin hit the Bloody Mary’s at a bar. 🙂 We had a hilarious afternoon navigating the streets and strolling (or speed walking because it was cold) and talking. The last time I saw my family was for the wedding, so it was nice to catch up.

Read more: Travel Tips: Traveling with Family



Sine everyone else had to work, Will and I conquered the city alone today. And conquer we did! Here’s some of what we did on Monday:

  • American Museum of Natural History
  • World Trade Center Memorial
  • St. Patrick’s Cathedral
  • Lots of other churches I would randomly pop into to get warm
  • Rockefeller Center
  • Marveled at 5th Avenue store prices
  • Radio City Music Hall for the Rockettes Christmas Show
  • Chinatown
  • Little Italy



We only had a half-day available to us today because our Amtrak Train was leaving Penn Station at 3:30pm. Will and I decided to split up today because we had different goals for our last day in New York. I ambled along the paths of Central Park slowing making my way to the Frick Collection and Will went for a run in Central Park. We met up for lunch and then tidied up for the train ride to Providence where his sister, Courtney, was meeting us.



If you remember my summer Massachusetts posts, Will’s aunt lives on the Cape about an hour away from Boston. We spent the next few days here cozying up to my “new” family. On Wednesday we popped into Boston for the day and spent time walking around, finishing up things we didn’t get to last time like Bunker Hill and the last floors of the Museum of Fine Arts.



THANKSGIVING DAY! We obviously didn’t have any plans for Thanksgiving, and enjoyed a leisurely day grading (I know….it never ends) and eating!

Read moreTravel Tips: How Not to Break the Bank for Holiday Travel



Courtney, Will, and I drove up to Salem (about 1.5-2 hours from us) to see the sights. I thought the museum was really well done and then we popped into a few punny “witches” shops. Not much else there but I’ve always wanted to go.


Will and I had a late afternoon flight so we drove into Providence in the morning to sight-see a bit and then hopped on a plane to home sweet Orlando.

Tickets were WAYYY cheaper Saturday than Sunday so we flew out Saturday evening. It worked out well because we got a day back home to get ready for work Monday morning.


P.S. Kayak has a Thanksgiving Travel Tips page



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