Boston to New York City Itinerary

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Since we don’t have a lot of time off from work, we have to plan our vacation wisely. This Boston to New York City itinerary hits some highlights in Massachusetts, Connecticut, Rhode Island, and New York.

We spent a few days in Boston before heading south to New York City. It was a really fast paced week and there is a lot more you can do in these areas. Stay tuned for added information to this itinerary.

First stop: Boston

Boston has SO much to enjoy. My favorite thing about the Boston area is the history. Walking along the Freedom Trail and visiting the sites brings the history books to life. I really enjoyed learning more about our country.

Boston is one of the most walkable cities in America. However, some of the places you may want to visit are farther away than a few miles you may want to walk. We used a Hop on Hop off bus to tour the city for a few days. This makes it easier to get to Harvard and Fenway Park. Oh, and if you are in the area of Fenway Park, stop at Boston Burger Company to eat. You WON’T be disappointed.

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Acorn street. Do you know why this is one of the most photographed streets in America? When you walk down this street you feel as though you are stepping back in time. Acorn Street is one of the last places to still have a cobblestone street. The Beacon Hill area is now one of Boston’s most expensive and desirable neighborhoods. It sure is beautiful, don’t ya think?
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Click here for things you can’t miss out on in Boston.

Here’s a video of our trip to Boston.

Heading south on 3a

Stop number one was the first Dunkin Donuts located in Quincy. We had noticed there were Dunkin Donuts all over Boston. I felt like there were more of them than Starbucks. This original location opened in 1950. I’m not sure if it was because Chris was hungry, but he said it was the best donut he had ever eaten.

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Next stop: Plymouth

This is the town I read about in history class growing up where the Pilgrims landed. There’s a rock where they supposedly came upon shore. You have to remember that the landscape was probably different back then. But, the rock is there, protected.

Did you know the Pilgrims landed in Provincetown first? Then, after about 5 weeks, set sail and landed in Plymouth.

There’s also a National Monument to the Forefathers here in Plymouth. Dedicated to the Pilgrims, it is actually the world’s largest freestanding solid granite monument. It was built in the late 1800s, took 30 years to build, and is 81 feet tall.

I really wanted to visit the Mayflower II that is located nearby. Unfortunately, the Plymoth Plantation is closed during the winter. In addition, the Mayflower II is currently being restored and will not be available until 2019.

Searching for the Sandwich Police

The sole purpose of stopping in the town of Sandwich was to find the Sandwich police! Of course, it didn’t take long to find the police station to snap a quick picture. Now, I wish I had eaten a sandwich while in Sandwich!

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Cape Code here we come!

Cape Cod is beautiful no matter what time of year you visit. But, beware if you visit during the winter time. Many restaurants and businesses are closed during the cold winter months.

We used our time wisely by avoiding the traffic and crowds. We had the whole beach to ourselves and we didn’t have to deal with any traffic on the 2 lane road.

I highly recommend visiting the Cape Cod National Seashore.

Not far from it is the lighthouse found on the Cape Cod chip bags.

In Provincetown, you will find the Pilgrim Monument that commemorates the Pilgrims’ first landfall in 1620 and the signing of the Mayflower Compact in Provincetown Harbor.

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Rolling to Rhode Island

Next stop was Rhode Island. It was on my bucket list to stay in the Chanler on Cliff Walk. This accommodation is one of the original homes in the Cliff Walk area of Newport and was rumored to be one of the most romantic places to stay in America. I was really amazed by the beauty of the Chanler and Newport, as well.

Many of the old homes are available for tours. Some of these homes were abandoned because they were so big they were hard to maintain as just summer vacation homes. Plus, many of the owners didn’t want to vacation back to the same place every year. These homes became known as “white elephants.” We went on a Christmas tour of the Breakers house. It is named that because of the sound of the waves as they crash on the side of the cliffs.

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Pizza in Connecticut

I am a BIG fan of Julia Roberts and have collected almost all of her movies. One of her earlier movies is called “Mystic Pizza.” In fact, the movie was shot in the town of Mystic, Connecticut. You can visit the pizza restaurant made famous by the movie.

The restaurant is decorated with pictures of Julia Roberts on the wall. The pizza is so yummy. I definitely recommend this quick stop for lunch on the way through Connecticut.

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New York City!!!!!

There’s SO much to do in New York City. I guess that’s why it’s known as the city that never sleeps. 🙂 More to come on things to do in NYC on an upcoming post. So stayed tuned!

In the meantime, if you are planning a trip to New York City, make sure to add Black Tap to your list of places to eat. Go after 10 PM to avoid the long hour + wait. When we went to the SOHO location at that time, we were seated right away. Or, go a few minutes before the doors open to avoid the line (learned the hard way on our second trip there after waiting over an hour!).