A trip to Boston on points!

I shared about the first half of our trip to the east coast in another blog post that you can find here. We started off in Newport, Rhode Island, but shifted gears halfway through and headed to Boston.

I had previously been to Boston several years ago, but my husband had never had the chance to explore the city and my daughter had never been. I loved visiting the city the first time I went and had been wanting to go back for a while. So we made it part of our New England summer adventure!

We decided to stay at the Hyatt Regency Boston. There are several options in Boston, and several Hyatts, but this one seemed like a good central location for our activities. This hotel worked out really well for us. It wasn’t the most luxurious stay I’ve ever had, but it was perfect for what we needed and the location couldn’t be beat! We would definitely stay there again!

We arrived late one afternoon because we had spent the morning finishing our time in Rhode Island. So, we didn’t do much our first day. It was also pretty rainy and gloomy so we explored close to the hotel, and grabbed dinner at the hotel restaurant.

The next day we got up, ate our comped Globalist breakfast at the hotel and headed out to catch the Old Town Trolley Boston! I remembered doing this years ago in Boston and we also loved doing this in DC last year. What I love about the Old Town Trolley in Boston, is that it is a hop on/off trolley. So, we spent the day taking the trolley around the city with a tour guide giving us lots of info. But, we were also able to hop off when we wanted, for as long as we wanted at any given spot. So, we learned a lot about Boston and also didn’t have to worry about walking everywhere or catching an Uber/train. Some of our stops included: Faneuil Hall, The North End, USS Constitution, Cheers Bar, and Boston Commons.

One of the highlights of the day was hopping off the trolley and heading to the Boston Tea Party Ships & Museum. This was a super fun/interactive museum that gives a history lesson in an immersive way. It’s a great one for families and was definitely one of the highlights of our trip. We loved tasting the different “teas” at the end of the tour as well.

That evening, we ventured to The Boston Sail Loft for some New England Clam Chowder, shrimp, and Boston Cream Pie.

The next day we hopped on the subway (which was super easy and convenient) over to Fenway for our ballpark tour. I was bummed that the Red Sox weren’t in town when we booked our trip. If you are a baseball fan at all, you know that Fenway is a must (I went to a couple Royals/Red Sox games on my visit years ago). But, I remember the tour being so interesting, so I made sure we booked it this time as well.

After the morning tour, we went to the hotel for a bit to relax and then grabbed a quick lunch at Cheers since it was walking distance.

Next, we walked just a few blocks over to Escape the Room Boston. One thing we are trying to do more of is including our 11 year old in the planning. I knew Boston would have a lot of “history”, but wanted to mix things up a bit. She suggested doing an escape room because our family always loves the challenge these have to offer. So, we did just that, and booked a room! It would also be a great idea for a rainy day or if the temps aren’t the best while visiting Boston. Our family had a great experience and made it out of our room with just a couple minutes to spare! It was a blast!

My husband and daughter took a little break afterwards and swam for a bit in the indoor pool at the hotel. Then we got freshened up and headed to La Famiglia Giorgio’s Restaurant for a delicious family style Italian dinner.

Our last day was our travel day, so we took some time to walk over to the Beacon Hill area to check out the shops and Acorn Street to get a picture (it’s one of the most photographed streets in America),then we made our way to the airport. Since it was the first day of August, I was able to use another monthly Lyft credit on my premium card. Next, we headed to the airport lounge thanks to that same premium card for a free lunch before our flight.

I didn’t realize it when I was booking, but Southwest does have a few nonstop flights, and Saturday is one of those days, so we were able to grab a direct flight back to KC!

Our family really did enjoy this trip- we tried to mix things up from some beautiful scenery, delicious food, history and some family fun time!

There are so many things to do in both Newport and Boston, and we just scratched the surface!

If you are looking for points to take a trip to the New England area, grabbing a card that earns flexible points can help you get there! You can find the cards we used here!

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    Hi, we're Lauren and Keri! 

    We are teachers and moms raising our families in the Midwest and we know how special it is to make memories as a family while traveling.

    Learning to travel on points has been life changing for both of us and has allowed us to take trips we never could have taken on our teacher salaries. We'd love to teach you how to make that happen for your family!

    Nice to meet you!

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