4 Days in Massachusetts and Rhode Island (Vlog Included)

After many long months of quarantine and travel restrictions, I was ecstatic when my brother came to me and asked if I wanted to go on a road trip. I jumped at the opportunity and probably would have done the same regardless of where he wanted to go.

He expressed his interest in going to Boston and a few other places nearby. We had both been to Boston before, but not for very long and there were still things that each of us wanted to see and do there. Plus, we were both getting the travel itch and dying for some good seafood. It was a perfect fit!

Unfortunately, Jacob wasn’t able to go in this trip as he just started a new job and couldn’t take the time off. After almost a year apart, it was nice to hang out with my brother anyway. So, after a quick refresher of my road trip tips post, we headed out on our six and a half hour journey to Boston.

New England Road Trip Vlog

Now I know, you can’t base your fondness of a place on your hatred of their sports teams.

We decided to stay in Boston and take a few day trips to Cape Cod and Newport Rhode Island. Although it was very unlike me, we went with a few loose plans and figured things out as we went. This felt like a very foreign strategy as someone who usually plans very thoroughly for trips.

We were able to find lots of cool things to do on our own, luckily, and I want to share them so others can enjoy them as well. I’ll add links to all restaurants we ate at and places we went to add to your next trip itinerary.

Boston, MA

We stayed in a cute one bedroom Airbnb in Jamaica Plain Hills. The apartment was nice and clean and equipped with everything we needed. Here’s the link to our place for your next trip to Boston. It was a conveniently located neighborhood. A 10 minute walk go us to the subway station and a short drive found us right in downtown Boston.

The first night, we took the subway to the Back Bay station and found a nice southern style restaurant to eat at. With COVID and the fact that it was a Tuesday night, not many places were open. We weren’t necessarily looking for this type of food, but it was absolutely delicious and we were glad we found it.

The restaurant was called Buttermilk & Bourbon and I would definitely recommend it. I ordered the Bon Temps cocktail and Shane had the Whodi Smash. To eat we shared an order of the Brisket Croquettes, New Orleans BBQ Shrimp and their specialty fried chicken. All so yummy and just what we didn’t know we needed!

The next morning, we made our way downtown again to see some staples of Boston. The Boston Harbor, Paul Revere’s house and the Quincy Market were on the list.

After walking around in the rain, we settled down for a nice lunch at the Neptune Oyster Bar. Here we had some delicious local oysters served with lemon and red wine vinegar. Along with that, hot overstuffed lobster rolls with butter. This was perhaps my favorite meal of the trip because I’m a newly converted oyster lover.

Due to the torrential downpour in the afternoon, we decided to purchase some locally caught clams to cook ourselves for dinner. We made steak along with it and had ourselves a proper feast!

Cape Cod, MA

The next day we set off to explore Cape Cod. It was raining for most of the drive out, so we decided to stay in the car and drive all the way to Provincetown. I’m so glad we did because this small town is wonderfully quaint, yet lively and colorful.

We checked out Race Point Beach where we observed two seals swimming along the shoreline. We walked in the water, picking up shells and enjoyed the fresh air and relaxing sounds of the ocean. Thankfully, we didn’t go too far in the water as sharks are known to swim close to the shore. In fact, just a few days later there was a shark spotted only 10 feet from the shoreline at the same exact beach!

Later, hungry from all our fun at the beach, we sat down at The Canteen restaurant in Provincetown for some yummy drinks and fish and chips. I loved this place because it was right on the beach and had a very casual and laid back vibe. We were actually dining at a table on the sand.

The food was also excellent. The fish was super fresh and cooked perfectly. After eating, we decided to walk a little bit more along the beach before heading back to Boston.

On our way back, we stopped in Chatham to check out one of the oldest lighthouses on Cape Cod. Surrounding the lighthouse are a beautiful beach and walking area. A perfect ending to the day!

Newport, RI

On our last day, we drove down to Newport, Rhode Island. I really loved the charming feel of this town’s streets lined with little shops and restaurants. The rocky coasts and beautiful views also contributed to this being my favorite stop on the trip.

First, we had lunch at a place right next to a marina called @ The Deck. We sipped on some Coronas and enjoyed more lobster rolls, cold this time because it was hot and sunny!

Next, we drove out to the coast and walked along the cliff overlooking the water. The views from here were stunning and we also got to see some of the old-money mansions on the water.

This cliff walk was really nice because it went on for 3.5 miles so you can get in some good exercise and views at the same time. The terrain varied from paved paths to walking across large rocks, so if you decide to check it out, I recommend wearing sturdy shoes!

For our last dinner, we went to another relaxed place in Wakefield called Ocean Mist. The seating was literally on the edge of a cliff by the water. We each ordered a New England favorite- Narragansett beers, as well as two stuffies (stuffing with clams inside) and an order of steamed clams. We definitely got our seafood fix from this trip!

After dinner, we wandered down to the nearby town beach and just sat along the fence and enjoyed a couple hours of talking, listening to music and watching the water until the sun set.

We both agreed that this was our single favorite part of the trip despite all of the other cool things we saw. I learned from this moment to be more spontaneous and allow myself more time to rest and be mindful when I’m in a new and beautiful place. It was something I definitely needed to learn and now want to remind others to do as well!

We finished off the night in Narragansett, snacking on some clam cakes from Iggy’s Doughboys and Chowder House. We sat on a wall by the water and chatted while we watched the orange-colored moon slowly rise over the horizon. Pictures absolutely didn’t do this justice, but I tried anyway.

I had never seen anything like this happen before and it all definitely felt like the most blissful way to cap off such a memorable day.

Where are your favorite places to go in New England? What did you think of our choices?


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I am a 25 year old American girl trying to see the entire world with my travel partner/boyfriend, Jacob. We find beauty in the biggest and smallest places and the journey it takes to get there.

20 thoughts on “4 Days in Massachusetts and Rhode Island (Vlog Included)

  1. I’ve worked in Provincetown for 4 months, several years ago, and loved it there! The food that I had at the Canteen restaurant was amazing back then! It was so nice reading your blog post and being able to immerse myself once again into that atmosphere. Thank you, Kristen, great blog post!

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  2. Haven’t been to this part of the states yet but it looks like there are some great places to get some food and drinks – and the beaches look amazing too!

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  3. I live in Toronto, Canada which is just a short flight from Boston! I’ve always wanted to visit this region of the USA, but I guess it’ll have to wait until the border reopens. Either way, thanks for this great guide – pinning it for when I can finally make the trip!

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  4. What an awesome spontaneous road trip…I tend to plan also, but every now and then it feels so freeing to let go and see what happens! I lived in Vermont for five years so am a huge fan of New England. I had friends who lived on the Cape so it has a special place in my heart.

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  5. I’m also a plan everything to the t kind of traveller, so I feel super proud that you went on a spontaneous trip, and look how beautiful it turned out to be!! Newport looks adorable, and right up my street- love a good cliff walk!

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  6. I think sharks are cool, but maybe not swimming with them. Never realized the came so close to shore. I do love a spontaneous trip, figuring things out as you go. It has been a really long time since I’ve done that. Newport Rhode Island looked so beautiful.

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