My first cold-weather trip of the year was to New England! This was my first time in this region, spending four days with my two Instagram besties Sam (@soudersam) and Jules (@bejulesed). We’ve been on several trips together but this one was extra special because it’s Jules’s hometown!

She’s the best tour guide… we got the full tour of her city, Boston, Massachusetts, and then road-tripped to Newport, Rhode Island to see the quaint coastal beach town in the midst of its off-season. We had a blast per usual, packing all kinds of city sightseeing, eating, hotel hopping, and laughing into our short stay. 

This isn’t the longest travel guide I’ve published considering we only had two days in each spot but I’m still sharing all the details of our trip including hotel stays, restaurant recommendations, must-see spots, and a detailed packing list of what to bring. Enjoy! 

Boston, Massachussetts 

Where To Stay 

For my time in Boston, Massachusetts, I checked into Stay Pineapple, the cutest boutique hotel located in the South End. I stayed in one of their South End Corner King rooms and although it was tiny, I’ve been told this size room is pretty typical for Boston.

My room had a large, comfy king bed, a gorgeous view of the city, and cozy robes to lounge in. This was the perfect spot for our little galantine’s day celebration with champagne and new matching pajamas! 

The bathroom here was small but so adorable—entirely marble with amazing lighting and a walk-in shower.

Stay Pineapple offers free water, tea, and pineapple cookies in the lobby and is known for being a dog-friendly property. This specific location also has a restaurant attached that serves amazing brunch on the weekends. They also are open for dinner and drinks nightly. If you’re interested in booking a stay with Stay Pineapple, click here for current availability and the best rates! 

Restaurant Reccomendations 

Ciao Roma 

Menu // Directions

We had the most amazing three-hour-long dinner at Ciao Roma, an adorable Italian restaurant located in the North End. We started off with their incredible arancini and calamari. Both were super tasty! For the main courses, we split the penne a la vodka (my personal favorite), shrimp scampi, and chicken parmesan. I couldn’t believe how huge the portions were, or how tasty everything was. 

Paired with a few of the cranberry Aperol Spritz’s this was the perfect night. I cannot say enough good things-=0 about this restaurant—the girls and I have been to hundreds of restaurants together but the vibe of this one was unbeatable. 

Greystone Cafe

Menu // Directions

One of our friends recommended this place to Jules because they are known for their to-go coffee window. I’m not a caffeine drinker so I ended up getting a Caprese sandwich instead. Originally I was bummed that this was a cold sandwich but to my surprise, I ended up enjoying how fresh it tasted. The mozzarella was amazing and the balsamic glaze was so tasty. Perfect spot if you’re looking to bring your laptop and work for a bit or just need a quick coffee on the go. 

Levain Bakery

Menu // Directions

This adorable bakery is known for its chocolate chip cookies. It’s nestled right between the cutest stores on Newbury Street and is the perfect spot to pick up a sweet treat and mid-day coffee. I’m a foodie at heart so I can’t say it was the best chocolate chip cookie I’ve ever had but it was a good afternoon pick-me-up.

Cafe Vittoria

Menu // Directions

Jules took us to Cafe Vittoria claiming that it was her go-to spot when she was in college to grab a sweet treat after dinner. I tried their red velvet cake and it was amazing. Sam ended up getting their lobster tail which was three times the size she expected and five times too big for her to finish, haha. This would be a good first date spot—young people chatting everywhere. Gotta love that diner feel! 

Frank Pepe 

Menu // Directions

Sadly I don’t have any photos of my margarita pizza from Frank Pepe but it was so yummy! I’m not usually a pizza fan so I was shocked to find out how much I enjoyed this. Perfect place to get takeout for a girl’s night in. 

What To Do 

Just explore. Boston is far bigger and more spread out than I imagined so we found ourselves just wandering around taking in the sights. Jules spewed all kinds of fun facts about different neighborhoods and buildings. I’m not usually one for restless, aimless exploring like this but unlike other cities, this isn’t really one with landmarks that you just have to see. Plus, it was like five degrees during our visit so we didn’t have it in us to do as much as we would have liked, haha.

Rather than a tourist destination, Boston felt more like a city with a lot of young people who just loved to be living in it.  

Newbury Street 

You can’t come to Boston and not go to Newbury Street. This adorable strip reminded me of so many quaint European cities I visited abroad. There are all kinds of adorable boutiques, local artisans, and bookstores along this strip. Plus, you can find favorite retailers like Lululemon and Sephora. We spent a few hours popping in and out of different stores, window shopping, and attempting to keep warm. 

Prudential Center

Jules told us you can’t come to Boston and not go to the Prudential Center. This is essentially a huge mall with tons of designer stores and favorites like Urban Outfitters and Altard State. There’s also a fun little market inside here that has tons of different food vendors. I stopped at Eataly and got myself an overpriced gelato because I’m missing Italy more than I ever imagined! 

Quincy Market 

Quincy Market is a food hall full of different restaurants. They have anything and everything you could imagine—Thai, Chinese, Italian, chowder, sandwiches, sweet treats, and more. Definitely a good spot to come to if you’re wanting variety! If you walk down the stairs you can also find a few local artisans and all kinds of Harvard merchandise! 

Newport, Rhode Island 

Where To Stay 

For my time in Newport, Rhode Island I checked into The Cliffside Inn, a beautiful family-owned inn nestled just a block from the water. This was my first time staying at an Inn—this had that cozy bed-and-breakfast feel and an interior that looked right out of a Gilmore Girls scene.

We stayed in their Tower Suite which was located just off the main house. This was a gorgeous two-story suite, separate from the rest of the property. It was so quiet here, you could’ve heard a pin drop!

The upstairs was truly the most beautiful bedroom. Complete with a large queen bed, funky wallpaper, and antique furnishing, the character of this room speaks volumes. However, the large window nook and huge windows are what make this room so memorable. Watching the sunrise over the water here is priceless.

And of course, because this is the Tower Suite, this room has beautiful tall ceilings with windows wrapped all the way around. The natural light in here is just phenomenal! I’ve never stayed in a room so unique—it feels more like a bedroom and less like a hotel.

A spiral staircase leads down to the ground level where there’s the hugest bathroom you’ve ever seen: a beautiful walk-in shower and the largest bathtub I’ve ever been in. I filled this to the brim one morning and took the longest bubble bath—truly the perfect spot to relax.

The owner of the Cliffside Inn makes breakfast from scratch in the main kitchen each morning. We enjoyed fresh berries, egg casserole, avocado wraps, and muffins. With a cozy fireplace and inviting interiors, I loved this Inn more than I ever could have imagined. I’d take many more weekend getaways right here.

If you’re interested in booking a stay at The Cliffside Inn, click here for current availability and the best rates!

Restaurant Reccomendations 

We were only in town for one day so I don’t have as many recommendations as I usually would. However, we did spend our sole night wisely, hopping from place to place to experience a few different atmospheres!

Clarke Cooke House 

Menu // Directions

Jules claims that Clarke Cooke House has the best clam chowder she’s ever had, lighter and thinner than most served in New England. I’d never had clam chowder until this day so unfortunately I don’t have anything to compare this to, but I will say it was mighty tasty. A cup with a few pieces of bread was the perfect appetizer while sipping a few cocktails!

Plus I loved the vibe of this restaurant—it was chic yet coastal giving all the New England vibes. If you’re wanting a pricey seafood meal with a beautiful oceanfront view, stay here for your full meal!

Bar and Board 

Menu // Directions

We came to the Bar and Board for a couple of drinks before dinner. We were expecting more of a college crowd but got here a little early (and on a weekday) so we ended up sitting down and just mingling amongst one another. Still a cute vibe for an Aperol Spritz with your girls!

Brick Alley Pub 

Menu // Directions

We ended up venturing over to brick Alley Pub per a follower’s recommendation and it did not disappoint! This place was packed full of locals and had the largest menu you’d ever seen. I ended up getting their jalapeno cheddar burger with chipotle mayo and bacon and it was phenomenal. Full of flavor and cooked perfectly.

Jules got their blackened fish tacos which I just had to snag a bite of. These were coated in cajun seasoning and a fruity slaw. The portion of food was insane for the price and so delicious. I would highly recommend it! This was the spot place for a casual night out and a cheap (yet strong) drink. I would definitely come again!

What To Do 

Shopping along the Newport Harbor

Back in my OG Styledby day’s, I was obsessed with New England style—Lily Pulitzer, The Black Dog, and of course, everyone’s favorite—Kiehl James Patrick. I’ve always wanted to visit the storefront and was stoked to see it along the Newport Harbor. I had to go in and buy a sticker after all of these years.

There are so many cute local boutiques along the water. I would have shopped for hours, admiring all of the classic preppy styles if most weren’t closed for the season. I definitely need to come back to Newport in the summer when it’s lively and full of summer tourists!

Check Out The Marina 

There is a gorgeous marina in Newport with dozens of boats parked along the water. It wasn’t even five degrees during our day of exploring and yet we still trekked out to watch the sunset… a must if you’re in the area. There are tons of different bars and restaurants along the marina so if you’re wanting to grab a bite to eat while watching the sun go down, there’s plenty of opportunities in this area.

Cliff Walk

Right outside of The Cliffside Inn is the popular Cliff Walk. This is a beautiful place to go for your morning walk—a long path with gorgeous views of the water on one side and huge celebrity-owned mansions on the other. It was so peaceful here, especially on a chilly winter morning.

What To Pack

We visited New England in the midst of a brutal winter cold front. Temperatures barely crept above fifteen degrees and yet I still managed to stay warm enough during our days full of exploring. Sharing all of the outfits I wore during this trip + links to shop in this blog post.

In the meantime, here’s a packing list of things you need to pack for your trip to New England this winter.

• Your Warmest Jacket: I hate to admit it but Boston is not the place for your cute new pink coat… you’ll need the warmest jacket you’ve got! Preferably something that goes down to your knees to help keep the wind out.
• Hat/Ear Muffs: I laugh thinking back to the days when I was embarrassed to wear a hat when it was cold outside. What a silly thing to think?! I’ve got all kinds of cute beanies and earmuffs to keep my head warm and I brought every last one of them. These are not a suggestion but a must. 
• Scarf: Never underestimate the power of a good scarf. I swear these huge chunky plaid scarves are what kept me warmest in the midst of the cold front! Plus, they really do make every outfit 10x cuter.
• Gloves: Trust me; you’re going to want a pair of gloves. I know they are a pain in the butt, but just bring them with you.
• Leggings: Sometimes it’s just so cold that you need two pairs of pants on. That’s the kind of weather we got stuck with this trip—I slipped a pair of Aerie crossovers underneath my pants each day to give me an added layer and was so grateful I did.
• Warm Socks: I always wear my Cozy Earth cashmere socks for a day full of sightseeing. They are super thick, keeping your feet nice and toasty. I highly recommend investing in a pair they really are my go-to’s.

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Well, that’s a wrap on my mini trip to New England. Despite the cold, slower travel days I was surprised at how much I enjoyed both Boston and Newport. I hope to go back and visit in the summer to experience both states during their prime time…perhaps later this year!

In the meantime, I am off to Colorado for a snowy trip to the mountains. Stay tuned for more travels and more guides chock full of information coming your way very soon. Until then…

With love, McKenz

Latest Post: What to Wear in New England This Winter
Related Post: Chicago Travel Guide Summer 2021
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