Boston, Massachusetts
Updated: Apr 13
We had the opportunity to take a fun little weekend getaway to Boston, and we put together this itinerary for you to follow along! We focused on hitting the must-see spots in the city, along with a day trip to Cape Cod. Since we visited during the off-season, we didn’t get to explore as much as we would have liked—some shops and restaurants were still closed. That just means we’ll have to come back! We’d love to experience Cape Cod in the summer and enjoy everything it has to offer.
We truly fell in love with Boston—the architecture, the history, and the people make it such a beautiful and welcoming city. One of our favorite things was how walkable it is; you can easily get to most places in downtown Boston, which makes exploring so enjoyable. We had the best time wandering through different neighborhoods and taking in all the historic sites, and we hope you love it just as much as we did.
Friday Night
Fly into Boston Massachusetts Airport
Check into The Row Hotel at Assembly Row
We absolutely loved our stay at The Row Hotel at Assembly Row! The location, the vibes, and the service were all amazing. It’s part of Autograph Collection Hotels by Marriott Bonvoy, which we always try to book when we can because each property has its own unique style. The Row has a modern, industrial feel and is beautifully designed. Pricing was around $250–$320 per night, which felt very reasonable for a three-night stay. Plus, Assembly Row is filled with shops, restaurants, and coffee spots, making it such a fun and convenient area to stay in.
Dinner at Posto (right next to The Row Hotel) or if you're looking for something quicker, they have options such as Cava, Sweetgreen, and Shake Shack.
Saturday Morning- Day trip to Cape Cod
Leave early (7 or 8 AM at the latest) It is about a hour to an hour and a half from Boston, but the trip is so worth it!!
Chatham- the cutest little coastal town! They have so many things to see and explore, here are some of the places we got to see!
Chatham Perk- The coffee here was okay, what we really loved was their pastries! We had a Morning Glory muffin and it was delicious.
Main Street shops- very cute local stores where you can find lots of Cape Cod souvenirs! The Mayflower was our favorite store, they have a little bit of everything!
Chatham Lighthouse Beach- the classic Cape Cod photo spot! You can see the lighthouse and then go down to the beach and get some sun!
Chatham Bars Inn- the cutest hotel with the most stunning views of the ocean! They have a restaurant where you can get a drink and a bite to eat.
West Dennis- about a 20 minute drive from Chatham!
Cuffy's of Cape Cod: The cutest store and boardwalk! It reminded us a lot of Disney World! They have a great selection of sweatshirts, beachwear, and souvenirs. They also have a sweet's shop where you can find fudge, chocolates, and many other fun candies.
West Dennis Beach- such a stunning view of the ocean, the water was so blue here! We got to beach comb for seashells and watch the birds and ducks.
Captain Parker's for lunch! I cannot recommend this place enough! We had the best meal of our trip here. We ordered their Lobster Roll, the Clam Chowder, and the Coconut Shrimp. Everything was beyond amazing, and the restaurant itself is so coastal and fun.
After lunch we headed back to Boston! It was around 1:00 PM and it took us about 2 hours to drive back since the traffic had built up on the roads. But once we got back to our hotel we got ready to go into the city to visit some iconic spots!
Beacon Hill
Acorn Street- the most photographed street in all of Boston!
Beacon Hill Library and Café- such a cute and small 5 story library! They have a small sit down café on their 1st level.
Brownstones on Beacon Hill- stroll down the residential streets here. The cobblestone roads and brownstone homes are stunning and picturesque.
Saturday Night in Boston
There are so many amazing and aesthetic restaurants in Boston! Since they are very popular and good, they book really quickly! Make sure you make reservation about a week in advance if you can! We were able to snag a reservation at Coquette in the Omni Hotel.
This restaurant is so cute—very pink and perfect for photos! The food and drinks we tried were great, though in our opinion the cocktails were on the pricier side (basic drinks started around $20). I ordered a glass of rosé prosecco and it was divine, and my husband had the Rush Hour cocktail and really enjoyed it. You’re definitely paying a bit for the presentation, but it’s part of the experience.
We started with the Nonna Buns, which were essentially four fluffy dinner rolls topped with butter, parmesan, and garlic—so good. For our main, we shared the Spicy Salami Capri-style pizza, which we loved because the thin crust kept it light and not too heavy. Overall, we really enjoyed this spot and, if we lived in Boston, it would definitely be a go-to for a fun girls’ night out!
After Dinner drinks:
Contessa: Iconic rooftop, views of the city and the Public Garden! Definitely a dressy vibe.
Oak Long Bar & Kitchen: Glamorous, chandeliers, old money aesthetic.
The Liberty Hotel Lobby Bar: A very unique spot! Its is located inside a former jail, super cool for content.
Sunday Morning
Coffee Shops to visit near Beacon Hill, Boston Common, and Newbury Street.
Tatte Bakery and Cafe: Parisian aesthetic, amazing pastries, sit down available.
Blue Bottle Coffee: Small coffee shop but the coffee is amazing!
Central Perk Coffee Shop: Just like the show FRIENDS!
Blank Street Coffee: a lot of people in Boston claim this as the best coffee!
Walk around Newbury Street- This is the spot for shopping and café hopping. It is lined with brownstones, local boutiques, designer stores, and cozy coffee shops. Here are some of our favorite stores to visit:
Zara
H&M
Brandy Melville
Uniqlo
Anthropologie
Ralph Lauren
Le Labo
Aesop
FP Movement
Visit the Boston Public Library- it is one of the most beautiful spots in Boston! Think grand architecture, marble staircases, and it even has a courtyard that feels European. It was such a great place to stop and take pictures!
Head to The Boston Public Garden- It is right in the heart of the city and it is known for its iconic weeping willows. It is super peaceful and perfect for a stroll, a picnic, or just a cute break between exploring!
Walk across the street to Boston Common and walk around the park to start the Freedom Trail walk! It is a 2.5 mile red-brick path through Boston that takes you past 16 of the city's most iconic historic sites. You can do a self guided tour of the story of the American Revolution. Even if you are not big on history, like us, it is a really pretty way to explore the city, wander through different neighborhoods, and stop for coffee, shopping, and take pictures along the way!
Dinner in Boston
Try to get a reservation at any of the following restaurants:
Contessa Boston- amazing views of the city, dress up vibe!
Mooo- a terrific steakhouse in Beacon Hill
Saltie Girl- Oysters, Caviar, Lobster!
The city has so much to offer and places that we did not have time to visit on this trip such as Harvard University, Charles River Esplanade Walk, and Copley Place. We absolutely love Boston- from the charm of its streets to the mix of history, shopping, and cozy vibes, it is a city we would come back to in a heartbeat. Our day trip to Cape Cod was the perfect little escape, and it left us already dreaming about experiencing it in peak summer. Next time, we would love to see Boston in the fall for all the crisp, colorful magic- and head back to Cape Cod when its sunny, beachy, and in full swing.
If you have any questions about this itinerary or need any more information please reach out to us via email at thecarryontwins@gmail.com. And follow our instagram for live travel updates and photos @thecarryontwins.
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