Boston Itinerary: tips for a weekend trip to Boston

Can you believe that I’ve been living in New York City for over 9 years, and I’ve never been to Boston? I don’t know about you, but I have a tendency to procrastinate about traveling to some destinations when these places are close – for some reason, I feel there’s no rush since it’s close, lol. Well, I finally changed that cause last week I spent a weekend in Boston – I was invited by Meet Boston – Tourism Bureau – and I was so excited to share everything with you! Boston is charming and beautiful and whether you’re a history buff, a foodie, or a lover of the arts, the city has something to offer everyone.

In this blog post, we’ll guide you through a weekend itinerary packed with exciting things to do and see – so let’s dive into some activities and attractions! I traveled with my friend Laura Giromini, a content creator and influencer.

Where to stay in Boston

We stayed at XV Beacon Hotel – a boutique hotel in Beacon Hill, considered one of the best hotels in Boston, and I couldn’t recommend the place better! The rooms are very spacious, the bed is so so so comfortable, and the decor is so chic. Also, love the fact that there is a gym – with even a Peloton bike! – and a rooftop with beautiful views of the city. My room was always so neat and clean. The staff is really nice and sweet. As you can see, I really loved my stay!

Oh, and there’s a restaurant at the hotel called Mooo, which offers breakfast, lunch, and dinner, plus room service. Laura and I had breakfast there, and it was so delicious. I wish I had time to have dinner there, I bet it’s really good as well.

How to get to Boston

If you live in New York City, there are so many ways to get to Boston! You can rent a car, you can catch a flight, you can hop on a bus or you can go by train – which was our choice! Amtrak trains depart from Moynihan Train Hall – the “new” Penn Station – and the trip is smooth! It takes around 4h15 min to get to Boston – there are some stops on the way. The seats are comfortable; there’s plenty of space to store your luggage, plus every seat has an outlet to charge and a little table. Also, the train features a coffee shop, quiet car, and business class. In Boston, you will arrive at South Station.

It was my first time traveling with Amtrak and I couldn’t recommend it more. Such a comfortable and convenient way to explore destinations near the city!

Things to do in Boston – our itinerary!

We arrived in Boston on a Thursday night – around 8 pm – and we departed on Sunday, at noon. It was short and sweet – and still, we managed to do so many things! I will share our itinerary, with attractions, tours, activities and restaurants – and I will also add some other suggestions of more things to do!

Day 1 – Thursday

As I mentioned, we arrived at South Station around 8 pm, and we called an Uber to the hotel – I would like to highlight that Laura and I used Uber a lot because we had a lot of pre-booked activities and reservations at restaurants, so, for us, it was more convenient and fast to use Uber. But, be aware that Boston has a “T” subway system, which includes subways, trains, and trolleys along five separate lines. Also, you can rent bikes. I would say that, if the weather is good, exploring the city by bike or by walking are probably the best choice!

After checking in, we left the hotel to have dinner at Lola 42. This is an upscale neo-global bistro & sushi bar, and the menu features sushi, Japanese izakaya-style bites, and global dishes. We started with the Spanish Octopus with cauliflower puree and it was divine! We also ordered some sushi rolls and, for dessert, we had the Classic Brownie Sundae, with vanilla ice cream. OMG, the brownie was so so so good! Definitely recommend this spot – the environment is super cool!

Day 2 – Friday

I’ve become this person that wakes up early and gets happy if the hotel has a gym, so, as you can imagine, I started my day running 4km on the treadmill, lol. After that, we headed to Mooo, the restaurant at the hotel, to have breakfast. We ordered yogurt bowls and avocado toast. Everything was super tasty.

We requested an Uber to our first activity of the day: Innovation Trail, a walking tour in Cambridge. For those who are not familiar, Cambridge is situated just across the Charles River from Boston, and, as you probably know, it is widely known for its prestigious educational institutions, including Harvard University and the Massachusetts Institute of Technology (MIT).


This walking tour was really interesting! We learned a lot about the innovations that have happened and that are in the works – from anti-aging technology to gene editing. We walked past The Broad Institute, Google, Microsoft, Novartis, Akamai, and a myriad of other Info- and BioTech giants. We heard a lot of interesting stories. Absolutely loved it – such an interesting focus! After the tour, we stayed around the Killian Court – MIT – to take some pictures at the waterfront, with beautiful views of Boston.

We headed to our next destination: Time Out Market Boston – I was so excited to check this place because I love the Time Out Market concept (I’ve been to the NYC and Lisbon locations). Time Out is a media company and these markets are dining-and-culture experiences curated and vetted by their editors. The idea is that a meal at Time Out Market Boston means you’re truly digging your fork into the city’s most delicious dishes, cooked by some of New England’s most decorated chefs. Expect seafood, Italian food, tacos, burgers, donuts, drinks and more. Laura had the famous Lobster Roll from Cusser’s Roast Beef and Seafood and I tried the Nori Tacos from GoGo Ya – and if you are into sushi, you NEED to try these. Yep, you read it right: like sushi tacos. SO SO SO GOOD! We also got a cold brew from Say Cofee Co – and it was probably the best cold brew I’ve ever had, seriously.

From Time Out Market, we walked to our next destination: the Museum of Fine Arts, which is one of the largest and most comprehensive art museums in the United States. The museum showcases over 450,000 objects, including paintings, sculptures, decorative arts, photographs, prints, textiles, and more. Among the collection, you will find galleries dedicated to ancient Egyptian and Nubian art plus European paintings from renowned artists like Monet, Van Gogh, and Rembrandt. The Monet Gallery is a must-visit! So many paintings. You can easily spend hours at this museum.

Next, we visited one of the most famous attractions in Boston: Isabella Stewart Gardner Museum, which is a short walk from the Museum of Fine Arts. A lot of locals recommended us this place. It’s an enchanting art museum showcasing the personal collection of its founder, Isabella Stewart Gardner. The museum’s collection comprises more than 7,500 works of art spanning various periods and cultures. It includes paintings, sculptures, furniture, textiles, ceramics, and rare books. The pieces are displayed in a manner reminiscent of the original arrangement Isabella Stewart Gardner herself envisioned. The museum’s centerpiece is the stunning Venetian-style palazzo, designed to resemble a 15th-century Venetian Renaissance palace. The courtyard is definitely a highlight!

Also, an interesting fact is that several valuable artworks were stolen in 1990 – and the heist was never solved, and there’s a documentary on Netflix about it (it’s on my watchlist!)

After visiting the museum, we took an Uber back to Beacon Hill – Laura wanted me to try Tatte Bakery, a French Bakery chain with many locations in Boston. This area is super charming, with many shops and cute corners, so I recommend walking around and exploring. At Tatte, we tried the chocolate mousse; it was perfect in texture and flavor. Then, we headed to Acorn Street, a cute cobblestone street.

We then walked back to the hotel – passing by Boston Common on our way, a beautiful and charming park  – for a quick stop before heading to the next stop: View Boston! I absolutely love observatories and was so glad we were there just when they opened. View Boston is a 360 observation deck offering breathtaking and orienting views from high above the heart of Boston, featuring an indoor enclosed area and a terrace. Unfortunately, it was a bit cloudy that day, and there was no sunset – but still, the views are fantastic! Besides the views, View Boston features an immersive theater and an interactive neighborhood discovery tool to explore various neighborhoods and locate attractions, restaurants and landmarks of interest based on your individual taste – there’s also a fantastic scale model of the city with light projections – can we please have something like that in NYC? You will also find a restaurant – The Beacon – and a bar – Stratus. Make sure to reserve a spot!

We returned to Time Out Market to eat something and tried tacos from Taqueria El Barrio. So good!

Day 3 – Saturday

The weather was not good, so we had some changes of plans – but nothing that prevented us from exploring the city. I started my day with breakfast with a friend that lives in Boston at another Tatte Bakery at Seaport. I had the yogurt granola bowl and another avocado toast. My friend and I also shared a pistachio and berries tart, which was perfect—absolutely loved Tatte; such a great spot for breakfast, brunch, or a quick snack!

Laura met me after breakfast, and we had tickets to ICA -The Institute of Contemporary Art  – which is a dynamic and innovative museum dedicated to showcasing contemporary art in various forms. Situated on the waterfront in the city’s Seaport District, the ICA is known for its striking architecture and thought-provoking exhibitions. With your ticket, you can also take the shuttle ferry to East Boston to visit The ICA Watershed, which is their museum across Boston Harbor, open in the summer months.  Every summer, this space in a formerly condemned copper pipe factory is transformed with a new exhibition. In East Boston, you can also visit  The Tall Ship Boston, which is a 245′ vessel turned floating oyster bar moored on Pier One. Unfortunately, it was closed that day due to the weather.

We had lunch at ReelHouse Oyster Bar – please when in Boston, take advantage and have seafood because everything is so fresh! This restaurant has beautiful waterfront views! I had oysters and more sushi tacos because why not? Laura had their Lobster roll. They also brought us some Tuna nachos. Make a reservation, because they we really busy!

We then headed to Lyric Stage Company of Boston to see a play – Rooted. Make sure to check their calendar; there are always great productions! After the play, we took a Duck Tour – make sure to include this in your itinerary when you visit Boston, was another highly recommended activity! It’s a very popular and unique way to explore the city’s landmarks and historic sites. You are probably wondering about the name… You will ride in a specially designed amphibious vehicle known as a “duck,” which can travel both on land and in water. Yep! You will see a lot of spots in Boston while the guide tells interesting and fascinating stories and facts, and then the vehicle heads to the Charles River and tou will have beautiful views as it floats along the water.

We finished our day at the North End – Italian District – an area in Boston with a lot of Italian Restaurants. We had a glass of wine at Ciao Roma, and then past at Forcella and dessert at Caffè Paradiso – because the line at Modern Pastry was too long, lol.

Day 4 – Sunday

We had a train to catch at noon, so I woke up early to run. After packing and checking out, we had brunch at The Beehive, a cute restaurant with live music. We shared a delicious French toast and, you guessed, I had another avocado toast because why not? Lol! We got to the train station around 11:15 am, and we had a great trip back to NYC!

I loved Boston! There’s a lot of history, and if you are into cultural experiences, there are plenty of things to do- and many amazing restaurants. Definitely, a great getaway if you live in New York City!

Other places and activities you can consider when in Boston

  • Cycleboat
  • Faneuil Hall
  • Freedom Trail
  • Brattle Book Shop
  • Harvard

We had such an amazing time in Boston! Thanks, MeetBoston, for having us!

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