Spend a Weekend in Boston
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Let's explore Boston, the birthplace of the American Revolution. Between work and visiting friends, I've been to Boston quite a few times and still manage to discover something new each time I visit.
This northeastern gem has something for any type of vacationer. Whether you're lounging on beaches in the south end or savoring mouth-watering eats in Little Italy on the north end. History buffs are in for a real treat, too. You'll spot the costume-clad tour guides roaming the city guiding hoards of groups, regaling them with the tales of our nation's founding.
On my latest trip to the city, I stayed for two days. This itinerary will center Downtown and Back Bay neighborhoods. Ready to have a fantastic weekend in Mark Walhberg's hometown? Let's go!
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Boston is a big little city. Many of the attractions are scattered among three major areas: Downtown, Seaport and Back Bay. The city is easy to navigate so a stay in any of these areas will be accessible to all that Boston has to offer.
Dagny Hotel
Omni Seaport
The Godfrey
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Boston is definitely a foodie city here are some must try restaurants:
Mike's Pastries
Kane's Donuts
Tatte's Bakery&Cafe
Buttermilk & Bourbon
Quincy Market
Anywhere in Little Italy
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But First Coffee!
Tradesmen Coffeehouse - Co-located with Dagny
Thinking Cup
Ogawa Coffee
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Top Activities and Attractions:
Shop and Eat at Quincy Market and Fanuiel Hall
Visit the Public Garden
Stroll along Beacon Hill
See The View at Prudential
Paul Revere House Tour
Getting Around
You'll arrive at the Boston International airport, conveniently located about a 10 minute drive from the city limits, allowing you to start your vacation right away! Catch a rideshare at the designated spot in the airport and you're on your way.
For my chronic illness breadren, be prepared: Boston airport is huge. And I swear I always arrive at the gate farthest away from the exit. If you're having a tough day, don’t hesitate to ask the flight attendants for help arranging transportation. Getting to the ground transportation area from the terminals is quite a trek.
Boston is one of the most walkable cities I've been to. Many of the top attractions this town has to offer are central to one another, and strolling past the beautiful brownstones of Beacon Hill and the breezy seaport makes it easy to forget how much ground you're covering.
If you need to travel across the city, Boston's transit system has you covered. Their subway system is quick and convenient with numerous stations throughout the city. It's about $5 for two trips or $11 for an all day pass, giving you access to all of Boston's public transportation options. You can also purchase tickets to the “Hop-On Hop-Off” bus to get a guided tour, while bopping around.
I highly suggest NOT DRIVING, unless you're planning an excursion outside the Boston area. Boston traffic is crazy and frankly the roads make no sense. Between the walkability, public transportation and rideshare, there really isn’t a need.
Where to Stay
We stayed at the Dagny Boston, located within the Downtown Financial District. Surrounded by high rises, swanky coffee shops and restaurants it's peaceful yet central spot. Many attractions are within 10 minutes and public transit is close by.
I've stayed at the Dagny a few times and always have a great experience. The rooms are surprisingly spacious for Boston. Many of the hotels here are, well, cozy -- but the Dagny even has a little seating area at the foot of the bed, a rarity, in my experience.
I'd suggest staying within the Downtown area for the best access to city attractions. Other great places would be Back Bay and the Seaport. This city is very easy to navigate so it's hard to go wrong with picking a location.
Each neighborhood gives a different taste of the city. I've enjoyed stays in both Downtown and Seaport locations.
Day 1 : Arrival + Downtown
Highlights Include
Kane's Donuts
Fanieul Hall
Quincy Market
Paul Revere House
The Wharf
Little Italy
Mariel
I arrived early, so we weren’t able to check in without incurring a fee. So, we left our bags with the concierge and journeyed off. First stop: coffee!
The Dagny hotel is co-located with the Tradesman coffeeshop, you even get a discount on your orders after staying one night. This spot hosts a range of freshly baked delights. You'll see them bringing in trays to restock the eye-catching display.
We resisted eating any of the mouth watering bites, as I had my mind set on trying Kane's Donuts. Less than 5 minutes down the road, you can find Kane's Donuts which boasts to have the best honey donut in America! Unfortunately, we missed out on this and their Saturday special, as they were already sold out.
You have to get there quickly! When we arrived at the take out only establishment the line was long and shelves were stocked with orders for hungry awaiting customers. We ended up getting a traditional glazed donut and a cinnamon cake donut.
These babies were huge, nearly the size of my face. The glazed was everything you want from a glazed donut, moist, sticky and perfectly sweet. The cinnamon cake, while flavorful, was a bit too crumbly for my taste.
With our bellies satisfied, we're off to explore starting with Faneuil Hall and Quincy Market. Despite having gone here a few times, I still enjoy the spot. This spot offers a host of local shops, restaurants and food stalls. You can find nearly any type of food you want, and it's also where you'll pick up your historical walking tour if you booked one. I did one on a previous trip and had a great time-- highly recommended.
We had lunch plans at High Street Market with a friend, so we couldn't indulge in anything this time. However, the mac+cheese and chowder spots are definite hits, if you're looking for a treat!
In this area you'll find the New England Aquarium, Public Market and the Wharf. The Wharf is a great spot to walk around and take in the sites of the harbor. You can also visit the Paul Revere House. For $6 you can take a short tour of the home and learn more about this historical figure.
After a quick lunch at the High Street Market, we just relaxed at the park before going back to check into our room. Remember, with a chronic illness you have to pace yourself on trips.
I had just returned from a jam packed trip to Savannah, so I was still recovering from that jaunt. Fortunately, I have the best understanding friend who was more than happy to lounge about and catch up in the room.
However, if you're still raring to go check out the Little Italy in the North End which is a quick 10 minute walk from Downtown. You absolutely must try Mike's Pastries and get one of their legendary cannolis.
I'm not even a big cannoli fan and they were some of the tastiest things I've eaten in Boston. They have so many flavors you're bound to find one -- or two that you must have. Plus, Little Italy is a great spot to grab a dinner reservation.
For dinner, we had reservations at Mariel, a Cuban restaurant serving sharing style plates. Their specialty? Mojitos. We both ordered the guava mojito, mine being a mocktail. It was delicious and refreshing -- I may have guzzled mine down a bit too quickly!
For plates we shared the calamari frito, fufu gnocchi, salmon cubitos and the chicken tots. It was just enough to leave us satisfied. The calamari, gnocchi and salmon were hits. The tots weren't my favorite, but the sauce was bomb.
During the evening this place converts into a lively club, so if you want to dance the night away, this is a place to check out.
After dinner we hopped on the subway to head over to the Prudential Center to meet my friend's brother and get some dessert at Venchi Chocolate, a cute little shop located within the mall. We picked some treats to go, then hopped back on the subway to enjoy them with some tea in the room.
It was a satisfying end to the day. Travel in itself tends to take a bit out of me, so I try not to pack too much on the first day at a place. It's all about finding that balance between exploration and relaxation.
Day 2 : Beacon Hill + Back Bay
Highlights Include
Tatte Bakery & Cafe
Beacon Hill
African American History Museum and African Meeting House
Public Garden
Buttermilk & Bourbon
Prudential Center
First stop: coffee and breakfast! We headed to Tatte Bakery & Cafe at One Boston Place. There are several locations around the city, but this one was closest to our hotel. I was craving a shakshuka, a dish I first tried on a previous visit to Boston at Stephanie's on Newbury. It was so good, but I hadn't had one since!
The place was bustling. Tables filled the restaurant and I could tell this was going to be a good choice and I was not disappointed. We ordered their iced seasonal latte, which had a delightful pistachio, almond flavor. I got the traditional shakshuka and a salmon avocado sandwich for my friend.
The shakshuka was the perfect size and the accompanying three pieces of sourdough bread were warm and soft. Best breakfast!
Then, we headed to Beacon Hill to visit the Museum of African American History, just a 15 minute walk away. Be forewarned: it's a bit of an uphill journey to the museum. After that hearty breakfast, I was not prepared.
Tickets are $15 and grants access to the museum and a guided tour of the African Meeting house next door. This was a great tour and was amazing to hear all the notable African American leaders that have gathered in those halls.
Afterward, we strolled along the beautiful streets of Beacon Hill, mesmerized by the gorgeous brownstones and tree-lined roads until we arrived at our next destination: Beacon Hill Books & Cafe. My friend I are avid book readers, so I knew she'd enjoy this spot. With four stories of books, it's a nice spot to browse about…though quite narrow. On the ground level there is a reservation-only cafe to dine at.
Five minute walk later and we were at the Public Garden, a sprawling green space in the middle of the city. With mature trees and a charming duck pond it's such a nice place to hang out. As luck would have it, we happened to come during the Japanese festival. There were a variety of food stalls and activities taking place. This spot is often the home to many of the city's events.
The park is so huge, that the festival only encompassed one side. After venturing around we went to the other side to simply sit and enjoy the beautiful day for a while. Remember, pace yourself when exploring.
At this point we're starting to get a bit hungry, so we journeyed off to find a clam chowder. I don't care what the temperature is, when I'm in New England I have to have a clam chowder, it's practically a tradition for me.
We ended up at the Banks Fish House, where I satisfied my chowder craving and enjoyed an authentic Caesar salad -- because let's face it if there are no anchovies it's not a real Caesar salad period. My friend opted for the fish tacos that were stuffed with fresh fried fish.
Afterwards, we leisurely hung out around the city, takin in notable sights like Harriet Tubman Square, Newbury Street and the Prudential Center.
Before we knew it, dinner time had arrived, and we headed to Buttermilk & Bourbon, a New Orleans themed restaurant on Commonwealth Ave. If it weren't for the distinctive orange umbrellas outside, I wouldn't even have recognized it as a restaurant. Situated on a street of impressive homes reconstructed into offices, I thought I was in the wrong place.
However, once you step inside you're transported to a cool and vibrant scene. Another sharing style place, we got a few different things. The fried chicken and beignets are absolute must tries.
Now, we're on our way to the View, an attraction located within the Prudential Center that takes you to the top of the Prudential building to soak in panoramic views of the city. Seems like every city has one of these at this point.
There are three floors of activities: the top floor contains the window-clad views of the city, one level down is the restaurant and you're able to go outside, and the last level houses the gift shop and an interactive display. It's a cool little destination and if you collect souvenir pennies, like me, you'll be able to grab some here.
Final Thoughts
There you have it, that's how I spent the weekend in Boston. Some things I didn't get to on this trip that are noteworthy are the plethora of Museums Boston has to offer. From the Museum of Science, Museum of Fine Arts and Boston Tea Party Ships & Museum, there is so much to see.
If you enjoyed this itinerary, I've created a Google List to help you plan your trip and get a layout of the city. Drop a follow and have an amazing trip!
