Boston Proper in 24,000 steps
a day trip itinerary // Boston, Massachusetts
In a whirlwind weekend in the Summer of 2023, Sean and I got to explore downtown Boston from head-to-toe, lovingly guided by our friends Ben, his wife, Armiew, and then-almost-1-year-old, Hazel. We clocked in 24,000 steps, 10.62 miles, walked from morning to sundown, ate at all of the important food spots, saw all the sights, and felt extremely blessed by the Lord to have done all of that within 12 hours. (can you tell I like my vacations intense?)
Below was our itinerary, plus a hand-drawn map and pictures 😊
📍280 Congress St. Garage // park here, if you’re driving into the city! This garage has great parking prices and also lands you a 3-5 minute walking distance from Boston Tea Party Ships & Museum, which is where this rigorous tour of Boston Proper begins 😉
📍Boston Tea Party Ships & Museum // we came for the Tea Room experience and had a lovely morning of sampling the 4-5 teas that were supposedly thrown overboard during the Boston Tea Party in 1773. (& from the Tea Room, you get the perfect view of people throwing fake tea overboard as part of the guided tour)
🚶♀️Atlantic Ave. // now begins the walking… take this road north! We did this on a beautiful sunny Saturday, so we saw many outdoor markets, and even got to pick up handmade earrings for my friend’s birthday. This path will also take you through scenic roadside greenery patches—something I didn’t expect Boston to have a lot of but was pleasantly surprised that it did!
📍EY-Parthenon // halfway up Atlantic Ave., you’ll see this beautiful building with an archway that opens up into the Boston Harbor. The way the American flag hangs in the middle, catching the light, took my breath away!
📍Faneuil Hall Marketplace // at this point, you’re probably starting to get hungry. Perfect time to browse the food stands at the famous Quincy Market, shop from over 40 local vendors, and if you’re lucky, enjoy some street performers! We tried the chowder here, because how can you not when you’re in the New England area?
🚶♀️The Freedom Trail // from Faneuil Hall Marketplace, you’ll begin following the Freedom Trail markings in the sidewalk. This is a super famous, 2.5 mile walking tour that hits 16 nationally significant historic sites that a lot of folks will recommend you do, but we’ll only hit a portion of the sites in this itinerary.
📍Little Italy // almost immediately when you cross into Boston’s North End, you’ll notice a dramatic increase of Italian everything. A lot of people find themselves here to figure out where they stand in the Mike’s Pastry vs. Modern Pastry vs. Bova’s Bakery cannoli debate, but for us, since we aren’t cannoli fans, we came for one of Ben’s favorite gelato places, Dolce! (I know, I know… did we even visit Boston if we didn’t get a cannoli? Don’t let this age-old question re-prioritize your travel plans!)
🚶♀️Hanover St. // walk this up from Dolce to see Paul Revere’s House, then Old North Church
📍The Paul Revere House // Paul Revere owned this home from 1770 to 1800; we did not pay for the tour, but the admissions tickets are affordable if you’re interested!
📍Old North Church // the launching point for Paul Revere’s revolutionary ride (say what!). The courtyard is large and was dotted with street performers/craft stands.
🚶♀️N. Washington St. // take this across the Charles River out of North End and into Charlestown (aka: “Old Boston,” or the O.G. as I like to call it)
📍City Square Park // is at the south-most corner of Charlestown, basically right when N. Washington St. ends. And it is the quaintest green space that ever did exist! There are plenty of metal park benches and trees to make for a pleasant outdoor destination.
🚶♀️Main St. to Monument Ave. // from the worn, character-filled brick buildings to the cobblestone streets, this strip is probably the most European of any town in America
📍Bunker Hill Monument // where the New England soldiers faced the British army for the first time on June 17, 1775, and wounded/killed 1000 out of the 2,400 British soldiers
🚶♀️Pleasant St. // this street runs parallel to Monument Ave. and leads right to Warren Tavern. It was crazy to find Sean’s dad’s childhood home among these town homes—naturally we had to take a picture!
📍Warren Tavern // first erected in 1780, and now touted as the oldest pub in Massachusetts (and probably in America), the vibes alone are worth your time (the interior makes you feel like you’re Hamilton waiting for his musical to be written). We took a break here to share some appetizers and get a beverage.
🚶♀️ Main St. // take Main St. back down the way you came, through City Square Park, and cross under the overpass and onto the walking paths along Paul Revere Park. As you keep walking West, you’ll pass Lynch Family Skatepark and North Point Park, which are all so beautiful!
🚶♀️Charles River Dam Road Bridge // once you run into Charles River Dam Road Bridge, turn onto it and take that back onto the main Boston Proper peninsula
📍West End // not much going on here, it’s just the north east area of Boston
🚶♀️Charles St. // soon the road will transition into Charles St.—a shopping street that also has a lot of European-cobblestone-worn-brick character—which will take you straight into the Beacon Hill area. It is one of the best places to buy something cute and local in Boston, so check it out if you’re looking for a super cute strip of boutiques and specialty restaurants!
📍Beacon Hill Books & Café // is 100% one of those said cute shops on Charles Street. The first floor is a café with coffee and light bites (you need to make a reservation for a spot) and floors 2-5 sell various genres of books, with the top floor being all children’s books! Super aesthetic.
📍Public Garden // at the end of Charles St. is the Public Garden, which is right next to Boston Common. The Public Garden differs from Boston Common in the sense that there are more plants and greenery, and even a small pond in the middle with a scenic bridge. They offer Swan Boats to ride at this lovely small pond!
📍Boston Common // the city’s largest green park, the layout and vibes are very similar to the Oval on The Ohio State University’s campus (which I know everyone knows about 😉). The entrance corners are laden with food trucks selling popcorn, hotdogs, funnel cakes, all that fun fair food. The smells are tantalizing!
📍 Chinatown // doesn’t dim sum sound nice after 24,000 steps? We ended the day with a nice and filling meal at Hei La Moon Restaurant. Which, strategically, is also a stone’s throw away from the 280 Congress St. Garage, where your lovely car has been napping in all day.
✨ Beacon St. // if you have more than a day to spend in Boston and enjoy window shopping, this street needs to be on your bucket list. It’s the heart & soul of the Back Bay East/Back Bay area and houses a mix of local boutiques and mall brands in its many storefronts. At the end of this street you’ll also be close to the Prudential Center, which is a large indoor mall that has Eataly (!!)
✨ Prudential Center // chillin’ at the end of Beacon St., this is a large indoor mall. But most importantly, it houses Eataly, which has gelato that truly tastes like it’s from Europe and is overall just stellar all around (shelf products, raw foods, pastries & coffee, food food, you name it, they have it and rock it).
~ cath!
That yellow skirt looks GORGEOUS on you!!
that gelato looks goood