Boston-a weekend itinerary

Boston-a weekend itinerary

As I discovered earlier this month, Boston is an utterly fantastic city to visit. Easily accessible from just about anywhere including a vast number of international cities, it’s the ideal destination for a long weekend. Not to say you couldn’t spend more time there because you could. However, in the span of three days you can really see and do a lot so be sure to follow along with my long weekend itinerary.

Day 1-late morning

Hopefully you’re like me and booked a flight that would have you arriving at Logan Airport in the mid-late morning. Or alternatively if you’re driving, a bright and early start is also the way to go. The airport isn’t located too far from the city center area and your options of getting to your hotel include either a taxi (estimate about $35 with tolls and a tip) or public transportation.

So, fingers crossed your room will be ready so you can deposit your bags and have a brief respite but otherwise head back on out! There’s a 385 year old city waiting to be explored!

Boston-a weekend itinerary

Day 1-early afternoon

Boston is very much a city to be enjoyed by foot so hopefully your hotel is close enough for you to head on over to its famous Chinatown (while small, it’s third only to New York and San Francisco’s which truly are the “big guns”). But if not, the T (the city’s underground train) does have a Chinatown stop right on the Orange Line. There are a mind boggling number of restaurants to try but like anything else, do your research. You certainly don’t want to squander your meal opportunities somewhere that’s just average. I personally recommend the Gourmet Dumpling House which offers delicious Szechuan fare. It’s cramped, hectic, and stressful but 100% authentic. If Chinese food isn’t really your thing, Pho Pasteur is touted as one of the city’s best Vietnamese restaurants.

Gourmet Dumpling House (Boston)-Restaurant Review

Be sure to wander the streets and check out the completely opposite world from the city’s historic sections. Then start walking the roughly 15-20 minutes up to the downtown neighborhood to start being immersed in all things colonial.

Boston-a weekend itinerary

Day 1-midafternoon

The Boston Tea Party, the Boston Massacre-some of the biggest events in American history happened right here in Boston. One of the first sites you come across will undoubtedly be the Old State House. It dates back to 1713 and was occupied by the British during the Revolutionary War. It also played tragic host to the Boston Massacre as the five innocent victims were killed right outside of its doors. A circle of cobblestones commemorates the event. Make sure you walk around to see all sides of the building-it’s quite striking and is a lovely example of Georgian style architecture.

Boston-a weekend itinerary Boston-a weekend itinerary

Next, make your way over to Faneuil Hall, which has served as a marketplace and meeting hall since 1742. Today, it’s home to some historical exhibits and numerous shops, many of which sell merchandise sporting Ben Franklin’s famous quotes regarding beer and farts (I kid you not). National Park Service rangers do offer historical talks every half hour so if you have the time be sure to check one out. And, of course, don’t leave without paying your respects to a certain Son of Liberty whose statue graces the front.

Boston-a weekend itinerary Boston-a weekend itinerary

And being in Boston, a city where alcohol is akin to breathing, check out one of the many pubs in the area. I recommend going the historical route. There’s the Green Dragon Tavern and the Bell in Hand Tavern. While the flat-screen televisions (majorly) detract from the historical ambiance, it’s still neat all the same to imagine individuals like Sam Adams and Jon Hancock sitting here enjoying a pint as they plotted against the British (supposedly plans for the Boston Tea Party were hatched in the Green Dragon).

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As they’re relatively in the area, be sure to seek out two non-colonial but equally important historical monuments-the Irish Famine Memorial which is right across the street from the Old South Meeting House and the Holocaust Memorial. Both employ unique designs that serve as powerful reminders of these two horrific events in history.

Boston-a weekend itinerary Boston-a weekend itinerary

Day 1-late afternoon

In a city as old as Boston, naturally there are going to be lots of cemeteries or burying grounds as they were once known. I recommend visiting Granary Burying Ground, which was founded in 1660 although it’s only the third oldest cemetery in Boston. It’s the final resting place to some of the city’s biggest players-John Hancock, Sam Adams, Paul Revere. It’s quite easy to find those graves as generally that’s where most of the mobs of people are. The five victims of the Boston Massacre are also buried here.

Boston-a weekend itinerary Boston-a weekend itinerary

And only a quick distance away is another famous burial ground-King’s Chapel which was founded in 1630 and was the first cemetery in the city. This is quite small when compared with Granary but pleasant all the same to walk around and look at the graves. I was fascinated by those tombstones in which more modern day development happened right on or near them.

Boston-a weekend itinerary

By now head back to your hotel for a rest although be sure to stop at one of the city’s coffee shops for a quick refresher. We went to Thinking Cup several times and were impressed especially by the Boston Cream Pie style tart.

Boston-a weekend itinerary

Day 1-evening

You’re in Boston, a sports obsessed city, and depending on what time of the year you’re there, I’d recommend checking out a sporting event. The baseball and hockey/basketball venues are both easily accessible via walking or public transportation and seeing a game is always a great way to experience the local culture. Fenway Park, home to baseball’s Red Sox, is rich in history (it’s one of the oldest sports stadiums still in operation in the country). I saw the Red Sox defeat the Philadelphia Phillies.

Boston-a weekend itinerary

Provided there aren’t extra innings, extra periods, etc, head back to the hotel after the game and crash.

Day 2-late morning/early afternoon

Start your first full day in the city with a food focus. Head on over to the North End neighborhood (a little past the downtown) and plan to stay a while as it’s an incredible spot. It’s existed ever since colonial times (it was Paul Revere’s stomping grounds) but over time became home to immigrant populations-first Eastern European Jews in the late 19th century followed by Italian immigrants in the late 19th to early 20th centuries. The Italians had the lasting influence and the North End is known as the Little Italy of Boston.

Boston-a weekend itinerary

Just like in Chinatown there are countless restaurants to check out here so do your research so you pick a good one. Not to mention save plenty of room for some of the great sounding treats-like gelato or cookies and cannoli from Maria’s Pastry Shop. A food tour is also not a bad way to go.

Boston-a weekend itinerary

Once your stomach has been satisfied, head to some of the historical attractions in the area (you are in Boston after all). Paul Revere’s house is tiny but interesting, considering less than a century ago it was at risk of being demolished.

Boston-a weekend itinerary

Then there’s the Old North Church which is a beautiful structure whose bell tower can be seen for some distance. This of course played a famous role in the legendary tale of the Midnight Ride of Paul Revere.


Day 2-midafternoon

Since you’re already pointed in the right direction, keep on walking and head across the Mystic River to nearby Charlestown (from the North End this will take about 20 minutes to walk). Luckily the Freedom Trail is well marked and will guide you precisely to one of the city’s most famous attractions, the Bunker Hill Monument. Once in Charlestown, you will pass by some beautiful, what appear to be 19th century homes.

Boston-a weekend itinerary

This large obelisk commemorates the Battle of Bunker Hill, the first major conflict between British and Patriot (the Americans) forces in the American Revolutionary War which was fought here on June 17, 1775. Visitors can climb to the top (294 steps in all, no elevators) for beautiful views of the city and surrounding area.

Boston-a weekend itinerary

Day 2-late afternoon/early evening

Even though your feet will start rebelling by now and feel like jelly, head back over to the North End/downtown area and get a light dinner. The food at the Bell in the Hand Tavern is quite good (clam chowder is a requisite and lobster grilled cheese an absolute delight). But really, you have no shortage of places to try out good ol’ fashioned New England fare.

Boston-a weekend itinerary

Return to your hotel and call it a day. Hopefully you were smart enough to get some Italian pastries to go earlier in the day that you can now feast on while relaxing in your room.

Day 3-late morning

You’ve been going quite strong since you first arrived so let your final full day in the city be a bit more relaxing. Since it’s Sunday after all, sleep in a bit and then head somewhere for brunch. If you’re interested in exploring some new neighborhoods that you haven’t been to yet, check out the areas of Copley Place and Back Bay. Both of them are home to some gorgeous, “simple” structures but especially Back Bay, which has no shortage of 19th century Victorian brownstones. Aquitaine’s wonderfully authentic ambiance makes diners feel as if they’re in Paris, with delicious food to boot.

Day 3-afternoon

You’ll be wanting to walk off the hearty brunch you just enjoyed so head on over to the Copley Square T stop, although be sure to admire the beautiful main branch of the Boston Public Library, Trinity Church, and the Old South Church.

Boston-a weekend itinerary

Two of Boston’s most famous museums are within minutes of each other-the Isabella Stewart Gardner and the Museum of Fine Arts. They’re both world renowned and you can’t go wrong with visiting either, although the beautiful Italian inspired courtyard found inside of the ISGM is certainly one of a kind. If you’re an avid art enthusiast, make time for both. Otherwise choose one.

Once you’ve had your fill of admiring centuries old works of art, hop on the T to go back to your hotel and rest although before you do so, definitely stop for a refresher (Cafe Nerro in the Theater District is an enjoyable spot).

Boston-a weekend itinerary

Day 3-evening

It’s your final night in this terrific city-so make it count. If you haven’t eaten too much seafood, make sure you remedy that before it’s too late, since Boston is one of the best places for fresh seafood in the country. Legal Seafoods is a popular restaurant group in the city and has numerous eateries all over (as well as in other states). Its Legal Harborside is quite popular and, as its name suggests, is right on the harbor and offers pristine views. Legal Crossing is also a good option.

Boston-a weekend itinerary

A nightcap would be a great way to bid a final evening adieu.

Day 4-morning

Hopefully your flight doesn’t leave too early in the morning so you have some time to enjoy yourself even if it does mean you’ll need to actually set an alarm to do so.

Boston Public Garden is a beautiful attraction in the city and the best part is that it’s free. It comprises 24 acres and was established in 1837, making it one of the oldest public parks in the country. It’s simply gorgeous-the flowers and greenery magnificent and I think even in the dead of winter when it’s covered in snow it would also be quite lovely. Be sure to check out the adorable Make Way for Ducklings statues which commemorate the children’s classic of the same name by Robert McCloskey.

Boston-a weekend itinerary

If your visit happens to fall during spring and summer, then ride one of the famous swan boats. They’re a fleet of dual-pontooned pleasure boats which operate in a pond in the garden. This cultural icon has been in existence since the 1870s if you can believe. Kids will simply love it and many adults will just appreciate the enchanting nature of it.

Boston-a weekend itinerary

And before you say bye to Beantown for good, make a quick stroll over to nearby Beacon Street, basically the Elfreth’s Alley of Boston. It’s a narrow lane paved with cobblestones and is home to some of the most beautiful town homes, thus making it one of the most photographed streets in Boston.

Boston-a weekend itinerary

So there you have it-how to spend a wonderful weekend in one of America’s most historic and beautiful cities. You won’t see everything there is but you sure will see a ton.

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  • Reply
    September 23, 2015 at 6:21 pm

    Wow I feel like I have visited Boston with you! So many things to see and do!

    If I ever get the chance to visit Boston I would take this post with me. I wouldn’t want to miss any of the sights that you mentioned. I might have to go hunting for a good veggie restaurant though. 🙂

    I love colonial architecture and historic sites! Boston’s Old State House is beautiful! Love the gorgeous details. However, I hate the fact that the modern buildings ominously loom over these lovely structures, but such is progress I guess. The cobblestone streets are so quaint.

    What is the “Green Dragon” crawling on? A very interesting piece. Although I’m not a drinker I would go just to experience the ambiance.

    Again, your photos are gorgeous and beautifully composed!

    I would go to Boston just for the Isabella Stewart Gardner Museum! Thanks for showing us how much there is to see in Boston!

    P.S. What type of sandwich goes with those french fries? 🙂

    • Reply
      September 24, 2015 at 11:52 am

      It was such a wonderful city-I’d return in a heartbeat and also live there! Such my cup of tea.
      I’m with you, colonial architecture in this country is simply lovely. I’m so fortunate to have grown up with in Philadelphia. To me, I somewhat like seeing the big, modern buildings right there-I like seeing how a city came to be. I’m not sure if you saw the movie Gangs of New York but my favorite scene is at the end when you see the New York skyline coming together. I imagined the same thing in Boston. But yes, the State House was beautiful.
      That was actually the beer tap-I couldn’t resist taking a picture. Very unique I thought.
      And thank you for your kind words, I’m definitely trying to be more artistic/have a better eye when it comes to picture taking.

      The sandwich was a lobster grilled cheese! We unfortunately never had our lobster rolls but this was at least something different 🙂

  • Reply
    September 24, 2015 at 9:48 pm

    You always express your love for travel so well in your posts! It makes me anxious to travel. Right now I am trying to find an apartment I can afford. Hopefully travel is in my future.

    Philadelphia is on my list of places to see. Seeing photos of the beautiful buildings and statues is just not the same as experiencing them for yourself. However, your photos come very close to it!

    Yes, I have seen Gangs of New York. I can appreciate what you are saying about watching the city evolve. Love that movie! 🙂

    • Reply
      September 28, 2015 at 12:25 pm

      I’m kinda torn as it’s my hometown and will always have a special place in my heart, but I found Boston to be equally worthy 🙂 Although hopefully you’ll have the chance to make it to Philly and then re-visit Boston once more! And thank you as always for the kind words about my photos-I keep trying to perfect my photography skills!

      Gangs of New York is a great movie. Such a fascinating albeit bloody piece of American history.

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    Bridget @ A Traveling B
    October 17, 2015 at 10:02 am

    What a great itinerary!! You really saw all the highlights Boston has to offer in a short period of time! I’m jealous that you made it to the Gourmet Dumpling House – it’s been on my list for a while and I still haven’t made it there! So glad you had such a great time in our city 🙂
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      October 17, 2015 at 8:20 pm

      Thanks Bridget! I’m really thankful for the blogging community since I probably never would have found out about the Gourmet Dumpling House otherwise 🙂 And yes, I absolutely LOVED Boston. History, walkability, wonderful food options, beautiful views-everything I love in a city. Can’t wait to return.

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