Boston Long Weekend Itinerary

Tuesday, May 31, 2016

I spend all winter waiting for Memorial Day Weekend, or at least I do, because that means it’s time to say bye to the harsh winter month. I’m always amazed by how many people who consider themselves travelers have never visited Boston. True, as a history nerd and lover of New England myself, I’m a bit prejudiced, but I’ve been to almost every city worth visiting and I can honestly say that none is more beautiful, especially the walk by the harbor and a glimpse look of old Italy in the North End of Boston.
Boston Bayback row houses. 

Day 1 (Friday late afternoon)

Depends on where are you traveling from, if you're traveling from NYC, there's a few afforable bus carriers you can book ranging from $10 - $30 for each way. Amtrack would be more comfortable and you can catch the train from all cities. Otherwise if you arrive at Boston’s Logan Airport, take the “T” (the region’s public transit system) to your hotel (cabs are quite expensive, especially after you pay tolls and airport fees, even though the airport is very close to the city proper).

Long known for only having a few grand dame hotels worth mentioning (e.g., The Ritz Carlton, now a Taj property, and the recently renovated Fairmont Copley Plaza), the city has seen a lodging boom in recent years. When I travel I usually either stay in a nice hotel and couchsurfing (platform for members to "surf" on couches by staying as a guest at a host's home, host travelers), this time I decided to couchsurfed with host (talanted and friendly Chris and Derek) and I stayed in downtown Boston by the Tuffs Medical University.


Getting around in Boston by public transportation and by foot are as easy as a piece of cake! With only a pair of high heels and flat, I walked over the city by foot and T trains in which Bostonian modestly call The Hub (as in the Hub of the Universe, no less).


Once settled, I suggest take a train to Mount Vernon Restaurant & Pub (Sullivan Sq / Orange line) for the twin lobster deal! I paid $19.99 for two lobster during peak season but I've been told during off peak season, you can get the deal for $12.99! 14 Broadway Somerville, MA 02145

Twin Lobster from Mount Vernon Restaurant in Somerville, Boston, MA 
Take the T (orange line) to downtown crossing and satisfied your shopping cravings. Downtown Crossing was Ben Franklin's stomping ground and a gathering place for the Sons of Liberty. Little more than a century after that, it had become Boston's chicest place to shop. The neighborhood's theaters—The Modern, the Opera House, the Orpheum and the Paramount—had all opened between 1900 and the 1920s as vaudeville palaces but later turned into X-rated movie houses or simply sat vacant.

Caffè Nero -  560 Washington St Boston, MA 02111 
Indeed, stop by in award winning European coffee house, Caffè Nero for a cup of joe, if you decided to have it to go, take your coffee wih you and visit Boston Common (also known as the Common) is a central public park in downtown Boston, Massachusetts. It is sometimes erroneously referred to as the "Boston Commons". Dating from 1634, it is the oldest city park in the United States.
Volunteers planted the flags for Memorial Day weekend to remember every Massachusetts service member killed in action since the Revolutionary War. The Massachusetts Military Heroes Fund organizes the tribute each year.
After a long walk in Boston Common, stopped by in the latest hidden gem, speakeasy bar - Yvonne's. Refined yet playful supper club in a handsome hideaway accented with marble & mahogany wood. When Boston’s historic restaurant Locke-Ober closed its doors in 2012, the reinterpretation of the classic restaurant, Yvonne’s (named for the subject of a classic painting in Locke-Ober) continues the tradition that Locke-Ober was so well known for while adding some new twists (think a champagne cart available by tugging a chandelier string and communal dining with shared plates). Located near Downtown Crossing at 3 Winter Place, Yvonne’s has a “secret entrance” through a blow-dry bar and is now divided into a classic Library Bar, main dining room and comfortable lounge. The iconic restaurant has remained true to its roots with Locke-Ober’s expansive Santo Domingo mahogany bar still prominently on display now with polished décor. As for dining, the menu here, which focuses on shared plates, was designed by Chefs Tom Berry and Juan Pedrosa with flavors of the Far & Middle East, Mediterranean, Europe and America. Sip on a classic cocktail here like Locke-Ober’s infamous Ward 8 or select a bottle of wine from their collection of more than 200 selections. (A separate drink list will be available in the Library Bar). 2 Winter Place, Boston, MA 02108


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After a few sips of the fancy cocktails, head to The Tam, a dive bar for dive bar connoisseurs, the Tam is a Boston legend—and rightly so. Everything here is just as it should be: the beer is cheap, the whisky is plentiful, the neon is garish, the music is loud, and the toilets…er, have running water. An eccentric, eclectic crowd gathers to sample its delights but be aware, don't flash your credit cards, it is cash only. The Tam - 222 Tremont St, Boston, MA 02116

Day 2 (Saturday)

Start the day early with a stroll around Chinatown (orange line). The neighborhood has a seemingly endless supply of dining spots both on its main drags and its side streets. And yes, the quality varies from place to place, with some restaurants being outstanding while others being so-so (or worse). So where to go while in Chinatown?


Well, if you are looking for great food at reasonable prices and don't really care about elegance or comfort, there is a little hole in the wall on Harrison Avenue called Hong Kong Eatery that is a truly great option, and a hidden gem to boot.
Your best bet for traditional Cantonese barbecue, this place offers specialties like char siu pork, and roast duck and chicken (try them in a combo rice plate). As seen here - Roast duck and chicken over rice $6.95
The menu features mainly Hong Kong style cuisine, including lots of seafood dishes as well as some pretty exotic entrees. Prices for nearly everything are downright cheap, with the majority of items being under $10. But if you are ok with a relative lack of atmosphere (or are looking to do takeout), Hong Kong Eatery is quite simply one of the best of many options in the Chinatown neighborhood of Boston. 79 Harrison Ave., 617-423-0838 

I'm a coffeeholic so I'm always on a hunt for the best coffee. I stumpled upon JAHO, a coffee bar by day, a wine bar by night in Chinatown/Downtown Crossing. In the daytime, the coffee offerings will be complemented by sandwiches. A large coffee roaster sits off to the side but is still very much a part of the room, with a small bar surrounding it, where guests can sit, sip, and watch the process. At the night, the bright lights will dim; it'll be time for craft beer (on tap and in bottles), wine, and an assortment of whiskies to take center stage. There will be small bites available, like charcuterie and cheeses, to accompany the beverages. 665 Washington St Boston, MA 02116


After spending some time in Chinatown, I suggest a walk. Indeed, if all you do is stroll Boston’s historic neighborhoods, that is reason enough to visit, but, of course, there’s much more to do and see. From the golden dome of the State House to the elegant homes of Louisburg Square, Beacon Hill (red line / Charles MGH stop) highlighting examples of early American architecture with particular emphasis on the work of Charles Bulfinch. Start at the corner of Beacon and Charles Streets, at the foot of Beacon Hill. Feel free to pop into the many unusual shops along this gas-lit thoroughfare, Among the notable residents of this beautiful square, past and present, are U.S. Senator John Kerry and Louisa May Alcott, who put pen to paper at No. 10. Combine its stately black-shuttered brownstones and old-world cobblestone streets with its contemporary amenities and central location, and it’s easy to understand why Beacon Hill boasts such a prestigious reputation. 

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On the red line, get off in Kendal/MIT stop. Across the Charles River from Boston proper, on the red line, get off in Kendal/MIT stop. Cambridge is best known for being home to the universities of Harvard and Massachusetts Institute of Technology (MIT). Largely because of this, Cambridge has established itself as a center of education and innovative science and technology. But there's so much more. Between museums, colonial architecture, historic university campuses and countless places to see and be seen, it's a place where you can relax, and explore one of the many "bests" of this area of Massachusetts. While on campus you will also find excellent museums and galleries. The Compton Gallery, among many galleries housed in the MIT Museum, and the outdoor sculpture collection on MIT's campus, provide a wide array of art offerings including frequently changing exhibits focused on science and technology.


No trip to the Boston area is complete without a visit to Harvard Square, where you can experience an wide array of delectable eats, and a simultaneously relaxing and stimulating atmosphere for shopping and taking in the sights. Take a leisurely walking tour or stop to watch an engaging street musician. Visit one of the many book shops bordering the square such as Harvard Coop, in operation since 1882 and with four floors of books to peruse. Nosh on some tasty victuals like a creamy New England clam chowder and a frothy Sam Adams beer at one of over 90 restaurants in the area. Russell House Tavern and Park Restaurant and Bar are right in the square. Various special events take place in and around the square all year.

Harvard Square - Red line stop
Hop in a cab or walk across Massachusetts Avenue’s Harvard Bridge to Central Square in Cambridge. Your destination is Toscanini’s, purveyors of arguably the best ice cream and sundaes in the United States. From here, it’s a lovely walk across the Charles back to Boston. Or heck, you’ve walked enough — take a taxi. Just ask the cabbie not to drive like a true Bostonian. 899 Main St, Cambridge, MA 02139

Day 3 (Sunday)

Great coffee shops is not hard to find in Boston, although Render Coffee just got in “America's 50 Best Coffee Shops” in America according to The Daily Meal. Hope over here for great breakfast sandwiches and a cup of cold brewed ice coffee, which will really get your day going! (Mass Ave / orange line) 563 Columbus Ave, Boston, MA 02118

After a delicious breakfast, walk to the elegantly simple Old State House (1713), one of the oldest public buildings in the United States, now a museum and a portal to the State Street T station. Cross over the site of the infamous Boston Massacre on your way to Faneuil Hall (1742), still used for public meetings, in the shadow of Quincy Market, once a collection of warehouses but now a beehive of upscale shops and restaurants. There's tons of things to do/see/eat in North End.

When you're in North End, you have to stopped by in Cannoli Factory, they claimed to have the best cannoli in Boston, although I heard Mike's pastry is pretty good too! Cannoli Factory - 272 Hanover St, Boston, MA 02113

A photo posted by Jessica Sophia Wong (@sillydrunkfish) on


A photo posted by Jessica Sophia Wong (@sillydrunkfish) on

In past years, you’d cross under the hideously green Central Artery (part of Interstate 93) on your way to the next stop, Paul Revere’s house - 19 N Square, Boston, MA 02113 (1690 - Boston’s oldest building), but that’s all gone now. In its place is a lovely park, the Rose Kennedy Greenway, now that the highway has been moved underground thanks to the multi-billion dollar “Big Dig” project, reputedly the biggest public works project in U.S. history. From here, it’s on to the Old North Church (1723). One of America’s most beautiful places of worship, this is where sexton Robert Newman hung the lanterns (the church still owns one of the two originals) that signaled the advance of British forces. Old North Church - 193 Salem St, Boston, MA 02113

A photo posted by Jessica Sophia Wong (@sillydrunkfish) on

From Boston North End walked to Haymarket area and visit Union Oyster House. Despite being almost 200 years old and a National Historic Landmark, Union Oyster House retains its reputation as one of the best seafood restaurants in Boston - a place for special celebrations and lobster dinners, as well as quick bites at the oyster bar.


Located near Faneuil Market on one of the first lanes laid out by the Puritans in 1636, Union Oyster House claims to be the oldest restaurant in Boston. In one of the upstairs dining rooms, you can see the favorite booth of another regular, President John F. Kennedy. 41 Union St, Boston, MA 02108

After fullfilling my stomach full of oysters and clam chowder, I walked to Boston's first public market, Faneuil Hall - adjacent to the site where Quincy Market now stands - was built in 1742, when the colony of Boston was still young. As a wholesale market, the building quickly became a gathering place for America's early citizens. 367 S Market St, Boston, MA 02109

Quincy Market - also called Faneuil Hall Marketplace - offers 100+ stores, artisan pushcarts, restaurants, and pubs right on Boston's famed Freedom Trail. More specifically, Quincy Market is actually the name of one of the four historic buildings making up the Marketplace.
A photo posted by Jessica Sophia Wong (@sillydrunkfish) on

It's only a short walk to the harbor by Quincy Market but of course, high heels are not recommended. To see a whole lot of waterfront and waterfront attractions, meander along Boston’s Harbor Walk, which right now includes almost 40 miles of pedestrian- and bike-friendly public access at the water’s edge. Boat watching in a breezy day or hop on one of the whale watching cruise to see whales in action.


A photo posted by Jessica Sophia Wong (@sillydrunkfish) on

Before ending the whole day of walking, follow the red line to Copp’s Hill Burying Ground, across from Boston’s narrowest house at 44 Hull Street (known as Spite House, this 10-foot-wide structure was built in 1874 as the result of a family dispute, and you can actually rent it for a short stay if you’d prefer living in a bit of history). “Old Ironsides,” the USS Constitution, oldest (1797) commissioned warship in the world, lies at anchor below in the Charlestown Navy Yard. It’s a 15-minute walk from here. 1 1st Ave, Charlestown, MA 02129

Day 4 (Monday)

Start the day in South End (Bay Back station / orange line) and check out Cathedral of the Holy Cross, the mother church of the Roman Catholic Archdiocese of Boston and is the largest Roman Catholic church in New England. When construction was finished, the cathedral rivaled both Old South Church and Trinity Church in grandeur, signalling the emergence of Roman Catholics in what was, at the time of construction, a largely Protestant city and state. Although the South End was initially developed for Boston's emerging Anglo-Saxon Protestant middle class, the neighborhood transitioned to new immigrants, especially Irish, as middle class owners moved to the new Back Bay neighborhood.

The cathedral is located in the city's South End neighborhood, at 1400 Washington St., Boston, MA 02118
It's brunch time in Boston! Head over to The Gallows and try the scoth eggs! Only boring people eat omelettes for brunch. At The Gallows, you can order anything from a pulled pork corn muffin to a sunnyside burger, but the real star is the scotch egg. It’s basically like a hardboiled egg inside a meatball, and they cook the egg so perfectly that you’ll have lots of opportunities for #yolkporn pics. 1395 Washington St, Boston, MA 02118

The “unique” New American comfort food on offer is “impressive” at this “lively” South End haunt known for its “crowded bar scene” and “fantastic” Sunday brunch
That's pretty much sum up my solo traveling in Boston during Memorial Weekend of 2016 and of course,  here is my sample itinerary for your references and you can always add or minus items on the list. On my last night in Boston, I went on a date with a recently MBA grad from Harvard and checked out the Harvard Business school residence as well, and a late night Chinatown supper with an über driver, (we became friends). So, create your own Bostonian journey!

A photo posted by Jessica Sophia Wong (@sillydrunkfish) on

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