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Jennifer O.

Boston, MA, USA Guide by Jennifer O. Status: Lived here (1 Dec, 1984 - 31 Aug, 2009)

What are some of your favorite memories of Boston, MA?
Evenings at Fenway on any summer night. As a kid, we’d go with my dad and bring our gloves in hopes of catching a fly ball. It never happened, but we didn’t care – the games and energy were all the fun we needed!

How would you spend 36 hours in Boston, MA?
I’d spend at least an hour trying to extend my stay! Then I’d face reality and head to Beacon Hill for a nice stroll around the neighborhood. After checking out the lovely townhouses and the State House, I’d walk to Faneuil Hall and Quincy Market for some fun shopping. Next I’d swing north to Hanover St and feast on some delicious Italian food! I’d hop on the T and go straight to Park St, and from there I’d continue my walk through Boston Common, the Boston Public Gardens, and Commonwealth Ave Mall. If I were lucky, I’d have tickets to a Red Sox game and would head straight to Fenway Park (also off of Commonwealth Ave). The next day I’d take a T bus out to Castle Island and go for a long walk around the lagoon. To wrap things up I’d walk from Castle Island up to Dorchester Heights (also in South Boston), where a monument stands commemorating the battle for the city in 1775. From this point one can take in all of Boston and feel good about having seen so much in just 36 hours time!

What kind of practical information should first-time visitors know about Boston, MA?
Prices in Boston vary a lot by neighborhood. You’ll get a lot of bang for your buck eating Italian in the North End, but be prepared to carry a doggy-bag home. Newbury St has some lux places, but be prepared to fork out the cash (pun intended). Transportation is very affordable. You can purchase a day or weekly ‘Charlie Card’ at any ‘T’ stop and use it on busses or trains. The city has many color-coded subway lines, and what you can’t access by train you can get to by bus. Like any city, rush hour brings with it delays and lots of people, so plan accordingly. Note that taxis are very pricey, so I’d strongly recommend relying on public transportation.

What are some precautions that people should take while exploring Boston, MA?
I’ve always felt very safe in Boston, and I don’t think it’s a scam-heavy place. The usual precautions will do (e.g., don’t go out alone late at night). Also, if you get sick in the city, no worries – Boston has some of the best hospitals in the world, so you’ll be in excellent hands!

Any other indispensable pieces of advice to share?
Boston has four seasons, so know when you’re going and dress appropriately. Personally, I would recommend visiting in late spring or early fall. Bostonians are known for having interesting accents. Most locals don't use the letter ‘r’. This can be very challenging for newcomers who are waiting for the train conductor to announce the ‘Park St’ or ‘Harvard Square’ stops. On the whole, though, it’s quite entertaining to hear ;) Finally, remember that Boston is a port city. Boats leave daily for ocean excursions or to drop you at neighboring coastal places. Consider a whale-watching trip or a leisurely boat ride while you’re in town!

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  • Beacon Hill, Boston, MA

When I think of Boston, I think of Beacon Hill, a posh but quaint borough of idyllic townhouses and cobblestone lanes that stirs thoughts of Boston’s colonial era. The best thing to do in Beacon Hill is to simply walk around and take in the peace and beauty. Be sure to stop at Louisburg Square (the house on the far left with the big American flag is Senator Kerry’s place), take a peak at the State House (and note its Bulfinch golden dome), and look out over vast Boston Common, a large and lovely green space in the heart of the city.

  • Commonwealth Avenue Mall, Commonwealth Avenue, Boston, MA

The greenery of Boston Common continues down Commonwealth Ave Mall. (In fact, the two areas are part of the larger ‘Emerald Necklace’, a network of parks and gardens that envelops the city.) Tall trees flank Commonwealth Ave Mall, starting from Arlington St. down to Hereford Ave. Rows of lovely brick townhouses provide parallel boundaries for this lovely walkway, which is often lit up at night. A stroll down the Mall or a nice rest on an abutting park bench is a great way to start any day in Boston.

  • Fenway Park, Yawkey Way, Boston, MA

In Boston, the Red Sox are religion, and devout followers go to Fenway Park to worship. There is truly no better way to spend a night in the city than to sit under the lights at this historic ballpark. Whether you’re behind home plate or up in the bleachers, grab a hot dog, sit back, and feel the energy of an entire city cheering on its home team.

  • Castle Island, Boston, MA

A true treasure of the city, its location in South Boston has kept it largely hidden from tourists and newcomers. The site earns its name from Fort Independence, built by the British back in the 1600s and still largely maintained today. The fort nearly touches the Atlantic and is surrounded by walkways and fishing piers. A man-made lagoon was constructed nearby and is full of bikers, runners, and skaters any day of the week. If you like pub-style food, stop by Sully’s for some great hot dogs and fries. Be prepared to wait, though; this is a neighborhood favorite. If you’re lucky enough to get some grub, be sure to guard it well from the seagulls. They love Sully’s too!

  • Hanover Street, Boston, MA

Ask anyone on the streets of Boston, ‘where can I get good Italian food’, and they’ll all say the same thing: the North End. Boston’s very own ‘Little Italy’ doesn’t disappoint, either! You’ll find excellent lasagna, meatballs, and chicken parm all up down Hanover St. An iconic stop for cannolis is Mike’s Pastry, also on Hanover St. If you have trouble finding the North End, just look up: the Old North Church, from where Paul Revere took his colonial cues, still sits in the neighborhood.

  • Neptune Oyster, Salem Street, Boston, MA

Boston is known for its seafood, and if you’re looking for good oysters, this is the place! Tucked away in the North End, one could easily walk past this small restaurant, but that would be a big mistake. At Neptune, oysters are sourced from across the Eastern coastline and can be custom ordered based on the beach from where they were collected. Unfortunately the small interior can mean long lines, so try going at an off-peak time with only a small group of friends. If nothing else, you should be able to grab a seat at the bar itself.

  • Eastern Standard Bar, Commonwealth Avenue, Boston, MA

Boston is known for its Irish Pubs, and there are plenty to choose from, but if you’re looking for a slightly less rambunctious scene, check out this place. In the spring and summer, the front panes of Eastern Standard open to let the sounds of Kenmore Square rush in – quite a scene after a Red Sox game! And the bartenders here are some of the most talented in the city. If you can’t decide which cocktail you’re in the mood for, give them one or two flavors you like and they’ll be sure to whip up something tasty.

  • Top of the Hub, Boylston Street, Boston, MA

While this place is often thought of upscale and snooty, the lounge is surprisingly cozy and well-priced. Request a table by the windows facing Back Bay and behold some of the best views in the city. From some 50 floors above Boston, you’ll be able to take in the Charles River, Trinity Church, Old North Church, and many more sights! My favorite dishes to order are the margherita pizza, chicken lollypops, and crème brulee.


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