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Boston: An Essential Guide

With a rich cultural history and striking modernity, no city combines old and new better than Boston. A port city that sewed the seeds for the American Revolution, Boston came to define the American story. But, as extensive as the city’s legacy may be, Boston is actually quite small in size. The city itself encompasses just 125 square kilometres (48 square miles), has a population well under a million at about 650,000, and is known as one of the most walkable cities in the world. Age-old architecture plus an iconic skyline and famous parks equal an aesthetically pleasing cityscape in almost every part of town.

Whether in town for work or pleasure, this essential guide to Boston will help you figure out how to get around, what to see, and where to go when you’re yearning for a bit of history in the city.


Boston proper is broken up into loosely defined neighbourhoods. While change is constant, each part of town maintains unique characteristics that have remained intact over time. With vehicular traffic notoriously terrible and unavoidable most times of the day, coupled with a public transit system that may remain forever dated and unreliable, few cities rival the navigational ease of Boston by foot.

“Downtown” is defined by business. Trading, large department stores and historic attractions-turned commercial tourist traps are all found here. Just north of downtown you’ll find the North End. This is Boston’s “Little Italy.” Here you’ll find famous Italian restaurants, bakeries, cafés and landmarks, such as Paul Revere’s House and the Old North Church.

Head south and you’ll find the South End. The once seedy section is now a thriving LBGT-friendly neighborhood filled with boutiques and restaurants. Still further south you’ll find Chinatown, which isn't as famous as those in other cities). Cross the bridge over the highway and there's Fort Point Channel; head even further south and you’ll find yourself in South Boston, the primarily Irish neighborhood affectionately referred to as “Southie.” The neighbourhood is gentrifying, with new shops, lofts, galleries and restaurants popping up all the time.

Just west of downtown is Beacon Hill. True to the old ideal of a “city on a hill,” this is where you’ll find the State House, local government and brownstones owned by the richest and oldest families around. Head further southwest and you’ll reach Fenway and Back Bay. Fenway is home to world famous museums, fields of natural beauty and the grand church of baseball, Fenway Park. Back Bay’s cityscapes and squares offer plenty of Instagrammable moments, while the stretch of commerce and wealth known as Newbury Street is great for shopping and people watching alike.


Public transit

The Massachusetts Bay Transit Authority (www.mbta.com) runs an integrated network of public buses and subways within the Greater Boston area. Ironically named after the famous Kingston Trio folk song about a man named “Charlie” who can’t get off of the train because of the hike in fares, Boston bases its transit on the CharlieTicket and CharlieCard.

Fare for the subway is $2.65, but $2.10 if you manage to find a place that sells rechargeable CharlieCards. Buses cost $2.10 for a single ticket or $1.60 with a CharlieCard. Day passes are $12.00 and weekly passes are $19.

Residents complain constantly about the delays and inefficiency of the T. But, being America’s oldest subway, there’s not much that can or will change. There are five different lines, each defined by color and each with varying degrees of frequency and expediency. Transferring from one to the other is free with your original purchase.

Taking the Silver Line bus from the airport is free and conveniently drops you off at South Station where you have access to the Red Line, Boston’s most convenient route.

Once again, walking is the best way to navigate Boston. Trains come next. Most lines run underground and are not defined by the traffic that exists above. But, be advised, post-work rush hour and events like Celtics, Bruins or Red Sox games cause trains to become overcrowded and too uncomfortable to bear.


Base fare: The initial charge is $2.60, plus $.40 for each 1/7mi; waiting time is $28 per hour.

Cabs in the city are plentiful and easily hailed in the downtown core. Compared to other major U.S. cities, cabs in Boston can be quite expensive. There are flat rates posted from the airport to various popular destinations so the customer knows what to expect, but because of bridge/tunnel tolls they tend to range between $25 and $40 excluding tip. Because of city ordinances, Boston cabs cannot pick you up in Cambridge (even if it’s the only one around), and vice-versa. Many a heated argument and fines have resulted when taxis are caught in violation. There are several cab companies, and getting a cab is very easy at any hour, especially on major streets. If you don’t see one, call one. Getting to your destination, however, is a different story. With bridges often closed due to construction and limited connectors to major highways jam-packed due to traffic, waiting in a cab during rush hour, watching your meter tick away can be the most stressful travel experience in town.

While the conversation continues and cab companies continue to try to outlaw Uber, it is still a viable option—not to mention the cheapest and often most convenient, cleanly and efficient.  


• Radio: For current affairs, human-interest stories and cutting-edge interviews, tune in to WBUR (90.9 FM), Boston’s local National Public Radio (NPR) outlet. For a wide variety of music that strays from the mainstream and the homogenized trends of radio programming, stick with college radio. WMBR (MIT, 88.1FM) WZBC (Boston College 90.3) are arguably some of the best in the country. For a real treat, switch over to the “Memories Station,” WJIB at 740 on the AM dial for a mesmerizing trip to the lost sounds of yesteryear. There aren’t left many like this.   

• On the hotel TV: CNN is the principal 24-hour cable news outlet, and for local coverage turn to NECN (New England Cable Network). Other local channels provide news coverage periodically throughout the day.

• Listings for arts and culture, events, food and drink are not as easy to pin down as they once were. For the most complete, yet still lacking coverage, check out www.digboston.com or pick up today’s edition of the reliable Boston Globe.

• LGBT-focused listings: www.lgbtmassvacation.com


To avoid lines – and only if you’re in a sightseeing kind of way – it’s best to get a City Pass. At $49, plus tax, the City Pass grants admission to four Boston attractions: The New England Aquarium, The Museum of Science, The Museum of Fine Arts and the Skywalk Observatory. The pass saves you money on full-price admissions and – most importantly – allows you to skip most ticket lines.

Sightseeing tips:

• The best views of Boston and its surroundings is from the Prudential Tower. Take the elevator to the 50th floor and head to the Skywalk to explore 360-degree views of Boston. The cost is $17 for adults and $12 for children. Pro Tip: take the elevator to the 52nd floor and you can explore the view for the price of a cocktail, snack or dinner at Top of the Hub.

• The Esplanade is a stretch of land that runs along the Charles River. You’ll see Cambridge and the buildings of M.I.T. across the way, and the natural beauty includes a paved path that is for bikers, joggers and walkers alike.

• The cheapest, easiest and map-free way to explore the complete history of Boston is to walk the Freedom Trail. Follow the painted red line marked on the sidewalk for a self-guided four-kilometre (2 ½-mile) walk that takes you that takes you to 16 of Boston’s most historic sites, including Boston Common, the Site of the Boston Massacre and Faneuil Hall. This is historic Boston at its finest, and without any hassle.

• Not only the scene of the most infamous and and unsolved art heist of all-time, the Isabella Stuart Gardner Museum is also a beautiful destination known for its architecture and the paintings, furniture and artifacts that are on display inside.

• The Museum of Fine Arts has been home to one of the world’s most comprehensive collections of art at its current location since 1909. From ancient Egypt to modern works, any trip to Boston should include a stop here.

• The Institute of Contemporary Art is worth visiting even just to enjoy a coffee in the waterfront café, let alone the actual contemporary art.

• You can visit Fenway Park, home to the Boston Red Sox, even when the famous baseball club is not playing. Little has changed since its 1912 debut besides the advertising, gourmet food options and seats on the Green Monster.

• Any trip to Boston should include a stop over the Charles River to Cambridge and Somerville. A world headquarters for higher education, Cambridge and Somerville have more of a laid-back, less touristy, vibe than Boston proper, not to mention a thriving arts scene.


Where to go if there’s something you need, and quickly

For everything you need under one roof, the Copley Square Mall and the Cambridgeside Galleria should have just about everything you’re looking for. Shop for clothes, electronics, souvenirs, luggage or a gift for a loved one while making a pit stop for fresh local fish at the famous Legal Seafoods.  

Beer, wine and liquor

Liquor stores can open as early 9 a.m. (noon on Sundays) and can sell until 11 p.m. Some grocery and specialty stores carry beer and wine, but not many. If you’re unsure, you’re better off going to a nearby liquor store. There’s one every couple of blocks.

Establishments in Boston proper can begin selling booze as early as 8 a.m. Monday through Saturday, and Sunday starting at 10 a.m. (not many open that early, however). Bars in Boston can serve until 2 a.m. every day, while Cambridge and Somerville close their doors at  1a.m., with some bars granted a 2 a.m. licence on Fridays, Saturdays and Sunday holidays.

You must be 21 years old to drink in Massachusetts.

Published Saturday, August 1st 2015

Header image credit: Getty Images



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