I recently found an excellent deal on roundtrip tickets to Boston. The catch was that it required making the reservations within the month, so my wife and I would be taking the trip on the spur of the moment with no planned budget. (The biggest cost was the Boston Red Sox American League Championship Series game tickets a few rows behind first base – but that was worth it!) We wanted to maximize seeing as much of Boston as possible without spending a ton of money, and since Boston has such excellent food of all varieties, we planned to splurge on some meals while exploring and learning about Boston on a dime.
For starters, we stayed at The Alise, a Staypineapple Hotel in Boston’s South End. It is a lovely boutique hotel with more charm and style than any of the standard hotels. The Alise is affordable at around $100/night, but what is even more attractive is its location. The South End is an excellent area of Boston to stay, and The Alise is within walking distance of the Boston Commons, Quincy Market, Fenway Park, the Blue Hills Bank Pavilion, Boston Symphony Center – plus, multiple museums and parks!
An alternative to staying in a hotel, Airbnb offers numerous options for the South End and Boston in general. For $80-100/night these homes are within walking distance of innumerable Boston treasures. Search Airbnb for Boston, MA near Boston Commons for the best locations near the sites mentioned here.
If walking is not an option, Boston has many alternatives for transportation. The Boston subway system is easily navigated, and Google Maps (or almost any phone app for maps) will deliver transit directions, including times of departure. Lyft and Uber are available and reliable. We used those services when a couple of our walks were interrupted by rain showers. Renting a car is NOT recommended as parking is difficult to find and often expensive.
There is a plethora of tours to enjoy, and most of them can be self-guided or purchased for a low cost. Be wary of promotions insisting these tours and sites are only available by purchasing tickets. Free Tours By Foot offers free tours in many towns including Boston. As long as your group is five or fewer, the tour is free – although tips are customary for the guides. Don’t feel as though a guide is always necessary, however, there are several interactive maps available, plus mp3 and pdf options of the information needed to learn while touring.
The Freedom Trail
One of the most popular walking tours is The Freedom Trail Tour. We did this tour in parts seeing the various sites as they fit in with other places we were eating at or touring. Walking the self-guided tour may take as little as 60 minutes or can last all day – especially if ducking into a classic Irish pub every couple of hours for “a pee and a pint” sounds appealing. Use the map below to go from sites A to L and read along with the free guide in pdf form. (Other options for completing all or part of this walking tour are included in the Reference section.)
Just a few blocks from the hotel, we found the quaint neighborhood of Bay Village centered along Arlington Street branched by Winchester, Melrose, Isabella and Cortes. The architecture is notable for both the Federal period style and the later Art Deco style. The Armory of the First Corps of Cadets is on Columbus Avenue. It’s the National Guard’s oldest volunteer militia unit.
Beacon Hill Walking Tour
With a short one mile walk from the hotel, we arrived at the Massachusetts State House where free tours are offered from 10:00 – 3:30. From there marvel at the incredible architecture along Beacon Street before heading over to The Nichols House Museum on Mount Vernon Street. (This museum does charge admission fees, however, even just a viewing from the outside illustrates the classic Charles Bulfinch design style.) The Louisberg Square and Church of the Advent show off more stunning architecture and luxurious homes of many notably rich and famous Americans including the lawyer and politician Daniel Webster, Henry Cabot Lodge, Sylvia Plath, Robert Frost and Louise May-Alcott. Conclude the tour at the Charles Street Meeting House on the corner of Mount Vernon and Charles, or wander over to Boston Public Garden or Boston Commons. Extra tip for a lazy stroll – just hit up Acorn and Chestnut Street – between the cobblestone lanes and the gas lit lights, it’s hard to beat for quintessential New England.
Boston Harbor Walk
A longer but perfectly enjoyable two-mile walk took us from the hotel over to the Boston Harbor where we met some friends for lunch at Legal Sea Foods Harborside – the food was amazing! Atlantic Avenue offers a diverse path to walk along with the harbor on one side and a series of parks on the other. The alternative – and a traveler favorite – is to do the Harbor Walk itself. Numerous art galleries, shops, cafes and restaurants line the walk, and the New England Aquarium, Boston Harbor Cruises and Christopher Columbus Park are on the route. A free audio mp3 guide for a Harborwalk tour can be found here.
Harvard Self-Guided Tour
Touring Cambridge/Harvard will require either a longer walk ~ 5 miles to get started, or catch a Lyft or the Red Line train from South End to Harvard University. The best guide I found for a self-guided tour was this Lonely Planet article. After touring Harvard for free, check out the other great spots in Cambridge just a step away starting at the Longfellow House where George Washington’s Headquarters used to be. The grounds are free and open daily, and the house opens seasonally usually May – September. Just down the street is the Hooper-Lee-Nichols House, now home to the Cambridge Historical Society. Stop in to visit and learn more about local history. On the way back across the Charles River, check out the Elmwood House, also known as the Oliver-Gerry-Lowell House. With a little more time, add the Cooper-Frost-Austin House and the Mount Auburn Cemetery to either end of the walk – both for free.
Little Italy in the North End
It is absolutely worth the extra effort to visit Little Italy. If for nothing else – the food. Flip a coin, it won’t matter. Every friend, family member and random website insisted that eating in the North End of Boston was as essential as doing the Freedom Trail. Yes, I’ll review it again in the “Eat” section, but I would be remiss if I didn’t include touring the area before, after or in between meals. Hanover Street (home to Mike’s Pastry), Salem Street (good food and history here) and the North Square (where Paul Revere’s House is) are must-dos.
We didn’t specifically set out to tour Chinatown. Much like our pieced together, self-guided Freedom Trail tour, we crossed most of Chinatown in our walks to and from other destinations like the Boston Opera House. Many visitors choose dedicated tour days for the area for the sightseeing, as well as, the food. See the Chinatown Gate while wandering down Beach Street (for a treat: Ho Yuen Bakery), and then peruse the local fare on Tyler Street (Peach Farm) and Washington Street (late night treat: Dumpling Café).
Museum of Fine Art
This wonderful collection can be viewed for free Wednesdays after 4pm.
Isabella Stewart Gardner Museum
Isabella Stewart Gardner was an avid collector, and this museum was the site of the 1990 $500 million art heist. There is still an excellent collection to enjoy. Admission is free on birthdays and to anyone named Isabella.
The Institute of Contemporary Art
Originally named Boston Museum of Modern Art, visitors can enter for free on Thursdays from 5 – 9pm.
See this collection for free Tuesdays and Wednesdays from 10am – 5pm at the University of Massachusetts.
Museum of African American History
An added bonus to this museum is the 1.6 mile Black Heritage Trail that is free to all who would like to walk it.
Boston Fire Museum
One of the nation’s oldest fire departments, the museum is free and open on Saturdays 11am – 4pm.
Boston Public Library
This library is a museum inside and out with some of the most elegant architecture in Boston, unique commissioned murals, and an art collection of its own. Always free to the public, they also offer guided tours throughout the week.
USS Constitution Museum
Open daily the museum is a Boston landmark. They don’t charge admission but do request a donation. While there, walk next door and tour the actual ship, the USS Constitution – “Old Ironsides” – the world’s oldest commissioned warship afloat and America’s ship of state. Active duty U.S. Navy sailors tell the stories of the USS Constitution and answer any questions.
Arnold Arboretum of Harvard University
This is North America’s oldest public arboretum, and they offer free guided tours.
Judson B. Coit Observatory
With both 10” and 14” telescopes, have a look on a Wednesday night when it’s open to the public.
Bunker Hill Monument and Museum
The museum and monument are open daily – weather permitting, and visitors are welcome climb the 294 stairs to the top!
Samuel Adams Brewery
The brewery offers four different kinds of tours, and the classic brewery tour can be done for free Monday – Saturday.
Even on a budget wandering through the various market places in Boston is a sightseeing, people-watching adventure of its own. Check out Quincy Market, Newbury Street, the SoWa Open Market, and, of course, Faneuil Hall Marketplace where in addition to shopping and dining, there are street performers daily and special events year-round.
One of my favorite parts of traveling is trying out new foods, particularly those unique to that region and culture. Boston is no exception. We ate delicious meals at classic Boston locations from a hotdog at Fenway Park to New England clam chowder to pints of brews in Irish pubs. Here are some local favorites we got to try out:
- Top of the Hub is an upscale restaurant with gorgeous views of the Back Bay and the South End from atop the Prudential Center. If having supper there doesn’t fit the budget, stop in for cocktails in the bar.
- Legal Harborside is one of Legal Seafoods’ numerous locations around Boston serving fresh seafood among the wharfs of Boston Harbor.
- The Union Oyster House is one of America’s oldest restaurants – running continuously since 1826. The classic Boston fare is served right on the Freedom Trail.
- Fanneuil Hall and Quincy Market are both essential stops when touring Boston and each has a wide variety of formal restaurants, pubs, cafes and food carts.
- Trattoria il Panino is one of the dozens of fine Italian restaurants to be found in the North End and all over the rest of Boston, too. Try Mom’s Classic Meatballs and Ricotta.
- Mamma Maria was recommended to us by locals we ran into along the Harbor Walk. It’s in a 19th century row house with 4- and 5-star ratings on Zagat, AAA and Trip Advisor.
- Mike’s Pastry is another can’t-miss in North End’s Little Italy.
- The Friendly Toast Restaurant, a mere five-minute walk from our hotel, was a happy accident. Our brunch was delicious, and the décor and atmosphere wonderful.
Boston’s professional sports teams are legendary. Holding the NBA record for most Championships with 17, the Boston Celtics play in the Garden where the stars of basketball are regularly joined by Hollywood music, film and TV stars. Also playing in the South End’s Garden are the very first United States NHL team – the Boston Bruins. Conveniently located in the South End is Fenway Park, home to the Green Monster and the Boston Red Sox. If purchasing game tickets is not in the budget, there are several types of guided tours available at Fenway from $5 – $50 a ticket.
The Boston Opera House is a gorgeously refurbished space now used for Broadway shows, Boston Ballet performances and other cultural events. Boston Symphony Hall is home to the Boston Symphony Orchestra and often features other performances like the Boston Pops. The Boch Center provides information on the theater scene in Boston including shows in the Wang Theatre where parts of movies like Ghostbuster, Witches of Eastwick and American Hustle were filmed. Another source for art information is ArtsBoston, a nonprofit arts service organization.
Boston Harbor hosts a number of water adventures and travel options. Public ferry routes are available through the Massachusetts Bay Transportation Authority, and private companies, such as Bay State Cruises, offer more cruise-like ferry routes including routes to Provincetown in the Cape Cod Bay. Boston Harbor Cruises is the most versatile with cruises to the Boston Harbor Islands, history cruises, and whale-watching cruises in addition to the destination cruises like the one to Provincetown.
Bus and Trolley Tours
Numerous types of trolley, bus and even amphibious vehicle tours are available. Boston Duck Tours combine a cruise and a bus-like tour for around $45, and a Boston Ghosts and Gravestones tour is available for about $40. An easy way to combine traveling through the city, sightseeing, touring and even dining and art events is to utilize the hop-on-hop-off tour options. Grayline offers one of these on its Beantown Trolley, and Old Town Trolley Tours also offers hop-on-hop-off as well as other types of tours.
Some people prefer to have a slate of tours and admissions lined up, and Boston has several serving the area. One option is Boston CityPass with access to New England Aquarium, Skywalk Observatory, Museum of Science and a choice between discounts at the Museum of Fine Arts or Boston Harbor Cruises. Another popular choice is the Go Boston Card with All Inclusive (43 attractions), Explorer Pass (3-5 attractions) or Build Your Own Pass.
Boston is an amazing city rich with history and culture, and there are more than ample attractions to fill 3, 5, 14… days of vacationing there. The city is easily accessible both to travel by foot and to use public transportation. We only had five days there and definitely plan to return for a longer stay to experience more of Boston.
MBTA (Subway) ¯
Freedom Trail Free PDF ¯
Free Freedom Trail/Historical Tours and Guides ¯
Beacon Hill ¯
Harbor Walk ¯
Harvard and Cambridge ¯
Miscellaneous Sites ¯
Bus and Trolley Tours ¯
Paid Combination Tours ¯
Boston Public Information ¯