Boston Shopping Areas (Self Guided), Boston

One of the top shopping destinations in the US northeast, Boston has a strong network of interesting stores, galleries and boutiques to visit along with its many high-class shops, some of which are nestled inside historical buildings. Shopping here in more than one way mirrors the city itself: an amalgamation of classic and vanguard, the handmade and the high-end, and both local and international sensibilities. Take our self-guided tour to experience the best shopping Boston has to offer, starting with bargains aplenty in the Downtown Crossing area.
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Boston Shopping Areas Map

Guide Name: Boston Shopping Areas
Guide Location: USA » Boston (See other walking tours in Boston)
Guide Type: Self-guided Walking Tour (Sightseeing)
# of Attractions: 6
Tour Duration: 2 hour(s)
Travel Distance: 3.2 Km or 2 Miles
Author: anna
Sight(s) Featured in This Guide:
  • Downtown Crossing
  • Beacon Hill / Charles Street
  • Newbury Street
  • Boylston Street
  • Prudential Center
  • Copley Place Mall
1
Downtown Crossing

1) Downtown Crossing (must see)

Downtown Crossing is a shopping district in Boston located due east of Boston Common and west of the Financial District. It features large department stores as well as eateries, music stores, souvenir sellers, general retail establishments, and many street vendors – you could, literally, make a day of it! The section of Washington St. between Temple and Bromfield streets (and portions of Winter and Summer streets) are closed to most vehicular traffic; pedestrians may walk freely.

The whole area is safe and vibrant with street entertainers/musicians frequenting on a structured basis to entertain all in the mood for such; quirky, innovative and always enjoyable – a colorful insight into the lot of a Bostonian. And finally, it is quite smart and picturesque, too, with characterfully designed buildings most impressive on the eye.

Why You Should Visit:
Fantastic shopping area not just because it houses Boston's edition of Macy's but, for some at least, because it is the location of the best supermarket that you'll ever come across anywhere in the USA – Roche Bros. Not so much an opportunity to shop – more an experience to be savored.

Tip:
Check out the Summer Street Markets, as well as the holiday market that happens here!
2
Beacon Hill / Charles Street

2) Beacon Hill / Charles Street

If you're looking for a lively shopping area with local shops and independent retailers rather than chain stores, Charles Street is hard to beat. The main thoroughfare of Boston's Beacon Hill neighborhood, it has a quaint, village-like air, and many on-trend boutiques (ouimillie, Paridaez, Crush Boutique, Holiday Boutique), specialty shops (Helen's Leather Shop, December Thieves, E.R. Butler & Co.), well-stocked gift shops (Black Ink, Flat of the Hill, Tibet Emporium), antiques shops (Eugene Galleries, Devonia, Marika's), coffee houses and restaurants (Artu, The Paramount, Ristorante Toscano, Bin 26 Enoteca, Tatte Bakery and Cafe) that you'll never see elsewhere – so grab a drink and prepare to enjoy the window shopping and the walking in and out of these!

Even without frequenting any of the shops, one is completely taken with the design and character of the homes and buildings, and the care that all owners seemingly take not only to preserve such but to present them to best effect.
3
Newbury Street

3) Newbury Street (must see)

Traditionally for Boston, Newbury Street has been a mixture of fashion and trend similar to New York's 5th Avenue when it comes to higher-end and designer stores. The thing about this street is that it's always changing, due to the rents and trends – even more so over the last few decades. Due to Newbury's reputation as a shopping Mecca, many chains from out of state tend to set up shop, with a plethora of tiny specialty shops, ultra-modern art galleries, salons and dazzling jewelers thrown into the mix (just take note that the closer you get to Arlington Street, the pricier the stores you will encounter).

Stores/restaurants/cafes are also ever-changing and eclectic, featuring national chains as well as independents. Many of the restaurants and bars have patio seating and stylish bay windows, making this the perfect sunny-weather spot to see and be seen while indulging in an invigorating coffee or some ethnic delicacies. Highlights include the Rustic Italian eatery PIATTINI (10am–10pm); the intimate LA VOILE (12–3pm, 5–9:30pm), known for its super-authentic French cuisine; and BEANTOWN PHO & GRILL (11:30am–10pm) serving Thai, Vietnamese, and other Asian dishes.

Sidewalks are wide enough to accommodate the foot traffic and the street is lined with beautiful architecture and foliage.
4
Boylston Street

4) Boylston Street

Probably the best-known Boston street in the world, Boylston is recognizable not only as the finish line of the Boston Marathon but also as a place packed with monuments, notable churches, top-tier restaurants and bars...

Scattered around the chains and restaurants you will find a few standout stores like Anne Fontaine (for clothing that flatters women's bodies), Pompanoosuc Mills (for fantastic handcrafted furniture), and Marathon Sports (for both serious and beginner runners – and posers, also).

Whatever the reasons, you can't help coming across this street at some point, and you might as well arrive at nightfall when everything lights up and invites you to have fun with open arms.
5
Prudential Center

5) Prudential Center

Take a trip to the Prudential Center's 50th-floor observation deck for some outstanding views over the city and further afield, or simply spend a while exploring the building's vast interior at the tower's base. With over 75 specialty retailers, the choices for shopping are good for an out-of-town visitor to choose from, and there are many places to eat any meal of the day. Even if you are not here to shop, the experience of an Italian marketplace is worth the stop, so check out "Eataly", the huge open area of restaurants and specialty shops that can cause sensory overload! There is even a small Catholic chapel in the mall – the St. Francis Chapel – with frequent masses.

Opening Hours:
Mon-Sat: 10am-9pm: Sun: 11am-7pm
6
Copley Place Mall

6) Copley Place Mall

This nice upscale mall located across from (and directly connected to) Prudential Center will cater to all your upscale needs with boutiques ranging from Chanel and Louis Vuitton to Salvatore Ferragamo, Dior and even Moncler. They even have mid-range names like J. Crew, Gap, and Sur La Table. Legal Sea Foods is the only sit-down eatery, however.

The interior lacks architectural interest but has a very nice and chic design nevertheless, especially with the spaced-out luxurious storefronts. When combined with the shops at Prudential Center next door, its network of glass walkways makes for a perfectly safe way to traverse the Back Bay at all hours while being sheltered from the elements.

Opening Hours:
Mon-Sat: 10am-8pm; Sun: 12-6pm

Walking Tours in Boston, Massachusetts

Create Your Own Walk in Boston

Create Your Own Walk in Boston

Creating your own self-guided walk in Boston is easy and fun. Choose the city attractions that you want to see and a walk route map will be created just for you. You can even set your hotel as the start point of the walk.
City Orientation Walk

City Orientation Walk

The capital of the Commonwealth of Massachusetts, Boston is one of the oldest cities in the United States which played a key role in the country's struggle for independence. The city was founded in 1630 by Puritan settlers from England and witnessed many events of the American Revolution, including the Boston Massacre, the Boston Tea Party, the Battle of Bunker Hill, and the Siege of Boston....  view more

Tour Duration: 2 hour(s)
Travel Distance: 3.4 Km or 2.1 Miles
Historical Cambridge and Harvard University Walking Tour

Historical Cambridge and Harvard University Walking Tour

Once a quiet New England farming village-turned capital of the Massachusetts Bay Colony, today's Cambridge, MA is a university town that dazzles visitors as the home of renowned Harvard University – alma mater of many intellectuals, literary geniuses, celebrities, and wealthy and powerful. Many of America’s elite have spent some time at Harvard, and their contributions to Cambridge have...  view more

Tour Duration: 2 hour(s)
Travel Distance: 3.5 Km or 2.2 Miles
North End Sightseeing

North End Sightseeing

The North End was the city's first neighborhood, and one that has been key to its fortunes. Known as Boston's Little Italy, it has been home to Italian immigrants through much of the 20th century, and still retains an European flavor in its many restaurants, cafés, and specialty shops. This neighborhood is one of those where it's easy to get lost, so take this self-guided walk to...  view more

Tour Duration: 1 hour(s)
Travel Distance: 0.9 Km or 0.6 Miles
Boston Churches Walking Tour

Boston Churches Walking Tour

Boston's many great churches are among the most precious of the city's numerous architectural jewels. What makes these artworks special are their unique styles, elegant facades and long history. Take this self guided walk to witness these architectural wonders of Boston.

Tour Duration: 2 hour(s)
Travel Distance: 3.6 Km or 2.2 Miles
Bunker Hill Walk

Bunker Hill Walk

If you're a history buff or simply interested in understanding more of America's past, take this walk covering part of the Freedom Trail in Boston, Massachusetts. On this tour you are going to visit some of the places associated with the origin of the United States of America as an independent nation and more!

Tour Duration: 1 hour(s)
Travel Distance: 1.5 Km or 0.9 Miles
North End Food Walk

North End Food Walk

Boston’s North End is famous primarily for its Italian food. By far not as big as New York's Little Italy, this one-square-mile waterfront community is the oldest in the city, and is packed to the brim with a cornucopia of Italian eateries – restaurants, cafes, espresso bars, pizza and sandwich shops – lined next to each other within just a few short blocks to ensure visitors both, a...  view more

Tour Duration: 1 hour(s)
Travel Distance: 0.8 Km or 0.5 Miles

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