Best Shopping in Boston

Fill Your Bags with Buys from Boston's Best Shopping Spots

Shopping in Boston allows you the chance to create your own perfect excursion. Enjoy the landscape that Boston has to offer and explore the small shops that add personality to the shopping scene. Fills your bags with staple items at the popular big box stores that you'll find in most area malls, or pick out quirky, unique pieces at boutiques and specialty shops. Shop the couture lines like Chanel, and Burberry or just as easily locate a steal at a second hand store or outlet mall.

Enjoy the outdoor options alongside the rich and famous by popping into the small shops along Beacon Hill, where you'll find something new, different and interesting or stroll Newbury Street where high end fashion and hip, trendy shops can be found nestled in the brownstones that line the sidewalks.

Head indoors and take advantage of the temperature controlled environment at one of the many malls that surround the Boston area and are jam packed with the most popular brands available. Boston proper is home to the Prudential Center and Copley Place while the well stocked malls in the 'burbs are ideal for those with a car since parking is free so you can spend more on what you're shopping for.

Head less than hour outside the city and be treated to bargains in all forms at the Wrentham Village Premium Outlets where popular brands come together to offer deep discounts on designer merchandise.



Harvard Square is a delight for the senses. Hear the music playing from street performers as you pass, see history come to life as you step through the gates of Harvard University, smell the food cooking when you walk by the restaurants that are all around, taste what those restaurants have to offer, and touch the goods sold in the many specialty stores within the four square miles that is Harvard Square. Shopping here is an eclectic mix of mainstream and funky finds that will delight even those who have it all. Smaller shop owners are often inside to offer you the personal touch as you peruse their shelves.

Recommended for Best Shopping because: A collection of funky shops make their home in Harvard Square where you'll find items you just won't find everywhere.

Jessica's expert tip: A perfect place for people watching as well as shopping. Street performers provide entertainment as you pass from place to place.

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Beacon Hill

Beacon Hill is a cozy community that offers residents a prime downtown location as well as great shopping and sightseeing for the masses. Approximately one-half mile square, Beacon Hill is one small section of the city that packs a big punch. Home to many retailers this is not the shopping destination for those seeking to save a buck. Small boutiques, specialty stores and antique shops line the length of Charles Street, the main street through Beacon Hill and home to most of the stores. Here you'll encounter shop proprietors who care, and who want to make you happy, and who have things that can't be found everywhere. You'll be sure enjoy the keepsake you'll find in Beacon Hill.

Recommended for Best Shopping because: Beacon Hill's charm is as exciting as its shopping. Many small boutiques and independent retailers make a home on the Hill.

Jessica's expert tip: Parking is hard to come by in Beacon Hill. Public transportation is recommended.

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Outside the City

Shop the South Shore Plaza for a climate controlled experience less than 20 minutes south of Boston's center. This multi-level mall has it all: excellent places to eat and drink, department stores and smaller more specialized shops as well as common retailers you don't want to miss. You'll be sure to find what you're looking for within these walls be it fashion, food, or home goods. With plenty of free parking, your car will be in easy reach when your arms get full and you need to unload your haul. You'll be so comfortable shopping at the South Shore Plaza that you may find the entire day has passed and you are still shopping.

Recommended for Best Shopping because: Two floors of fashion make for excellent shopping at the South Shore Plaza where ample parking makes hauling bags a breeze.

Jessica's expert tip: Start at one end and make your way to the other on one level, then work back on the other to cover the entire mall most efficiently.

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Wrentham Village Premium Outlets was built with bargain hunters in mind. Wrentham Village Premium Outlet Center is home to one hundred and seventy high end retail outlets, all offering reduced pricing on their premium goods. Less than an hour away from Boston, Wrentham Village Premium Outlets is worth the drive to buy the Tory Burch clutch you've been eyeing or the Brooks Brothers suit you've been dying to buy. Shopping at the Wrentham Village Premium Outlets you can outfit the entire family from head to toe and most of your home. Like any shopping in Massachusetts, all clothing purchases are made tax free.

Recommended for Best Shopping because: The Wrentham Village Outlets is a bargain hunters dream; you'll find the best of the best at deep discounts.

Jessica's expert tip: AAA members receive free coupon books at guest services as well as discounts in many stores just by showing your card. Ask in every outlet store to see just how deep a discount you can get.

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Copley Place
Photo courtesy of Copley Place

Copley Place located in the Back Bay, offers high-end stores with a variety of quality merchandise. This indoor shopping "mall" is a sight to see. The two story design with extra wide walkways allows guests to enjoy the space while shopping at their favorite retail stores. Here are retailers and stores that make Copley Place unique in Boston and additional spots to buy gifts: Neiman Marcus, Tiffany & Co., Barney's New York, and Tory Burch. Built with luxury in mind, the marble columns, gorgeous floors and rotunda are worth a look. Restaurants, and two hotels offer perfect places for a mid-shopping escape. Connected to the Prudential center by a glass encased bridge, the Copley Place Mall is ideal for mall hopping. It is also a great spot to enjoy some time shopping for yourself or a gift for someone special.

Recommended for Best Shopping because: Copley Place Mall offers a selection of high end retailers in a mall setting along with perks like a complimentary personal shopper.

Jessica's expert tip: Even if the stores housed here are beyond your budget; the beauty of the building is worth a walk through.

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Faneuil Hall, originally established as a market for merchants, fishermen and vendors in 174 is now a tourist attraction known for shopping, eating and drinking. One of America's premiere urban marketplaces, Faneuil Hall boasts more than 100 shops, 14 restaurants, and 40 food vendors. On a beautiful day a stroll outside along the pedestrian walkways lining each side and window shopping everyplace before entering anyplace is loads of fun. Street performers are out year round and their skilled performances always draw a large crowd. Also known as Quincy Market, Faneuil Hall is the perfect shopping destination to do it all.

Recommended for Best Shopping because: Faneuil Hall offers the best "Boston" gifts to take home and is also home to popular retailers.

Jessica's expert tip: Not just for shopping, Faneuil Hall is home to many places to eat and drink. Make time to do it all.

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The Shops at Prudential Center
Photo courtesy of Wrentham Village Premium Outlets/Facebook

One on New England's top shopping destinations, the Prudential Center has it all. An enclosed space that protects you from the elements, you can peruse all day without a worry about the weather. Offering outstanding stores to shop, a bright and airy setting, several excellent restaurant selections, a decent food court, and a room with a view, the Prudential Center is a shopping experience like no other. After you've shopped yourself senseless, enjoy the views from the Prudential Tower's Skywalk Observatory. With an unparalleled perspective of the city, your Skywalk ticket may the best "shopping" score of the day. And if you'd like a little food with your view Top of the Hub is located in the Prudential Tower to provide you with both scenery and sustenance.

Recommended for Best Shopping because: Indoor shopping in Boston's Back Bay where many popular retailers make their home sets the Prudential Center apart form area shopping malls.

Jessica's expert tip: A great way to avoid the elements for a day.

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The Natick Mall is the largest mall around. Home to two hundred retail stores, the Natick Mall is anchored by lavish retailers like Neiman Marcus and Nordstrom as well as affordable stores such as JC Penney, sears and Macy's. You'll also find the hottest chains around as well as a few smaller merchants providing quality goods. The Natick Mall's indoor architecture has been updated from the run of the mill to a spectacularly serene setting. With more than 7,000 parking spaces, including valet and premium parking, Natick Mall offers more parking options than any surrounding retail destination to ensure your bags find their way home with ease.

Recommended for Best Shopping because: With an entire section of upscale shopping, the Natick Mall the go-to of locals who want to do it all under one roof.

Jessica's expert tip: The Natick Mall customer service desk is worth a stop as they know of any special events taking place as well as coupons.

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Newbury Street shopping has everything from fun and funky finds at stores like the hip chain Urban Outfitters to the classic couture that is offered at Chanel. Plus everything in between. Newbury Street is known as a high end shopping spot like New York's Fifth Avenue, or California's Rodeo Drive. Shopping starts at Massachusetts Avenue and continues to Arlington Street, spanning a mere eight city blocks. The historic storefronts offer charming glimpses of Boston during the mid-to-late 19th century. Open air cafes and restaurants can be found lining the sidewalks and offer the perfect place for people watching when you tire of shopping.

Recommended for Best Shopping because: From high end to hip and inexpensive, Newbury Street's vibe is classy and its clientele often rich and famous.

Jessica's expert tip: Begin at Mass Ave and make your way to Arlington Street, the closer you get to Arlington the pricier the stores you encounter.

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Hip, contemporary CambridgeSide is an indoor mall that draws locals for easy indoor shopping at all the shops you love: Ann Taylor, Gap, Victoria's Secret, Best Buy, Banana Republic, Old Navy, and J Crew. Easily accessible by MBTA, Boston area locals enjoy the mix of stores that call the CambridgeSide close to home. Home to a decent food court and several sit-down restaurants you can enjoy a side of food with your shopping. Paid parking is available in their indoor garage. Located a block from the Museum of Science you can add a "quick" mall stop to a museum day. Best of all, CambridgeSide hosts many events throughout the year to make your shopping experience extra special.

Recommended for Best Shopping because: CambridgeSide an actual mall in the city; offering reasonable parking rates and an impressive selection of retailers; it's your one stop for Boston shopping.

Jessica's expert tip: The CambridgeSide placement along the MBTA makes it easy to shop without a car.

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Meet Jessica Polizzotti

Born and raised in Boston, Jessica knows her city like the back of her hand.  Always looking to uncover something new, Jessica keeps up on the latest and greatest Boston offerings. 

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