Looking forward to the end of November and another hearty Thanksgiving feast, we can all get ready for another exciting season of holiday shopping. Once you’re finished licking your wounds from the mad dash of Black Friday, enjoy some more competitive bargain hunting from the comfort of your own bed on Cyber Monday. Go ahead and score yourself a number of amazing deals, then take those savings and splurge during a trip to Boston, Massachusetts. 

First Off, What Is Cyber Monday? 

For decades, the unofficial start of the holiday shopping season has been on Black Friday—the day following Thanksgiving. In 2005, a pair of innovative minds named Ellen Davis and Scott Silverman from the National Retail Federation created Cyber Monday as an internet-based followup after Black Friday Weekend. The concept made its debut with Shop.org, and has since blossomed into a massive holiday championed by major online retailers like Amazon, as well as countless boutique operations around the world. 

Cyber Monday At The Boxer Boston

To discover special discounts for upcoming trips to Boston, check out these amazing Hotel Deals at The Boxer. Also, be sure to keep an eye out for the release of our upcoming Cyber Monday Package. 

Holiday Shopping in Boston

After you’ve made a killing with your online purchases for this holiday season, you can take those savings and find even more amazing gifts right here in Boston. For those who get the shopping bug, this is an incredibly easy and fun city to get lost in. We are home to numerous retail destinations, as well as boutiques from acclaimed designers, international brands, and local artisans. 

Newbury Street

Located in Downtown Boston, Newbury Street is the area’s most famous destination for shopping. The picturesque stretch features red-brick buildings housing impressive shops from the gorgeous Boston Public Gardens all the way down to the Fenway area. When visiting, you can find some upscale and stylish caps at the famous Goorin Bros. Hat Shops, which is rife with retro flare. For some upscale women’s fashion, we recommend checking out shops like L’elite occasions, and Mulberry Road. 

You can truly while away a lot of time when shopping on Newbury, and to make a day of it, we recommend stopping for something sweet at Teuscher Chocolates of Switzerland, or Emack & Bolio’s Ice Cream. For a nice lunch, some of our favorite options include the classy bistro Sonsie, French favorite La Voile, and local haunt Cafeteria Boston. 

Shopping Local in Boston

In addition to Newbury Street, Boston has a large number of inspired local shops that are well worth including on your holiday spree. You can find unique bottles for gifting at City Winery, and also treat yourself to a dish from its onsite Meditrranean restaurant with a glass from the wine bar. Faneuil Hall Marketplace comes to life during the holiday season with specials, vendors, tree lighting ceremonies, and Santa photo opps. For that bookworm in your life, we recommend shopping at the historic Brattle Book Shop, which is the country’s largest and longest-running Antiquarian book shop. 

Celebrating The Holidays in Boston

Another way to utilize your Cyber Monday savings to create great memories in Boston, is to get out and soak up the city’s romantic seasonal charm. If you’re here for it, be sure to check out the annual Boston Common Tree Lighting Ceremony on December 5th, and travelers coming in anytime after in December should absolutely visit the colorful spectacle. On that trip to the Boston Common, you can also indulge in some hot chocolate and ice skating on the world-famous Frog Pond. 

The holiday season in Boston will also come to life with the Boston Christmas Festival at the Seaport World Trade Center on November 8th, and the Holiday Lights of Boston event in the Boston Public Garden on the same day. Famous holiday markets and trees will also pop up at Faneuil Hall and Hynes Convention Center this season. 


Following your Cyber Monday shopping spree, consider giving back to a good cause of your choice. We’ll celebrate our favorite organizations, and charities this #GivingTuesday, and invite you to join us.

Planning a visit to Boston? Experience it like a local with our insider’s guide at the Boxer Boston blog!