The Best of Boston Holiday Guide


We may be biased, but Boston is one of the best cities to spend the holidays. From cozy cobbled streets to historic holiday markets and impressive tree displays, Beantown won’t let your spirits down.

Where to See the City Glow


During the holiday season, Boston shines even brighter. Here are a couple of our favorite places to see the lights.


Copley Square

Splashed with red-velvet wreaths and tolls of the Old South Church bell, Copley Square is straight out of a storybook. When the tree is lit, you can catch glimpses of Santa, Rudolph and Frosty. Live music performed by local groups like the Boston Pops Brass Quintet also adds to the atmosphere. 560 Boylston Street, Boston, MA 02116

Boston Common

For the last 48 years, Nova Scotia has donated a stunning 45-foot white spruce to the city of Boston. The gesture gives thanks for relief efforts provided in 1917 following the explosion of a munitions ship in the Halifax Harbor. The tree is lit with over 7,000 lights and hugged by 80+ other glowing trees. Admire the lights on a crisp night and if you need to warm up, go for a skate on the Frog Pond139 Tremont Street, Boston, MA 02111

The Best Places to Holiday Shop

The best place to holiday shop

‘Tis the season for splurging. From shopping villages to locally loved boutiques, treating yourself is expected here and getting ahead of holiday gift-giving is easy. Two birds, one satisfying stone.


SoWa Winter Festival

9-minute walk – Free for all, this is the biggest holiday festival in Boston where you can knock out gifting needs with handmade goods from 130 of the region’s top makers. Do so while enjoying festive cocktails, full stomachs from the best food trucks in town and entertainment including live ice sculpting and holiday workshops.


5-minute walk – Embodies the iconic feel of New England with a curation of timeless goods ranging from winter jackets to warm flannels and candles. Check out their Gift Guide for extra inspo. Sault517 Tremont St., Boston, MA 02118

Olives & Grace

8-minute walk – Winner of ‘Best Gifts’ in Boston, this boutique focuses on introducing emerging food and craft makers to the community. A place to discover well made, beautifully designed goodies. 623 Tremont St, Boston, MA 02118

The Wine Emporium

6-minute walk – Serving the South End for over 40 years, the Emporium is a great place to find curated beverages ranging from single malt scotches to liqueurs, grappa, wines and more. There’s nothing like unwrapping a nice bottle, and then promptly uncorking it. 607 Tremont St, Boston, MA 02118

It’s Always Sporting Season

Its always sporting season

Awww yeah, game (or should we say games) on. Patriots, Bruins, Celtics and beyond – Boston lives and breathes them all. Don’t miss the array of showdowns happening in town throughout the holidays. And if you need team gear, I love Boston Sports has you covered.

Drink and Eat Your Heart Out

Drink and eat your heart out

The South End is spilling over with bars, restaurants and cafes – each with unparalleled personalities perfect for winter wanders. Here are a few of our favorite walkable options.



0-minute walk – Coming soon to The Revolution Hotel, Cosmica is a vibrant Mexican eatery and bar serving up a selection of Cal-Mex specialties like tasty tacos, snacks and tequila-based cocktails. The Revolution Hotel40 Berkeley Street, Boston, MA 02116

Wink & Nod

2-minute walk – This sultry speakeasy with modern flair is home to a rotating pop-up culinary program, where featured Chef’s create an entirely new menu based on their own backgrounds. Plus, beverage selections ranging from seasonal craft cocktails to cordials are guaranteed to keep you warm on chilly nights. 3 Appleton Street, Boston, MA 02116


4 minute walk – Beehive is a popular Bohemian restaurant recognized as one of the top 100 Jazz clubs in the world. It’s a funky yet elegantly artistic joint offering rustic dishes from the Middle East, Eastern Europe and America. Eat, drink, be merry and groove to some tunes.

The Butcher Shop

4 minute walk –This spot is pays tribute to the old world European boucheries. With a wine bar and menus featuring ingredients from local farms and vendors, it’s the perfect place to stop for a quick bite and glass of wine or settle in for a full evening of feasting.

Coppa Enoteca

6 minute walk – An intimate enoteca featuring Italian treats such as made-in-house pastas, pizzas and a specialized charcuterie program. Just peep their Instagram and your mouth will water.

Gettin’ Down at The Revolution Hotel


We have plenty of revolutionary festivities happening here this holiday season, head over to our Facebook for a look at the latest lineup.