What’s more comforting that a warm meal on a chilly winter day? Treat yourself to some grilled cheese during your stay in Boston at one of our favorite places for these comforting sandwiches.


What began as a grilled cheese food truck in 2011 has now morphed into three brick and mortar locations in the Boston area. Roxy’s offers over ten different types of grilled cheese—hot honey bacon, muenster club, double fried, the mighty rib melt–and make sure to order with one of their delicious milkshakes and a side over of truffle tires.

Roxy’s. 292 Massachusetts Ave Cambridge MA. (617) 945-7244


On the tip of Newbury Street, Trident Booksellers & Cafe serves food and books to the literature lovers of Boston. The extensive menu can be overwhelming, but you needn’t look further than the deluxe grilled cheese, with provolone, bacon, avocado on grilled challah bread: the perfect lunch on cold winter day.

Trident. 338 Newbury Street Boston, MA. (617) 267-8688


In the heart of Harvard Square, Crema is beloved for its delicious coffee, cozy atmosphere and scrumptious pastry items. Treat yourself to the grilled cheese with a side of the daily soup selection, and be sure to try some coffee and espresso offerings for dessert.

Crema Cafe. 27 Brattle St, Cambridge, MA. (617) 876-2700

Luke’s Lobster

In one of Boston’s favorite shopping districts, Luke’s Lobster is there when you need some fuel for the rest of your shopping endeavors. Check out the limited-time seasonal winter menu, featuring lobster and gruyere grilled cheese. Or if you’re not into lobster, try the crab grilled cheese.

Luke’s Lobster. 290 Washington Street, Boston, MA. (857) 317-4843

Thinking Cup

At this Stumptown-serving coffee shop, you can build your own grilled cheese. Choose from a variety of bread, cheeses, meats and veggies to satisfy your cravings. Pair with one of the decadent desserts to complete your Thinking Cup experience.

Thinking Cup. 165 Tremont St Boston, MA. (617) 482-5555