Things To Do
Tatte Bakery & Cafe | Charles St
A lovely spot to sit outside on a summer morning and see the bustle of the neighborhood. Close to Beacon Hill Books and other shops.
Sofra Bakery & Cafe
A bit out of the way, but this place has fantastic array of Middle Eastern inspired foods and baked goods. Right by Mount Auburn Cemetery
Bagelsaurus
One of the hottest commodities in Boston. Must show up before 10 am on the weekends. Grant’s personal favorite: Honey Rosemary cream cheese.
Contessa Boston
An Italian rooftop restaurant with beautiful view of the Boston Public Garden. While they have a great dinner, the brunch is even better! FYI: on the pricier end.
Pammy's
Fun, energetic Italian restaurant in Cambridge. Love the communal table.
Krasi
Made to order tzatziki and natural wine. What else can you ask for!
Alden & Harlow
Worth the journey for the pickled corn pancakes alone. If you don't have a reservation, could always put your name down and get a frozen margarita (or two) at Felipe's rooftop across the street.
Brewer's Fork
While Brewer's Fork versus Area 4 is a tough decision, Brewer's Fork slightly takes the edge with their outdoor patio and original pizza toppings.
Neptune Oyster
The line may be long, but it is worth it! Fresh, excellent seafood in a fast-moving environment. Great spot after wandering around the North End (perhaps on our Harbor Walk!)
Fox & The Knife
We were probably riding the high of graduation... but this meal was one of the best we have had in the city!
Dear Annie
Whether classified as a place to eat or a place to drink, this is currently our favorite spot in Boston. Great for a walk in date night. (Featured in NY Times America's Best Restaurants 2022).
haley.henry
A staple date night spot. Excellent service, even better wine.
Felipe's Taqueria
Best rooftop + frozen margarita + burritos
Night Shift Esplanade
On a warm summer evening, the most popular spot to be in Boston. The line can be long right around sunset. Can always just (unofficially) bring your own beverages and picnic on the esplanade.
Time Out Market Boston
Nice outdoor patio, particularly fun around Red Sox games. Generally easy to get a spot.
Lamplighter Brewing Co. - Cambridge Crossing
If you happen to find yourself in this newer neighborhood, the patio is great (and the beer even better).
Trillium - Fort Point
One of our favorite breweries in Boston! They have multiple locations, but we love this one as there is a great rooftop deck and ample space. Try one of their "Daily Servings" beers.
Harpoon Brewery & Beer Hall
A classic Boston brewery. If you're into tours + unlimited samples, you can pay $5 for an 30 minute brewery tour that ends with a tasting (you can buy tickets beforehand or day of) - highly recommend.
Charles River Esplanade - Walk
Take a stroll around Boston's Charles River on the Esplanade - it's our FAVORITE part of this city!!! For a nice 3 mile loop, we recommend starting from the Charles Street entrance, walking to the Harvard Bridge and going across, then looping back along Memorial Drive to finish by going over the Longfellow Bridge (where we got engaged)! Stunning at sunset.
Boston Public Garden - Walk
For a nice morning walk, we recommend strolling through the beautiful Boston Public Garden followed by walking down Commonwealth Avenue. You can cross over to Newbury Street for some coffee and shopping.
Boston Harbor - Walk
A uniquely Boston walk (and generally less busy), we enjoy the Harbor Walk from near the Battery Wharf Hotel to the Marriott Long Wharf Hotel. While the Charles often feels like the heart of Boston, this walk is a great reminder that we are on the ocean! Easy to add on the North End and/or the Rose Kennedy Greenway as well.
The Fens - Walk
If you happen to find yourself in Fenway, the Fens two mile loop is a peaceful spot in the heart of the city. Easy to stop by the Museum of Fine Arts, Isabella Steward Gardner, Harvard Medical School, or Time Out.
Red Sox Game at Fenway Park
If you'll be in Boston through Labor day, catch a Red Sox game at Fenway Park! On Sunday (8/31), they play the Pirates at 1:35pm and on Monday (9/1), they play the Guardians at 1:35pm.
Institute of Contemporary Art
Grant's favorite museum in Boston! Enjoy modern art with a gorgeous view of Boston's harbor.
Museum of Fine Arts, Boston
A beautiful museum with an extensive and diverse collection of art - a can't miss if this is your first time in Boston!