Start at Boston Public Market with iced coffee and Union Square Donuts. The vegan ones are so good. I’m not vegan, but the coconut oil adds this chewiness and texture that is really appealing.
Then walk down the greenway and admire the art installations. Maybe even take a ride on the carousel, if you’re feeling child-like.
You can pick up picnic ingredients in the North End to eat on the greenway with the sun shining on your face. Get salamis, cheeses, and olives from the Salumeria on Richmond St. and bread from the basement wonder bakery, Bricco.
On the other hand, if you’re feeling too lazy to assemble any foods, grab an Italian sandwich with everything--everything--from Monica’s on Salem, and if you have a companion, also get the steak bomb from Dino’s across the way. The steak bomb tastes like a much nicer version of a McDonald’s cheeseburger, in the best way possible.
Then walk toward the aquarium, and continue down the harborwalk. You can walk all the way to the ICA. And on the way back, you can stop for a lobster roll. There’s this one place called like, “Amazing Fresh Lobster,” or something just really straightforward like “This is Fresh Lobster.”
Then go to the Lawn on D, and have some stuff from the food trucks. Sheherazad is the best food truck in Boston. There is cinnamon in the hummus!
Then walk off your snack along the Charles River. Walking along the Charles isn't the most convenient thing, but you know, at this point you've eaten like four meals, so I think you can deal with it.
Then I’d go to Picco for ice cream, because I just love Picco. Mint chocolate chip ice cream, and dark chocolate sorbet. I insist on the sorbet. I insist.