In the cover story for Yankee’s March/April 2019 issue — “Food Town Showdown” — I took a side-by-side look at the top food spots in Boston and Portland to determine which city is the true dining capital of New England (to find out who won, click here). Now I’d like to invite you to come along as I visit my (current) favorite food destinations in Boston, which also happens to be my hometown. The city is always changing, and so will this list; still, these Boston food crawl picks are reliably good.

In an effort to present as many options as possible in Greater Boston, I’ve created this crawl for the city proper and another one for Cambridge and Somerville. The Boston itinerary is mostly walkable, though you might want to hop the Green Line to get out to Fenway. The Cambridge crawl will require some wheels.

To be clear: There’s no way you could actually visit all these spots in a single day, nor should you. But if you stretched them out over a weekend, I guarantee you’d be full and happy.

The Ultimate Boston Food Crawl

We begin, naturally, with coffee…

8:00 a.m.Gracenote

This petite roastery and café is a great first stop if you’re stepping off a bus or train at South Station, and a worthy trip from anywhere else in the city. Order a macchiato, but save room for a pastry at …

9:00 a.m.: Modern 

Home to the city’s best cannoli, Maria’s also makes a killer sfogliatelle, which is a clam-shaped pastry filled with delectable semolina custard cream — the Neapolitan breakfast of champions. The name translates as “leaves,” which refers to the many layers of crisp-tender pastry. If you’re lucky, you’ll get yours still warm from the oven.

[Editors Note: We were sad to learn that Maria’s, the beloved North End bakery and winner of this “Best Cannoli” taste-off, closed in September, 2019. Fortunately, there are many wonderful Italian bakeries in North End (namely Mike’s, Modern, and Bova’s) to start your day off right.]

10:45 a.m.: Galleria Umberto

Pizza before 11? Well, this cult Sicilian pizzeria is so popular that unless you want to wait in line, it’s best to arrive early. The Deuterio brothers make the most tender crust and top it with ample cheese and San Marzano tomatoes. Add an arancino (fried stuffed rice ball) and a Dixie cup of red wine, and your meal will still cost less than $10.

12:00 p.m.: Cusser’s Roast Beef & Seafood or Gene’s Chinese Flatbread Café

Cusser’s, the casual downstairs sibling to Mooncusser Fish House, serves an exemplary chowder and one heckuva roast beef sandwich. (The swordfish souvlaki is great, too.) If it’s Chinese you’re craving, head to Gene’s Chinese Flatbread Café, on the border between Downtown Crossing and Chinatown. Its hand-pulled noodles, with or without braised lamb, are tender and rich with spice — the perfect comfort food.

2:00 p.m.:L.A. Burdick or Eataly Boston

For an afternoon pick-me-up, I recommend either L.A. Burdick’s famous hot chocolate, which is rich and pudding-thick, or an espresso at Eataly Boston. The latter may be part of a chain, but it has enriched our food scene mightily (and a visit here is much cheaper than a nonstop to Rome).

5:00 p.m.: The Butcher Shop

There’s no Boston food crawl without Barbara Lynch. Her Butcher Shop was acing the wine bar concept before anyone else, and I can’t think of a nicer place to sip a boutique Italian red while nibbling on house-made charcuterie and antipasti. And now that you’re in the South End, it’s time to think about dinner …

7:00 p.m.: SRV

There’s pasta magic happening at SRV, and the tapas-style bites, called cicchetti, are irresistible (don’t miss the meatballs).

10:00 p.m.: Fool’s Errand

Tiffani Faison and Kelly Walsh are two of Boston’s most beloved restaurateurs, and their three properties — Sweet Cheeks Q, Tiger Mama, and Fool’s Errand — have been major drivers in the revitalization of the Fenway neighborhood. Fool’s Errand is a standing room–only “adult snack bar” where you can grab a European-inspired nightcap (the bar menu is wise in the ways of vermouth and amaro) and a nosh (try the croquettes) before slipping happily into a food coma.

What places would you put on your own Boston food crawl? Let us know!

This post was first published in 2019 and has been updated.