Progressive Dining in Boston’s North End

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progressive dining Boston north end

My husband and I love progressive dining experiences for daytime dates. If you haven’t tried progressive dining before, you must! Simply choose an area that’s populated with restaurants, and then frequent several places on foot, only sampling a small plate and/or drink from each. Our favorite destination for this kind of date is Boston’s North End (Little Italy). Autumn is the best time of year to give this a try in order to avoid the usual crowds and long wait times. Just make sure to bring your appetite and wear some stretchy pants! In random order, here are my suggestions for the perfect North End stroll:


1. Galleria Umberto, 289 Hanover Street
Umberto’s is my favorite take-out spot in the North End. It’s a “Plain Jane” establishment, but I guarantee there will be a line whenever you arrive. No worries though, it moves fairly quickly, and it will totally be worth any wait. Their arancini are the best I’ve ever had— deep fried on the outside, with a cheesy ground beef mixture on the inside. Seriously delish! Their Sicilian cheese pizza slabs are another must try. They do have seating if you’d like to stay, though we typically like to find a park bench to enjoy our bites outdoors. 
Pro tip: Umberto’s is a cash only establishment, and they are closed on Sundays.

2. Bricco Salumeria & Pasta Shoppe, 11 Broad Alley
Bricco is a literal gem located down a tiny alley (more likely a hidden walkway). If you want an authentic Italian sub, or any specialty Italian sandwich, then look no further. You will not find fresher, higher quality meats and cheeses anywhere. Bricco has a full deli and a slew of homemade pastas, so if you’re able, order some cold cuts and pasta to go.
Pro tip: The deli can be hard to miss, so look for their sister restaurant on Hanover, also named Bricco, and follow the signs down the alley. While you’re there, check out Bricco Panneterria (fresh bread bakery) right next door. Try their prosciutto & parmesan loaf.

3. Giacomo’s, 355 Hanover Street
While Umberto’s is my favorite to-go spot, Giacomo’s is my favorite sit-down restaurant. It’s a hole-in-the-wall eatery that specializes in linguine with seafood, and there’s a reason why they constantly have a line out the door. Their house sauce, aptly named Giacomo’s sauce, is a must try on their homemade pasta. Additionally, their fried calamari and lobster ravioli are some of the best I’ve had and pair well with their house wine.
Pro tip: The service at Giacomo’s is known to be abrupt. If you’re looking for a leisurely meal, then this might not be the place for you.

4. Quattro, 264 Hanover Street
Quattro is a chic spot to grab a drink on Hanover. Of course, they have an extensive Italian wine list, but my favorites are their blood orange sangria and their blueberry basil lemonade. Salute!
Pro tip: Sit at the bar and watch staff prepare and bake brick oven pizzas while you sip your beverage of choice.

5. Bova’s Bakery, 134 Salem Street
Bova’s is a North End staple that’s been around since 1926. Although they offer a variety of calzones, pizza, and arancini, I’d say its their pastries and dessert that make them shine. Their cannoli rival Mike’s Pastry, though slightly smaller and not as wide of a variety. Try the Pinwheels, assorted Italian cookies, and the tiramisu.
Pro tip: You can go anytime— Bova’s is open 24/7 365!

6. Mike’s Pastry, 300 Hanover Street
Mike’s is a tourist hot spot, but for good reason! They specialize in cannoli. Alllll the cannoli. The Florentine is an absolute must try, and the chocolate covered is a close second. Aside from cannoli, you can also find pretty much any other Italian specialty treat along with more traditional options as well.
Pro tip: Ask them to fill your cannoli shell fresh in the back.

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