Boston’s North End is basically Italian food Disneyland. Every corner smells like fresh bread, marinara, or espresso, and everywhere you look there’s a line of hungry people waiting for pizza, cannoli, or a lobster roll. Sure, you could book a guided tour, but honestly? Half the fun is making your own food crawl—skipping what doesn’t appeal to you, lingering at places you love, and going back for seconds without anyone judging.
Here’s my version of a self-guided North End Boston food tour—with exactly what to order, why it’s special, and a few personal notes on how much food you can reasonably cram into one stomach. (Spoiler: it’s a lot.)
If you’d rather let someone else lead, read my North End Boston Food Tour Review to see if it’s worth booking.
Start with caffeine because you’re going to need it. Walking into Polcari’s Coffee feels like stepping into an old-world Italian market—coffee beans, spices, herbs, the whole place smells like comfort.
Order this: Their house blend coffee or a bag of espresso beans. If it’s summer, don’t leave without a cup of their fresh Italian lemon slush. It’s tart, icy, and made with real lemons—basically an Italian grandmother’s lemonade stand.
This place never sleeps. Bova’s Bakery is open 24 hours, which means you can grab a cannoli with your morning coffee or stumble in at 2 a.m. after the bars. Both are equally valid life choices.
Order this: Their Florentine cannoli. The shell is made from a delicate lace-like cookie, thin and crunchy, and it’s their best seller. At $10, it’s basically the Prada bag of cannoli—but once you bite into it, you stop caring about the price tag.
Why it’s special: Unlike Mike’s or Modern, Bova’s makes their shells in-house. Some locals swear these are the best in Boston. Personally? I’m still debating, but I will say I ate mine leaning against a lamppost outside because I couldn’t wait.
One slice at Ernesto’s is basically two anywhere else. The slices are oversized, loaded with toppings, and taste exactly like what you need when you’re deep into a food crawl.
Order this: A pepperoni slice or a combo slice with everything.
Pro tip: Don’t try to be delicate. Fold it in half, New York-style, and just go for it.
This bakery doesn’t look flashy, but it’s been feeding Boston since 1907.
Order this: A slice of their pizza or a loaf of bread to take home.
Why it’s special: A lot of North End restaurants secretly use Parziale’s bread and pizza shells—so if you eat here, you’re going straight to the source.
If there’s one place that sums up the North End’s no-nonsense attitude, it’s Galleria Umberto. Cash only. Closed Sundays. Closed for all of July because, as they’ll tell you, “it’s too hot to work.”
Order this: Their Sicilian pizza or an arancini (rice ball).
Storytime: They won a James Beard Award in 2018 and hung it between two beer signs because they didn’t even know what it was. They open at exactly 10:45 a.m. (not 10:30, not 11), and when they sell out, they shut the doors. Respect the schedule.
Time to take a sweet detour. Petrova Chocolate is like walking into a European boutique—wine, truffles, and bon bons so pretty you’ll hesitate before biting into them.
Order this: A box of truffles or a couple of their handmade bon bons. (If you’re still full from pizza, save these for later—they travel well.)
Two hidden gems side by side:
La Panetteria: A blink-and-you’ll-miss-it bakery down an alley, down some stairs. Their olive loaf bread is ridiculously fresh.
Bricco Salumeria & Pasta Shop: Grab some of their homemade pasta or sauces, or pair their raspberry balsamic with fresh mozzarella for foodie bliss.
Here’s stop #2 in the great cannoli debate. Modern has a cult following, and once you taste their desserts, you’ll understand why.
Order this: The Boston cream cupcake (trust me) and a mini ricotta cannoli with chocolate chips.
Fun fact: Modern doesn’t make their own shells—they source them from Golden Cannoli, a third-generation local company that’s basically the Beyoncé of cannoli shells. They sell to shops nationwide, but Boston gets the fresh stuff.
You didn’t think one pizza stop was enough, right? The original Regina’s has been around since 1926, and it’s still run out of the same North End location with the same brick oven.
Order this: A classic cheese for the pure experience, or the Giambotta if you want everything but the kitchen sink.
Why it’s special: This place once ranked as TripAdvisor’s #1 pizza in the U.S. Jay Leno and Ben Affleck both swear by it—and if you can’t trust a Boston boy’s pizza rec, who can you trust?
This isn’t just a sandwich shop—it’s an event. The line is always out the door, but people wait because the sandwiches are that good.
Order this: The Italian sub “with everything.” They cut the meat ultra-thin to order, pile it onto fresh baguette bread, drizzle with olive oil and balsamic glaze, and top it with cheese sourced from Connecticut.
Storytime: I tried eating mine politely but gave up and ate half standing on the sidewalk. Zero regrets.
Need a seafood break? Mare Oyster Bar is a little upscale, but worth sliding into for a sit-down pause.
Order this: The stuffed zucchini blossom with lobster.
Vibe: Perfect if you want something lighter before tackling more carbs.
Technically just outside the North End, but if lobster rolls are on your Boston bucket list, this is where you check it off.
Order this: The lobster roll.
Why it’s special: They’ve been at it for over 100 years, and they still make one of the best in the city.
Brace yourself: the line here is legendary. People start waiting at 10:30 a.m. for an 11 a.m. opening. And yes—it’s worth it.
Order this: The hot buttered lobster roll and a bowl of clam chowder.
Why it’s special: GQ once called it one of the top food experiences you can’t live without. Rich, decadent, and unforgettable.
The oldest Italian café in Boston and the perfect place to caffeinate before your final stop.
Order this: A cappuccino and their famous tiramisu. If you’re in the mood, go all-in with a pistachio martini.
Why it’s special: They actually use Modern’s cannoli shells—proof the neighborhood is more interconnected than it seems.
End your tour at the most famous bakery of them all: Mike’s Pastry. The line wraps down Hanover Street, but it moves fast.
Order this: The classic ricotta cannoli with chocolate chips.
Why it’s special: Mike’s makes their shells in-house and fills them to order. Plus, you get the iconic blue-and-white box tied with string. It’s practically a Boston souvenir.
A must-stop if you want something cold and sweet. Small-batch, super creamy gelato-style ice cream that’s the perfect finisher for a summer day food crawl.
The North End is a food crawl that doubles as a workout—you’ll walk, you’ll wait, and you’ll eat more carbs than you thought possible. But every bite has a story behind it, from bakeries that never close to sandwich shops where the line is a rite of passage. Between bites pop into Loft & Vine for cute home décor and gifts or I AM Books for Italian cookbooks and kids books — perfect North End souvenirs.
My advice? Don’t try to hit every stop in one day unless you have the appetite of a college football player. Pick 5–6, share with a friend, and come back for round two next time. And yes, you still need to pick a side in the cannoli wars: Mike’s, Modern, or Bova’s. Choose wisely—Boston locals will fight you on it.
When you’re ready to branch out beyond Italian food, here’s my Where to Eat in Boston (Outside the North End).
Sky Ranch Lodge, Sedona. Booked it for the location, stayed for the sunsets.
This is not a five-star resort with ten restaurants and a spa menu the length of a novel. It’s a family-owned boutique hotel on Airport Mesa that knows exactly what it’s good at: red rock views from basically everywhere and one of the best sunset spots in town, private, with maybe four other couples instead of a crowd.
We booked a Premier Rim Room and I’d do it again in a heartbeat. Watched the sunset from our own patio one night and it’s still one of my favorite moments of the whole trip.
✨ Six acres of botanical gardens to wander morning and evening
✨ Pool + hot tub that hit exactly right after a day of hiking
✨ On-site food truck for easy breakfasts and lazy room service nights
✨ Complimentary shuttle so you’re not fighting Sedona parking
✨ Robes, slippers, and a staff that felt genuinely happy to help
Two stays in and I’d book it again without a second thought. This is where to stay in Sedona if you want it to actually feel like Sedona.
Thank you to @skyranchlodge for having us, link in bio for the full review 🌵
Four hours on a train through a canyon you can’t reach by car — such a fun experience! We picked the indoor seats with unlimited access to the open-air viewing car, which honestly felt like the only right call. You’re not stuck in an assigned seat the whole time we bounced between the two, snacks in hand, chasing the best light.
The scenery is the whole point. Red rock cliffs, the Verde River, a 734-foot tunnel, historic trestle bridges views most people visiting Sedona never see, because you literally can’t drive to them.
The charcuterie box that comes with your ticket is shockingly filling ✨ so skip lunch at the Copper Spike Café beforehand, save your appetite for dinner back in Sedona.
Four hours with no stops did start to feel long by the end, but the trade-off for scenery like this? Worth it.
Would I ride it again? Yes. Would I buy lunch first again? No.
Link in bio for the full review cost breakdown, what to pack, and exactly how early to arrive 🚂
I ate chilaquiles while a Cessna taxied past the window, and that’s just a normal Tuesday breakfast in Sedona.
@mesa_grill_sedona sits right beside the Sedona Airport Scenic Lookout, so along with your food you get red rock views stretching in every direction and a front-row seat to tiny planes lifting off. Chef Mercer Mohr runs the kitchen, serving up Southwestern comfort food from breakfast through dinner, chilaquiles, elevated diner classics, burgers, steaks, seafood, all of it.
The view is what pulls people in the door, but the food actually holds its own. Good enough that this place stays packed with locals, not just tourists passing through on their way to the lookout. It also picked up the 2025 Tripadvisor Travelers’ Choice and OpenTable Diners’ Choice awards, so it’s not just me saying it.
Indoor seating if you want the AC, a pet-friendly patio if your dog’s along for the trip. Either way, get there before plane-spotting turns into a wait for a table.
Link in bio for the full Sedona breakfast roundup ✈️🌵
Confession: my newsletter is where the good stuff lives. Not the polished, edited-for-the-grid stuff, the “here’s the hole-in-the-wall I almost skipped” stuff, the packing lists I actually use, the “don’t book this hotel” warnings before you waste your money on them.
The newsletter is basically me texting you before a trip instead of after one. Sign up and you’ll be the first to know where I’m headed next, plus a few things I’ll never post here.
Link in bio if you want in. ✈️
Yes, it’s only July. Start planning anyway. Fall books faster than people expect, and a few of these destinations are worth getting ahead of. Here are five places worth putting on your radar right now.
Ireland: Cooler temps, moody skies, dramatic coastline fall was made for it. Tourist crowds drop, the green stays, and the whole country feels a little more like itself.
Great Smoky Mountains, TN/NC: Fall foliage in the Smokies is the real thing. The color peaks mid-October and the views from the ridgelines are hard to argue with. It’s also one of the most visited national parks in the country, so going on a weekday makes a real difference.
New York City: Fall is NYC at its best comfortable temps, the energy of the city shifting into a new season, and every neighborhood doing something worth showing up for. It’s also just a great walking city when it’s not brutally hot.
Japan: Fall foliage season is as good as spring cherry blossoms and somehow less talked about. The colors are dramatic, the temples and gardens are stunning, and it’s worth planning around peak dates by region.
Mystic, Connecticut: Small, walkable, genuinely charming Mystic in fall feels like exactly what a New England autumn is supposed to look like. Easy to pair with a broader New England road trip if you want to extend it.
Full guides linked in bio 🍂
Follow @travelwithwendyplummer for Beautiful Beach Destinations, City Guides, Foodie Spots, and Luxury Hotel Recommendations.
