• Galleria Umberto

By now you know the drill: get here at 11:30am or earlier, or face the possibility that they might run out of dough. Get two slices. They will be Sicilian. Get a beer. Walk outside and ask the old Italian guys sitting on the stoop and whistling at girls if they mind if you sit on the stoop with them. Eat the pizza. Drink the beer. Don’t bring up Roberto Baggio.

• The Barking Crab

What you're getting: Stuffies and a mixed crab bowl

It sat out over Fort Point way before sitting out over Fort Point was a thing. Its yellow and red tent can be seen for miles, and when you see people filling it, stretching out along those communal tables dotted with paper towel rolls and Tabasco, you know that summer has returned to Boston and that is indeed a great thing. Start with the quahog, chourico (Portuguese spelling!), and Ritz cracker “Stuffies,” and move onto the crab cake slider sandwich if it’s lunch, or throw on a bib and make yourself gleefully messy with a mixed crab bowl, then Water Taxi back to whence you came.

• Mike & Patty's

You can't go wrong with any of the sandwiches at beloved six-seat Boston institution Mike & Patty's, from the breakfast torta to the sa-té-sauced PBGC to the caramelized Banana OG on brioche (with Nutella!). But our advice is to go Fancy. Multigrain bread is the canvas, painted with two yolk-bulging fried eggs, cheddar, bacon, avocado, red onions, and just the right amount of house-made mayo. It's truly a work of art.

• Grill 23 & Bar

If you're gonna open shop in one of the sexiest neighborhoods in America, then you not only have to serve some great steaks, but your interior’s gotta get people excited too. And the mahogany walls, giant marble columns, and sexy bar in this Back Bay steakhouse don't disappoint. Neither do the steaks -- you're going with the famous 100-day, dry-aged ribeye.

• Townsman

Am I including Townsman on the list because Chef Matt Jennings and I hail from the same town outside of Boston? Or because I kind of think he named the restaurant after our town newspaper? Or because, once, I was named Athlete of the Week in that small town newspaper and got to do an interview and see my picture up at the Linden Store?!?! Unfortunately, no, because I didn’t realize any of this stuff until after the fact. For several years, Chef Jennings (and his Pastry Chef wife, Kate) ran a very cool, nationally recognized restaurant in Providence called Farmstead. But eventually, he came to realize that the Rhode Island accent is somehow much more jarring than the Boston one, and decided to come home and open Townsman, a New England brasserie, which celebrates the beauty of our coastal cuisine without getting into the depressing snow and cold stuff. Definitely start with the fried dumplings, that amazing clam chowder, and the New England charcuterie board. And then maybe get the prawns and the mussels in the Narragansett lager, which provides just enough acidity to balance out the garlic and brown butter. After that, you’re a fool not to get the lamb or the pork shank, and you’re even more stupid if you don’t wash it all down with one of the cocktails from their gloriously gin-heavy menu. -- KA

• Blackbird Doughnuts

The Gallows is one of my favorite Boston restaurants, with a burger worthy of an out-of-town journey. When it opened up a donut shop, I was excited but confused, as running a restaurant and successfully pulling off damn good donuts are two things that don’t necessarily intersect. But clearly I worry too much. Blackbird’s donuts (made on site, which, as touted on the website, is actually a rarity in Boston proper) have that artisanal look, meaning they're impeccably dressed up in beautiful glazes and offer up weird-ish flavors (when I was there the shop had a blueberry white chocolate Bismarck and a cold-brew coconut). I always get the simple donuts, though, when trying out new shops (because, basically, if you can’t do a layup, how're you going to hit a half-court shot?), and both the simple raised-style vanilla glazed and the cinnamon-sugar cake donuts checked off all the boxes: airy, pillowy dough in the raised, and that moist cake without the oil in the latter. It also has soft-serve, I should point out, in case you don’t feel like a donut alone poses much of a challenge to your system.

• The Hawthorne, Hotel Commonwealth

The Hawthorne beneath the Hotel Commonwealth looks like a friend's living room -- a friend with a good design sense, of course! -- and is a relaxed space to order up a cocktail or four while sitting fireside and contemplating the inevitably of death, traffic, and dropped R's. But mostly traffic. Also, it's a big supporter of Tiki culture in the summer, so get ready for some wicked-cool patio partying.

• Posto

Chef/owner Joe Cassinelli makes fresh mozzarella for his Neapolitan pies every day, and the triple-threat of creamy mozzarella, light basil, and crusts baked in a wood-fire oven creates pizza cravings. Cassinelli started a pizza truck, Posto Mobile, a couple of years ago, and although it’s used only for catering events, we still might chase it down like it’s the ice cream man.

• Beacon Hill

Beacon Hill is one of Boston’s most sought after neighborhoods to live in and visit. BH is also home to the most photographed street in the US – Acorn Street. Don’t believe me? Google it! With beautifully built brownstones displaying flower pots, custom door knockers, quintessential New England window shutters, overgrown ivy and gardens tucked away in secret alleys, Beacon Hill is seriously #facadegoals (especially if you come during Halloween or Christmas). A few popular spots are in front of Rouvalis Flowers, Chestnut Street and Louisburg Square. John Kerry’s house in Louisburg Square is also a popular spot for picture takers. If you visit in the morning, you’ll avoid crowds, but if you come in the evening, you’ll instantly be transported to Europe with its gas-lit streets and pretty sunset views. Beacon Hill is also home to a ton of equally adorable, locally-owned shops that line Charles Street. For food try Figs, Tatte Bakery and Sweet Cupcake. For shopping check out Follain, Dress Boston, The Holiday Boutique and NRO. Pro-tip: Get to Acorn Street before 9am to avoid engagement shoots and other tourists trying to get that perfect snap.

• Bricco
• Mamma Mia’s
• Monica’s Trattoria
• Mike’s Pastry
• Bovas
• Modern Pastry
• Luke’s Lobster
• James Hook + Co.
• Island Creek Oyster Bar
• Neptune Oyster
• Row 34
• Select Oyster Bar.
• The Envoy Hotel Rooftop
• Legal Seafood Harbourside in the Seaport district
• The Sinclair in Cambridge
• Pro-tip: Skip the Skywalk Observatory at the Top of the Hub. Instead, go enjoy some eats at the restaurant on the 52nd floor for free (you just have to pay for the food of course).
• Cambridge is home to Harvard University and the popular Harvard Square area where you’ll find all types of dining and shopping experiences. For dining check out Giulia, Alden & Harlow or Beat Brasserie. For shopping check out Mint Julep and Black Ink.

Pro-tip: Bring or rent a bike so you can travel between Boston to Cambridge. You’ll get to experience beautiful city views as you cross the bridge between areas.

• Hong Kong

One can't imagine that -- when the Hong Kong was founded in Cambridge in 1954 -- its founders knew that over the next 64 years, their humble Harvard University-adjacent restaurant would be transformed into the three-tiered palace of debauchery it is today. Its more farsighted guests start on the first floor, padding their stomachs with hot & sour soup and beef & broccoli, only to continue to the second floor to mingle over drinks (that's code for sharing multiple scorpion bowls full of alcohol while raucously laughing) before inevitably shedding their inhibitions on the gigantic, laser-filled dance floor upstairs. Of course, you could be forgiven for unwinding the opposite way, as many Boston-area residents have found themselves doing on Sunday morning at 3am. And as funny as it is to imagine intense conversations about physics and philosophy happening next to straightforward observations on the alcohol content of certain rum cocktails, it's definitely happened here. And it always guarantees an entertaining evening.

• Coppa Enoteca

For aperol spritzes

• John F. Kennedy Presidential Museum and Library

Inside a striking exterior designed by I.M. Pei, the John F. Kennedy Presidential Museum and Library in Boston examines the life of America’s35th Commander in Chief from childhood through his political career, marriage and assassination.