Since we spent our first two years together living in different cities, we don't have a local first date spot to share with you. But in lieu of that, we have Central Square, where we spent a lot of time in and around DigitalOcean's Cambridge office. With small plates perfect for sharing, Little Donkey holds a little spot in our hearts and on our expense reports. Naco Taco is a low-key option for lunch and margs, and Darwin's is solid for coffee and sandwiches. When you're done in Central, walk or T over to Harvard Square, most famously known for being home to one of the best burgers in the area at Alden & Harlow (and some college).
Conveniently located mere steps away from the weekend's festivities, the waterfront path is one of our favorite places to run. Though it's arguably more enjoyable if you're taking a casual stroll (stop at Lolita for a marg if you need a break from the harbor's chilly wind💨).
Visit the "Make Way for Ducklings" statues, check out the swan boats, and enjoy the people watching. This is also a great starting point for sightseeing; from here you can walk to most neighborhoods and points of interest. Across the street from the Common, towards Downtown Crossing, is Silvertone. It doesn't look like much (if you manage to see it at all - the entrance is subterranean), but serves shockingly delicious diner food and is a great option for a casual lunch.
Looking for the perfect black tie outfit?! Look no further than Newbury Street: home for bougie retail and restaurant experiences. Pavement and Thinking Cup for coffee. Salty Girl, Stephanie's, or Sonsie for an overpriced cocktail and a snack. Pro tip: drink first, then shop 😈 💸
In the morning, stop at Flour early for a homemade poptart. If they're out (likely, if you're not there before 10) get literally anything else because Joanne Chang will not do you wrong. Boston Chops is Aaron's favorite steakhouse. Coppa, Beehive, or Banyan are also good for dinner and atmosphere. Frenchie is your place to cap the night with one to two to ten espresso 'tinis.
You've heard to wait in line for cannolis at Mike's, and maybe even Modern. But skip the tourist hot spots (though they are really good) and go to Bova's. They're open 24/7 and if you order the Florentine cannoli you will thank us forever (unless you're allergic to nuts; in that case, do not order because they are chock-full of almonds). La Famiglia Giorgio's has huge portions of homemade pasta. Bacco is romantic and delicious. For slices, get fried eggplant at Ernesto's, and even though it's overhyped, Regina's is 😗🤌 Also can't go wrong with a personal-sized rugola at Ducali. Unfortunately, the one thing you won't find in the North End is good ole South Shore bar pizza. Columbus Park is waterfront perfection, and also where Dave and Claire got engaged. Wander through and feel the love 🥰
This spot is a leeettle out of the way if you're trying to stay downtown and/or on the T, but worth the Uber. Good beer, good snacks, good for groups.
If you're looking for a Sunday activity, the SoWa market in the South End has food trucks, local vendors, and dozens of artists' studios in the building next door.
The Sox are away on our wedding weekend, but you can still head to Fenway for Time Out Market. There are bunch of food and drink options, including a Union Square Donuts location and GoGo Ya, the little sister to fancy and tough to get in o ya.
If you're coming from out of town and planning to spend extra time in Boston or New England, let us know if you want any help planning your trip! Or, if you're local and realizing how much taste we have 💁🏻♀️ we're happy to help plan your staycation or night out.