If its your first time in Boston, and you’re here just for the day, or just for the night, here are my top picks for seeing all the city has to offer:
1. I won’t tell you to start with this (but you really should), just squeeze it into the day when someone can give you a ride to this out-of-the-way spot: free tour (and 3 free beers!) at the Sam Adams Brewery
2. Where you really should start your day is Boston Common. Get a coffee (at Dunkin’ Donuts, if you must), and lounge or wander until you’re awake. Then, follow the brick-line away from Boston common along the Freedom Trail (you may need a map/guidebook to do this effectively without getting lost, and without missing the pertinent historical stops). When you reach Quincy Market and Faneuil Hall, take a break.
3. Have lunch at the historic Union Oyster House. Billing itself as America’s oldest restaurant, the Oyster House also features fantastic (albeit uninspired) seafood, and the booth frequented by JFK himself. Around the corner from the Oyster House are other historic bars, The Bell in Hand and The Green Dragon.
4. Make your way from the Quincy Market area, across the Rose Kennedy Greenway, to the Italian neighborhood of the North End. Here, you can wander through bakeries (be sure to stop at Lyndell’s on Hanover St.), wine stores (my favorite is always Cirace’s, for its unbeatable selection of liquors), and grocers (if you didn’t have lunch at the Oyster House, pick up some antipasti at the Salumeria Italiana for a picnic near Paul Revere’s statue in the North End). If you’re lucky, you’ll find the hidden (and well-maintained) bocce courts, or will score a table at Giacomo’s (which always has a line out the door – this is a great place for cheap/fast/delicious food, but the wine list leaves something to be desired…many more inventive Italian restaurants are throughout the North End – but make a reservation, and don’t expect to find parking). Other North End favorites: the cigar bar downstairs at Stanza dei Sigari (bosomy waitresses, vintage and smoky atmosphere, nice cocktails, and hookas, too); and the coffee shop at Vittoria Caffe (great espresso drinks and biscotti).
5. By now, you should be satiated and exhausted. Take a cat nap (if the weather is nice, you can do this on the Greenway overlooking the docked and moored boats in the harbor), and prepare to spend the evening out and about. There are many neighborhood options for bar hopping. Harvard Square, Central Square, or Davis Square (Cambridge/Somerville areas) are great for being close to the T (which ends at about 12:30pm by the way), and a lot of interesting bars in walking distance. Or, head to the Quincy Market area for Irish pubs and dancing with youngsters (and tourists). Or, move to the more edgy student-centric Allston/Brighton area (and don’t miss Sunset Cantina, with over 100 beers on tap). For more interesting experiences to impress the ladies, try these: Drink, Beehive, Cucci Cucci, Eastern Standard. Or check out our lists of old-timey bars in Boston, if you want that historic or speakeasy feel.
Or if you’re more into dinner and a movie (with parking!) try Brookline (sushi at Fugakyu, movie at the vintage and independent Coolidge Corner Theater), or Kendall Square (The Friendly Toast or the Blue Room, and a movie at Kendall Square Cinema).
And if you’re around for breakfast in the morning, try brunch at Highland Kitchen, bring your Buddy Holly glasses to The Other Side Cafe, or people-watch over your banana-caramel-french toast at Sonsie on Newbury Street.
These 5 steps will get you started for your first day in Boston. From there, the options are endless for visiting museum and other sites, exploring the shopping, interesting dining, or discovering the eccentric.
Stay tuned for our list of a Bizarre-Day Out in the Boston-Area and the list: Foodie Day Out In Boston