Play: Although only allowed during off-peak hours, it's a wonderful thing to be able to ride the T around town with the dog at your feet. Whether you choose to throw the frisbee in Boston Common (off-leash hours are before 9 a.m. and after 4 p.m.), mingle in South End's Peters Park Dog Run, or picnic with your pooch in Harvard's Arnold Arboretum, rest assured a trip to Boston means everyone's tail will be wagging.
Stay: In addition to hosting a Wednesday "Yappier Hour" party, the Beacon Hill-based Liberty Hotel (from $395/night, plus a $100 pet fee) comes with cool human perks like complimentary bikes, yoga classes, and expansive views of the city. If you'd rather spend the pet fee on dinner at O Ya, Kimpton's Hotel Marlowe (from $144/night) in Cambridge welcomes dogs for no extra charge.
Eat: There are over 40 pet-friendly restaurants in Boston, but local favorites include Granary Tavern, Cambridge Brewery Company, Coppa, and Wired Puppy, where you can sit indoors with the dog while you enjoy a chocolate chip muffin and iced coffee.