Boston! (a mini travel guide)

Mapping of Places of Interest

A: Coolidge Corner, Brookline; B: Alden Castle; C: Fenway Park; D: Newbury Street; E: Charles Street; F: Fanueil Hall; G: South End

Brookline (where Alden Castle is located) is, more or less, a suburb of Boston but very close to the heart of town and super close when considering the green line T runs straight through the center of it. I'll reference the letters up top when recommending; the spot will be close to the letter, though perhaps not directly on top of it.

Places to Stay
Same list as in the hotels section, only this time with letters corresponding to the map!  

• Liberty Hotel : old jail turned fancy spot (fabulous bar). (E)

• Hotel Buckminster : right next to Hotel Commonwealth, where we are staying. (C) 
• Marriott Courtyard : 5 minutes to Alden Castle. (B) 
• Copley Mariott : classic spot, in the (fancy) mall, near ABP/great sports bar. (D)
• Beech Tree Inn & Longwood Inn: Literally walkable to the ceremony site. They are small B&B's that looked charming when we drove by... cannot vouch for them personally. (B)
• AirBnB: choose a local's apartment near Newbury Street or in the South End.

Foods. (Brunch highlighted.)

• Metropolis : an old stand-by in the South End. Simple, classic. (G) brunch
• Eastern Standard : French. Heated outdoor seating. Enough? (C)  brunch, also cocktails, dinner, snacks, everything. (C)
• Toro : Tapas. Loud. Delectable.(G)
• Stephanie's : Popular, dependable food. (D)
• Zaftig's: If you're staying in Brookline, you must. Proper Jewish sit-down deli type. (A) brunch
• Michael's Deli : Brookline deli, to go. (A) brunch
• Petit Robert : Small & French.  (C--the Kenmore Sq. option)
• Matt Murphy's Pub : a favorite from college. (B) brunch

Coffee

•  Peet's : It's a chain, but it's good. And in Coolidge Corner. [There is also a Starbucks & Panera on Harvard St.] (A)
• Espresso Royale : You probably won't go here, but its my college favorite and I'm obligated/nostalgic to put it on here. Also, it's SORTA near Hotel Commonwealth. (C)
• L'Aroma Cafe : The best on Newbury Street. (D)
• Francesca's : Perfect paired with Metropolis. (G)

Sights, etc.

• Newbury Street for high-end shopping.
• Charles Street for boutiques.
• Faneuil Hall for elements of history and crowded lanes.
• Boston Commons for gorgeous scenery, especially in the autumn.
• South End for the best food & cobble stone streets.
• SoWa flea market is open on Sundays in the South End, by the way.
• ICA for contemporary art.
• MFA for art from the beginning of time in a gorgeous museum.
• A duck tour if you're feeling touristy.
• Copley Mall if it's raining.
• Chinatown for dim sum.
• North End for small streets and great Italian food.
• Harpoon Octoberfest: October 4th & 5th.
• Harvard Square for cobble stones and Will Hunting.
• Which brings me to Kelly's Roast Beef; a sandwich rooted firmly in history.
• Want to leave Boston? Go to Salem, MA. Witches, quaintness.

Professional Advice: Food & Wine-Boston & Design*Sponge Boston / Salem &  3 Days in Boston from Trip Advisor