There are several great restaurants, people watching and places for drinks and cafe. Some favorites for food are Lucca, Parla and Galleria Umberto (only open a few hours a day for a slice). Drinks and coffee/espresso: We also love Caffe Paradiso for their pistachio martini and similarly Cafe Vittoria for their espresso martini. Both have great espresso, too! Desserts can be quite controversial, with everyone having an opinion on which is better: Mike's Pastry, Modern Pastry, (or for real Bostonians, Bova's). Bova's is less touristy, so it has less of a line, it's open 24/7, and it has the best cannolis (there, I said it!). Get one from each and throw your opinion into the ring!
The Isabella Stewart Gardner Museum - Many people have heard of the art theft of 1990 at this estate turned museum where 13 works of art worth 500+ million were stolen, and as of today still not recovered. The museum has the frames displayed where the art was cut out of said frames. This is probably the most interesting (and beautiful) museum in Boston and worth a look if you have time. The MFA - 20th largest art museum in the world. We are members of this incredible art museum and if you are in Boston for a longer trip we highly recommend it!
This upscale neighborhood, with its iconic brownstone-lined streets built atop landfill that filled in the "back bay", is great for high-end shopping, dining. Walk down the Commonwealth Ave ("Comm ave") Mall for a nice tree-lined median park. Walk over to the Charles River Esplanade for a beautiful park along the Charles River to hang out on a bench or our favorite, sitting on Adirondack chairs on the docks in the river (like Fiedler Dock) Head to Newbury Street for all shopping and dining. Some dining favorites on Newbury St include La Voile, Sonsie, Stephanie's, Rochambeau and Lolita. A homing beacon to Back Bay is the Prudential Center building which hosts an indoor mall and a renovated View Boston observation deck where we got engaged! The Boston Public Library has grand architecture and and an extensive collection. Head to the newer wing to see where GBH hosts some of its local NPR radio programming where Manny would go to watch their Boston Public Radio show live.
The newest neighborhood of Boston is the Seaport, located next to the historic and artsy neighborhood of Fort Point. The Seaport is Boston's newly built "Innovation district" (most buildings were built after 2015 - Like Ashley's new work headquarters). Congress St, Seaport Blvd, and Northern Ave are the main in streets in this area. Walk down the harborwalk and enjoy a very picturesque view of Boston. Throw some tea into the harbor at the Boston Tea Party Ship. Check out the ICA, also with harbor views, if contemporary art is your jam. Cisco Beer Garden is a favorite hang out in the neighborhood -- try one of Manny's favorite beers, Grey Lady. Legal Harborside (Legal Seafood has multiple, unique, locations in the city) has great harbor views on each of its three floors. Row 34 is an amazing local seafood restaurant, their warm buttered lobster roll is a favorite.