For those coming to Boston for the first time, the Freedom Trail is an ~3 mile walk that brings you past some of the most historical aspects of Boston. Self guide or sign up for a tour! Start out in the Boston Common and follow the painted red line (sometimes it switches to brick). Some highlights include the MA State House, site of the Boston Massacre, the Old North Church, and Bunker Hill. Be sure to take a break in the North End to refuel! Bruce and Gloria recommend the Behind the Scenes- Old North Church Tour (http://oldnorth.com/btstours/) for a more in-depth view of the Old North Church.
You will find great cannoli here! If you need something a little stronger, pop downstairs to the lesser known (and usually less crowded) Modern Underground bar- they will serve you pastry down here too!
One of our staples for wine, bread, and cheese when we were living in the North End! With Monica's, Chris put together a very impressive charcuterie plate the first time I went over to his apartment. We also went to the Trattoria di Monica across the street on one of our first dates. In case you haven't caught on, we love all the Monica's establishments, check out one (or all three) if you have the time!
After eating your way through the North End, head over to Ward 8 for cocktails. Another one of our favorite establishments when we lived in the North End!
Stop in for a taste of local fare! Some of our favorites include Union Square Doughnuts and SQ Nuts, but we haven't had anything here that wasn't delicious!
Check out the esplanade for a pleasant walk along the Charles River. Chris and Marissa have spent many hours running countless miles along the loops here. Cross over to the Cambridge side to get great views of Boston, or to check out MIT! (Although if you really want to get a historical, Ivy League feel, you may want to keep heading north to Harvard..)
Catch a game at the Green Monster and enjoy a Fenway Frank!
A beautiful place to spend an hour or two!
A Cape Cod favorite of the Brennan's. If you like clam chowder, definitely stop in!
The go-to beach for us whenever we are on the Cape, no matter the weather! Faces out to the true Atlantic Ocean.
Candlepin bowling. Great tap list and BBQ (trust us) too!
A great place to play games while sipping on some local beer.
Very classic Cape Cod beach, part of the protected National Seashore. Follow the signs to Marconi station if you just want a nice view. Otherwise, you can pay to park to hang out at the beach.
Check out the lighthouse on the beach, then head into picture perfect downtown Chatham for shops. Finish up with food and drink at The Squire.
Watch the sunset over Cape Cod Bay! If it's low tide, you will be able to walk out on the sand bars for over a mile. Tricky to put into Google Maps, but if you are coming from the south on Rock Harbor Road, take a left at Capt'n Cass Rock Harbor Seafood (onto Bay View Drive) and follow the road to the parking lot at the end.