Know more. Do more.
Whether you're hoping off the trolley for a bit or setting off for a day on your own, hopefully this here page will help more efficiently navigate the city so you can make the most of your time and experience!
The Waterfront & The Greenway
This section of town includes the areas along both sides of Atlantic Ave from the Rose F. Kenndy Greenway to the Harbor and roughly from Seaport Blvd. to Christopher Columbus Park.




The North End
The Waterfront: Boston's waterfront (along with the Seaport District) probably benefited the most from the notorious Big Dig. Once cut-off and separated, now open and vibrant. A great, free activity would be to do this part of the Harborwalk. Enjoy some of the best views in the city by starting at Boston's historic Long Wharf, behind the Boston Harbor Hotels iconic archway (where most days a wicked big American flag will be hanging) and end at James Hook & Co with the city's best lobstah roll! If you want to spend a few bucks there's a multitude of harbor cruises day and night. Perhaps a whale watch? Or, go visit one or multiple of the Boston harbor islands by ferry. My favorite is Spectacle to collect some sea glass. The Rose Kennedy Greenway: OK, so yes, most of this will pertain to the warm-weather months but the Greenway is truly a treasure. A little less than 2 mile stretch of parks and green spaces that was once where the big, ugly, elevated, expressway used to be. Sure, there's places to buy stuff like at the Trillium open beer garden or the seasonal open-air markets on the weekends but most of Greenway is free fun! From spray parks and fountain pads to light installations to sculptures and artwork the Greenway is an urban oasis with something for everybody. Get more info and an interactive map of the Greenway here. Crafty's Best Eats: Overall winner would be the Sail Loft. Technically, it might be in the North End but it's right on the line, located on the back side of Christopher Columbus Park on Commercial Ave. The Chart House on the Long Wharf is a little more upscale but very nice. The aforementioned, James Hook & Co is always a winner or perhaps try the Granary Tavern. Located on the other side of the Greenway at the corner of Surface and Milk.
Ahhh, Boston's oldest residential neighborhood, the Italian Noth End. This is where it all started way back in 1630. Sure, it's changed a little since then. But....not much! If you like "old school", the North End is for you. If you like plenty of parking on the other hand.....:) You can easily spend a full day just here in this little section of town. There's 4 big, major attractions. The Paul Revere house (North St.) and the Paul Revere Statue & Mall (Hanover St.) The Old North Church (Salem St.) and Copp's Hill Burial Ground (Hull St.) For a couple off-the-beaten-path choices? Try the Printing Office of Edes & Gil. Super cool! They'll show ya how it was done back in Paul Revere's day. Also, while there, see if you can find the Memorial Garden. It's pretty touching. Or, for the real history nerd, go find the site of the Thomas Hutchinson house on Garden Court. Of course, if the North End is known for anything these days, it's food! And yes, Italian food. For my older readers, you might recognize Prince Street. That's where the Prince Spaghetti factory started and yes, where, Anthony lived. "Hey Anthony!" You know. Wednesday's WAS Prince Spaghetti Day. Crafty's Best Eats: Oh boy, where to start?! Look, you almost can't go wrong. However, my long-time favorite, Mother Anna's is gone so while I search for a new one, I'll stick with what I know, pizza! Here's my top 3: Ducali's (Commercial St), Earnesto's (Salem St.), and Giacomo's (Hanover St.). Please, by all means, let me know what you enjoyed most in the North End and I'll add it to the list!
Connect
© 2025. All rights reserved.
Venmo: @Steve-Crafts-1


CraftyTheTourGuide.com is in NO WAY, SHAPE OR FORM associated with Old Town Trolley or Historic Tours of America. I am personally responsible for all the content on this site. In other words, don't blame them for anything here or vice versa:)