​Who knew Boston has one of the biggest “Little Italy” neighborhoods in the USA? We did! The North End has everything you’d expect given its namesake – food worth salivating over, historic sites, and a cadre of locals staking out the best people-watching spots. Follow our itinerary for the perfect mix of history and fun!

1. Paul Revere’s House
Start your morning off with some history! Paul Revere’s house stands out against the typical North End brick architecture. It was built in 1680 and owned by Revere from 1770 to 1800. With a self-guided tour, you can explore the hall, kitchen, and bedchambers – ending in their new Visitor Center, which highlights Revere’s life and role in the American Revolution. 

2. Old North Church (and Crypt!)
Wander up the back roads of the North End to Old North Church. Built in 1723, the windows near the top of this 191-foot high steeple had two lanterns hung on the night of April 18, 1775. The lanterns warned Charlestown that British soldiers were traveling to Lexington “by sea.” If you take the tour, you’ll get to go up to the bell tower (where Paul Revere was a bell ringer when he was a young lad!) and down into the crypts. It’s still a functioning church with service on Sundays, so plan ahead. 

3. Regina Pizzeria
Ready for lunch?  Head to Regina Pizzeria, a North End institution open since 1926.  The family-owned establishment has been firing up brick-oven pizzas for over three generations.  You’ll get some delicious pizza and perhaps a side of Boston attitude, though we like to call it flair! If there’s a line, it usually moves quickly and is worth the wait. 

4. Ye Olde Tavern Tour along the Freedom Trail
Walk off that pizza and learn more about the decade before Paul Revere’s midnight ride by joining us on Ye Olde Tavern Tours of the Freedom Trail!  Spoiler: Revere loved drinking in Boston's taverns, so you’ll be following in his footsteps by enjoying New England craft beer at three historic taverns. Bonus: We end minutes away from the North End, so head over for a little dessert after the tour.

5. Grab some Dessert
Cannolis from the North End are definitely a thing  if you're visiting Boston. While most people knows about Mike's Pastry, act like a local and go to Modern Pastry across the street or even more local, Bova's Bakery, a couple blocks over. If cannolis aren't for you, there are plenty of other tempting desserts. All three bakeries have been around since at least the mid-twentieth century, so it's a great way to end your day of history and fun.

The Freedom Trail connects 16 historic sites in Boston and is a must do. Join our tours to see 10 of the sites and drink beer along the way. Afterward, you can explore some of favorite free stops, listed below.

1. Massachusetts State House Tour
The Massachusetts State House atop Beacon Hill is at the start of the Freedom Trail. This is the “new” State House, built in 1798 (the Old State House is also a stop on the Freedom Trail, now a museum with paid admission). The building’s staff provides free tours on weekdays between 10am and 3:30pm, lasting 30-45 minutes. You’ll learn about the building’s history and see the House/Senate chambers. Advance reservations required. 

2. Granary Burying Ground
Around the corner from the State House you’ll find Granary Burying Ground, established in 1660. Your self-guided tour will take you by over 2,000 grave markers, including some belonging to Boston’s famous Revolutionary-era inhabitants. The Puritans, who settled Massachusetts Bay Colony in 1630, didn’t believe in religious iconography, so keep an eye out for skulls, depictions of the Grim Reaper, and winged cherubs. 

3. USS Constitution 
​On the other end of the Freedom Trail in Charlestown Navy Yard, you’ll find the USS Constitution. “Old Ironsides” is the oldest commissioned war ship still afloat, first launched in 1797 and most famous for her role in the War of 1812.  You can visit the ship for free (after showing a valid ID or passport), with tours kicking off every 15 minutes Wednesday-Sunday, 10am to 4pm. You'll even get to see the ship's officer's quarters, which is a fun sneak peek. 

4. Bunker Hill Monument 
Finish up at the Bunker Hill Monument in Charlestown, across the harbor from Boston proper. The 221-foot tall, granite obelisk marks the spot of the bloodiest battle of the Revolutionary War fought on June 17, 1775. If you have a few more steps in you, head up the staircase to the top! There’s also a free museum across the street where you can learn more about the battle, including a diorama of the troops' placements.