Boston has one of the biggest “Little Italy” neighborhoods in the United States. The North End is the city's oldest neighborhood and is a must-visit. It has everything you need – 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 purchased by Revere in 1770. We recommend going inside--the admission fee is nominal. With a self-guided tour, you can explore the hall, kitchen, and bedchambers – ending with a museum exhibit that explores Revere’s life in Boston and his role in the American Revolution.
2. Old North Church
Wander along the narrow streets of the North End--you can follow the red brick Freedom Trail--to the Paul Revere Mall with the Old North Church steeple in the background. The church was built in 1723 and the windows near the top of this 191-foot high steeple showcased two lanterns the night of April 18, 1775, which warned Paul Revere that British soldiers were starting their journey to Lexington “by sea.” There are special tours that will take you up to the bell tower and down into the crypts! It’s still a functioning church with service on Sundays, so plan ahead.
A bonus stop: head just up the hill from the church to Copp's Hill Burying Ground, Boston's second oldest burying ground. Keep your eye out for a black cat that wanders the grounds.
3. Cannoli Competition
There is debate among locals and visitors about who has the best cannolis in the North End, so we recommend going to three of the most famous and celebrated shops and trying for yourself. Visit Modern Pastry Shop, Mike's Pastry, and Bova's Bakery and then pick your favorite.
4. Pizzeria Regina
Ready for lunch? Head to Regina Pizzeria, a North End institution open since 1926. The family-owned establishment has been firing up brick-oven, thin-crust 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. There are a few other historic restaurants in the North End we recommend checking out--our ebook has more details.
5. Ye Olde Tavern Tour
Finish your day walking off that pizza and learning more about the decade before Paul Revere’s midnight ride by joining us on Ye Olde Tavern Tours along the Freedom Trail! Spoiler: Revere stopped by taverns to rally the local militia for Lexington, so you’ll be following in his footsteps by enjoying New England craft beer at three historic taverns to top off a day full of history and fun! Bonus: We end minutes away from the North End… so if you’re ready for round two, you can head back over for a lovely Italian dinner. Huzzah!