Historic Icons & Upscale Italian in the North End
5 activities
TRIP'N'AI
Boston, MA, USA
Experience Boston's iconic history, upscale dining, charming neighborhoods, live music, and vibrant culinary scene—including Italian fare and fresh seafood. Enjoy top-tier accommodations and seasonal events during a memorable spring visit.
Daily Itinerary
Activities
Day Theme: Historic Icons & Upscale Italian in the North End
Freedom Trail Self-Guided or Private Tour
Walk the 2.5-mile Freedom Trail, exploring Boston’s Revolutionary-era landmarks like Boston Common, State House, Granary Burying Ground, Faneuil Hall, and Paul Revere House. Guided tours depart several times daily or you can explore at your own pace.
Price Range: Expect to pay $17 (guided tour)
Duration: Plan for about 3-4 hours
Entrance Fee: Entry fee: $17 (guided)
Opening Hours: Open Guided tours start 11am-1pm
Popular Times: To avoid crowds, visit outside of Late morning, early afternoon
Popularity Rating: 4.8/5
Here's what you need to know: Follows the historic brick line through 16 major sites from Boston Common to Bunker Hill.
Walk the 2.5-mile Freedom Trail, exploring Boston’s Revolutionary-era landmarks like Boston Common, State House, Granary Burying Ground, Faneuil Hall, and Paul Revere House. Guided tours depart several times daily or you can explore at your own pace.
Price Range: Expect to pay $17 (guided tour)
Duration: Plan for about 3-4 hours
Entrance Fee: Entry fee: $17 (guided)
Opening Hours: Open Guided tours start 11am-1pm
Popular Times: To avoid crowds, visit outside of Late morning, early afternoon
Popularity Rating: 4.8/5
Here's what you need to know: Follows the historic brick line through 16 major sites from Boston Common to Bunker Hill.
Lunch at Neptune Oyster
Iconic, intimate oyster bar serving some of Boston’s most coveted seafood, from fresh oysters to their legendary hot lobster roll.
Price Range: Expect to pay $$$
Cuisine: Specializes in Seafood cuisine
Duration: Plan for about 1-1.5 hours
Opening Hours: Open 11:30am–9:30pm
Popular Times: To avoid crowds, visit outside of Lunch, early dinner
Popularity Rating: 4.7/5
Hot Buttered Lobster Roll
If you're wondering what to order, Succulent lobster on a toasted roll, drenched in butter.
Here's what you need to know: Frequently ranked Boston’s best seafood spot.
Iconic, intimate oyster bar serving some of Boston’s most coveted seafood, from fresh oysters to their legendary hot lobster roll.
Price Range: Expect to pay $$$
Cuisine: Specializes in Seafood cuisine
Duration: Plan for about 1-1.5 hours
Opening Hours: Open 11:30am–9:30pm
Popular Times: To avoid crowds, visit outside of Lunch, early dinner
Popularity Rating: 4.7/5
Hot Buttered Lobster Roll
If you're wondering what to order, Succulent lobster on a toasted roll, drenched in butter.
Here's what you need to know: Frequently ranked Boston’s best seafood spot.
Explore North End & Italian Bakeries
Wander Boston’s ‘Little Italy’, peruse charming streets, and sample cannoli from rival bakeries—Mike’s Pastry and Modern Pastry.
Price Range: Expect to pay $
Cuisine: Specializes in Italian/Bakery cuisine
Duration: Plan for about 1-1.5 hours
Opening Hours: Open 8am–10pm
Popular Times: To avoid crowds, visit outside of All day, dessert hours
Popularity Rating: 4.6/5
Cannoli at Mike's Pastry
If you're wondering what to order, Cream-filled, hand-piped classic Boston dessert.
Here's what you need to know: Bustling, authentic Italian enclave with old-world ambiance.
Wander Boston’s ‘Little Italy’, peruse charming streets, and sample cannoli from rival bakeries—Mike’s Pastry and Modern Pastry.
Price Range: Expect to pay $
Cuisine: Specializes in Italian/Bakery cuisine
Duration: Plan for about 1-1.5 hours
Opening Hours: Open 8am–10pm
Popular Times: To avoid crowds, visit outside of All day, dessert hours
Popularity Rating: 4.6/5
Cannoli at Mike's Pastry
If you're wondering what to order, Cream-filled, hand-piped classic Boston dessert.
Here's what you need to know: Bustling, authentic Italian enclave with old-world ambiance.
Dinner at Mamma Maria
Refined, romantic Italian dining in a historic townhouse featuring handmade pasta and locally sourced ingredients.
Price Range: Expect to pay $$$$
Cuisine: Specializes in Upscale Italian cuisine
Duration: Plan for about 2 hours
Opening Hours: Open 5pm–10pm
Popular Times: To avoid crowds, visit outside of Dinner
Popularity Rating: 4.7/5
Osso Buco
If you're wondering what to order, Slow-braised veal shank with saffron risotto.
Here's what you need to know: One of the city’s most romantic Italian restaurants.
Refined, romantic Italian dining in a historic townhouse featuring handmade pasta and locally sourced ingredients.
Price Range: Expect to pay $$$$
Cuisine: Specializes in Upscale Italian cuisine
Duration: Plan for about 2 hours
Opening Hours: Open 5pm–10pm
Popular Times: To avoid crowds, visit outside of Dinner
Popularity Rating: 4.7/5
Osso Buco
If you're wondering what to order, Slow-braised veal shank with saffron risotto.
Here's what you need to know: One of the city’s most romantic Italian restaurants.
Live Jazz at The Beehive
Catch live music and creative cocktails at this iconic, artsy South End venue known for its bohemian vibe.
Price Range: Expect to pay $$$
Cuisine: Specializes in Global/Modern American cuisine
Duration: Plan for about 2 hours
Entrance Fee: Entry fee: Varies, usually free cover on weekdays
Opening Hours: Open 5pm–12am
Popular Times: To avoid crowds, visit outside of 8–11pm
Popularity Rating: 4.5/5
Beehive Julep
If you're wondering what to order, Signature cocktail with bourbon and mint.
Here's what you need to know: Intimate jazz and art scene, extensive spirits list.
Catch live music and creative cocktails at this iconic, artsy South End venue known for its bohemian vibe.
Price Range: Expect to pay $$$
Cuisine: Specializes in Global/Modern American cuisine
Duration: Plan for about 2 hours
Entrance Fee: Entry fee: Varies, usually free cover on weekdays
Opening Hours: Open 5pm–12am
Popular Times: To avoid crowds, visit outside of 8–11pm
Popularity Rating: 4.5/5
Beehive Julep
If you're wondering what to order, Signature cocktail with bourbon and mint.
Here's what you need to know: Intimate jazz and art scene, extensive spirits list.
Accommodation
The Langham, Boston
Luxury hotel in a former Federal Reserve Bank, walking distance to the North End and Downtown. Features plush rooms, top-tier amenities, and acclaimed on-site dining.
Local Tips
- Wear comfortable shoes for the Freedom Trail.
- Book restaurant reservations in advance.
- Try both Mike’s and Modern Pastry’s cannoli for the full North End experience.
Photo Spots
- Boston Common
- Paul Revere Statue in North End
- Quaint alleyways of North End
Share Trip
Share this amazing trip itinerary