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Roam Around

Ultimate 21-Day New England Adventure

Ultimate 21-Day New England Adventure Itinerary

Last updated: 2024 Jun 14

Historic Beginnings and Culinary Delights

Morning

Start your Boston journey with a guided walking tour of the Freedom Trail, visiting iconic landmarks like the Massachusetts State House, Granary Burying Ground, and the site of the Boston Massacre. After the tour, enjoy a delightful breakfast at Lincoln Tavern & Restaurant.

Afternoon

Immerse yourself in the rich history of the Boston Tea Party Ships and Museum with an interactive tour. For lunch, savor the flavors of the city on the North End Secret Food Tour, exploring the culinary gems of Boston's Little Italy.

Evening

Witness the city come alive on the Boston Harbor Sunset Yacht Cruise, enjoying stunning views and a gourmet dinner onboard. After the cruise, take a leisurely stroll through the vibrant Faneuil Hall Marketplace.

Bedtime

Find amazing hotels in Boston.

4.61
Freedom Trail
Book Now

4.75
Boston Tea Party Ships and Museum
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Seafaring Tales and Haunted Trails

Morning

Dive into the maritime history of Salem with the Salem Pirate Museum with Authentic Treasures Entry Ticket. Afterward, grab a quick bite at The Bell In Hand Tavern, one of the oldest taverns in the United States.

Afternoon

Explore the hidden history of Salem on a guided walking tour, Secrets of Salem Hidden History Walking Tour. For lunch, indulge in the fresh seafood at Fin Point Oyster Bar + Grille.

Evening

Experience the eerie side of Salem with the Salem Night Tour Haunt and History Guided Night Tour. After the tour, enjoy a comforting dinner at Mr. Dooley's Boston.

Bedtime

Find amazing hotels in Boston.

4.91
Salem Pirate Museum with Authentic Treasures Entry Ticket
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4.56
Secrets of Salem Hidden History Walking Tour
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Academic Wonders and River Views

Morning

Begin your day with a student-guided walking tour of the prestigious Harvard University in Cambridge. Enjoy breakfast at OAK Long Bar + Kitchen before the tour.

Afternoon

After the tour, take a leisurely stroll along the Charles River and enjoy the scenic views. For lunch, head to 21st Amendment for a casual dining experience.

Evening

Explore the innovative exhibits at the MIT Museum and learn about the cutting-edge research at the Massachusetts Institute of Technology (MIT). End the day with a delightful dinner at CLINK. and The Liberty Bar.

Bedtime

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4.25
Harvard University
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4.54
Charles River
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Festive Trolley Rides and Holiday Cruises

Morning

Embrace the holiday spirit with the Boston Holiday Sights and Festive Nights Trolley Tour, taking you to the city's most enchanting holiday displays. Enjoy a warm cup of cocoa at the end of the tour.

Afternoon

Glide through the waters on the Boston Cocoa and Carols Holiday Cruise, accompanied by live holiday music. For lunch, savor the comfort food at The White Bull Tavern.

Evening

Continue the holiday celebration with the Boston Harbor Gourmet Brunch or Dinner Cruise, indulging in a lavish meal with panoramic views of the city. After the cruise, take a serene walk in the Boston Common.

Bedtime

Find amazing hotels in Boston.

3.86
Boston Holiday Sights and Festive Nights Trolley Tour
Book Now

4.75
Boston Cocoa and Carols Holiday Cruise
Book Now

Sports Legends and Evening Observatory

Morning

Step into the historic Fenway Park with a guided ballpark tour. After the tour, enjoy a classic breakfast at Cheers, the famous bar from the TV show "Cheers."

Afternoon

Visit the View Boston Observatory and take in the city's skyline. For lunch, head to The Point Boston for a casual dining experience.

Evening

Dine at Emmets, a cozy Irish pub, and then enjoy the city lights at After Dark at View Boston Observatory (Adults Only), an exclusive evening experience.

Bedtime

Find amazing hotels in Boston.

4.19
Fenway Park
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4.65
View Boston Observatory
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Literary Legacies and Waterfront Wonders

Morning

Begin your day with a visit to the Longfellow House (Washington's Headquarters) in Cambridge, the former home of poet Henry Wadsworth Longfellow. Enjoy breakfast at JJ Foley's Bar & Grille, a classic Irish pub.

Afternoon

Explore the vibrant Kendall Square in Cambridge, known for its innovative tech scene. Have lunch at Bar 10, offering a diverse menu in a lively atmosphere.

Evening

Take a relaxing cruise on the Boston Harbor Sunset Yacht Cruise, enjoying the cool breeze and the city's skyline. Conclude the evening with a sumptuous dinner at Broadside Tavern.

Bedtime

Find amazing hotels in Boston.

4.33
Longfellow House (Washington's Headquarters)
Book Now

4.82
Kendall Square
Book Now

Museum Marvels and Historic Harbor

Morning

Spend the morning at the Harvard Museum of Natural History in Cambridge, exploring its fascinating exhibits. Grab a quick breakfast at The Street Bar before heading out.

Afternoon

Visit the USS Constitution, the world's oldest commissioned warship afloat, and the adjacent Museum of Science. Enjoy lunch at Tavern in the Square South Station before or after your visit.

Evening

Dine at Corner Tavern, a local favorite, and then take a serene walk along the Charles River, enjoying the city lights reflected on the water.

Bedtime

Find amazing hotels in Boston.

3.80
Harvard Museum of Natural History
Book Now

4.74
USS Constitution
Book Now

Theatrical Tales and Culinary Journeys

Morning

Begin with a guided tour of the iconic Harvard Square in Cambridge, a hub of academic and cultural activity. Enjoy breakfast at The Dubliner Irish Pub to start your day.

Afternoon

Explore the vibrant Cambridge Common, a historic park with a lively atmosphere. For lunch, head to The Sevens Ale House for a casual meal and a wide selection of beers.

Evening

Immerse yourself in the world of theater with a performance at the renowned Huntington Theatre Company. After the show, enjoy a sophisticated dinner at Theater District Brasserie, just a short walk from the theater.

Bedtime

Find amazing hotels in Boston.

4.20
Harvard Square
Book Now

4.89
Cambridge Common
Book Now

Revolutionary Trails and Local Eats

Morning

Embark on a guided walking tour of the Freedom Trail, revisiting the historic sites with a focus on their culinary connections. Enjoy a breakfast with a twist at Local Eats on the Freedom Trail, where you'll sample traditional New England fare.

Afternoon

After the tour, continue your exploration of the trail, making stops at the Paul Revere House and the Old North Church. For lunch, head to Union Oyster House, the oldest restaurant in continuous service in the United States, and savor their famous seafood dishes.

Evening

Relax and unwind at Boston Harbor Sunset Yacht Cruise, enjoying the beautiful views of the city from the water. Indulge in a gourmet dinner onboard and raise a glass to a day well spent.

Bedtime

Find amazing hotels in Boston.

4.61
Freedom Trail
Book Now

4.49
Paul Revere House
Book Now

Artistic Explorations and Elegant Dining

Morning

Start your day with a visit to the Institute of Contemporary Art (ICA), where you can immerse yourself in contemporary art and enjoy stunning views of the Boston waterfront. Breakfast is served at Waterfront Bistro, a perfect spot to begin your day.

Afternoon

After the museum, take a leisurely walk along the Rose Kennedy Greenway, a linear park that winds through the city. For lunch, head to Harborview Restaurant & Lounge and enjoy a meal with a view.

Evening

Dress up for an elegant evening at Top of the Hub, where you can enjoy fine dining and panoramic views of the city. After dinner, take a romantic stroll through the Public Garden and enjoy the beauty of the park at night.

Bedtime

Find amazing hotels in Boston.

4.54
Institute of Contemporary Art (ICA)
Book Now

4.65
Public Garden
Book Now

Literary Legends and Waterfront Wonders

Morning

Begin your day with a visit to the Longfellow House (Washington's Headquarters) in Cambridge, the former home of poet Henry Wadsworth Longfellow. Enjoy breakfast at JJ Foley's Bar & Grille, a classic Irish pub.

Afternoon

Explore the vibrant Kendall Square in Cambridge, known for its innovative tech scene. Have lunch at Bar 10, offering a diverse menu in a lively atmosphere.

Evening

Take a relaxing cruise on the Boston Harbor Sunset Yacht Cruise, enjoying the cool breeze and the city's skyline. Conclude the evening with a sumptuous dinner at Broadside Tavern.

Bedtime

Find amazing hotels in Boston.

4.33
Longfellow House (Washington's Headquarters)
Book Now

4.82
Kendall Square
Book Now

Museum Marvels and Historic Harbor

Morning

Spend the morning at the Harvard Museum of Natural History in Cambridge, exploring its fascinating exhibits. Grab a quick breakfast at The Street Bar before heading out.

Afternoon

Visit the USS Constitution, the world's oldest commissioned warship afloat, and the adjacent Museum of Science. Enjoy lunch at Tavern in the Square South Station before or after your visit.

Evening

Dine at Corner Tavern, a local favorite, and then take a serene walk along the Charles River, enjoying the city lights reflected on the water.

Bedtime

Find amazing hotels in Boston.

3.80
Harvard Museum of Natural History
Book Now

4.74
USS Constitution
Book Now

Theatrical Tales and Culinary Journeys

Morning

Begin with a guided tour of the iconic Harvard Square in Cambridge, a hub of academic and cultural activity. Enjoy breakfast at The Dubliner Irish Pub to start your day.

Afternoon

Explore the vibrant Cambridge Common, a historic park with a lively atmosphere. For lunch, head to The Sevens Ale House for a casual meal and a wide selection of beers.

Evening

Immerse yourself in the world of theater with a performance at the renowned Huntington Theatre Company. After the show, enjoy a sophisticated dinner at Theater District Brasserie, just a short walk from the theater.

Bedtime

Find amazing hotels in Boston.

4.20
Harvard Square
Book Now

4.89
Cambridge Common
Book Now

Revolutionary Trails and Local Eats

Morning

Embark on a guided walking tour of the Freedom Trail, revisiting the historic sites with a focus on their culinary connections. Enjoy a breakfast with a twist at Local Eats on the Freedom Trail, where you'll sample traditional New England fare.

Afternoon

After the tour, continue your exploration of the trail, making stops at the Paul Revere House and the Old North Church. For lunch, head to Union Oyster House, the oldest restaurant in continuous service in the United States, and savor their famous seafood dishes.

Evening

Relax and unwind at Boston Harbor Sunset Yacht Cruise, enjoying the beautiful views of the city from the water. Indulge in a gourmet dinner onboard and raise a glass to a day well spent.

Bedtime

Find amazing hotels in Boston.

4.61
Freedom Trail
Book Now

4.49
Paul Revere House
Book Now

Artistic Explorations and Elegant Dining

Morning

Start your day with a visit to the Institute of Contemporary Art (ICA), where you can immerse yourself in contemporary art and enjoy stunning views of the Boston waterfront. Breakfast is served at Waterfront Bistro, a perfect spot to begin your day.

Afternoon

After the museum, take a leisurely walk along the Rose Kennedy Greenway, a linear park that winds through the city. For lunch, head to Harborview Restaurant & Lounge and enjoy a meal with a view.

Evening

Dress up for an elegant evening at Top of the Hub, where you can enjoy fine dining and panoramic views of the city. After dinner, take a romantic stroll through the Public Garden and enjoy the beauty of the park at night.

Bedtime

Find amazing hotels in Boston.

4.54
Institute of Contemporary Art (ICA)
Book Now

4.65
Public Garden
Book Now

Literary Legends and Waterfront Wonders

Morning

Begin your day with a visit to the Longfellow House (Washington's Headquarters) in Cambridge, the former home of poet Henry Wadsworth Longfellow. Enjoy breakfast at JJ Foley's Bar & Grille, a classic Irish pub.

Afternoon

Explore the vibrant Kendall Square in Cambridge, known for its innovative tech scene. Have lunch at Bar 10, offering a diverse menu in a lively atmosphere.

Evening

Take a relaxing cruise on the Boston Harbor Sunset Yacht Cruise, enjoying the cool breeze and the city's skyline. Conclude the evening with a sumptuous dinner at Broadside Tavern.

Bedtime

Find amazing hotels in Boston.

4.33
Longfellow House (Washington's Headquarters)
Book Now

4.82
Kendall Square
Book Now

Museum Marvels and Historic Harbor

Morning

Spend the morning at the Harvard Museum of Natural History in Cambridge, exploring its fascinating exhibits. Grab a quick breakfast at The Street Bar before heading out.

Afternoon

Visit the USS Constitution, the world's oldest commissioned warship afloat, and the adjacent Museum of Science. Enjoy lunch at Tavern in the Square South Station before or after your visit.

Evening

Dine at Corner Tavern, a local favorite, and then take a serene walk along the Charles River, enjoying the city lights reflected on the water.

Bedtime

Find amazing hotels in Boston.

3.80
Harvard Museum of Natural History
Book Now

4.74
USS Constitution
Book Now

Theatrical Tales and Culinary Journeys

Morning

Begin with a guided tour of the iconic Harvard Square in Cambridge, a hub of academic and cultural activity. Enjoy breakfast at The Dubliner Irish Pub to start your day.

Afternoon

Explore the vibrant Cambridge Common, a historic park with a lively atmosphere. For lunch, head to The Sevens Ale House for a casual meal and a wide selection of beers.

Evening

Immerse yourself in the world of theater with a performance at the renowned Huntington Theatre Company. After the show, enjoy a sophisticated dinner at Theater District Brasserie, just a short walk from the theater.

Bedtime

Find amazing hotels in Boston.

4.20
Harvard Square
Book Now

4.89
Cambridge Common
Book Now

Revolutionary Trails and Local Eats

Morning

Embark on a guided walking tour of the Freedom Trail, revisiting the historic sites with a focus on their culinary connections. Enjoy a breakfast with a twist at Local Eats on the Freedom Trail, where you'll sample traditional New England fare.

Afternoon

After the tour, continue your exploration of the trail, making stops at the Paul Revere House and the Old North Church. For lunch, head to Union Oyster House, the oldest restaurant in continuous service in the United States, and savor their famous seafood dishes.

Evening

Relax and unwind at Boston Harbor Sunset Yacht Cruise, enjoying the beautiful views of the city from the water. Indulge in a gourmet dinner onboard and raise a glass to a day well spent.

Bedtime

Find amazing hotels in Boston.

4.61
Freedom Trail
Book Now

4.49
Paul Revere House
Book Now

Artistic Explorations and Elegant Dining

Morning

Start your day with a visit to the Institute of Contemporary Art (ICA), where you can immerse yourself in contemporary art and enjoy stunning views of the Boston waterfront. Breakfast is served at Waterfront Bistro, a perfect spot to begin your day.

Afternoon

After the museum, take a leisurely walk along the Rose Kennedy Greenway, a linear park that winds through the city. For lunch, head to Harborview Restaurant & Lounge and enjoy a meal with a view.

Evening

Dress up for an elegant evening at Top of the Hub, where you can enjoy fine dining and panoramic views of the city. After dinner, take a romantic stroll through the Public Garden and enjoy the beauty of the park at night.

Bedtime

Find amazing hotels in Boston.

4.54
Institute of Contemporary Art (ICA)
Book Now

4.65
Public Garden
Book Now

Literary Legends and Waterfront Wonders

Morning

Begin your day with a visit to the Longfellow House (Washington's Headquarters) in Cambridge, the former home of poet Henry Wadsworth Longfellow. Enjoy breakfast at JJ Foley's Bar & Grille, a classic Irish pub.

Afternoon

Explore the vibrant Kendall Square in Cambridge, known for its innovative tech scene. Have lunch at Bar 10, offering a diverse menu in a lively atmosphere.

Evening

Take a relaxing cruise on the Boston Harbor Sunset Yacht Cruise, enjoying the cool breeze and the city's skyline. Conclude the evening with a sumptuous dinner at Broadside Tavern.

Bedtime

Find amazing hotels in Boston.

4.33
Longfellow House (Washington's Headquarters)
Book Now

4.82
Kendall Square
Book Now

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