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Ultimate 14-Day Massachusetts Exploration

Ultimate 14-Day Massachusetts Exploration Itinerary

Last updated: 2024 Jun 14

Historic Beginnings and Scenic Views

Morning

Start your Massachusetts adventure with a hearty breakfast at Mike's Pastry, famous for its delectable pastries. Afterward, take a stroll through the picturesque Boston Common, the oldest city park in the United States, and continue to the adjacent Public Garden to enjoy the iconic swan boats.

Afternoon

Savor a traditional New England lunch at Legal Sea Foods, known for its fresh seafood. Spend your afternoon exploring the historic Freedom Trail, visiting sites like the USS Constitution ("Old Ironsides") and the Bunker Hill Monument.

Evening

Dine with a view at Top of the Hub, offering panoramic scenes of the city skyline. After dinner, experience the Boston Harbor on a Boston Harbor Sunset Yacht Cruise, enjoying the cool breeze and the lights of the city reflecting on the water.

Bedtime

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4.49
Boston Common
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4.14
Public Garden
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Cultural and Culinary Delights

Morning

Enjoy a morning coffee and breakfast at Eastern Standard Kitchen & Drinks. Then, immerse yourself in marine wonders at the New England Aquarium, where you can skip the line with your entry ticket and explore the vibrant undersea world.

Afternoon

For lunch, head to Row 34 and indulge in their exceptional seafood offerings. Afterward, take a leisurely walk through the charming North End, also known as Little Italy, and explore the historic streets and shops.

Evening

Dine at Neptune Oyster, a local favorite for its fresh oysters and seafood. Cap off the evening with a spooky adventure on the 1.5-Hour Ghosts and Gravestones Tour, exploring Boston's darker history and haunted spots.

Bedtime

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4.47
New England Aquarium
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4.51
North End
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Harbor History and Culinary Cruise

Morning

Start your day with a buffet breakfast on the water with a Buffet Lunch or Dinner Cruise on Boston Harbor. As you dine, enjoy the views of the city's iconic landmarks from the harbor.

Afternoon

After your cruise, visit the Boston Tea Party Ships & Museum for an interactive tour, reliving the historic event. Then, take a walk along the waterfront and explore the shops at Quincy Market and Faneuil Hall Marketplace.

Evening

For dinner, experience the vibrant atmosphere and delicious Italian cuisine of the North End at Mamma Maria. Later, take a stroll to the nearby Paul Revere House and the Old North Church to immerse yourself in the history of the American Revolution.

Bedtime

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4.51
Buffet Lunch or Dinner Cruise on Boston Harbor
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4.22
Boston Tea Party Ships & Museum
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Literary Legacies and Academic Icons

Morning

Begin your day with breakfast at Toro, offering a delightful Spanish menu. Then, take a walk through the prestigious grounds of Harvard University and explore the campus, including the famous Harvard Square and the John Harvard Statue.

Afternoon

Enjoy a sumptuous lunch at Giacomo's Ristorante, known for its mouthwatering Italian dishes. Afterward, visit the Harvard Museum of Natural History to marvel at its impressive collections and exhibitions.

Evening

Dine at No. 9 Park, where you can enjoy a sophisticated meal in an elegant setting. Cap off the evening with a visit to the Longfellow House (Washington's Headquarters), once home to the renowned poet Henry Wadsworth Longfellow.

Bedtime

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4.25
Harvard University
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4.20
Harvard Square
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Innovative Minds and Culinary Finds in Cambridge

Morning

Start your day with a visit to the Massachusetts Institute of Technology (MIT), where you can explore the campus and its innovative exhibitions. Enjoy breakfast at Craigie on Main, known for its creative and locally sourced menu.

Afternoon

For lunch, head to Union Oyster House, the oldest restaurant in the United States, and savor their famous oysters. Spend your afternoon strolling through the vibrant Kendall Square, exploring its shops and galleries.

Evening

Dine at Oleana, a restaurant celebrated for its inventive and award-winning Mediterranean-inspired cuisine. Conclude your day with a relaxing walk along the serene Charles River, enjoying the picturesque views.

Bedtime

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4.33
Massachusetts Institute of Technology (MIT)
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4.82
Kendall Square
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Freedom Trail and Haunted Pubs

Morning

Start with a delicious breakfast at Myers + Chang, offering a mouthwatering menu with a fusion of flavors. Then, embark on a Small Group Freedom Trail History Walking Tour, immersing yourself in the rich history of Boston.

Afternoon

Enjoy a delightful lunch at Santarpio's Pizza, a local favorite known for its thin-crust pizzas. Afterward, visit the Boston View Boston Observatory Entry Ticket to get a bird's eye view of the city.

Evening

For dinner, head to The Capital Grille for an elegant dining experience with perfectly prepared steaks and an extensive wine list. Then, join the Boos and Brews Haunted Pub Crawl in the evening, exploring Boston's haunted history while visiting its iconic pubs.

Bedtime

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4.91
Small Group Freedom Trail History Walking Tour
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4.65
Boston View Boston Observatory Entry Ticket
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Literary and Culinary Delights

Morning

Start your day with breakfast at L'Espalier, offering a sophisticated start to your morning. Then, visit the Longfellow House (Washington's Headquarters), the former home of poet Henry Wadsworth Longfellow, and explore the beautiful gardens and historic house.

Afternoon

Enjoy a luxurious lunch at Menton, known for its fine French cuisine and elegant ambiance. Spend your afternoon at the MIT Museum, exploring the world of science, technology, and innovation.

Evening

Dine at O Ya, a contemporary Japanese restaurant that offers a unique dining experience with its innovative dishes. Conclude your day with a leisurely walk through the serene Kendall Square, enjoying the vibrant atmosphere and public art installations.

Bedtime

Find amazing hotels in Boston.

4.33
Longfellow House (Washington's Headquarters)
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4.91
MIT Museum
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Salem's Haunted History and Mystical Tours

Morning

Begin your day with a visit to the Salem Witch Museum Admission Ticket, where you'll learn about the infamous witch trials. Enjoy breakfast at Top of the Hub with a panoramic view of Boston before heading to Salem.

Afternoon

Have lunch at Row 34 in Salem, and then explore the Salem Witch Trials Walk to visit the sites associated with this dark period in history. Continue with the Secrets of Salem Hidden History Walking Tour to uncover the lesser-known stories of the city.

Evening

Dine at The Capital Grille back in Boston, savoring their dry-aged steaks and fresh seafood. Conclude your day with the Salem Night Tour Haunt and History Guided Night Tour, where you'll hear chilling tales of Salem's past.

Bedtime

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3.95
Salem Witch Museum Admission Ticket
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4.26
Salem Witch Trials Walk
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Fenway Park and Culinary Surprises

Morning

Start with a breakfast at Neptune Oyster, a local favorite known for its fresh seafood. Then, take a guided tour of the iconic Boston Fenway Park and learn about the history of this legendary ballpark.

Afternoon

Enjoy a casual lunch at Santarpio's Pizza, where you can taste some of the best pizzas in the city. Spend your afternoon exploring the interactive exhibits at the Boston Science Park and Museum Entry Ticket.

Evening

Dine at Craigie on Main, a restaurant celebrated for its innovative American cuisine. Cap off the evening with a visit to Harvard Square in Cambridge, where you can explore the vibrant shops and street performances.

Bedtime

Find amazing hotels in Boston.

4.19
Boston Fenway Park
Book Now

4.81
Boston Science Park and Museum Entry Ticket
Book Now

Literary Legacies and Scenic Strolls

Morning

Start your day with a delightful breakfast at Giacomo's Ristorante, known for its authentic Italian dishes. Then, visit the Longfellow House (Washington's Headquarters), the former home of poet Henry Wadsworth Longfellow, and explore the beautiful gardens and historic house.

Afternoon

Enjoy a sumptuous lunch at No. 9 Park, where you can indulge in award-winning cuisine. Spend your afternoon at the Harvard Museum of Natural History, marveling at its impressive collections and exhibitions.

Evening

Dine at Menton, a fine dining restaurant that offers an exceptional culinary experience. Conclude your day with a leisurely walk through the serene Charles River, enjoying the picturesque views.

Bedtime

Find amazing hotels in Boston.

4.33
Longfellow House (Washington's Headquarters)
Book Now

3.80
Harvard Museum of Natural History
Book Now

Aquatic Wonders and Historic Trails

Morning

Start your day with breakfast at Eastern Standard Kitchen & Drinks, known for its classic American dishes. Then, head to the New England Aquarium to explore the vibrant marine life and engage with interactive exhibits.

Afternoon

For lunch, visit Legal Sea Foods and savor their fresh seafood in a casual, nautical-themed setting. Afterward, take a self-guided tour of the Freedom Trail, visiting sites like the USS Constitution and the Bunker Hill Monument.

Evening

Dine at O Ya, a contemporary Japanese restaurant that offers a unique dining experience with its innovative dishes. Cap off the evening with a visit to the Boston Harbor Sunset Yacht Cruise, enjoying the cool breeze and the lights of the city reflecting on the water.

Bedtime

Find amazing hotels in Boston.

4.47
New England Aquarium
Book Now

4.61
Freedom Trail
Book Now

Innovative Minds and Culinary Finds in Cambridge

Morning

Start your day with a visit to the Massachusetts Institute of Technology (MIT), where you can explore the campus and its innovative exhibitions. Enjoy breakfast at Craigie on Main, known for its creative and locally sourced menu.

Afternoon

For lunch, head to Union Oyster House, the oldest restaurant in the United States, and savor their famous oysters. Spend your afternoon strolling through the vibrant Kendall Square, exploring its shops and galleries.

Evening

Dine at Oleana, a restaurant celebrated for its inventive and award-winning Mediterranean-inspired cuisine. Conclude your day with a relaxing walk along the serene Charles River, enjoying the picturesque views.

Bedtime

Find amazing hotels in Boston.

4.33
Massachusetts Institute of Technology (MIT)
Book Now

4.82
Kendall Square
Book Now

Salem's Haunted History and Mystical Tours

Morning

Begin your day with a visit to the Salem Witch Museum Admission Ticket, where you'll learn about the infamous witch trials. Enjoy breakfast at Top of the Hub with a panoramic view of Boston before heading to Salem.

Afternoon

Have lunch at Row 34 in Salem, and then explore the Salem Witch Trials Walk to visit the sites associated with this dark period in history. Continue with the Secrets of Salem Hidden History Walking Tour to uncover the lesser-known stories of the city.

Evening

Dine at The Capital Grille back in Boston, savoring their dry-aged steaks and fresh seafood. Conclude your day with the Salem Night Tour Haunt and History Guided Night Tour, where you'll hear chilling tales of Salem's past.

Bedtime

Find amazing hotels in Boston.

3.95
Salem Witch Museum Admission Ticket
Book Now

4.26
Salem Witch Trials Walk
Book Now

Fenway Park and Culinary Surprises

Morning

Start with a breakfast at Neptune Oyster, a local favorite known for its fresh seafood. Then, take a guided tour of the iconic Boston Fenway Park and learn about the history of this legendary ballpark.

Afternoon

Enjoy a casual lunch at Santarpio's Pizza, where you can taste some of the best pizzas in the city. Spend your afternoon exploring the interactive exhibits at the Boston Science Park and Museum Entry Ticket.

Evening

Dine at Craigie on Main, a restaurant celebrated for its innovative American cuisine. Cap off the evening with a visit to Harvard Square in Cambridge, where you can explore the vibrant shops and street performances.

Bedtime

Find amazing hotels in Boston.

4.19
Boston Fenway Park
Book Now

4.81
Boston Science Park and Museum Entry Ticket
Book Now

Top Boston Travel Videos

Adjacent Cities

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