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Ultimate 20-Day Boston and Surroundings Adventure Itinerary
Last updated: 2024 Jun 14Historic Boston Kickoff
Morning
Start your Boston exploration with a hearty breakfast at Mike's Pastry, known for its delicious pastries. Afterward, immerse yourself in history with a visit to the Boston Tea Party Ships and Museum Interactive Tour.
Afternoon
For lunch, savor the fresh seafood at Legal Sea Foods. In the afternoon, take a Boston Freedom Trail Small Group History Walking Tour to visit the city's iconic landmarks.
Evening
Enjoy a sunset dinner cruise on Boston Harbor with a buffet onboard, a perfect way to end your first day in the city.
Bedtime
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Boston Boston Tea Party Ships and Museum Interactive Tour
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Boston Freedom Trail Small Group Guided Walking Tour
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Harbor and Skyline Views
Morning
Indulge in a delightful breakfast at Neptune Oyster, known for its seafood. Then, take a Boston Harbor Codzilla High Speed Thrill Boat for a fun and thrilling experience on the water.
Afternoon
For lunch, head to Union Oyster House, the oldest operating restaurant in the U.S. Afterward, visit the New England Aquarium to explore the marine life.
Evening
Dine at Top of the Hub for a fine dining experience with panoramic views of the city. After dinner, take a leisurely stroll around the harbor.
Bedtime
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Boston Harbor Codzilla High Speed Thrill Boat
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New England Aquarium
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Fenway Park and North End Delights
Morning
Enjoy a classic Boston breakfast at Mamma Maria, known for its Italian cuisine. Then, take a Boston Fenway Park Guided Ballpark Tour with Options to learn about the history of this iconic stadium.
Afternoon
For lunch, have a slice of pizza at Santarpio's Pizza, a local favorite. Afterward, explore the Boston North End on a self-guided food tour, trying different Italian specialties.
Evening
End your day with a dinner at Giacomo's Ristorante, a cozy restaurant known for its delicious pasta dishes.
Bedtime
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Boston Fenway Park Guided Ballpark Tour with Options
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Boston North End
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Innovation and History
Morning
Start your day with a breakfast at Myers + Chang, offering a unique fusion of flavors. Then, take a Massachusetts Institute of Technology Public Tour to explore the campus and its innovations.
Afternoon
For lunch, enjoy the vibrant atmosphere and Spanish tapas at Toro. Afterward, visit the MIT Museum to delve into the world of science and technology.
Evening
Dine at Oleana, a renowned restaurant offering Mediterranean-inspired cuisine. After dinner, take a leisurely walk along the Charles River.
Bedtime
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Massachusetts Institute of Technology Public Tour
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MIT Museum
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Literary and Culinary Delights
Morning
Enjoy a leisurely breakfast at Flour Bakery + Cafe, known for its pastries and sandwiches. Then, visit the Boston Public Library to admire its architecture and literary treasures.
Afternoon
For lunch, experience the farm-to-table concept at Craigie on Main. Afterward, take a Boston North End Pizza Tour with 3 Slices and Cannoli to sample the best pizza in the city.
Evening
Dine at L'Espalier, a fine dining institution in Boston. After dinner, take a stroll through the Boston Public Garden.
Bedtime
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Boston Public Library
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Boston North End Pizza Tour with 3 Slices and Cannoli
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Revolutionary Boston
Morning
Start your day with a classic American breakfast at The Paramount, a popular spot in Beacon Hill. Then, take a Boston Freedom Trail, Bunker Hill, & USS Constitution Tour to delve into the city's revolutionary history.
Afternoon
For lunch, enjoy the local and sustainable cuisine at Island Creek Oyster Bar. Afterward, visit the USS Constitution and the Bunker Hill Monument.
Evening
Dine at Row 34, known for its seafood and oyster selection. After dinner, take a leisurely walk around the historic North End.
Bedtime
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Boston Freedom Trail, Bunker Hill, & USS Constitution Tour
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Chengdu Giant Panda Breeding Research Base Ticket
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Boston Harbor Islands National and State Park
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Art and Culture in Boston
Morning
Enjoy a leisurely breakfast at Tatte Bakery & Cafe, known for its pastries and Mediterranean-inspired dishes. Then, visit the Museum of Fine Arts to explore its world-class collection.
Afternoon
For lunch, head to Sportello, a modern take on the classic diner. Afterward, take a walk down Newbury Street for some shopping and people-watching.
Evening
Dine at Sorellina, a contemporary Italian restaurant. After dinner, attend a performance at the Symphony Hall or the Boston Opera House.
Bedtime
Find amazing hotels in Boston, Massachusetts.
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From Interlaken Local Canyoning Trip
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Freedom Trail
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Relaxation and Recreation
Morning
Start your day with a leisurely breakfast at Stephanie's On Newbury, a popular spot for brunch. Then, take a walk or a bike ride along the Esplanade.
Afternoon
For lunch, enjoy the laid-back atmosphere and seafood at Atlantic Fish Company. Afterward, you can rent a kayak or paddleboard to explore the Charles River.
Evening
Dine at Deuxave, a fine dining restaurant known for its French-American cuisine. After dinner, take a romantic evening stroll along the river.
Bedtime
Find amazing hotels in Boston, Massachusetts.
Day Trip to Martha's Vineyard
Morning
Catch an early ferry to Martha's Vineyard. Upon arrival, rent a bike or a moped to explore the island at your own pace.
Afternoon
For lunch, enjoy the fresh seafood at The Black Dog Tavern with a view of the harbor. Afterward, relax on the beach or visit the Aquinnah Cliffs.
Evening
Catch the ferry back to the mainland and have a casual dinner at Chesca's, known for its Italian and seafood dishes.
Bedtime
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Colorado River
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Culinary Tour of Boston
Morning
Start your day with a delicious breakfast at Flour Bakery + Cafe. Then, embark on a Boston Public Market Tour and Hands-On Cooking Class to learn about local ingredients and prepare a traditional New England meal.
Afternoon
Enjoy the fruits of your labor for lunch. Afterward, take a Sweet and Savory South End Food Tour to sample a variety of dishes in this vibrant neighborhood.
Evening
For dinner, indulge in a multi-course tasting menu at O Ya, a renowned sushi restaurant. After dinner, take a leisurely walk around the South End.
Bedtime
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Death Valley National Park
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Whale Watching and Waterfront Dining
Morning
Have a hearty breakfast at The Friendly Toast, a quirky spot known for its creative dishes. Then, embark on a Boston Whale Watching Catamaran Cruise for a chance to see these majestic creatures in their natural habitat.
Afternoon
For lunch, enjoy the seafood and the view at Chart House on the waterfront. Afterward, take a walk along the Harborwalk and visit the Institute of Contemporary Art.
Evening
Dine at Legal Harborside, a three-story seafood restaurant with a roof deck. After dinner, enjoy the sea breeze and the city lights.
Bedtime
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Boston Whale Watching Catamaran Cruise
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Fountains of Bellagio
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Salem Witch Trials and Haunted History
Morning
Start your day with a spooky breakfast at Gulu-Gulu Cafe in Salem. Then, immerse yourself in the history of the Salem Witch Museum and the Salem 1692 Witchcraft Trials Walk.
Afternoon
For lunch, try the eclectic dishes at A Bit Bazaar. Afterward, take a Salem, MA History and Hauntings Guided Walking Tour to explore the city's dark past.
Evening
Dine at Opus, a restaurant housed in a former fire station. After dinner, join the Salem Night Tour Haunt and History Guided Night Tour for a spine-tingling experience.
Bedtime
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Fremont Street Experience
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Salem 1692 Witchcraft Trials Walk
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Salem, MA History and Hauntings Guided Walking Tour
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Salem Night Tour Haunt and History Guided Night Tour
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Literary and Maritime History
Morning
Enjoy a leisurely breakfast at Pour House Bar and Grill in Boston. Then, visit the Harvard University and take a Cambridge Explore Harvard University on a Student-Led Tour to learn about its history and famous alumni.
Afternoon
For lunch, try the classic New England clam chowder at Union Oyster House. Afterward, visit the Longfellow House (Washington's Headquarters) and the Charles River.
Evening
Dine at Harvest, a restaurant known for its farm-to-table cuisine. After dinner, take a Charles River Sunset Cruise for a different perspective of the city.
Bedtime
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Harvard University
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Cambridge Harvard University Student-Guided Walking Tour
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Longfellow House (Washington's Headquarters)
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Charles River
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Gondola Rides at the Venetian
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Revolutionary War and Maritime Adventure
Morning
Start your day with a breakfast at The Breakfast Club, a cozy spot in Allston. Then, take a From Boston Full-Day Historical Lexington & Concord Tour to explore the sites of the first battles of the Revolutionary War.
Afternoon
For lunch, enjoy the casual atmosphere and the lobster roll at Neptune Oyster. Afterward, visit the USS Constitution Museum and take a Boston Harbor Sunset Cruise.
Evening
Dine at The Capital Grille, a classic steakhouse. After dinner, take a walk along the waterfront and enjoy the sea breeze.
Bedtime
Find amazing hotels in Boston, Massachusetts.
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From Boston Full-Day Historical Lexington & Concord Tour
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Boston Boston Harbor Sunset Cruise
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Harvard and MIT Exploration
Morning
Have a leisurely breakfast at The Friendly Toast in Cambridge. Then, take a Massachusetts Institute of Technology Public Tour to learn about its cutting-edge research and innovation.
Afternoon
For lunch, try the diverse and flavorful dishes at Oleana. Afterward, visit the Harvard Museum of Natural History and take a Massachusetts Institute of Technology (MIT).
Evening
Dine at Harvest, a restaurant known for its farm-to-table cuisine. After dinner, take a Charles River Sunset Cruise for a different perspective of the city.
Bedtime
Find amazing hotels in Boston, Massachusetts.
Popular
Massachusetts Institute of Technology Public Tour
click to access prices
Popular
Harvard Museum of Natural History
click to access prices
Popular
Massachusetts Institute of Technology (MIT)
click to access prices
Popular
Gondola Rides at the Venetian
click to access prices
Literary and Culinary Delights
Morning
Enjoy a leisurely breakfast at Tatte Bakery & Cafe, known for its pastries and Mediterranean-inspired dishes. Then, visit the Boston Public Library to admire its architecture and literary treasures.
Afternoon
For lunch, head to Sportello, a modern take on the classic diner. Afterward, take a walk down Newbury Street for some shopping and people-watching.
Evening
Dine at Sorellina, a contemporary Italian restaurant. After dinner, attend a performance at the Symphony Hall or the Boston Opera House.
Bedtime
Find amazing hotels in Boston, Massachusetts.
Popular
Boston Public Library
click to access prices
Popular
Freedom Trail
click to access prices
Revolutionary Boston
Morning
Start your day with a classic American breakfast at The Paramount, a popular spot in Beacon Hill. Then, take a Boston Freedom Trail, Bunker Hill, & USS Constitution Tour to delve into the city's revolutionary history.
Afternoon
For lunch, enjoy the local and sustainable cuisine at Island Creek Oyster Bar. Afterward, visit the USS Constitution and the Bunker Hill Monument.
Evening
Dine at Row 34, known for its seafood and oyster selection. After dinner, take a leisurely walk around the historic North End.
Bedtime
Find amazing hotels in Boston, Massachusetts.
Popular
Boston Freedom Trail, Bunker Hill, & USS Constitution Tour
click to access prices
Popular
Chengdu Giant Panda Breeding Research Base Ticket
click to access prices
Popular
Boston Harbor Islands National and State Park
click to access prices
Art and Culture in Boston
Morning
Enjoy a leisurely breakfast at Tatte Bakery & Cafe, known for its pastries and Mediterranean-inspired dishes. Then, visit the Museum of Fine Arts to explore its world-class collection.
Afternoon
For lunch, head to Sportello, a modern take on the classic diner. Afterward, take a walk down Newbury Street for some shopping and people-watching.
Evening
Dine at Sorellina, a contemporary Italian restaurant. After dinner, attend a performance at the Symphony Hall or the Boston Opera House.
Bedtime
Find amazing hotels in Boston, Massachusetts.
Popular
From Interlaken Local Canyoning Trip
click to access prices
Popular
Freedom Trail
click to access prices
Relaxation and Recreation
Morning
Start your day with a leisurely breakfast at Stephanie's On Newbury, a popular spot for brunch. Then, take a walk or a bike ride along the Esplanade.
Afternoon
For lunch, enjoy the laid-back atmosphere and seafood at Atlantic Fish Company. Afterward, you can rent a kayak or paddleboard to explore the Charles River.
Evening
Dine at Deuxave, a fine dining restaurant known for its French-American cuisine. After dinner, take a romantic evening stroll along the river.
Bedtime
Find amazing hotels in Boston, Massachusetts.
Culinary Tour of Boston
Morning
Start your day with a delicious breakfast at Flour Bakery + Cafe. Then, embark on a Boston Public Market Tour and Hands-On Cooking Class to learn about local ingredients and prepare a traditional New England meal.
Afternoon
Enjoy the fruits of your labor for lunch. Afterward, take a Sweet and Savory South End Food Tour to sample a variety of dishes in this vibrant neighborhood.
Evening
For dinner, indulge in a multi-course tasting menu at O Ya, a renowned sushi restaurant. After dinner, take a leisurely walk around the South End.
Bedtime
Find amazing hotels in Boston, Massachusetts.
Popular
Death Valley National Park
click to access prices
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