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How To Plan Sightseeing For One Week In And Around Boston


by Quinta Bedolla



Welcome to the vibrant city of Boston! If you’re planning a week-long sightseeing trip in and around Boston, you’re in for a treat. With its rich history, diverse neighborhoods, and picturesque landscapes, Boston offers a plethora of exciting and educational experiences for visitors. Whether you’re a history enthusiast, a nature lover, or an art aficionado, this itinerary will help you make the most of your time in this captivating city.


From exploring the iconic Freedom Trail to hopping on a ferry to the enchanting Martha’s Vineyard, this week-long guide will take you on an unforgettable journey through Boston and its surrounding areas. You’ll have the opportunity to immerse yourself in the history of the American Revolution, soak in the beauty of the harbor, and discover the vibrant culture of nearby Cambridge.


Throughout your adventure, you’ll have the chance to indulge in delicious local cuisine, explore world-class museums, and experience the charming charm of Boston’s neighborhoods. So, put on your walking shoes, grab your camera, and get ready to discover the best that Boston has to offer!


Note: This itinerary is designed for those who have a week to explore Boston and its surroundings. Feel free to adjust the schedule based on your interests and preferences.


Day 1: Exploring Historic Boston

Start your week in Boston by immersing yourself in its rich history and exploring the iconic sites that played a significant role in the American Revolution. Begin your day by visiting the Boston Common, the oldest public park in the United States. Take a leisurely stroll through the park and soak in the serene atmosphere before making your way to the nearby Massachusetts State House, an architectural gem that houses the state government.


From there, head to the nearby Granary Burying Ground, the final resting place of many notable historical figures, including Paul Revere and John Hancock. Take a moment to pay your respects and marvel at the intricate gravestones that tell stories of Boston’s past.


Next, make your way to the historic Faneuil Hall Marketplace. This vibrant marketplace is a hub of activity with its blend of shops, restaurants, and street performers. Explore the Quincy Market building and indulge in some delicious New England clam chowder or grab a lobster roll for lunch.


In the afternoon, take a guided tour of the USS Constitution Museum and the nearby Charlestown Navy Yard. Step aboard the USS Constitution, the world’s oldest commissioned naval vessel still afloat, and learn about its remarkable history. Take in breathtaking views of the Boston skyline from the ship’s deck.


As the evening sets in, make your way to the North End neighborhood, also known as Boston’s Little Italy. This charming enclave is famous for its narrow streets, historic buildings, and delicious Italian cuisine. Sample some mouthwatering cannoli from one of the local bakeries, and end your day with a delightful dinner at one of the authentic Italian restaurants in the area.


Note: Remember to check the opening hours and any COVID-related restrictions for each attraction before visiting.


Day 2: Harbor and Island Hopping

On your second day, embark on a waterfront adventure and explore the picturesque Boston Harbor and its surrounding islands. Start your day by taking a scenic harbor cruise, where you can admire the stunning skyline of Boston and learn about the city’s maritime history.


After the cruise, make your way to the Boston Harbor Islands. These pristine islands offer a peaceful retreat from the hustle and bustle of the city. Hop on a ferry and head to one of the islands, such as Spectacle Island or Georges Island. Enjoy a day of picnicking, hiking, or swimming, and take in the breathtaking views of the harbor.


In the afternoon, return to the mainland and visit the New England Aquarium. Explore the fascinating exhibits, including the Giant Ocean Tank, where you can witness a diverse range of marine life up close. Don’t miss the opportunity to catch an animal feeding or watch a thrilling IMAX movie at the aquarium.


As the day winds down, head to the Seaport District, a vibrant neighborhood located on the waterfront. Enjoy a delicious dinner at one of the many seafood restaurants in the area, and soak in the lively atmosphere of this dynamic district.


Before calling it a day, consider catching a sunset harbor cruise to witness the enchanting lights of the city reflecting on the water. It’s the perfect way to end a day of exploring the harbor and its surrounding islands.


Note: Be sure to check the ferry schedules and availability for the Boston Harbor Islands, as they may vary depending on the season.


Day 3: Discovering Cambridge

On day three, venture across the Charles River to explore the vibrant city of Cambridge, home to two prestigious universities: Harvard University and the Massachusetts Institute of Technology (MIT). Start your day by visiting Harvard Square, the heart of the Harvard University campus. Take a guided tour of the university and admire the historic buildings, lush green spaces, and iconic Harvard Yard.


After exploring Harvard, make your way to nearby MIT. Known for its innovative research and cutting-edge technology, MIT offers a unique glimpse into the future. Explore the campus and visit the MIT Museum, where you can learn about the scientific breakthroughs and technological advancements pursued by the institution.


In the afternoon, take a leisurely stroll along the banks of the Charles River. Enjoy the scenic views and relax in one of the picturesque parks along the riverfront. If you’re up for it, consider renting a kayak or paddleboard to explore the river from a different perspective.


As evening approaches, head to Central Square, a lively neighborhood in Cambridge known for its diverse culinary scene. Indulge in a delectable dinner at one of the many restaurants offering cuisines from around the world. Afterward, catch a performance at one of the local theaters or live music venues to immerse yourself in Cambridge’s vibrant arts and culture scene.


Note: Harvard University and MIT offer guided tours, so be sure to check their websites for tour schedules and any COVID-related guidelines before your visit.


Day 4: Exploring the Freedom Trail

Day four is dedicated to immersing yourself in the history of the American Revolution by following the famous Freedom Trail. This 2.5-mile-long trail takes you through 16 historically significant sites, allowing you to experience the rich heritage of Boston firsthand.


Start your day at the Boston Common Visitor Information Center, where you can pick up a map and gather information about the trail. Begin your journey by walking through the charming streets of Beacon Hill, one of Boston’s oldest and most picturesque neighborhoods. Admire the well-preserved federal-style architecture and visit the Massachusetts State House, a symbol of democratic governance.


As you continue along the trail, don’t miss the Old Granary Burying Ground, where you can pay your respects to prominent figures such as Samuel Adams, John Hancock, and Paul Revere. Stop by the Old South Meeting House, the site where the colonists gathered to protest the British taxes and played a pivotal role in the events leading up to the American Revolution.


Next, make your way to the historic Faneuil Hall, often referred to as the “Cradle of Liberty.” Explore the marketplace and step inside the hall, where many influential speeches and debates took place. Grab a quick bite to eat at Quincy Market before heading to the Paul Revere House in the North End. Step back in time as you visit the home of the famous midnight rider and learn about his role in the Revolution.


Continue your journey along the trail, passing by the Old North Church, where the signal for Paul Revere’s ride was famously given. As you approach Charlestown, you’ll see the Bunker Hill Monument, a tribute to the Battle of Bunker Hill.


End your day by crossing the Charles River and enjoying the stunning view of the Boston skyline from the USS Constitution Museum and Charlestown Navy Yard. Explore the museum dedicated to “Old Ironsides,” the world’s oldest commissioned naval vessel afloat.


Throughout the day, immerse yourself in the stories and history surrounding each site along the Freedom Trail. It’s a truly captivating journey that allows you to step back in time and appreciate Boston’s role in shaping the United States.


Note: Wear comfortable shoes and be prepared for a lot of walking. Consider taking breaks and hydrating along the way, especially during warmer months.


Day 5: Visiting the Museum District

On day five, delve into Boston’s vibrant cultural scene by exploring the Museum District. This area is home to several world-class museums that offer a diverse range of art, history, and science exhibits. Start your day by visiting the Museum of Fine Arts (MFA), one of the largest art museums in the United States. Explore its vast collection of artwork from various eras and cultures, including renowned works by artists such as Monet, Van Gogh, and Picasso.


After enjoying the art at the MFA, make your way to the neighboring Isabella Stewart Gardner Museum. Step into a stunning Venetian-style palace filled with a remarkable collection of art, including masterpieces by Rembrandt, Vermeer, and Michelangelo. Take a leisurely stroll through the beautiful gardens and courtyards, which are equally as impressive as the artwork.


For history enthusiasts, the next stop is the Museum of African American History. Learn about the compelling stories of African Americans’ journey and contributions to the nation’s history and culture. Explore exhibits that delve into topics such as slavery, the Civil Rights Movement, and the influence of African Americans in Boston.


In the afternoon, venture to the nearby Museum of Science, where education and entertainment intersect. Discover interactive exhibits on various scientific disciplines, including astronomy, biology, engineering, and more. Marvel at the living exhibits, catch a show at the planetarium, or even watch a thrilling IMAX film.


Wrap up your day by visiting the Institute of Contemporary Art (ICA), located on Boston’s waterfront. Explore the thought-provoking contemporary artworks, attend a lecture or performance, and enjoy the breathtaking views of the harbor from the museum’s terrace.


As evening falls, consider exploring the nearby Seaport District, where you’ll find a variety of dining options to satisfy your appetite. Treat yourself to a delicious dinner at one of the waterfront restaurants, and enjoy the vibrant atmosphere of this bustling area.


Note: Check the museums’ websites for current exhibitions, operating hours, and any special COVID-related guidelines before your visit. Some museums may require advanced reservations.


Day 6: Venturing to Salem

On day six, take a day trip from Boston to the historic and bewitching city of Salem. Known for its infamous witch trials of the late 17th century, Salem offers a fascinating blend of history, maritime heritage, and spooky attractions.


Start your day by visiting the Salem Witch Museum, where you can learn about the witch trials through interactive exhibits and informative presentations. Explore the museum’s collection and gain insight into the events that unfolded in Salem during that dark period of history.


Next, immerse yourself in Salem’s maritime heritage by visiting the Peabody Essex Museum. This world-class museum showcases a wide range of art, artifacts, and interactive exhibits that highlight the city’s strong ties to the sea. Marvel at the intricate maritime models, explore the East India Marine Hall, and learn about the trading history that shaped Salem.


As you wander through Salem’s charming streets, make sure to visit the House of the Seven Gables. This iconic mansion, made famous by Nathaniel Hawthorne’s novel of the same name, offers guided tours that provide insight into the lives of New England’s early settlers.


For a dose of spooky entertainment, head to the Salem Witch Trials Memorial. Pay homage to the victims of the witch trials and reflect on the lessons learned from this dark chapter in history. Afterwards, take a leisurely stroll through the atmospheric streets of downtown Salem, lined with shops selling witchcraft-related souvenirs and quaint cafes.


Before you leave Salem, make a stop at the Salem Maritime National Historic Site. Explore the historic buildings, including the Custom House and the Derby Wharf, and learn about Salem’s role in the early days of maritime trade.


If you’re visiting during the Halloween season, be sure to check out the haunted attractions and events that Salem has to offer. From haunted houses to ghost tours, there’s no shortage of spooky experiences to indulge in.


As you return to Boston in the evening, take some time to reflect on the intriguing history and cultural significance of Salem. Enjoy a delicious dinner in one of Boston’s many dining establishments, and prepare for your final day of adventure in the beautiful city.


Note: Salem is easily accessible from Boston by train or ferry. Check the schedules and plan your transportation accordingly.


Day 7: Exploring Cape Cod and Martha’s Vineyard

On your final day, embark on a scenic journey to Cape Cod and Martha’s Vineyard to experience the beauty of New England’s coastal landscapes. Start your day by driving or taking a ferry to Cape Cod, a renowned vacation destination known for its charming towns, picturesque beaches, and distinctive Cape Cod architecture.


Begin your exploration of Cape Cod by visiting the Cape Cod National Seashore. This pristine stretch of coastline offers stunning views, sandy beaches, and dunes to explore. Spend some time walking along the shore, enjoying the fresh sea breeze, and taking in the natural beauty that surrounds you.


In the afternoon, make your way to Hyannis, a bustling town located at the heart of Cape Cod. This vibrant community is famous for its connection to the Kennedy family. Visit the John F. Kennedy Hyannis Museum to learn about the legacy of the 35th president and his deep ties to Cape Cod. Take a walk along Hyannis Harbor and enjoy the atmosphere of this charming waterfront location.


Next, head to the village of Woods Hole, where you can catch a ferry to Martha’s Vineyard. This picturesque island is renowned for its idyllic beaches, quaint towns, and charming lighthouses. Explore the historic streets of Edgartown, visit the charming fishing village of Menemsha, or relax on the pristine beaches in Oak Bluffs.


While on Martha’s Vineyard, be sure to visit the famed Gingerbread Cottages in Oak Bluffs. These whimsical and colorful cottages are a sight to behold and are a testament to the island’s rich history and unique architectural style.


As the day draws to a close, catch the ferry back to Cape Cod and reminisce about the beautiful landscapes, charming towns, and cultural experiences you’ve enjoyed throughout the week. Consider stopping in one of Cape Cod’s seafood shacks for a delicious lobster roll or fresh local seafood before heading back to Boston.


Remember to check the ferry schedules, parking availability, and any COVID-related guidelines before planning your day trip to Cape Cod and Martha’s Vineyard.


As you conclude your week-long adventure, take a moment to reflect on the incredible experiences you’ve had exploring Boston and its surrounding areas. From delving into history on the Freedom Trail to embracing the maritime heritage of Salem and venturing to the coastal beauty of Cape Cod and Martha’s Vineyard, you’ve made unforgettable memories and gained a deeper appreciation for the rich culture and heritage of New England.



As your week-long sightseeing journey in and around Boston comes to a close, you can reflect on the incredible experiences, rich history, and breathtaking landscapes that you have encountered. From immersing yourself in the footsteps of American Revolutionaries on the Freedom Trail to exploring the enchanting coastal destinations of Cape Cod and Martha’s Vineyard, you have embarked on a memorable adventure in one of the most culturally significant regions of the United States.


Throughout your journey, you discovered the historical landmarks and iconic sites that shaped the nation’s history, such as Harvard University, the Boston Harbor Islands, and Salem’s witch trials. You also had the opportunity to indulge in the vibrant arts and culture scene of the Museum District and explore the maritime heritage of Boston’s harbor.


Beyond the historical and cultural sites, you enjoyed the picturesque landscapes of the region. Whether it was walking along the serene shores of Cape Cod, admiring the sunset from a harbor cruise, or strolling through the charming neighborhoods of Boston, you witnessed the natural beauty that New England has to offer.


From the delectable seafood of Boston’s waterfront restaurants to the charming cafes of Cambridge, you savored the local cuisine and experienced the diverse culinary scene that Boston and its surrounding areas are known for.


As your week of exploration comes to an end, cherish the memories you’ve made, the knowledge you’ve gained, and the friendships you’ve forged along the way. Boston and its surroundings hold a wealth of history, culture, and natural beauty that will continue to inspire and captivate visitors for years to come.


Whether you’re a history buff, a nature lover, or simply seeking new experiences, Boston offers something for everyone. So, until your next visit, carry the spirit of adventure and exploration that defined your time in Boston, and continue to uncover the beauty and wonders that the world holds.