Ultimate 22-Day Boston and Beyond Adventure Itinerary

Embark on the Guided Walking Tour of the Freedom Trail to explore the heart of Boston's history. Refuel with a morning pastry and coffee at Emmets, a local favorite known for its warm hospitality.

After the trail, visit the Granary Burying Ground and Faneuil Hall Marketplace. For lunch, head to The Tip Tap Room for their extensive beer selection and diverse menu featuring steak tips and more.

Experience the vibrant atmosphere of the North End, Boston's Little Italy. Enjoy a delightful evening on the Boston's North End Secret Food Tour, sampling the best Italian cuisine. Conclude with a stroll along the charming streets.

Cross the river to Cambridge and start your day with a guided tour of the prestigious Harvard University. For breakfast, indulge in the creative dishes at 4th Wall Restaurant & Bar.

Explore the innovative campus of Massachusetts Institute of Technology (MIT) and visit the MIT Museum. Have lunch at Bukowski Tavern, a laid-back spot with a wide beer selection and tasty burgers.

Enjoy a leisurely walk in the scenic Kendall Square area, and for dinner, head to Birch Bar for their craft cocktails and a menu that highlights local ingredients.

Begin with an insider's look at the historic Fenway Park on the Fenway Park Guided Ballpark Tour with Options. Grab a quick breakfast at The Point Boston, known for its fresh and vibrant dishes.

After the tour, take a relaxing stroll along the Charles River or enjoy a picnic in the Cambridge Common. For lunch, visit Tavern in the Square for a casual dining experience.

Witness the city lights come alive as you take the Boston Harbor Winter Holiday Weekend Brunch Cruise. Indulge in the festive atmosphere and enjoy a memorable dinner on the water.

Start with a spooky Salem Night Tour Haunt and History Guided Night Tour in the nearby town of Salem, known for its witch trials. Enjoy a hearty breakfast at Mr. Dooley's Boston, a traditional Irish pub with a welcoming atmosphere.

Return to Boston and spend the afternoon at the Longfellow House (Washington's Headquarters) and the John Harvard Statue. For lunch, head to The Black Rose, an iconic pub serving classic Irish dishes.

Dive deeper into Boston's eerie past with the Boston Ghost Tour. Conclude your night with live music or stand-up comedy at 21st Amendment, a lively venue in the heart of the city.

Hop on the Hop-on Hop-off Old Town Trolley Tour to get an overview of the city's major attractions. Disembark at the Boston Harbor for a refreshing morning breeze. Grab a quick bite at Solas Irish Pub, known for its traditional Irish fare.

Continue the trolley tour and visit the USS Constitution and the Bunker Hill Monument. For lunch, enjoy the comfort food at The Bell In Hand Tavern, one of the oldest taverns in the United States.

Explore the vibrant atmosphere of Quincy Market and have dinner at French Quarter, where you can savor Cajun and Creole dishes in a lively setting.

Start with a delightful Boston Harbor Winter Holiday Weekend Brunch Cruise, enjoying the seasonal menu and the views of the city waking up. Have brunch at the Porters Bar and Grill, known for its waterfront dining experience.

After the cruise, take a Boston Cocoa and Carols Holiday Cruise, immersing yourself in the holiday spirit. Warm up with a cup of cocoa and some caroling. For lunch, visit Rock & Rye American Bar for their creative American cuisine.

Explore the holiday lights and decorations around the city, and for dinner, indulge in the upscale menu at The White Bull Tavern, offering a mix of classic and contemporary dishes.

Enjoy a morning at the Boston View Boston Observatory Entry Ticket, taking in the panoramic views of the city. Pair this with a visit to the View Boston Observatory Coffee and Donut Combo experience. For breakfast, continue the theme with a visit to jm Curley, where you can enjoy their famous donuts and a cup of coffee.

After the observatory, take a leisurely walk along the Rose Kennedy Greenway and enjoy the public art installations. For lunch, head to 21st Amendment for their diverse menu and a relaxed atmosphere.

Experience the city after dark at the After Dark at View Boston Observatory (Adults Only), and for dinner, try the innovative dishes at Birch Bar, known for its creative cocktails and locally sourced ingredients.

Begin with a Boston Historical Sightseeing Cruise, learning about the city's maritime history and passing by iconic landmarks. Enjoy a breakfast sandwich at 21st Amendment to fuel up for the day.

Disembark at the Charlestown Navy Yard and visit the USS Constitution Museum. Then, head to Harvard Square in Cambridge for an afternoon of exploring the shops and cafes. Have lunch at Tavern in the Square, offering a variety of options in a casual setting.

Return to Boston and enjoy a sophisticated dinner at Yvonne's, known for its elegant ambiance and creative menu. Afterward, take a stroll through the Back Bay neighborhood, admiring the beautiful brownstones and upscale boutiques.

Start your day with a visit to the Boston Public Library, where you can explore the stunning architecture and literary treasures. For breakfast, enjoy the cozy atmosphere and delicious pastries at Silvertone Bar & Grill.

After the library, take a walk down Newbury Street, known for its upscale shops and galleries. For lunch, head to Bostonia Public House and indulge in their modern take on classic American dishes.

As the sun sets, experience the Boston Literary Historical Walking Tour, delving into the city's rich literary history. Conclude the tour with a dinner at The Tip Tap Room, where you can enjoy a wide selection of beers and a menu featuring various cuts of meat.

Spend your morning at the Isabella Stewart Gardner Museum, admiring the stunning collection in a unique setting. For breakfast, visit Emmets and enjoy their Irish-inspired dishes.

After the museum, take a guided tour of the Boston Symphony Hall and learn about its rich history and world-class acoustics. For lunch, head to The Bell In Hand Tavern, where you can enjoy a meal in the oldest tavern in America.

Enjoy a performance at the Huntington Theatre Company or the Boston Opera House. For dinner, visit French Quarter and savor the flavors of New Orleans in the heart of Boston.

Start your day with a visit to the Arnold Arboretum, where you can enjoy a peaceful morning walk among the trees and gardens. For breakfast, head to Mr. Dooley's Boston and fuel up with a hearty Irish breakfast.

After the arboretum, spend your afternoon at the Franklin Park Zoo, exploring the diverse range of animals. For lunch, visit The Black Rose and enjoy a traditional Irish meal in a lively pub atmosphere.

Conclude your day with a pub crawl through the South End, visiting local favorites like Porters Bar and Grill, Bukowski Tavern, and The Tip Tap Room. Enjoy a variety of beers and delicious pub fare as you explore the neighborhood.

Take a day trip to the historic towns of Concord and Lexington. Visit the Minute Man National Historical Park and the Louisa May Alcott's Orchard House. For breakfast, stop by Tavern in the Square for a quick bite.

Explore the Walden Pond State Reservation and enjoy the natural beauty that inspired Henry David Thoreau. Have lunch at 21st Amendment before heading back to Boston.

Relax and unwind with a dinner at The White Bull Tavern, where you can enjoy a mix of classic and contemporary dishes in a welcoming atmosphere.

Start your day with a visit to the Museum of Fine Arts, Boston (MFA), where you can explore a world-class collection of art. For breakfast, enjoy the elegant setting and delicious pastries at Yvonne's.

After the museum, take a leisurely walk through the Back Bay Fens (Victory Gardens) and enjoy the beautiful green space. For lunch, visit Rock & Rye American Bar and try their creative American cuisine.

Spend a relaxing evening at The Spa at Mandarin Oriental, Boston, where you can indulge in a range of luxurious treatments. Afterward, enjoy a peaceful dinner at Birch Bar, known for its locally sourced ingredients and innovative dishes.

Start your day with a visit to the Museum of Science, Boston (MOS), where you can explore interactive exhibits and learn about a variety of scientific topics. For breakfast, visit 21st Amendment and enjoy their diverse menu.

After the museum, take a walk along the Charles River Esplanade and enjoy the beautiful views of the city. For lunch, head to Tavern in the Square and relax with a meal in a casual setting.

Conclude your day with a visit to the New England Aquarium, where you can see a wide variety of marine life. For dinner, visit The Black Rose and enjoy a traditional Irish meal in a lively pub atmosphere.

Spend your morning exploring the shops on Newbury Street, known for its upscale boutiques and galleries. For breakfast, enjoy the cozy atmosphere and delicious pastries at Silvertone Bar & Grill.

After shopping, visit the Prudential Center and take a ride to the Top of the Hub for panoramic views of the city. For lunch, head to Bostonia Public House and indulge in their modern take on classic American dishes.

Conclude your day with a Guided Delicious Donut Tour with Tastings, where you can sample some of the best donuts in the city. For dinner, visit The Tip Tap Room and enjoy a wide selection of beers and a menu featuring various cuts of meat.

Start your day with a visit to the Institute of Contemporary Art (ICA), where you can explore a range of contemporary art. For breakfast, visit Emmets and enjoy their Irish-inspired dishes.

After the museum, take a walk along the Harborwalk and enjoy the views of the waterfront. For lunch, head to The Bell In Hand Tavern and enjoy a meal in the oldest tavern in America.

Conclude your day with a performance at the TD Garden or the House of Blues Boston. For dinner, visit French Quarter and savor the flavors of New Orleans in the heart of Boston.

Start with a visit to the John F. Kennedy Presidential Library & Museum, where you can learn about the life and legacy of the 35th President of the United States. For breakfast, enjoy the elegant setting and delicious pastries at Yvonne's.

After the museum, take a ferry to the Boston Harbor Islands National and State Park and spend the afternoon exploring the natural beauty and rich history of the islands. For lunch, visit Rock & Rye American Bar and try their creative American cuisine.

Conclude your day with a dinner at Birch Bar, known for its locally sourced ingredients and innovative dishes. Afterward, take a leisurely walk along the Rose Kennedy Greenway and enjoy the public art installations.

Begin your day with a visit to the Arnold Arboretum, where you can enjoy a peaceful morning walk among the trees and gardens. For breakfast, head to Mr. Dooley's Boston and fuel up with a hearty Irish breakfast.

After the arboretum, spend your afternoon at the Franklin Park Zoo, exploring the diverse range of animals. For lunch, visit The Black Rose and enjoy a traditional Irish meal in a lively pub atmosphere.

Conclude your day with a pub crawl through the South End, visiting local favorites like Porters Bar and Grill, Bukowski Tavern, and The Tip Tap Room. Enjoy a variety of beers and delicious pub fare as you explore the neighborhood.

Start your day with a visit to the Museum of Fine Arts, Boston (MFA), where you can explore a world-class collection of art. For breakfast, enjoy the elegant setting and delicious pastries at Yvonne's.

After the museum, take a leisurely walk through the Back Bay Fens (Victory Gardens) and enjoy the beautiful green space. For lunch, visit Rock & Rye American Bar and try their creative American cuisine.

Spend a relaxing evening at The Spa at Mandarin Oriental, Boston, where you can indulge in a range of luxurious treatments. Afterward, enjoy a peaceful dinner at Birch Bar, known for its locally sourced ingredients and innovative dishes.

Start your day with a visit to the Museum of Science, Boston (MOS), where you can explore interactive exhibits and learn about a variety of scientific topics. For breakfast, visit 21st Amendment and enjoy their diverse menu.

After the museum, take a walk along the Charles River Esplanade and enjoy the beautiful views of the city. For lunch, head to Tavern in the Square and relax with a meal in a casual setting.

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