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5-Day Boston Adventure

5-Day Boston Adventure Itinerary

Last updated: 2024 Jun 14

Historic Boston Exploration

Morning
Start your day with a visit to Freedom Trail. This 2.5-mile-long path through downtown Boston passes by 16 locations significant to the history of the United States. It's a great way to get acquainted with the city's rich history.
Afternoon
After a morning of exploring, head over to Neptune Oyster for lunch. This highly-rated seafood restaurant is known for its fresh oysters and lobster rolls. Post-lunch, visit Boston Old State House, one of the oldest public buildings in the U.S., and learn about its historical significance.
Evening
In the evening, enjoy dinner at Ostra, a sophisticated seafood restaurant offering Mediterranean-inspired dishes. After dinner, take a leisurely stroll through Beacon Hill, one of Boston's most picturesque neighborhoods with its narrow streets and brick row houses.
Bedtime
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Academic and Cultural Day

Morning
Begin your day with breakfast at Tatte Bakery & Cafe in Cambridge before heading to Harvard University. Take a guided tour of this prestigious institution and explore Harvard Yard.
Afternoon
For lunch, dine at Mamma Maria, an Italian restaurant in the North End. Afterward, visit MIT Museum where you can explore fascinating exhibits on science and technology.
Evening
Enjoy dinner at Myers+Chang, an Asian-inspired eatery known for its creative small plates. Conclude your day with a visit to Boston Symphony Hall for an evening concert.
Bedtime
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Seaside and Science Fun

Morning
Start your day with breakfast at Flour Bakery & Cafe before visiting New England Aquarium. Spend your morning exploring marine life exhibits and watching entertaining shows.
Afternoon
Have lunch at Island Creek Oyster Bar, renowned for its fresh seafood. Post-lunch, head over to the nearby Museum of Science Boston where you can engage with interactive exhibits and watch an IMAX film.
Evening
For dinner, make reservations at No. 9 Park, offering French-Italian cuisine in an elegant setting. After dinner, take a scenic walk along the Charles River Esplanade.
Bedtime
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Artistic and Historical Insights

Morning
Kick off your day with coffee from Thinking Cup before visiting the iconic Fenway Park. Take a guided tour of this historic baseball stadium.
Afternoon
Lunch will be at Toro Boston, known for its Spanish tapas. Following lunch, explore the art collections at the Isabella Stewart Gardner Museum or alternatively visit the nearby Museum of Fine Arts.
Evening
Dine at The Capital Grille for an upscale steakhouse experience. End your evening by exploring the vibrant nightlife in Back Bay or catching a live performance in one of Boston's many theaters.
Bedtime
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Exploring Boston's Hidden Gems

Morning
Start your day with a hearty breakfast at Mike & Patty's, a beloved local spot known for its delicious breakfast sandwiches. Afterward, head to Boston Public Garden, the first public botanical garden in America. Take a leisurely stroll through the beautifully landscaped grounds and enjoy the serene atmosphere.
Afternoon
For lunch, visit Sarma, a Mediterranean-inspired restaurant offering a variety of small plates. After lunch, explore Copley Square, an architectural gem surrounded by historic buildings like Trinity Church and the Boston Public Library. Don't miss the chance to step inside and admire the stunning interiors.
Evening
In the evening, dine at Oleana, known for its innovative Middle Eastern cuisine. Conclude your day with a visit to Boston Symphony Hall for an evening concert or performance, soaking in the rich cultural heritage of Boston.
Bedtime
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