A Five-Day Itinerary for Boston
A city rich in American history, culture, and innovation, Boston is at the heart of New England. There’s something for everyone in Boston, whether you’re a history buff, a foodie, or a lover of outdoor adventure. Visit the city’s iconic landmarks, vibrant neighborhoods, and unique attractions during this five-day itinerary.
Discover the city’s revolutionary roots, savor delicious seafood, and stroll through charming streets that weave together centuries of history during your stay. For an authentic Boston experience, this itinerary balances must-see sites with local favorites.
What makes Boston so special?
With its rich history, world-class museums, and beautiful parks, Boston is one of the oldest cities in the United States. The city is easy to navigate, and most major attractions can be reached by foot or public transportation. Boston’s compact size makes it easy to explore at a comfortable pace, soaking up its unique blend of past and present.
The key takeaways are:
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Major attractions are close together in a walkable city.
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The area is great for history, culture, food, and outdoor activities.
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The city is easily accessible by public transportation, making it easy to get around without a car.
Day 1: Exploring the Historic Core
Your first day in Boston will be spent learning about the city’s revolutionary past. We will visit some of the most iconic landmarks that shaped American history, so wear comfortable shoes!
Morning: Freedom Trail Tour
The Freedom Trail is a 2.5-mile-long route that takes you through 16 historically significant sites, tracing Boston’s role in the American Revolution. Start your tour at Boston Common, the oldest public park in the U.S., and make your way to landmarks like the Massachusetts State House, Paul Revere’s House, Old North Church, and Faneuil Hall.
- Boston Common
- Massachusetts State House
- Park Street Church
- Granary Burying Ground
- King’s Chapel Burying Ground
- Benjamin Franklin statue and the former site of Boston Latin School
- Old Corner Bookstore
- Old South Meeting House
- Old State House
- Site of the Boston Massacre
- Faneuil Hall
- Paul Revere House
- Old North Church
- Copp’s Hill Burying Ground
- USS Constitution
- Bunker Hill Monument
Tips:
- Opt for a guided tour (prices typically range from $14 to $20 per person) for in-depth historical insights.
- Alternatively, you can download a free self-guided tour app to explore at your own pace.
Key Stops:
- Boston Common is the starting point of the Freedom Trail. Free to visit.
- Granary Burying Ground—the resting place of revolutionaries like John Hancock and Samuel Adams. Free to visit.
- Old South Meeting House—where the Boston Tea Party was organized. Admission: $6.
- Paul Revere’s House: Admission: $5 for adults, $1 for children.
Lunch Recommendation:
- Head to Quincy Market at Faneuil Hall, a historic marketplace with diverse food vendors. Try the famous New England clam chowder from Boston Chowda Co. for around $8.
Afternoon: Boston Tea Party Ships & Museum
After lunch, continue your historical adventure at the Boston Tea Party Ships & Museum. This interactive museum recreates the event that sparked the American Revolution. You’ll get to throw tea into the Boston Harbor and learn about the significance of this act through live reenactments and multimedia exhibits.
- Admission: $31.95 for adults, $23.95 for children (5-12).
- Hours: Open daily from 10:00 AM to 5:00 PM.
Traveler Tip: Book tickets in advance as this museum is popular, especially during peak tourist season.
Evening: Dinner in the North End
Conclude your day in Boston’s famous North End, also known as Little Italy. This historic neighborhood is home to some of the best Italian restaurants in the city. Giacomo’s and La Famiglia Giorgio’s are local favorites, offering generous portions of pasta and seafood dishes. Expect to pay around $15 to $25 per entrée.
After dinner, take a walk to Mike’s Pastry or Modern Pastry for a delicious cannoli (about $5 each)—both are legendary dessert spots in the North End.
Review: “The North End is a charming mix of old-world Italy and Boston history. You can’t go wrong with any restaurant here, but Giacomo’s is a must if you love fresh seafood with a local flair. Be prepared to wait in line, but it’s totally worth it!” (4.7/5 stars on Google Reviews)
Day 2: Museums and Waterfront Exploration
Now that you’ve experienced Boston’s revolutionary past, it’s time to delve into its cultural and artistic side.
Morning: Museum of Fine Arts
Start your second day at the Museum of Fine Arts, one of the largest art museums in the U.S., boasting over 450,000 works of art. From ancient Egyptian artifacts to contemporary art, the museum covers a wide range of artistic periods and styles.
- Admission: $27 for adults, $10 for children (7-17).
- Hours: Open Wednesday-Monday from 10:00 AM to 5:00 PM.
Afternoon: Lunch and a Stroll Along the Charles River
After your museum visit, grab a bite at Flour Bakery + Cafe, famous for its mouth-watering pastries and sandwiches. Prices range from $8 to $15. Afterward, take a leisurely stroll along the Charles River Esplanade, a beautiful waterfront park perfect for walking or cycling.
Evening: Dinner in Seaport District
Head to the trendy Seaport District for dinner. This area has transformed into one of Boston’s most exciting neighborhoods, with sleek modern architecture, vibrant restaurants, and rooftop bars. Try Legal Harborside for fresh seafood with views of the harbor.
Day 3: Harvard and Cambridge
Take a day trip across the Charles River to explore the academic and cultural hub of Cambridge, home to two of the world’s most prestigious universities: Harvard and MIT.
Morning: Harvard University Tour
Start with a guided tour of Harvard University, which offers a fascinating look at the history and architecture of this Ivy League institution. Tours are usually led by Harvard students and cost around $15 per person.
Pro Tip: Visit the Harvard Museum of Natural History ($15 admission) to see the famous Glass Flowers exhibit and explore the extensive collection of minerals and fossils.
Afternoon: Lunch in Harvard Square and MIT
Enjoy lunch in Harvard Square at Tatte Bakery & Cafe, known for its Mediterranean-inspired dishes and cozy atmosphere. Prices range from $12 to $18. Afterward, head to nearby MIT and explore the innovative MIT Museum, which features exhibits on science, technology, and robotics. Admission is $10 for adults.
Day 4: Boston’s Green Spaces and Neighborhoods
After several busy days of sightseeing, slow down and enjoy Boston’s natural beauty and charming neighborhoods.
Morning: Boston Public Garden
Start your day at the Boston Public Garden, a beautifully landscaped park filled with flowers, ponds, and swan boats. If you’re traveling in the warmer months, take a swan boat ride for $4 per adult.
Afternoon: Beaver Hill and Back Bay
Explore Beacon Hill, one of Boston’s most picturesque neighborhoods with cobblestone streets, gas lamps, and historic brick homes. Stop by Acorn Street, one of the most photographed streets in the U.S. From there, walk to Back Bay to admire the brownstones and shop along Newbury Street.
Evening: Dinner in South End
End your day in the South End, a foodie haven known for its diverse range of restaurants. Toro is a great spot for Spanish tapas, while The Gallows offers New England-inspired pub fare. Expect to pay around $25 to $40 per person for dinner.
Day 5: Fenway Park and Final Exploration
No trip to Boston is complete without experiencing its sports culture.
Morning: Fenway Park Tour
Start your day with a tour of Fenway Park, home to the Boston Red Sox and one of the most iconic baseball stadiums in the U.S. Tours last about an hour and cost $25 for adults.
Afternoon: Lunch and Final Stops
For lunch, head to Sweet Cheeks Q, a Southern BBQ spot near Fenway, where you can indulge in hearty sandwiches and sides for around $15 to $20. Spend your afternoon exploring any sites you may have missed, such as the Isabella Stewart Gardner Museum ($20 for adults) or the New England Aquarium ($32.50 for adults).
Evening: Final Dinner at Union Oyster House
Finish your Boston adventure with dinner at Union Oyster House, the oldest continuously operating restaurant in the U.S. Enjoy classic New England seafood dishes like lobster and oysters. Prices range from $25 to $50 per entrée.
Other Things to See and Do in Boston
- Boston Public Library: A beautiful historic library with free admission and frequent exhibitions.
- Newbury Street: Great for shopping, dining, and people-watching.
- Duck Tours: A fun way to explore the city by land and water. Tickets cost $50 for adults and $35 for children.
FAQs
1. Is Boston expensive to visit? Boston can be pricey, especially for accommodation and dining. However, there are plenty of free and low-cost activities, like walking the Freedom Trail or exploring Boston Common.
2. What’s the best way to get around Boston? Boston is very walkable, and the MBTA (Boston’s subway) is an affordable and efficient way to travel longer distances. A single ride on the T costs $2.40.
3. When is the best time to visit Boston? The best time to visit Boston is in the spring (April to June) or fall (September to November), when the weather is mild and the city’s parks are especially beautiful.
You’ll learn about Boston’s history, culture, and modern attractions by following this itinerary. A Red Sox game at Fenway, exploring the cobblestone streets of Beacon Hill, or dining in the North End, Boston offers a unique blend of old and new.
