Trip highlights
- 1Freedom Trail
- 2Fenway Park
- 3Harvard and Cambridge
- 4North End Italian food
- 5Boston Harbor
Daily spend
Where you're going
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Day-by-day plan
Arrival & Freedom Trail
Tuesday, September 21
Est. spend
$160
per person
🌅 Morning
Arrive at Logan International Airport (BOS)
Logan International Airport
The Silver Line bus connects the airport to downtown Boston in about 20 minutes, free in the airport direction.
The Silver Line bus to South Station is free from the airport — a great budget option into the city.
☀️ Afternoon
Freedom Trail: Boston Common to Faneuil Hall
Boston Common to Faneuil Hall
Walk the first half of the famous red-brick trail past the Massachusetts State House, Park Street Church, the Granary Burying Ground, and Faneuil Hall.
Pick up a free Freedom Trail map at the Boston Common Visitor Center to follow the painted red line.
🌙 Evening
Dinner at Quincy Market
Quincy Market, Boston
Faneuil Hall's historic Quincy Market food hall offers a huge variety of Boston classics, from clam chowder to lobster rolls.
🍽️ Meals
Airport or hotel breakfast
American · $12
Faneuil Hall area lunch
American · $18
Quincy Market dinner
New England · $30
North End & Freedom Trail Continued
Wednesday, September 22
Est. spend
$175
per person
🌅 Morning
Freedom Trail: North End to Bunker Hill
North End to Charlestown, Boston
Continue the trail through the North End past Paul Revere's house and the Old North Church, crossing into Charlestown to climb the Bunker Hill Monument.
Climb the 294 steps of the Bunker Hill Monument for a panoramic view over the harbor and city.
☀️ Afternoon
North End Italian food crawl
Hanover Street, North End
Boston's historic Italian-American neighborhood, packed with red-sauce restaurants, cannoli shops, and espresso bars along Hanover Street.
The cannoli rivalry between Mike's Pastry and Modern Pastry is a local institution — try both and pick a side.
🌙 Evening
USS Constitution and Harbor walk
Charlestown Navy Yard, Boston
Visit the world's oldest commissioned naval vessel still afloat, then stroll the Charlestown waterfront as the sun sets over the harbor.
🍽️ Meals
Hotel breakfast
American · $12
North End pasta lunch
Italian-American · $22
North End dinner
Italian-American · $40
Harvard, Cambridge & Fenway Park
Thursday, September 23
Est. spend
$220
per person
🌅 Morning
Harvard Yard and Cambridge
Harvard Square, Cambridge
Cross the Charles River to explore Harvard University's historic yard, the quirky shops of Harvard Square, and the broader Cambridge academic atmosphere.
Free student-led walking tours of Harvard Yard run regularly from the Smith Campus Center.
☀️ Afternoon
Lunch in Harvard Square
Harvard Square, Cambridge
Cambridge's lively square has an excellent mix of casual eateries and bookshops worth browsing before heading to the ballpark.
🌙 Evening
Boston Red Sox game at Fenway Park
Fenway Park, Boston
America's oldest operating ballpark, home to the Red Sox since 1912, complete with the iconic Green Monster left-field wall.
If no game is scheduled, book the Fenway Park stadium tour instead for behind-the-scenes access to the Green Monster.
🍽️ Meals
Hotel breakfast
American · $12
Harvard Square lunch
American · $18
Fenway Park ballpark food
American · $25
Boston Harbor & Departure
Friday, September 24
Est. spend
$150
per person
🌅 Morning
Boston Harbor Islands ferry
Boston Harbor Islands
A short ferry trip out to the Boston Harbor Islands, offering walking trails, beaches, and views of the city skyline from the water.
Georges Island, with its Civil War-era fort, is the easiest island to reach for a half-day visit.
☀️ Afternoon
Final souvenir shopping near Newbury Street
Newbury Street, Boston
Boston's premier shopping street, lined with boutiques and cafés in elegant brownstone buildings, perfect for a final stroll.
🌙 Evening
Transfer to Logan Airport
Logan International Airport
Allow at least 2.5 hours before an international flight given TSA wait times.
🍽️ Meals
Hotel breakfast
American · $12
Newbury Street lunch
American · $20
Airport food
American · $18
Before you go
📅 Best time to visit
May-June and September-October offer mild temperatures (15-24°C) and fewer crowds than peak summer.
🛂 Visas
International visitors from visa-waiver countries (most of Europe, UK, Australia, and others) need ESTA pre-authorization before flying to the US; other nationalities require a B1/B2 tourist visa arranged in advance.
💱 Currency
US Dollar (USD). Cards are accepted almost everywhere; tipping 18-20% at restaurants is standard and expected.
🆘 Emergency numbers
police: 911
ambulance: 911
💬 Things you won't find in a guidebook
- The Freedom Trail's full 4 km route is best split over two days to properly explore each stop rather than rushing through.
- Buy Red Sox tickets well in advance for popular matchups — Fenway Park is one of the smallest and most in-demand parks in MLB.
- Harvard's free student-led tours offer better insider context than paid commercial tours.
- The MBTA Charlie Card is cheaper per-ride than paying cash fares — pick one up at any subway station.
- Mike's Pastry vs. Modern Pastry cannoli is a genuine, good-natured local rivalry in the North End — try both.
One thing worth not skipping
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