Boston
THE AMERICAS · CITY · HISTORY
The oldest big city in America and the most walkable, packed onto a peninsula with a 4km red line painted on the pavement connecting sixteen Revolutionary sites. It's a college town at heart — 250,000 students across the river and in the city — which keeps the bars cheap and the food scene sharper than its reputation. Autumn here is worth planning a trip around.
The plan
The Freedom Trail
Follow the red line 4km from Boston Common through the North End to the USS Constitution. Do it early.
The North End
Italian Boston since the 1860s — Hanover Street for dinner, then the cannoli argument between Mike's and Modern.
Isabella Stewart Gardner Museum
A Venetian palace built around a courtyard, with the empty frames from the 1990 heist still hanging.
Fenway Park
The oldest ballpark in the majors, 1912, with the Green Monster. Take the tour if there's no game.
Charles River Esplanade and Beacon Hill
Gaslit brick streets and Acorn Street, then the river path with the sailboats.
Book before you fly
Freedom Trail walking tours
Costumed guides from Boston Common; book the morning departure.
Fenway Park tours & Red Sox
Tours daily; game tickets go on sale in December for the whole season.
Isabella Stewart Gardner
Timed entry, and free forever if your first name is Isabella.
Getting there
Fly Logan (BOS)
Fifteen minutes from downtown — the Silver Line bus is free inbound and drops at South Station.
Take Amtrak
The Acela from New York in three and a half hours arrives at South Station in the middle of everything.
Getting around
The T is the oldest subway in America and covers everywhere you'll go. Do not drive here — the street grid predates cars.
When to go
Best time to go
September to October for New England autumn — clear, 18°C, and the leaves an hour in any direction.
Cheapest months
January to March, when it's genuinely cold and hotels are at their cheapest.
Priciest & busiest
Late May graduation weekends and the Boston Marathon in April, when every room in the city is gone.
If you've got one day
Morning
The Freedom Trail
Late morning
The North End
Lunch
Santarpio's Pizza
Afternoon
Isabella Stewart Gardner Museum
Evening
Dinner at Neptune Oyster, then Fenway Park
If you've got a week
Day 1
Arrive, settle in around Four Seasons One Dalton, and take it slowly — Santarpio's Pizza for dinner.
Day 2
The Freedom Trail.
Day 3
The North End. Dinner at Neptune Oyster.
Day 4
Day trip — Cape Cod.
Day 5
Isabella Stewart Gardner Museum. Giulia at some point.
Day 6
Fenway Park.
Day 7
Charles River Esplanade and Beacon Hill. Finish with Union Oyster House.
Staying longer?
Nearby & day trips
Cape Cod
Ninety minutes to Provincetown's dunes and the National Seashore.
Salem
Thirty minutes by commuter rail; a maritime town that becomes a circus every October.
Three and a half hours by Acela.
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