Boston
Boston is America's most walkable historic city: a red line in the pavement joins sixteen Revolutionary sites, the centre follows old cart tracks rather than a grid, and Harvard is one stop across the river. Two or three nights, the airport bus free inbound, and leaf season in October.
Boston in a nutshell
Boston: what to expect
What follows sits on 450,000+ stops planned across the United States on Stippl.
Boston is two or three nights on foot, and the Freedom Trail is the spine of the first one. Four kilometres of red line in the pavement join sixteen Revolutionary sites from the Common to the Charlestown Navy Yard, the North End's Italian streets sit on it, Harvard Yard is one Red Line stop across the Charles, the Gardner Museum hangs its empty frames, Fenway Park is the oldest ballpark in the majors and the harbour islands are a national park a short ferry from the centre. Most travellers give Boston 2 nights on Stippl.
Boston is the Northeast's door as often as New York is, and it is planned for the autumn. The city opens 39.9% of the trips it appears on, of everyone who plans it on Stippl, and October draws a larger share of Boston plans than of American plans generally, because New England's colour reaches the city last and the Head of the Charles falls in the same fortnight.
Sleep in Back Bay, walk everything inside the old centre, take the free Silver Line in from Logan, and rent the car only on the day you head for the Cape or Maine. The street plan is why it walks and why nobody drives it. Skip Boston between January and March unless the museums are the point, since it is cold, dark and cheap, and skip the marathon weekend in April without a booking, because the city closes and the hotels sell out months ahead.
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First-timers
One painted line joins the sights, the whole centre is walkable, and the airport bus into it is free.
History buffs
The Revolution started here and the buildings it started in are still standing, from Faneuil Hall to the Old North Church.
Foodies
An oyster and lobster city with an Italian quarter attached, and cannoli filled to order in the North End.
Families
Short distances, a free-to-walk trail, the harbour islands by ferry and a duck-boat ride that children remember.
Autumn planners
October draws a larger share of Boston plans on Stippl than of American plans generally, for the colour and the rowing.
Northeast starters
Boston opens 39.9% of the trips it appears on, of everyone who plans it on Stippl, with the train to New York or the drive to Maine next.
Maybe not for you: anyone arriving between January and March, when it is cold and dark; and anyone who wants a bargain, because Boston is one of the most expensive American cities to sleep in.
The best time to visit Boston
Leaf season
late September to October
The reason to plan around a date: New England's colour peaks north of the city first and reaches Boston last, with the Head of the Charles regatta in the same fortnight.
Summer
June to August
Harbour cruises, the Esplanade, the islands and the ballgames, and the most crowded months, with the Fourth of July on the Charles the biggest night.
Spring
April and May
The marathon, the students leaving and weather that has not settled; the cheapest good window once the marathon weekend is over.
Winter
December to March
Cold, dark and genuinely cheap, with the museums and the North End as the argument and snow that shuts the T for a day at a time.
- Most travellers give Boston 2 nights on Stippl, and 28.8% of stops are a single night. Two covers the trail and Cambridge; the third night is the Gardner, Fenway and the islands.
- The Boston Marathon on Patriots' Day, the third Monday in April, closes the city. The hotels sell out months ahead and Back Bay is fenced from the morning, so the week is booked early or avoided.
- Boston's Fourth of July brings one of the largest crowds of the American year. The Boston Pops and the fireworks over the Charles, with the Esplanade full from the afternoon and the T packed until midnight.
- The Head of the Charles in mid-October is the largest rowing event in the world. It collides with peak leaf season and the rooms across the river in Cambridge go weeks ahead.
- Most travellers plan Boston about 90 days days ahead on Stippl, and 16.6% inside a fortnight. Nothing sells out months ahead except the marathon and a Red Sox game at Fenway.
- The T's fare pilot means free transfers for two hours. Subway, bus and ferry on one tap, paying only the highest single fare, provided you use the same card throughout.
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Things to do in Boston
Walking the Freedom Trail
Four kilometres, sixteen sites, a red line in the pavement and two to three hours end to end from the Common to the Charlestown Navy Yard; free, and the spine of a first visit.
Harvard Yard and Harvard Square
One Red Line stop into Cambridge, with the campus open to walk, the bookshops around the square and MIT's campus a mile down the river.
The Gardner Museum
A Venetian palazzo built around a courtyard in the Fenway, with the empty frames from the 1990 theft still hanging where the paintings were, and free on Thursday evenings.
Fenway Park
The oldest ballpark in the major leagues, tourable on non-game days and worth a game on the others, with the Green Monster and the hand-turned scoreboard.
The Boston Harbour Islands
A national park a short ferry from the centre, with a fort on Georges Island and beaches on Spectacle, for the afternoon the city gets too tight.
The Museum of Fine Arts
One of the largest collections in America, in the Fenway next to the Gardner, with the Japanese and Egyptian rooms the ones people come back for.
The neighbourhoods of Boston
Back Bay
Brownstones and a shopping street
Central, walkable to the Common, the trail and the T, with Newbury Street's shops, the Public Garden and the best-connected hotels in the city. For first visits.
Central to everything on foot, but the highest room rates in an already expensive city.
Beacon Hill
Gaslit cobbles
Acorn Street and the most photographed lanes in the city, five minutes from the Common, with the State House on top and Charles Street's antique shops below. For couples.
The prettiest streets and the Common at the door, with few hotels and steep, uneven brick.
North End
Little Italy on the oldest streets
Two hundred metres of Italian restaurants and bakeries on the Freedom Trail, the Old North Church and Paul Revere's house, and the cannoli queue. For food and history.
The best eating in the city and the trail underfoot, in the loudest, narrowest lanes.
Cambridge
University, bookshops, river
Harvard Yard, MIT's campus and a bookshop density unmatched in America, one Red Line stop across the Charles, a city of its own with its own square. For history and a second base.
Harvard and the river, and a train under the Charles to every Boston sight.
Seaport
New, glassy, on the water
The newest restaurants, the Institute of Contemporary Art and the harbour walk on reclaimed dockland, with the free airport bus ending nearby. For food and a modern hotel.
New hotels and the waterfront, with no history and a walk to the old city.
Jamaica Plain
Residential, green, cheaper
The Arboretum, a pond you can walk around and rents that make sense, on the Orange Line south of the centre. For longer stays and remote workers.
Green and cheaper, and twenty minutes on the T to anything a visitor lists.
See every Boston neighbourhood on one map
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Where to stay in Boston
Sleep in Back Bay, the right default, central to the Common, the trail and the T, or across the river in Cambridge for a second visit and a lower rate. Most travellers give Boston 2 nights on Stippl, the city is one of the most expensive in America to sleep in, and the marathon, the regatta and the graduation weeks move every rate in town.
Back Bay
€190–320
Grand and chain hotels on Boylston and Newbury, €200 to €450 a double.
Beacon Hill
€200–340
A handful of small inns in the brick lanes, €180 to €350 a double.
North End
€170–280
Guesthouses and apartments above the restaurants, €150 to €300 a double.
Cambridge
€160–270
University-area hotels and inns around Harvard Square, €160 to €320 a double.
Seaport
€200–330
New glass hotels on the harbour, €180 to €400 a double.
Jamaica Plain
€120–200
Apartments and guesthouses on the Orange Line, €110 to €200 a double.
What to eat in Boston
Cream, potato and clams, thick enough to stand a spoon in
Lobster meat in a split-top bun, warm with butter or cold with mayo
Cold-water Wellfleet and Island Creek, shucked to order
Filled to order in the North End, and the queue is the point
A sponge cake with custard and chocolate, and the state dessert
A North Shore speciality, three ways, on an onion roll
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Boston customs and what not to do
Tip 18 to 20 percent
In sit-down places and at the bar a dollar or two a drink, the same as the rest of the country, with the tax on top of the menu price.
Jaywalking is the local sport
Drivers expect it, which does not make it safe; the street plan produces blind corners and the drivers who take them.
Do not mention the Yankees
The rivalry is genuine and the joke is old, and a Red Sox cap is the local uniform from April to October.
Leave the accent alone
It is a class and neighbourhood marker rather than a costume, and imitating it lands badly.
The Revolution is local
The sites on the trail are treated as the city's own history rather than a theme park, and the reenactors are volunteers who know the dates.
Cannoli are filled to order
The North End's bakeries fill them when you ask, the queue is the point, and the two rival shops have their partisans.
Do
- Take the free Silver Line from every Logan terminal to South Station
- Walk the Freedom Trail end to end on the first morning
- Cross the river to Cambridge for at least an afternoon
- Book a Red Sox game if the season is on
- Rent the car only on the day you leave for the Cape or Maine
Don't
- Drive inside the city; the street plan follows cart tracks and parking is dear
- Arrive on marathon weekend without a booking
- Mention the Yankees in a bar
- Expect the leaves in September; the colour reaches Boston last, in October
- Skip the Gardner because the Museum of Fine Arts is next door
What a Boston trip costs
Budget
€80–120
A hostel bed, the T on a CharlieCard, the free trail, the free Silver Line, chowder from a counter.
Mid-range
€138–198
A mid-range hotel in Back Bay, the Gardner and the MFA, a lobster roll, a harbour ferry.
High-end
€260+
A Back Bay grand hotel, Fenway seats, oysters in the Seaport, a duck-boat tour.
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Fun facts about Boston
Harvard was founded in 1636, which makes it older than calculus. Its yard is open to walk through, one Red Line stop from the centre of Boston.
Thirteen works are still missing from the Gardner Museum after the 1990 theft. The museum hangs the empty frames where the paintings were, and the reward still stands.
Anyone named Isabella gets free lifetime admission to the Gardner. By reservation, in the founder's honour, and the museum keeps a list.
The street plan of Boston follows old cart tracks. Which is why the centre has no grid, why the walking is short and why nobody who lives there drives it.
Fenway Park in Boston opened in 1912 and never closed. It is the oldest ballpark still in use in the major leagues, with a hand-turned scoreboard on the Green Monster.
The Freedom Trail's red line was painted in 1958. A journalist proposed it to join the Revolutionary sites, and the city has repainted the four kilometres ever since.
Local tips for Boston
The Silver Line is free inbound
SL1 picks up at every Logan terminal kerb and runs to South Station at no charge; you pay only on the way back out.
Tap a bank card on the T
A contactless card works alongside the CharlieCard, and the two-hour transfer pilot means one fare covers subway, bus and ferry if the same card is used.
Among the safer big US cities
The visitor core is safe day and night, and the ordinary rules are the only ones.
Traffic is the actual risk
The street plan produces blind corners and drivers who take them, and pedestrians are hit at a rate that surprises visitors, so the jaywalking habit is one to leave to the locals.
Cambridge is its own city
Harvard and MIT are one stop across the Charles on the Red Line, and Harvard Square is a destination in its own right with its own hotels.
Two nights, and October
Most travellers give Boston 2 nights on Stippl and 15.8% of stops run to four or more, the smallest tail of the two great American walking cities.
Boston questions, answered
Two or three nights: most travellers give Boston 2 nights on Stippl, and only 15.8% of stops run to four or more, the smallest long tail of the two great American walking cities. Two covers the trail and Cambridge, and the third is the Gardner, Fenway and the harbour islands.
Yes, the walk is free and marked by a red line in the pavement from the Common to the Charlestown Navy Yard, four kilometres and sixteen sites. Individual sites along it charge, the Old State House and Paul Revere's house among them, and the guided walks are ticketed.
At the start, or one end of the corridor: Boston opens 39.9% of the trips it appears on, of everyone who plans it on Stippl, with New York four hours south by train and Maine two hours north by car. Put Boston first in Stippl with three nights, then ask people who have done New England, in subreddits like r/boston, whether the Cape earns its day.
The Silver Line SL1 is free from every Logan terminal to South Station, and the Blue Line from the airport station reaches downtown for a single fare. Coming back out you pay, and a taxi through the harbour tunnel in traffic is the slowest of the three. 8.5% of Boston stops planned on Stippl are same-day, and the free bus suits those best.
Late September through October: New England's colour peaks north of the city first and reaches Boston last, and October draws a larger share of Boston plans on Stippl than of American plans generally. The Head of the Charles regatta lands in the same fortnight, so the rooms go early.
Not for the city: the centre follows old cart tracks, the T reaches Cambridge, the Fenway and the Seaport, and parking is among the dearest in the country. Rent one on the day you head for Cape Cod, Salem or Maine, and pick it up at the edge of town rather than downtown.
Every guide is written by the Stippl editors and checked against the trips our travellers actually plan. Spotted something out of date? Let us know.
Plan Boston in Stippl
Day-by-day planning, stays and budget in one app, with every place from this guide already on the map.
Download the app