Boston · City Break
A walkable history lesson by the harbour
Three ways to take on Boston, the Freedom Trail and the North End, the harbour and Fenway, and the neighbourhoods worth lingering in. Mix, match and we'll tailor the rest.
Itinerary One
The first-timer's day, Common to Charlestown
2.5 miles of red brick, four centuries of history, and the best lobster roll lunch of the trip.
Morning
- Coffee on Beacon Hill, then walk Acorn Street, the most photographed lane in America.
- Start the Freedom Trail at Boston Common and the State House gold dome.
- Pause at Granary Burying Ground, Paul Revere, Sam Adams, John Hancock.
- Lunch at Quincy Market inside Faneuil Hall, chowder, lobster rolls, cannoli.
Afternoon
- Cross into the North End for Paul Revere's House and the Old North Church.
- Espresso and a cannoli at Mike's Pastry or Modern Pastry (pick your side).
- Walk over the Zakim Bridge or hop the ferry across the harbour to Charlestown.
- USS Constitution and the Bunker Hill Monument finish the Trail.
Evening
- Sunset cocktails at Lookout Rooftop, Envoy Hotel, Seaport skyline views.
- Dinner at Neptune Oyster (go early, no reservations) or Row 34 in the Seaport.
- Catch the Boston Symphony, a show at the Wang Theatre, or jazz at Wally's.
- Nightcap at Yvonne's, a glamorous speakeasy hidden off Washington Street.
Itinerary Two
Harbour, islands and a night at Fenway
Two days on the water and at America's oldest ballpark, oysters, ferries and the Green Monster.
Day 1, Harbour & Islands
- Breakfast at Tatte in the Seaport before the queues build.
- Boston Harbor cruise, sail past the lighthouses to Spectacle Island.
- Lunch at Row 34: a dozen oysters and a cold local lager.
- ICA Watershed in East Boston, then a swan boat row in the Public Garden.
- Dinner at Legal Sea Foods on Long Wharf, harbourside.
Day 2, Fenway & the Sox
- Fenway Park tour, the Green Monster, the Pesky Pole, the dugouts.
- Lunch at Time Out Market, 15 of Boston's best chefs under one roof.
- Museum of Fine Arts or the Isabella Stewart Gardner, both within a block.
- Pre-game beer on Lansdowne Street, then nine innings at Fenway under the lights.
- Late-night slice at Regina Pizzeria back in the North End.
Where to Stay
- XV Beacon · The Liberty (a former jail!) · Encore Boston Harbor · Omni Parker House · The Newbury overlooking the Public Garden.
Itinerary Three
Boston by neighbourhood
Six pockets of the city worth a half-day each, pick the ones that fit your trip.
Back Bay & Newbury Street
Brownstones, boutiques and brunch, eight blocks of independent shops, the Boston Public Library and Copley Square.
The North End
Boston's Little Italy, family-run trattorias, espresso bars and Saturday-night queues that are entirely worth it.
Beacon Hill
Gas lamps, cobblestones and Charles Street antiques. Sunday brunch at Tatte and a walk down Acorn Street.
Seaport
Boston's newest neighbourhood, Time Out Market, the ICA, harbourfront breweries and rooftop bars.
Cambridge & Harvard Square
Cross the Charles to Harvard Yard, MIT's Stata Center and the bookshops, jazz clubs and tucked-away pubs in between.
Jamaica Plain
Local Boston, Sam Adams brewery tours, the Arnold Arboretum and brunch on Centre Street.
Top Things to Do
The best of Boston
From world-class museums and historic trails to harbour islands and championship sports, here's what not to miss.
Freedom Trail & Historic Walks
Follow the red-brick trail from Boston Common through 16 historic sites, the State House, Granary Burying Ground, Old North Church and Bunker Hill.
Museum of Fine Arts
One of the most comprehensive art collections in the Americas, from ancient Egyptian artefacts to Impressionist masterpieces and contemporary works.
Isabella Stewart Gardner Museum
A Venetian-style palace turned museum, famous for its stunning courtyard garden and the unsolved 1990 art heist.
Fenway Park
America's oldest ballpark, tour the Green Monster, sit in the dugouts, and soak up over a century of baseball history.
Boston Harbour Islands
Hop a ferry to Spectacle Island or Fort Warren, hiking trails, beaches, and lighthouse views just minutes from downtown.
The North End
Boston's Little Italy, cobblestone streets, historic churches, and legendary cannoli at Mike's Pastry and Modern Pastry.
Boston Sports
Catch the Celtics at TD Garden, the Red Sox at Fenway, the Bruins in winter, or the Patriots just down the road in Foxborough.
Harbour Cruises & Whale Watching
Sail past historic lighthouses, spot humpback whales on a summer excursion, or enjoy a sunset dinner cruise on the water.
Performing Arts & Music
The Boston Symphony Orchestra, Broadway at the Wang Theatre, jazz at Wally's, and live music venues across the city.
Ready to go to Boston?
Tell us which itinerary you're drawn to (or all three), we'll build the hotels, transfers and reservations around you.