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.
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.