Where to stay

Many of Boston’s luxury hotels are in the downtown area and Beacon Hill. A case in point is Raffles Boston, the city’s most exclusive hotel, which offers personal butler service and panoramic views of the prestigious Back Bay area. Once the Charles Street Jail, The Liberty in Beacon Hill has now transformed into a swanky, design-forward boutique hotel that’s popular with business travellers and creative types. Slightly edgier is The Verb near Fenway Park, a retro, music-themed property that nods to the city’s rock ’n’ roll history. Just a short drive from Logan International Airport, the luxurious Encore Boston Harbor by Wynn Resorts comprises a casino, lounges and restaurants specialising in everything from seafood to steak.

What to say

Bostonians celebrate their local heroes with a passion. Small talk about the city’s sports teams – Bruins (hockey), Celtics (basketball) or Red Sox (baseball) – is a foolproof ice breaker. Boston is located near many mountains and beaches, so asking colleagues and friends about their favourite weekend getaway spot is another excellent conversation starter.

What to know

Boston tends to go to bed early, a point of contention for many nocturnal denizens. (The city even recently appointed a new director of nightlife economy to rectify the situation.) However, you’ll find a higher concentration of nightlife-oriented venues at the Seaport district. Tipping 20 per cent or more for drinks and meals is customary.