A free planner from our editors. Choose your days, your base and your interests.
Build your Boston itinerary
Tell us how long you have, what you care about and how fast you like to move. You get a day-by-day plan built around your hotel, not a generic list of sights.
Your plan, day by day
How the plan is built
Each half-day slot is filled from the interests you ticked, weighted so that the things you selected appear early in the trip and nothing repeats. The neighbourhood you chose decides what lands on day one: the plan opens with what is on your doorstep, then works outwards, so you are not crossing the city before breakfast.
Pace changes the number of slots per day, not their quality — on the slow setting you get two anchors and room to wander, on the full setting three. If you tick very few interests the plan will repeat themes rather than invent filler; tick more and it spreads wider.
This is a starting structure to argue with, not a schedule. Opening days and times change, so check anything time-sensitive before you commit to it.
Questions people ask
How many days do you need in Boston?
Three full days covers the historic core, one museum, one harbour outing and enough eating to feel like you have been somewhere. Two works if you stay central. Beyond four, the city naturally opens onto day trips.
Can you walk everywhere in Boston?
Mostly, and that is the pleasure of it. The historic core, Beacon Hill, Back Bay and the North End link up on foot; the Seaport and Fenway are where you start reaching for the T.
What is worth doing on a first trip?
The Freedom Trail gives the city its shape, the North End gives it its appetite, and the harbour gives it its horizon. Most first itineraries that work have one of each.
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Club members get the editors’ notes: where to eat between the sights, and which hotel bar to end the day in.