Boston's got amazing walkable neighborhoods with tons of history and great food. The Freedom Trail is classic but not overwhelming, and definitely hit up some North End caferies for authentic Italian pastries. Parking can be tricky downtown so book a garage spot ahead of time. Fall is absolutely gorgeous for this route with all the foliage, and there are some nice stops in Connecticut and Rhode Island if you want to break up the journey. For comprehensive planning details and route suggestions for your Boston travel
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