Start near the harbor and let the town reveal itself in layers. Main Street and the surrounding side streets carry much of the walkable downtown energy, while the historic steps make the change in elevation impossible to ignore.
For a traveler, that means the best plan is usually a compact walking cluster rather than a long checklist. Pair the waterfront and downtown core first, then decide whether the climb toward the hillside viewpoints fits your heat, footwear, timing, and mobility needs.
VI Guide should help you understand that geography before it gives you more stops. Open the Living Map, keep the harbor as your orientation point, and use Concierge or Mobility when the hill becomes part of the plan rather than an afterthought.
Make the context actionable