Short answer: Sidmouth's esplanade is flat and level for its whole length, and it is where the town works best with wheels. The beach itself is large smooth pebbles, which are awkward underfoot and impossible with a buggy. Jacob's Ladder involves a steep slope or steps, and Weston is a long descent.
Sidmouth is unusually flat for a Devon seaside town — the esplanade runs level along the front with the white Regency hotels on one side and the sea on the other, and the town behind it is largely on the flat too. It is a genuinely easy place to push a chair or a buggy along.
The beach is the problem. Sidmouth's shingle is made up of large smooth pebbles known locally as Budleigh Buns, weathered out of the Triassic cliffs. They are beautiful and they are awkward to walk on, let alone push anything across. There is a paved promenade behind for most of the length, and that is where to stay.
Much of the beach is submerged at high water. On a falling tide, golden sand appears below the pebbles — firmer ground and a much better prospect if you do want to get down onto it. Check the tide table before you plan the day; it matters more here than the parking.
The clifftop gardens above Jacob's Ladder are well kept, free to walk around and have the Clock Tower café inside them with sea views from the tables and garden seating outside. Dogs are allowed downstairs. It is the best place in Sidmouth to sit with a view without tackling a beach.
The Pea Green Boat on the esplanade has both inside and outside seating facing the sea, with service coming out to you if you sit outdoors. Milsons Point on the High Street is on level ground and does the best breakfast in town. The Anchor Inn, in the middle of town, has a beer garden and is the pub of choice.
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