You can visit all three without carrying the stroller if you stick to the main paths.

Yes, for the most part. The main ferry docks, boardwalks, and paved trails on all three islands are wide enough for a standard stroller. You won’t need to lift it for the bulk of the trip.

The catch is the hidden gems. The best views, secret coves, and quieter trails often require stairs or narrow dirt paths. If you want to see absolutely everything, you’ll be carrying the stroller