Do Vista do Rei to the Boca do Inferno spur — flat-ish, an hour return, the postcard view. The full rim is a long exposed day; save it for a kid-free trip.
Azores
Sete Cidades viewpoint — is the crater rim walkable with kids?
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Whale watching — Ponta Delgada or a smaller port?
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The boats out of Ponta Delgada are bigger and steadier — that's your answer right there. Morning trips, calmer sea. Sperm whales are resident; April–June adds the migrating giants.
Furnas cozido — book a pot or turn up?
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Your restaurant books the pot — Tony's or Caldeiras & Vulcões, a day ahead. Watch the pots come out of the ground at 12:30, then eat what you watched.