You can’t come to Sydney and not visit the Harbour Bridge and Opera House, and this route happens to show off both. Start at the bridge’s northern landing, run across it, and follow the path around Circular Quay past the Opera House and the Botanic Garden to Mrs Macquaries Chair. Then turn back for the bridge. It’s about 12 km, and views are to-die-for. Make sure your phone is fully charged. No matter how many times I’ve run this, I always stop to take photos and videos. There are two fabulous outdoor pools—Olympic Pool, under the north side of the bridge, and Andrew Boy Charlton at Mrs. Macquaries Chair—great for photos, and post-run backstrokes.