3. 16th at Cypress Point -- Par 3, 235 yards -- Pebble Beach, Calif.
One of the most picturesque holes in golf is also one of the most punishing, requiring a hefty carry over the Pacific to a green fronted and flanked by bluffs. The safest option is a layup to a ribbon of fairway on the left. The penalty is the grief you’ll get from buddies when you tell them that you played the famous hole the wimpy way.