Andy --
Southward Ho is a Tillinghast design and many of his design favorites are at Southward Ho with a number of the holes featuring pear shaped greens flanked by deep bunkers.
The course is just under 6,500 yards from the tips (last time I played) and really starts slow. If you play the 1st hole downwind that is the usual prevailing wind out of the southwest off the Atlantic.
The best hole on the front is the mid-range par-4 8th hole which dog-legs right around trees and has a pond fronting the two-tiered green. Play smart on this hole or make space on the scorecard for a high number. Good hole.
The back nine really comes to life with the final five hole -- four of which play into the prevailing wind. If you are not doing well before you hit the 14th tee the likelihood for a low round is in clear doubt with the finishing holes.
The par-3 14th is one of the most underrated holes on the Island at 223 yards. You absolutely must "pure" a long iron or wood and get the ball to stay between the two large bunkers that pinch in tight to the putting surface. #15 and #16 are also good with the 15th dog-legging left and the 16th plays straight ahead and is a solid two-shotter.
The par-3 17th is the only one of the five that plays downwind and is also good but a notch below the quality at #14. The final hole is about 415 yards in change and your approach had best be accurate because the green is extremely big lengthwise.
Southward Ho will keep you on your toes particulary when the wind "freshens" a tad. I played the course a number of times during the annual Havemeyer event and the key is not getting careless or thinking the "short" yardage makes for plum pickings. Enjoy your day.
Hope this helps ...