Thanks all (via the board and IM) for the valuable insight and recommendations on all things Hamptons, North Fork, Montauk, Shelter Island, etc.
After much deliberation (read: my wife is the primary decision-maker), we're staying.... at the American Hotel in Sag Harbor. I figure it will be a good central "home base" for visiting the other villages, Shelter Island and other areas, too. Plus, it only cost 2/3rds of a mortgage payment.
Looking at Shelter Island, how would you spend part of a day there (other than golf)? Best place for lunch? Other sights?
American Hotel and Sag harbor are good choices-town will be buzzing
Hotel is very old world, the restaurant is excellent,and pricey.
Shelter Island: Mashomack Wildlife preserve covers 1/3 of island. Several loops can range from 1 mile to 20 miles. Home of the land for my fantasy golf course along the bluffs, through the fields and amongst mature trees,
Restaurants-many more-see trip advisor
upscale? Vine street cafe, Ram's head Inn,18 Vine
Local spots? i.e. affordable The Dory-nice views over lakelike inlet, Fresh (Goat Hill), The Islander, multiple others
Hamptony? Sunset Beach-$12 bar drinks
nice scenery
Dirty Dancing era? The Pridwin-great wednesday buffet/dancing in summer
Old world? Chequit
By Boat? Island Cafe also by car, nice secluded spot on water
DRIVE THOUGH AND PAST GOAT HILL dirt road parallels first fairway to clubhouse and 9th hole worth seeing-stop in for drink
Take a wine Tour on the north Fork via shelter Island(5 min ferry, 10 min drive, 10 minute ferry-each way but beautiful journey) -eat dinner on the island on way back to Sag Harbor-avoid shelter Island on departure day (Monday as traffic can be bead onto fery)