Day 1- North Shore- drive down HWY495 and turn at Jericho onto HWY106 north and visit Sagamore Hill, Vanderbilt Museum, Planting Fields Aboretum, stroll around Cold Spring Harbour, Mill Neck and Locust Valley.
Overnight stay at the Hampton Inn at Westbury. I like B&B's but the nice ones are very expensive, and since my group of 3 will just be sleeping, Hampton Inn seems to have good reviews ( noisy near highway?) and we can cancel with little notice in case the weather is bad and we cancel the trip.
Day 2- Drive to Long Beach, then back to mainland and then take the ferry to Fire Island. Then maybe visit Eastport and Hampton Bays if we have time.
Overnight at the Hyatt Hotel at Riverhead.
Day 3- Drive to South Fork all the way to Montauk, then to Shelter Island and ferry to North Fork. We are not wine drinkers, but we like to see the country side.
Day 3 night at Hyatt at Riverhead again,
Day 4- drive back to New York City.
I would appreciate your comments as to :
1)whether the trip makes sense as I cannot estimate driving time due to the traffic condition and along small side roads
2)will Fire Island and Montauk be too cold and windy to visit in the first week of October? Will restaurants be closed on Fire Island?
3) should we see the South Fiork only on Day 3 and stay on Monauk or Shelter Island on night of Day 3 instead of making it back to Riverhead, and then on Day 4, drive along the North Fork and then back to New York City?
Thank you for you r help :-)