From the vicinity of Rye or Greenwich it’s only about a 2 hour sail, so you can leave at noon, and be anchored in Oyster Bay for cocktails. The sand hole is on your port side as you enter Oyster Bay, but we only use it on weekends if we want to get stuck on a sand bar while dodging other boats. On a weekday, it’s pleasant and convenient when you don’t have time to go all the way into the harbor. If you continued straight in, you'd enter Cold Spring harbor. To reach Oyster Bay Harbor, pass through the channel to starboard and marvel at the lovely Seawanhaka Corinthian Yacht Club and its impressive fleet to port.

Continuing into Oyster Bay Harbor, another option is to anchor in Morris Cove, which is on your port, south of Seawanhaka. Depth is about 7-8 feet and it is quieter than the busy West Harbor. Look for the ospreys that nest in the trees and on the tops of navigation aids. Our favorite anchorage is in the cove that extends to port as you approach the Oyster Bay mooring field. There is plenty of room to swing, the holding is good (unless you happen to catch an oyster bed), it's protected and far from the main channel, and you can make your way by dinghy through the mooring field to town, inspecting the fleet as you pass. It's a fair distance to walk into town from the waterfront but worth it. Head in the direction of the fuel tanks on shore and you'll get to a couple of marinas that will let you tie up for a small fee. Be advised that Oyster Bay Marine has increased its prices for moorings, so you may want to check on pricing before committing to a mooring. If you're a member of a yacht club with reciprocal priviledges, you may try Sagamore Yacht Club. Great location for parking your dinghy and a wonderful Sunday brunch on their terrace overlooking the harbor to boot.