As long as you can actually navigate 2 day charters are very common on the Chesapeake. Docks are everywhere. Many also have shore accommodations.

Virgin Traders is known to do last minute short charters with a Captain. If the boat is free and they have a skipper Virgin Traders will book the deal.

In 2017 the BVI is a long way from home for the lightly traveled.

Again 15 day charters are the norm for us where we pick guests up for a night or a few days from hotels and houses from St. Thomas to Bitter End. Two days is plenty for many!