It is strongly recommended that Caribbean cruisers seeking to enter the Chesapeake Bay make their initial port of call in the Hampton Roads area. There are multiple marinas and protected anchorages available so
download the list. These recommendations are limited to those that enable readily accessible food and fuel resupply.
It is also strongly recommended that you make contact with a marina either by phone or email prior to arrival to ensure that space is still available and the entry rules have not changed. Once you’ve had a chance to catch your breath and resupply in Hampton Roads, there will be tons of information on options for proceeding north, either up the Bay or off-shore.