If you travel from Montauk to the Chesapeake, the trip takes approximately 54 hours (2-2 1/2 days). If you stop at Cape May Harbor first, you can anchor near the coast guard station. It's a thirty hour trip. From there, you can either go offshore to the Chesapeake, another 24 hours, or travel up the Delaware Bay to the C & D canal, an 8-10 hour trip with tides helping. You can spend the night at a marina on the C & D and then travel into the northern Chesapeake the next day. A longer journey would be heading south to Norfolk, VA. I prefer to do as much of my journey offshore as possible so I can avoid all the obstructions you find inland, i.e, tide changes, buoys, etc. In October, the winds assist you in your journey as they come off the land. They make the seas flatter and give you lots of speed. With a rumbline to the Chesapeake, that would be a beam reach all the way down. Even with that Cape May stop over, the next day would have the wind aft of the beam.
Little Creek is a great protected harbor, just a few miles in to the south when entering the mouth of the Chesapeake. There are numerous Marinas, such as "Little Creek Marina", "Cobbs", & "Cutty Sarks" with slips at great daily, weekly, or monthly rates. Haul out for your bottom paint job at great pricesor you can do it yourself. The Airport is minutes away. Norfolk is not that far north, where the ICW starts. Everyone is so nice & helpful.well, it's Southern hospitality! Tidewater Marina in Norfolk has all the amenities.dock up or anchor just outside the marina, there's plenty of room! It is a hard decision to make when you think of exploring the Chesapeake or exploring the ICW on the way to N. Carolinaboth have wonderful little towns and coves. You will make boating buddies in these areas as the parade of boats from the North head South during this time. They have business like cards with their boats' Name, E-mail address & Phone numbers, so staying in touch with new found friends is easy.
Depending on the weather, my trip south usually begins in October. The hurricane season is not over yet, so watching the Eastern Caribbean for new formations is prudent. It can take a few days to a few weeks for the hurricanes to arrive in area, so if one is coming, there's time to duck in a harbor. Check out websites that provide a global look at the weather by satellite and wind and wave forecasts. It's wise to have several sources of information to help you plan your trip. Also listen to your VHF radio to hear about formations or disturbances in the Atlantic and the Caribbean.
You can easily visit the Chesapeake area during a long weekend or extend your visit and your journey further south in North Carolina over the winter. If you sail the Neuse River, the widest in the USA, by Oriental, N. Carolina, take the ICW right into Beaufort. There are so many picturesque stops along the way and historical towns to visit. It's all so beautiful, you may not want to go home for the summer.
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