Discover Boats

Every year, I head down south for the winter in my sailboat. It’s nice to go down to the Florida Keys, if you can find the time. The Chesapeake area is a great place to spend the winter. Unlike the northeast area, the waters don’t freeze up in December, making it ideal for sailing. There are so many coves to explore that you can visit a new one on each journey. Conveniently located nearby is the Norfolk International Airport. North Carolina is another nice area to explore as its waters stay quite warm in the winter thanks to the gulfstream. Dowry Creek in Belhaven to Oriental and Beaufort (Bow-Fort) where they found Black Beards’ ship by the inlet are great marinas. The slip rates vary from $7 – $8 per foot per month. So for a 40′ boat you’re talking around $280.00 a month/6 months $1680.00 and sail her back up north in the spring. Very reasonable! The internet makes it easy to discover the numerous slips available there.

If you sail from Montauk to the Chesapeake, it would take about 54 hours (2-2 1/2 days). A great first stop is Cape May Harbor, a 30 hour trip. There you can anchor by the coast guard station. From there, you can either go offshore towards the Chesapeake, a 24 hour trip, or go up the Delaware Bay to the C & D canal, a 8-10 hour trip with the tide on your side. From a C & D marina, you can set sail for the northern Chesapeake. Norfolk, VA., with the beginning of the ICW, is south. That would be longer, but more inland. I prefer to sail offshore on my trip down to avoid the inland obstructions, tide changes, buoys, etc. Offshore you’re just clicking the miles off and getting into your watch routines. During October and November, the wind is on your side when heading south. They come from the northeast, off the land, making the seas flatter and giving you plenty 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.

When you first enter the mouth of the Chesapeake, you’ll find a great, protected harbor, Little Creek. “Little Creek Marina”, “Cobbs”, & “Cutty Sarks” marinas offer slips at cheap daily, weekly, or monthly rates. I find the kind and helpful southern hospitality second to none. Another great marina is Tidewater in Norfolk, where you’ll find lots of room to dock or anchor nearby. I have a hard time choosing between sticking around the Chesapeake area or taking the ICW to North Carolina. Either way, I find so many great coves and towns to check out. There are many other boaters enjoying their winter voyage and you’ll make friends with many of them.

My trip usually starts in October, as long as no hurricane is on its way. It’s still the hurricane season, but in the Chesapeake there’s plenty of time to head for a safe harbor. The storms take several days to several weeks to reach this area. I make it a habit to have several sources of information for weather, wind, and wave information. There are several good websites, and, of course, the VHF radio will keep you up-to-date on any formations or disturbances in the Atlantic and Caribbean.

There’s so much to explore, whether your trip is just for a long weekend or over the winter. But, who says you have to go home for the summer. Another adventure always lies ahead.