Written by Bob Ruegsegger
October 2017

When the English Colonists who established Jamestown sailed through a watery passage into the New World in 1607, there were no charts, lighthouses, or daymarks. They often used familiar English sobriquets as names for the places and rivers that they “discovered” in Virginia — Cape Charles, Cape Henry — but Captain John Smith’s map of Virginia, in use for seventy-five years, also recorded many of the native tags given by the indigenous people, including the Chesapeake Bay.

These days, the area at the confluence of the James River, Elizabeth River, and the Chesapeake Bay — collectively known as Hampton Roads — is still a great place to explore by water.

Norfolk and Portsmouth are on opposing banks of the eastern branch of the Elizabeth River, and the shipyards and marinas lining both sides make this a splendid starting point for a cruising adventure in the region. On the Norfolk bank are the Waterside Festival Marketplace, Waterside Marina (757-625-3625), and Town Point Park. The naval museum, Nauticus, which has the World War II-Era Battleship Wisconsin as its centerpiece, is adjacent to Town Point Park and is an easy five-minute walk from Waterside Marina. Also, a former 1873 church now turned into a tavern, the Freemason Abbey Restaurant, is only a four-block trek from Town Point Park.

The Elizabeth River Ferry provides a convenient, interesting, and inexpensive means of crossing the river from Norfolk to Portsmouth. A one-way ride costs $1.75 and runs every 30 minutes. Portsmouth boasts a plethora of boatyards and marinas. Tidewater Yacht Marina (757-393-2525), located at mile marker “0” on the Intracoastal Waterway (ICW), houses some of the best marine facilities in Hampton Roads along with Ocean Marine Yacht Center (757-321-7457). Both are set in the heart of Portsmouth’s Olde Towne, a charming historic maritime district with the country’s oldest operating U.S. Naval Hospital and loads of shopping and dining options. The Naval Shipyard Museum, Portsmouth Lightship Museum, and the Children’s Museum of Virginia are also nearby, and the Olde Towne Courtesy Shuttle provides passenger service within the Olde Towne district.

Cruisers who like to explore should check out this Historic Hampton Roads boating itinerary.

DAY ONE – Waterside/Olde Towne to Lynnhaven Inlet

Lynnhaven Inlet, on the Chesapeake Bay side of Virginia Beach, is approximately 22 nautical miles from Waterside and Olde Towne. The voyage requires sailing down the Elizabeth River, around Lambert’s Point and into Hampton Roads. Along the way, cruisers will sail past the Norfolk Naval Base, over and under the Hampton Roads Bridge-Tunnel and the Chesapeake Bay Bridge-Tunnel, and under the Lesner Bridge into the Lynnhaven River.

Lynnhaven Bay was the site of a notorious 18th-century pirate battle, and Lynnhaven oysters gained renown worldwide for their succulence and distinctive flavor. Long Bay Pointe Marina (757-321-4550) is located on Wolfsnare Creek, a tributary of the Lynnhaven River. This first-rate boating resort is about five minutes from the Chesapeake Bay and ten minutes from the Atlantic Ocean. The 215-slip marina with floating docks can accommodate boats from 20 to 200 feet. Amenities include a tackle shop, fish-cleaning facilities, climate-controlled restrooms, showers, laundry facilities, and easily accessible parking. Restaurants are located on the premises.

First Landing State Park, the site where English colonists first came ashore in 1607, is within walking distance. The park features 20 miles of hiking and bicycling trails and a mile and a half of beach.

Cape Henry and its two lighthouses are located ten miles east of Lynnhaven Inlet via Shore Drive (Route 60), on the Joint Expeditionary Base-Fort-Story. The Old Cape Henry Lighthouse, built in 1792, is open to visitors for a fee.

DAY TWO – Virginia Beach to Cape Charles

Passing through Lynnhaven Inlet into the Chesapeake Bay on a northerly heading will put sailors on course to Cape Charles. An easterly bearing will put the crew on a course to Cape Henry — and the Atlantic

Cape Charles, on Virginia’s Eastern Shore, is 25 nautical miles from the mouth of Lynnhaven Inlet. The cruise to Cape Charles will involve passing through the Chesapeake Bay Bridge-Tunnel at some point. While small craft may pass under the bridge trestles, larger craft must pass over either the Thimble Shoals Channel Tunnel or the Chesapeake Bay Tunnel Channel. On the Eastern Shore side of the bridge tunnel, larger vessels can pass under the North Channel Bridge.

The town of Cape Charles was founded by Alexander Cassatt and William L. Scott in 1864. It was the southern terminus of the New York, Philadelphia, and Norfolk Railroad. The outgrowth of railroad tracks from Maryland to Cape Charles opened markets in the Northeast to Eastern Shore produce and seafood. By employing steamboats and railroad barges, the newly established port created a link to Norfolk. Cape Charles grew rapidly and quickly became the economic and domestic hub of Northampton County.

These days, Cape Charles is the gateway to the ecosystem of the Virginia Coast Reserve, a coastal barrier biosphere comprised of mainland watersheds, lagoons, and tidal marshes. Because of where it’s situated, it also serves as a kind of “convenience store” for super yachts in need of fuel and provisions as they cruise the Atlantic coast.

Cape Charles Yacht Center (757-331-3100) is a full-scale service facility, with short-term and long-term
boat slips and dry storage. All types of mechanical systems are designed, serviced, and installed on site. Guests also get complimentary shuttle service to all Cape Charles attractions. The 75-ton Marine Travel Lift (a 650-ton lift is currently under construction), gently and expeditiously removes and returns bigger craft to the water, and the deep-water floating docks can easily accommodate large yachts for transient or longer visits.

DAY THREE – Cape Charles to Hampton

Hampton is in the heart of the Hampton Roads region, about 22 nautical miles from Cape Charles on Virginia’s Eastern Shore. The entrance to the Hampton River is just beyond Old Point Comfort, where the channel passes between Fort Monroe National Monument and Fort Wool and over the Hampton Roads Bridge-Tunnel.

Bluewater Yachting Center (757-723-6774) is adjacent to Blackbeard’s Point on the port side at the mouth of the Hampton River — where Blackbeard’s severed head was posted on a pole as a warning to other pirates in 1718. The full-service marina offers diesel and premium gasoline, a full parts department, and factory-trained technicians. It also has a swimming pool, a coin-operated laundry, bicycle rentals, and the ever-popular Surfrider Restaurant.

A complimentary water shuttle is available on demand to transport guests from the marina to the center of downtown, where the Hampton History Museum illuminates the city’s past, from the native Kecoughtan Indians through the 20th century. The Hampton Carousel was built in 1920, and its 48 intricately carved horses and two elegant chariots were recently restored. The Virginia Air & Space Center serves as the official visitor site for Hampton’s NASA Langley Research Center.

Hampton has had a reputation for hospitality since Captain John Smith and his men were welcomed and treated kindly by the Kecoughtan people during the winter of 1608-1609. The four-centuryold tradition continues to this day. The Hampton River Waterfront has five marinas all on its own, and is an ideal stopping point for boaters traveling the Chesapeake Bay or the Intracoastal Waterway. If you can, hit the town during the annual, nationally acclaimed Blackbeard Pirate Festival in June — it’s a swashbuckling good time.