In the tiny village of Weems, not far from the town of Irvington on Virginia’s Northern Neck, Clay Dingledine, dressed in a flannel and khakis with his long hair tied at the nape of his neck, offers a friendly wave from the dock of Carter’s Cove Marina. As the afternoon sun begins its decent to the west, Captain Clay—a native of the area whose love of sailing began at the age of 13—welcomes us aboard Galene, the 36-foot 1968 Columbia sailboat originally built in Portsmouth and painstakingly restored by Dingledine after he rescued it from a state of disrepair in 2017.
The laidback vintage vibes of this vessel and its cool captain are all part of the charm as we set out on the “Sunset Cruise,” one of several charter sailing excursions offered by Sail & Surf Adventures, the company founded by Dingledine in 2021 after he decided to dock his day job in favor of a professional life on the water, giving passengers the chance for at least a couple of hours of “reflection and rejuvenation from busy life ashore.” With two decades of sailing experience under his belt, the captain will put you at ease as you soak up the scenery and take in the brackish breezes of the Rappahannock River.
Sail & Surf Adventures offers sailing charters departing daily from Weems including the Sunset Cruise, the Breezy Brunch Cruise, the Moonlight Cruise and a Half-Day Sail on The Bay—most for up to four passengers with prices ranging from $250-$600. My Coastal Virginia Magazine colleague and I got a taste of the Sunset Cruise, special thanks to Captain Clay. But we are most looking forward to a return trip for another decidedly foodie-friendly experience also offered by Sail & Surf: the Sail & Savor Trip to Merroir Tasting Room. Merroir is a well-known nearby destination for oyster connoisseurs, where fresh-shucked local bivalves are beautifully complemented by a selection of small plates, wines and craft brews overlooking the river.
This got us to thinking of other places around Virginia where we might be able to experience the unique pleasure of sailing—from small private boats to large replicas of historic ships—along with good eats and drinks for a weekend getaway or vacation outing. Here are a few ideas for pairing a quick sailing adventure with some signature bites and sips.
An iconic sight with its red sails on the Norfolk waterfront for more than three decades, this 135-foot, 125-passenger, topsail schooner has given thousands of locals and visitors a unique view of the Elizabeth River and the Port of Virginia. Cruises depart from the Waterside Marina and include Sunset Cruises (with live entertainment), Harbor Tours and Private Boat. Public cruises last about two hours and cost between $27-$45. Cruises for special events like 4th of July are also available. Prices vary.
What to Eat and Drink Nearby: Stripers, Cogan’s Pizza, Starr Hill Market Bar, Brothers Norfolk
Northern Virginia Sailing School
Known as a sailing school with an iconic and historical significance on the Potomac River, they also offer easy-breezy charters. Relax and unwind as an experienced captain treats you to the beauty of the Potomac at its best. See Maryland’s shores, scenic and historic points and wildlife April through October. Northern Virginia Sailing School is nestled at the marina in Leesylvania State Park, directly on the lower Potomac River in Woodbridge. Two-hours tours for groups of one to four cost $150 and they offer flexible 24/7 scheduling.
What to Eat and Drink Nearby: Secret Garden Café, Water’s End Brewery, Potomac Point Winery, The Spot on Mill Street
With a fleet of sailboats from 34 to 51 feet, Norton Yacht’s charter program lets sailors experience all that the lower Chesapeake Bay has to offer. Departing from Broad Creek Marina at the mouth of the Rappahannock River, they offer easy half-day, bareboat charters to dozens of anchorages, dockside seafood spots, wonderful wildlife and picturesque points. Captains for charters can be hired separately if desired. Boats like their a 2015 Jeanneau 349 cruiser, AKA the FUNK 349, are meant for fun. Norton is also an ASA certified Sailing School.
What to Eat and Drink Nearby: The Table, Deltaville Tap & Raw Bar, White Dog Bistro, Gloucester Brewing Company
Onancock Sailing Adventures
You’ll be feeling thankful for the beauty and bounty of the Eastern Shore when you book a two-hour tour onboard the 26′ Nonsuch Catboat GRATITUDE, offering a laid-back leisurely way to experience the wildlife and history of Onancock Creek. All cruises begin and end at Onancock Town Wharf and carry two to five passengers at a rate of $50 per person. Morning, midday and afternoon cruises are available. While you’re there, don’t miss Onancock’s charming main street area, full of shops, eateries, art galleries and more.
What to Eat and Drink Nearby: Mallard’s at the Wharf, Janet’s Café, Corner Bakery, Blarney Stone Pub
Sail Away Charters
Operating since 1992, the Joie de Vie—a 33-foot Cape Dory, sloop rigged, fine sailing boat—sails the Chesapeake Bay from Kilmarnock, just north of the mouth of the Rappahannock River April through November, but they take reservations for skippered sails year-round. Full-day charters for up to four passengers run $495. Half-day and sunset trips are $295. Take in the splendors of the Chesapeake Bay or relax in the finely appointed teak interior with a fully equipped galley. Bring a picnic lunch or stop along the way.
What to Eat and Drink Nearby: Ditchley Cider Works, Northern Neck Burger, Good Luck Cellars, Kilmarnock Inn and Restaurant
History buffs, come aboard and explore the Chesapeake Bay. This 105-foot gaff-rigged schooner gets her new name from the French and American Alliance that was instrumental in winning the war of Independence and now sets sail daily from Riverwalk Landing Pier in historic Yorktown. Cost is $41 for adults for day cruises. Aaargh…they also offer a Pirate Adventure Cruise, onboard dining, private charters for up to 49 guests, and even a seven-day cruise to the Caribbean. Prices vary.
What to Eat and Drink Nearby: Water Street Grille, Umi Sushi, Carrot Tree, Mobjack Bay Coffee Roasters
Docked along the Elizabeth River at Nauticus, this reproduction of the last all sail vessel built for the Virginia Pilot Association serves the Nauticus Foundation as an education platform to engage the community in hands-on learning about everything from STEM to maritime history to environmental conservation. You might see her mainsail in full glory at Harborfest, but the Schooner Virginia is also available for private charters as are lessons through their First Sail program. Contact Sail Nauticus for pricing and details.
What to Eat and Drink Nearby: Todd Jurich’s Bistro, Saltine, Grain, Syd’s FishPig Cafe
757 Sailing Charters
The 35 and a half-foot Sailing Vessel Freedom lives up to its name with tours departing from historic Fort Monroe. With no set destination or typical route, no two trips are the same. Passengers may see work being done Hampton Roads Bridge Tunnel, large vessels like Naval aircraft carriers, kayaks, boats and birds like eagles, osprey and pelicans, all from a relaxing watery vantage point. Feel free to bring food aboard. Daytime and sunset cruises are available for one to four guests, last two to three hours and cost $300.
What to Eat and Drink Nearby: Fox Tail Wine Bar, 1865 Brewing Company, The Baker’s Wife Bistro & Bar, Fuller’s Raw Bar
Smith Mountain Lake Sailing
Smith Mountain Lake
This sailing school on Virginia’s picturesque freshwater lake, the “Jewel of the Blue Ridge” and a popular vacation spot for visitors from around the state, also invites you to spend a half day charter with Captain Pete for groups of up to four sailors. Relax and enjoy the ride while taking in the legendary mountain views surrounding the lake or help trim sail and steer the boat. Charters can be booked on either the J/24 Rascal or the O’Day 35 Joie de Vivre. The school is located on Smith Mountain Lake off Gills Creek, 45 minutes south-east of Roanoke.
What to Eat and Drink Nearby: The Landing Restaurant, AmRhein Cellars, Big Lick Brewing, Drifter’s
Kick back with Captain Clay aboard his 36-foot fully refitted sailboat, Galene, and “immerse your senses in life at sea.” Sailing from Weems, not far from The Tides Inn in Irvington, options includ the Sunset Cruise, the Breezy Brunch Cruise, the Moonlight Cruise, a Half-Day Sail on The Bay or the Sail & Savor Trip to Merroir Tasting Room, most for up to four passengers with prices ranging from $250-$600. Learn more in the intro story for this article. As the name suggests, they also offer surfing tours departing from Cape Charles for surfers looking for some sweet out-of-the way spots for waves.
What to Eat and Drink Nearby: Adrift, Merroir Tasting Room, Fish Hawk Cafe, The Local
Virginia Beach Sailing Charters
Departing daily from Tidewater Yacht Marina in Portsmouth for their two-hour Paradise Cruise ($50) on the Elizabeth River, Virginia Beach Sailing Charters lets you lend a hand setting the sails, take a turn at the helm or just sit back and enjoy as you cruise by the largest U.S. Navy base in the country. For a romantic evening or fun outing with friends, try their Sunset Cruise ($60) or go big with an overnight charter that includes light food. Ask about their part-time swashbuckling canine crew member, Cleo, an Afghanistan rescue.
What to Eat and Drink Nearby: Bier Garden, Fish & Slips, Café Europa, Stellar Wine Co.
Williamsburg Charter Sails
Choose from six unique charters sailing from York River Yacht Haven at Gloucester Point: an Adventures Cruise, Event Cruise, Appreciation Cruise, History Cruise, Lessons Cruise or Boat Buyers Cruise. Take in the natural beauty and history of Yorktown, Williamsburg and beyond aboard a 32-foot modern Hunter. Exhale and relax as you feel the wind in your hair or grab the wheel to become a member of the crew. Prices range from $150 to $350 for a unique experience for both Historic Triangle vacationers and locals. Sailing lessons are also available.
What to Eat and Drink Nearby: YROC Bar & Grill, Scoot’s BBQ, Yorktown Pub, Larry’s