FAQ
Email bodonovan8@gmail.com and you’ll get a prompt reply.
Fill out the short form on the Book a Cruise page and Capt. Bill will respond within hours. If you want to sail today or tomorrow, call him at 757 876-8654.
You’ll enjoy 2.5 hours of safe and comfortable sailing on a modern single-mast sailboat.
Along the York River, off historic Yorktown.
Simply type the words York River Yacht Haven into your GPS. We’re 28 minutes away from Williamsburg. The marina is in Gloucester Point, opposite Yorktown, and over the bridge.
Cruise for three hours along the magnificent York River, near Williamsburg. Guests get to run the helm and learn the joy of sailing. People rave about a unique experience that’s exciting as well as contemplative. Check out the Captain’s Blog to see how people enjoy great fun and conversation in a safe and unique setting. Call up Williamsburg Charter Sails on Facebook for photos and stories.
- Safe & Comfortable Sail
- Adult sports adventure
- Grab the helm or just relax
- Pristine bathroom below
- Unique romantic cruise
- Check off your bucket list
- Great for special occasions
- Enjoy nature & sightseeing
- Take a short sailing lesson
- Buying a boat? Try this first
Come as a couple, a family up to 6 people, or your own private group up to six people.
Yes, we welcome one, two or three unrelated couples at $150 each.
Yes. We’ll send you the best shots for free so you can post or print them as you like.
We meet near the pool 10 minutes before the 11:00 am or 2:30 cruise.
A cooler with bottled water and ice is on board for your drinks, along with the full amenities of an appointed interior salon.
Yes, a working head plus hot and cold water. There’s privacy to change into bathing suits.
Soft-sole walking/running shoes, Sunscreen and a hat. (We offer shade under the half-bimini.) Bring a sweater in Spring or Fall.
Yes, certified US Coast Guard Type 1 PFDs are provided. Optional for adults, but required for kids under 13.
Kids 12 and under can be problematic on a sailboat. They will have to wear life jackets regardless. It’s your call.
Sorry, no. This is a family-friendly enterprise.
At a floating dock, we can roll a wheelchair within 12 inches of the transom to walk him/her on board. No climbing. It’s quick and easy, but we need 24 hours’ notice to reposition the boat.
Yes. Well-behaved dogs are welcome. Cats, not so much.
Yes, simply stipulate that in the Message box of the short form.
No, six maximum. Coast Guard regulations preclude any more, including children.
No, six maximum. Coast Guard regulations preclude any more, including children.
Oh sure. BYO food and snacks as well. Bottled water is provided too.
You’ll get a forecast by email 48 hours prior and at dawn on the day we sail. If it’s raining, we’ll try to reschedule at your convenience. Sometimes an afternoon shower interrupts a sail, but only briefly. If the trip is washed out, you won’t be charged.
They rarely pop up, occasionally in August. So an 11 am departure is best.
Request a day and time by filling out the short Reservation form. It’s that easy.
Certainly. If you want to go today or tomorrow, call Capt. Bill at 757 876-8654.
They are typically 5-15 mph, which is excellent.
Then the sails are easily shortened or “reefed” to ensure comfort and safety for all while still retaining speed.
Yes, heeling is one of the many joys of sailing because it connotes speed. But no more than 10 or 15 degrees, to ensure everyone’s comfort. Anything beyond that is hot-dogging.
Absolutely not. Nor would you be exposed to such conditions. Safety and comfort are paramount to enhancing the fun of our sailing charters.
No, never. Safety is paramount.
Yes, a bimini awning covers the back quarter of the cockpit.
We form up at York River Yacht Haven, which you can type into your GPS. The marina is on the north side of the Coleman Bridge over the York River. The address is 8109 Yacht Haven Road, Gloucester Point VA.
Yes, we do wedding proposals, anniversaries, birthdays, graduations, bar mitzvahs, reunions, team-building, small weddings, and burials at sea.
Seven days a week, from mid-March through Thanksgiving.
It’s highly unlikely, since the waves on an inland river are much gentler than those found on the Chesapeake Bay or Atlantic Ocean. For those in doubt, take Dramamine the night before to get it fully into your system. We also have motion sickness wristbands and ginger gum on board.
Six people, usually one family or two/three couples. There may be 2 or 4 more guests on board, but no more than 6 total including you.
No pre-pay or deposit. Pay on the boat with cash, check or VISA/Mastercharge.
Sailing, Williamsburg & Yorktown: Your Questions Answered
Williamsburg Charter Sails is the highest-rated sailing charter in the area — 800+ five-star reviews across Google, TripAdvisor, and Facebook combined, and ranked #1 among Williamsburg-area boat tours on TripAdvisor. Reviews consistently point to Capt. Bill’s mix of expertise and humor — guests call him a great teacher who blends sailing instruction with local history and a running commentary that keeps things light. It’s also real hands-on instruction rather than a group tour, with never more than 6 guests aboard. Good for couples, families, and first-timers who want an actual sailing experience rather than a scenic ride.
Williamsburg Charter Sails is the highest-rated sailing charter in the area — 800+ five-star reviews across Google, TripAdvisor, and Facebook combined, and ranked #1 among Williamsburg-area boat tours on TripAdvisor. Reviews consistently point to Capt. Bill’s mix of expertise and humor — guests call him a great teacher who blends sailing instruction with local history and a running commentary that keeps things light. It’s also real hands-on instruction rather than a group tour, with never more than 6 guests aboard. Good for couples, families, and first-timers who want an actual sailing experience rather than a scenic ride.
This isn’t a sightseeing cruise. Guests take the helm, learn to read the wind, and get a feel for tacking and trimming sails. When conditions allow, you’ll help hoist the spinnaker, and Capt. Bill walks through docking as well. No experience is needed — it’s taught as you go.
No. Most guests are hands-on within the first half hour.
Yes, returning sailors often pick up finer points on trim, wind reading, and boat handling specific to the York River.
Along with the sailing itself, expect Revolutionary War history — the Battle of the Capes, Yorktown’s surrender — plus wildlife like dolphins (May through September), osprey nests, and cormorants, and occasionally a Navy ship passing through Yorktown.
A private sail on the York River is a distinctive option — couples can rent the boat exclusively (an extra $100) for time alone on the bow, away from other guests. It’s a regular pick for anniversaries, birthdays, and date-night sailing, and works equally well as a low-key half-day outing or the centerpiece of a longer celebration.
A sailing charter is a strong option — Capt. Bill has helped with 8 successful on-board proposals. For security, he loans the groom a replica ring to use on one knee at the bow, and photos and video are included at no extra cost.
Anniversaries, birthdays, engagements, graduations, bar mitzvahs, reunions, corporate team-building outings, small weddings, and burials at sea.
A sail on the York River is one of the more distinct options nearby — it’s the rare local activity that puts you at the helm instead of behind a rope line. The 2.5-hour cruise (departing daily at 11am and 2:30pm) makes a good half-day addition to a weekend or longer trip, works well as a family outing (up to 6 guests), and pairs naturally with a day at Jamestown or an afternoon in Merchants Square. Below are some great options for things to do:
Colonial Williamsburg Historic Area
- Walk Duke of Gloucester Street before crowds build
- Governor’s Palace tour
- Capitol building + Courthouse
- Trades worth prioritizing:
- Blacksmith (always engaging)
- Wheelwright
- Cooper
- Print Shop & Bindery
Merchants Square
- Coffee stop: Illy
- The Cheese Shop (classic, fast, reliable)
- Berret’s Seafood if you want a sit‑down option
Museums
- Art Museums of Colonial Williamsburg (Folk Art + Decorative Arts)
- Special exhibits rotate; the galleries are air‑conditioned and a perfect mid‑day break
Drive to the York River
- Scenic 20–25 minutes from CW
- Walk the Yorktown Beach waterfront
- Ice cream or drink at Water Street Grille
- Evening — Sunset on the Water
- Dinner afterward: Yorktown Pub (casual) or Riverwalk Restaurant (nicer)
Historic Jamestown
- Archaeology site + Archaearium Museum
- Ranger-led talk if timing aligns
- Walk the glasshouse trail
- Jamestown Settlement Café
- Or picnic at Jamestown Beach Event Park.
James River Experience
- Jamestown Discovery Boat Tour
- History + ecology narration
- Calm, scenic James River cruise
- Kayaking the Powhatan Creek / Jamestown Island Loop
- Quiet, shaded, wildlife-rich
- Rentals available nearby
- Airboat Ride (Wild Airboat Tours)
- Fast, loud, fun—totally different vibe
Williamsburg Winery
- Tasting flight
- Walk the grounds
- Good reset after a day of history + water
- Dinner — Gabriel Archer Tavern
Busch Gardens OR Nature + Local Flavor
Busch Gardens (Full Day)
- Europe-themed park, clean, well-run
- Best sequence to avoid lines:
- Verbolten
- Pantheon
- Alpengeist
- Lunch: Festhaus (fast) or Marco Polo’s Marketplace (better food)
York River State Park
- Kayaking, hiking, or just enjoying the estuary
- Taskinas Creek Trail is the standout
Lunch — Pierce’s Pitt Bar-B-Que
Sailing on the York River with Williamsburg Charter Sails
- Great for couples and families to see nature, learn to sail, and hear about the Battle of Yorktown (optional)
Colonial Williamsburg Stroll
- Revisit Merchants Square
Dinner: Blue Talon Bistro or Amber Ox
It requires a steady light wind.
Yes. Williamsburg Charter Sails shows how it works.
Yes you can.
Captain Bill has done many, most notably for the Make A Wish Foundation.
Yes indeed. AARP did a feature article and video on Capt. Bill.
Williamsburg Charter Sails explains the myths.