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Sailing in Virginia - Get Out on the Water Near Williamsburg

Sailing in Virginia and Exploring Peninsula

Beautiful waterways are a part of the natural landscape along the 180-mile-long Virginia peninsula, with streams, inlets, and two massive rivers – the York River and James River – less than a 20-minute drive away from Williamsburg, making sailing in Virginia an affordable and memorable day trip adventure during your stay at our historic bed and breakfast.

Since first setting sail in 2013, Williamsburg Charter Sails has developed a stellar reputation over the last decade for their 3-hour twice-daily trips along the York River side of the peninsula aboard a modern 32-foot sailboat, with a #1 Trip Advisor rating for tours and outdoor activities. You’ll learn about the unique history and wildlife of the York River, enjoy stunning views from the water, and it’s equally fun whether as a romantic couples’ outing or with the whole family. Billy and Sharon have sailed with Bill many times over the years! Being on the local waters is a favorite activity; no one does it better than Bill!

An Experienced Captain, History Coming Alive, and Nature on Display

Having been the publisher of the Williamsburg area newspaper, the Virginia Gazette, before switching gears to sailing full-time a decade ago, Captain Bill O’Donovan has well-established roots in the local community. He brings over 30 years of experience sailing in Virginia and a deep knowledge of local history, so while enjoying the scenery as Captain Bill guides you up and down the York River, you’ll learn about the fascinating chapters of history along its shores. You’ll pass by Yorktown, a decisive battlefield location during the Revolutionary War and where the British surrendered to George Washington. The York River coastline would prove crucial again in later years during the Civil War’s Virginia Peninsula campaign when Confederate troops dug in and held the 12-mile-long Warwick Line against successive Union attacks and movements toward Richmond.

In addition to the historical backdrop, you’ll be privy to the incredible diversity of birds and wildlife that make their home along the York River. The river is home to over 190 bird species, and birders will be in heaven, with osprey hunting from hundreds of feet above the water and herons floating effortlessly on the ocean breeze with their impressive 3-foot wingspan. During the spring and summer, when the water temperature is warmest, you’ll likely see bottlenose dolphins swimming alongside the boat and finding their next meal from the 250+ fish species in the river ecosystem.

Plan Your Perfect Sailing Afternoon and What to Expect

Start your morning with the Fife and Drum Inn’s continental breakfast, which starts at 8 am, and then enjoy a 25-minute scenic drive along the Colonial Parkway – one of the most historic stretches of road in the country – to the York River Yacht Haven in Gloucester Point, where you’ll set out for the 3-hour sailing session.

Captain Bill will tailor your sailing outing, or “charter,” to whatever best suits your desire for the day. An adventure cruise is for those who want to relax and enjoy the sailing sights; an event cruise focuses on a special celebration like an anniversary or wedding proposal; and a history cruise will satisfy the diehard history buffs in your family. Six different-themed charters are available, so just let Captain Bill know when you make your reservation. See his entertaining blog about a couple learning to sail before their upcoming pregnancy, another couple taking a celebratory sail after a successful life-saving surgery, and the surprise of seeing Coast Guard and Navy ships mid-sail.

Chartered sailing trips head out daily at 11 am and 2:30 pm, starting mid-April and going through mid-November. Midsummer is the busiest season, especially on weekends, so try to book as far in advance as possible to ensure you get a reservation squared away. Call Captain Bill at (757)876-8654 to reserve your spot, or email him at

Depending on whether you are going solo or as a couple (the cheapest rate), as a family (3-6 people and the second cheapest), or as a group (4-6 people), the cost varies, but it’s an affordable day of fun regardless of your group size. Children under 12 are allowed but must wear a life jacket.

A few other notes about the sailing experience: the boat conveniently has a bathroom on board, cold water is provided free of charge, Captain Bill is happy to take pictures of your group and send them to you afterward, and seasickness is less of a concern as you’ll be on river water rather than contending with Atlantic Ocean waves.

Stay with us in Williamsburg and get out for an unforgettable day of sailing in Virginia!