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Enjoy a day under sail aboard S/V StewardShip out of Cape Charles, Virginia. Experience the fresh breezes that the lower Chesapeake Bay has to offer while the sails fill and pull you and your crew toward no particular place. Perhaps a few dolphin will play with us along the way as we pass the remains of the Cherrystone Bar Light and the Old Plantation Flats Lighthouse. | ![]() |
Four Hour Day Sail with a light Lunch
| Choose the four hour day sail and get underway at 10 AM allowing the winds of the day to dictate our heading. We may head south towards Kiptopeke near the “concrete ships” or west to New Point Comfort Lighthouse. A northward course will take you and your crew to Cherrystone and the middle of the Bay. Whatever our course, drink in the vistas as the bow of StewardShip pushes water and your cares away. |
Four Hour Sunset Sail with an evening meal

A sail designed especially for the romantic at heart who wish to spend some time alone and on the water. Let S/V StewardShip harness the wind and take you and your loved one to sea for a few hours. Mate Hania’s exquisite fare will delight your palate as the sun slowly sets on the horizon. This cruise is not to be missed!
Spend a night at anchor
There is nothing quite so enthralling as spending a night in a quiet anchorage.
This cruise to an overnight anchorage is designed for the couple who wish to dropout for a day, chill and to simply
remain on the water enjoying what the southern Bay has to offer. We depart around noon and return the next day
around noon. This cruise is available Monday through Thursday only.
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| Rates* | |
| Four Hour Day Sail | $50 per person (4 people maximum) |
| Four hour Sunset Sail | $55 per person (4 people maximum) |
| Overnight Anchorage | $250 per couple (2 people maximum, double occupancy) |
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We will be happy to entertain your special cruising needs! S/V Stewardship carries a maximum of four passengers. |
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Interested in a private sailing lessons? Click here for information on learning to sail.
StewardShip is a 29’ sailing sloop with an auxiliary diesel engine. She is berthed in Cape Charles Harbor. Captain Dave is a USCG Licensed Captain and has been sailing the Bay for over 12 years. |
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Please click here to see a list of our partners and friends here in Cape Charles. |
*Does not include Cape Charles 3% admission tax.
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