Excellent Chesapeake sailing onboard Windsnap

(15 bookings)
26 ft
Boat length
Up to 6
Captain optional
This boat is rented with or without a captain
Owner’s response rate

The boat

S/V Windsnap is a 26 cruiser built in Ontario by the Grampian boat works. She was constructed back when fiberglass boats were laid up thick making a very solid hull.

Below she has full standing headroom in the main cabin. And can sleep four with dinette table down. Windsnap is equipped with a brand new 2021 fuel injected Suzuki four stroke 9.9 extra long shaft power tilt electric start outboard with cockpit controls.

Amenities include a built-in alcohol stove.

porta potty. ( please avoid #2 if possible) oil lamps LED cabin lights Clean interior canvas cushions in good shape.

Electric fresh water sink.

Gas grill.

Accessories include chart plotter with depth and speed. (A must for the Chesapeake)

Tiller auto helm

Led navigation lights

Illuminated masthead wind indicator “windex”

Self tailing jib sheet winches

Anchor bow roller with CQR ready to drop.

Sails are in good shape. Single reef Main Roller furling jib.

This is an older boat, well kept ,and a tough gal. Don’t expect gleaming flawless gel coat. I don’t have some nice extras like Bimini and cockpit cushions But then again you don’t need to worry about causing minor cosmetic damage to deck or hull either. This is why the rental fees are below similar listings. if you want to sail the treasure the Chesapeake is, Economically but safely, this is the opportunity for you.. as mentioned in another rental description this boat needs to get used and sits at the dock too long. I do have a boat partner but he doesn’t get out nearly as much either. A lot of the proceeds generated from the boat rental will go right back into boat improvements and projects.

Some basic sailing characteristic descriptions for Windsnap

. Higher winds, just adjust sail area accordingly and she will stay stable and manageable. Bottom is kept clean. In Lighter winds I often pass longer boats. Max Hull speed is 7k average is 5k. She’s not a high-performance racer, performs a little better off the wind, but still stands her ground sailing upwind.

Chesapeake entrance is about a 20 minute motor on the Rhode river, arguably the best protected and natural anchorage’on the Bay. Popular day sail destinations are Thomas Point light house, Annapolis, Chesapeake Bay Bridge for a long summer day St Michael’s (Admittedly, a better two day cruise). I’m open to the possibility of overnights under way and sleeping onboard overnight at the Marina slip. There’s also a complete sailing dinghy with a 4 horse outboard available in dry storage at the marina. Sail Windsnap in the river, anchor, and go dinghy sailing or go ashore and explore the Smithsonian conservation area and isolated beaches. Annapolis is a 15 minute drive and average 50 minutes from DC metropolitan area ( if you time traffic right). I’m a licensed USCG 100 ton captain ASA sail instructor, and I love sharing the knowledge of sailing. This is why I added the four hour captain option if you didn’t feel totally comfortable on a cruising Sailboat I could give a sailing refresher , boat run down, familiarization and then give you time by yourself. I am always available for any questions by phone and there is complete cell phone coverage in the cruising area described.

The “Shoulder seasons” especially fall, is the best on the Chesapeake. 70 degree days in November are not uncommon. Cool nights warm days and greater chance of wind.

I can book within 24 hours but sometimes can’t necessarily be available that quickly for greeting. Booking further in advance is best. I will soon be listing a car on Turo . I would consider a package deal if you were using the car to include a boat rental.

Please don’t hesitate to call anytime for more information.

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Owned by
(14 ratings)


Cooler / Ice chest
Swim ladder
Children's life jackets
Fish Finder
Depth finder
VHF Radio


26 ft.
26 Keel
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/ (excl. fees)
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Boat location

Exact location information is provided after a booking is confirmed.

Your crew

Boat owner
(14 bookings)
100 ton near coastal master sail power. I am voluntarily registered with the Maritime consortium drug testing program. I am a American sailing Association instructor ( not currently certified) I have skippered numerous inspected and uninspected sail charter vessels I enjoy sharing the sailing experience with others.
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  • Response rate: 91%
  • Avg. response time: < 24 hours

Things to know

Allowed on boat

kids under 12
red wine

  • Free cancellations until 24 hours before the booking start date.
  • Cancellations within 24 hours of the booking start date are non-refundable.
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A security deposit hold (not a charge) will be placed on your credit card 48 hours before your booking starts to cover any incidental damage that may occur during your rental. This hold is released 48 hours after the booking is complete, if no claims are made. The security deposit amount for the boat you are booking will be outlined during the check-out process.

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