Excellent Chesapeake sailing onboard Windsnap

(28 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 newer 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) , LED cabin lights, interior canvas cushions and

Electric fresh water sink.

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

Tiller auto helm

LED mast navigation lights,

Illuminated masthead wind indicator “windex” and

Anchor bow roller with bruce anchor ready to drop.

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

This is an older boat, well kept ,and a tough gal. Don’t expect gleaming flawless gel coat but then again you don’t need to worry so much 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. Majority of the proceeds generated from the boat rental will go right back into boat as improvements and projects. A new option which I am adding is a two hour captained combined boat orientation and instructional sail. This two hour option is designed for people that have some experience or may be recent sailing school Graduates who want to get out on the water And up their game but might not be comfortable or ready to take out A boat like this by themselves. My captain Dave is a certified American Sail Association instructor so you will be learning everything the right way by a professional captain. You won’t find a better deal as this one. Pending a captain evaluation you would be invited to bareboat charter Wind Snap.This Approach is the best way to build your confidence and set up your future sailing adventure for success.

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, sails 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 and the Chesapeake Bay Bridge. I’m open to the possibility of overnights under way and sleeping onboard overnight at the Marina slip. Annapolis is a 15 minute drive and average 50 minutes from DC metropolitan area ( if you time traffic right). I am always available for any questions by phone during your charter. There is complete cell phone coverage in the cruising area previously 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.

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

Read more
Owned by
(26 ratings)


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


26 ft.
26 Keel
See all
/ (excl. fees)
Start time
You won't be charged yet

Ratings & reviews

(0 rating)

Boat location

Exact location information is provided after a booking is confirmed.

Your crew

Boat owner
(26 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.
See profile
  • Response rate: 90%
  • Avg. response time: < 24 hours

Things to know

Allowed on boat

kids under 12

  • Free cancellations until 24 hours before the booking start time.
  • Cancellations within 24 hours of the booking start time are non-refundable.
See policy

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.

Learn more