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The Inn at Perry Cabin in ideally situated on Maryland's Eastern Shore, and is perfectly located for lovers of all things nautical!
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Offshore Sailing School
800-221-4326 Monday - Friday
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Discover sailing with America's #1 Sailing School on site at The Inn at Perry Cabin. Choose from a two-hour sailing lesson with a certified instructor where you take the helm, trim the sails and learn new skills or just sit back and enjoy the breeze.
Turbo-charge your team with the multi-day Corporate Sail-Race Challenge. This unique hands-on program provides proven team-building and leadership results. All instruction is on award winning Colgate 26 sailboats - choice of the U.S. Naval Academy. |  |

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"Let it Ride" Boat Charter
Captain Don Conley
410 758-2069
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This boat is docked at The Inn at Perry Cabin and offers beautiful scenic tours, memorable sunset cruises, fishing on the Bay, specialty events and occasions, corporate or private parties from April 1 through September 30.
Please note the following:
- 72 hour cancellation
- 1/3 charge if not cancelled 72 hours prior
- exclusive charge with group at $60 (i.e. 2 people at regular rate plus $60 additiional if only them)
- can hold up to 28 people
- fishing available must be confirmed by email or phone from Guest Services prior to arrival if weather is not good, no charge if cancelled by Captain
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Herman M. Krentz
Dogwood Harbor
Tilghman Island MD
410 745 6080
Can pick up guests at The Inn at Perry Cabin dock and is an authentic working Skipjack.
Nautical Destinations
410 269 4215
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Offering customized yacht charters for groups visiting the Chesapeake Bay! Specializing in larger private yachts – 74’ sailboat “Schooner Woodwind", 70’ Hatteras “Blue Horizons" and the 85’ 1935 classic wooden yacht “Enticer”, to name a few. Cruising ideas range from “Wine in the Wind” sunset sails, “Take the Helm” team-building or “Cruise to a Crabfeast”! Accommodating groups from 10 to 200 people! |
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