Chesapeake Sailing School


30 Ratings

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$130 54% $70
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In a Nutshell

  • 22 ft. keelboats
  • Sail on the Chesapeake Bay
  • Learn sailboat etiquette
  • Experienced instructors

The Fine Print

Promotional value expires Oct 5, 2011. Amount paid never expires. Limit 1 per person, may buy multiple as gifts. Valid only for option purchased. By appointment only 2 weeks in advance; subject to availability. 7-day cancellation notice required. Must be 16 or older. Must sign waiver. Light soled shoes (tennis shoes) required. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.

Before man conquered his fear of water, he amused himself with dust sports such as pushing boulders off cliffs, wrestling tumbleweeds, and falling in the dust. Opt for an aquatic adrenaline rush with today's Groupon for sailing sessions at the Chesapeake Sailing School in Annapolis. Choose between the following options:

Tide ticklers of any experience level can enjoy a four-hour cruise atop the Chesapeake Bay. Sailors can take the reigns of the keelboat or let the qualified skipper steer as the winds glide them around Annapolis scored by the soothing sounds of splashing waves and mollusk a cappella groups.

The Chesapeake Sailing School grants boat wings to landlubbers with interactive courses aboard the 22-foot Tanzer 22. The one-day 'Try It' Intro to Sailing course gives rookie water wanderers the chance to learn the basics of sailing on the open waves. After registering for the course, students will receive a guide in the mail detailing what to wear and what to expect on the day of the class. With proper aqua attire affixed to the body, students will begin the experience with instruction on tacking—or driving—the boat. From there, rookie sailors will head out onto Chesapeake Bay with the instructor for hands-on-deck learning of sailboat etiquette, safety procedures, and the proper, non-plank-walking ways to dismount a water vessel. A half-hour break for lunch is included.

Chesapeake Sailing School

Affiliates of the American Sailing Association, the instructors at Chesapeake Sailing School strive to keep the Chesapeake's seafaring heritage alive through classes spanning one-day sailing courses to five-day live-aboard cruises. The training fleet ranges from 22-foot boats for basic and intermediate instruction to 38-foot vessels for advanced cruise training. The school's team also assists students obtain their ASA certifications in preparation for careers as Popeye impersonators.

Beyond instruction facilities, Chesapeake Sailing School houses The Tiller Club, which grants members privileges such as unlimited daily use of the school's Tanzer 22 ships. The school’s team also coordinates charter excursions to give vacationers a from-the-water view of the Inner Harbor, St. Michael's the Archangel Church, and the bay's abundant wildlife.

Customer Reviews

30 Ratings

The instruction, both on and off the water, was exceptional and the entire sailing experience was wonderful. I would recommend it to anyone who would like to learn to sail, or who is interested in getting their credentials.
Kathleen S. · October 3, 2013
excxellent instructor -- fun and informative
Jill B. · September 13, 2012
There was a tiny hiccup when our assigned instructor was MIA the day of our class. The school found a solution quickly and easily, and we had a perfect day of sailing! I'd go back in a second.
Beth L. · August 19, 2012
Merchant Location Map
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    7080 Bembe Beach Rd.

    Annapolis, Maryland 21403

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