The Upper Bay Sailing School is an affiliate of Fair Wind Sailing Inc. and offers a wide range of live-aboard, sailing lessons for beginners and experienced sailors alike.

All sailing lessons follow the internationally recognized standards pioneered by the American Sailing Association, the organization with the most experience in developing standards. The ASA is now celebrating its 20th year and the land based part of the Basic Keelboat Sailing Course has been incorporated into the United States Coast Guard Auxiliary's teaching program. The Basic Keel Boat course is approved by the United States Coast Guard and the National Association of State Boating Law Administrators. ASA certification is awarded to all qualifying students. These certificates attest to the student's ability and are recognized world wide by many bareboat charter companies. Sailing lessons are held in the Chesapeake Bay from late April  to November and in the British Virgin Islands from November though July.

Upper Bay Sailing School Instructors are USCG licensed Captains and are expert sailors with many years sailing experience. The principal mission of the Upper Bay Sailing School is to provide a fun filled, supportive, teaching environment for mastering all the theoretical knowledge and practical skills needed to act as skipper or crew on your own boat or to bare boat charter. Three levels of courses are needed to accomplish this...Basic Keel Boat Sailing, Basic Cruising and Bareboat Chartering (Intermediate Cruising). These courses may be taken individually on the weekend, weekday or in any sequential combination. Advanced Coastal Navigation and Advanced Coastal Cruising Courses are also available.

We are also happy to arrange special live aboard programs for teenagers during the summer months. We are happy to match singles with other students. If that cannot be done we will run a class for a single person. Class sizes vary from 1 to 4.

Experienced sailors may challenge lower levels. For example the Basic Sailing standards can be challenged by completing the multiple choice quiz and demonstrating the on-the-water crew and skipper skills. We will do our best to match the class curriculum with your previous experience. Any person enrolling in any course may participate in all aspects of the course without taking the ASA examination. The cost would then be reduced by $50 per course. Young people can learn to sail too. The age limit for the first three courses is 12 years when accompanied by an adult.

Should two people request a yacht all to themselves the cost will be the same as for four people but with a 20% discount. A place in any class can be reserved for $200. 50% is due three months before and the balance is due one month before the class begins.

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Directions to Upper Bay Sailing School, Inc.

From Wilmington/Philadelphia/SE PA and NJ:
Take I-95 S. to Exit 4. Then the new highway # 1 S. Cross the new C & D Canal bridge and in about 5 miles turn right onto the connector for #301 S. Follow 301 S. into Maryland and 5 miles south of the state line turn right onto #290 S. for Galena and Chestertown. (There is a small super market in Galena called Ottwell's if you need supplies). At the stop light in Galena go straight on on #213 S. until you come to Vonnie's restaurant and fruit market. Now turn right on #298 and follow the road to Lynch and Butlertown where you are advised to watch out for speed traps. About 1 mile after the church in Butlertown turn right onto St. Jame's Newtown Rd and within about 0.4 miles turn left onto Green Point Road. Enjoy the drive along one of Maryland's most beautiful country lanes keeping an eye out for deer.

Approximately 65 minutes from Wilmington and the Delaware Memorial Twin Span Bridges and about 1 1/2 hours from Philadelphia.

There is an alternate more scenic but slower route from # 40 at Elkton along 213 S. to Galena crossing the C & D Canal and the Bohemia and Sassafras Rivers. Follow 213 S. by turning right at the stop light in Galena and then follow the directions above.

From Washington/Baltimore/Annapolis:
Cross the Twin Span Chesapeake Bay Bridge and at the #50/#301 split take #301 N. In about 12 miles turn left on #405 to Church Hill. At the junction with #213 turn right and continue to Chestertown. Immediately after the Washington College Campus you can turn right for a shopping center for supplies or left on Morganec Road (#291W) to continue to the marina which is at this point about 6 miles away. Next within 0.5 miles turn right onto #20 S. and then after 200 yds turn right onto #514. In about 3.8 miles the road bears sharply left to Melitola. Ignore this turn and continue straight for about 1.3 miles and then turn right onto #298 N. Within 0.1 miles turn left onto St. Jame's Newtown Rd. Next after 0.4 miles turn left onto Green Point Rd. and enjoy a drive along one of Maryland's most beautiful country lanes but keep a sharp lookout for deer. At the water's edge turn right into the marina.

Approximately 65 minutes drive from Annapolis.

Airport Limousine
The cost for a limousine from either BWI or Philadelphia is about $95 one way for the vehicle independent of the number of people.

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