Chesapeake Bay



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~ A Cut Above ~



Intensive sail training on Chesapeake Bay 
aboard an
 Island Packet Sailing Yacht

Professional Captain 
USCG Licensed & ASA Instructor Certified

Basic Keelboat Sailing (ASA 101) and Basic Coastal Cruising (ASA 103) are each four-day live aboard courses in which you'll learn to competently operate a 30+ foot cruising sailboat. At completion of both courses, you'll be able to skipper a boat of this size in coastal and bay areas during daylight. 

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Intermediate Coastal Cruising (ASA104): Learn extended cruise planning, equipment preparations, navigation, weather analysis, port-entry, anchoring and more while sailing to various destinations in Chesapeake Bay. 

You may live aboard the yacht during all courses

Request Additional Information

Online Course Registration

You may register for any course online
or email to
 or call us at 410-639-7030

Descriptions of Books can be found at our School Store

Four Day Course
Tuition: $975 + ASA Fee of $39
Includes Books & ASA Certification
2019 ASA101 Schedule
May 4-7 June 11-14 Sept 3-6
May 12-15 Jun 29-July 2 Sept 19-22
May 18-21 Jul 5-8 Oct 4-7
Women's Class
May 25-28 Jul 20-23
June 7-10
Women's Class
Aug 10-13 Oct 18-21
Four Day Course
Tuition: $975
Includes Books & ASA Certification
2019 ASA103 Schedule
May 8-11 July 9-12 Sept 7-10
May 29-Jun 1 July 24-27 Sept 23-26
June 15-18 Aug 14-17 Oct 22-25
June 20-23
Combined ASA101-103 Courses
Eight Day Course
Tuition: $1650 + ASA Fee of $39
(This is a $300 discount from the regular course tuitions)
Includes Books & ASA Certifications
2019 ASA101-103 Schedule
May 4-11 July 5-12 Sept 3-10

May 25-Jun 1

July 20-27 Sept 19-26

Jun 11-18

Aug 10-17 Oct 18-25
Five Day Cruise- Rock Hall to Rock Hall
Tuition: $1500
Includes Books, Onboard Food & ASA Certification
2019 ASA104 Schedule
May 12-16 July 13-17 Sept 11-15
Jun 2-6 Jul 28-Aug 1 Sept 27-Oct 1
Jun 19-23 Aug 18-22 Oct 26-30

Six-day, 130 mile one-way cruise from Norfolk, VA to Rock Hall, MD aboard our IP40 ocean sailing yacht for ASA104 certification.
 June 20-25. Fee $1600

Combined ASA103-104 Courses
Nine Day Course
Tuition: $2175
(This is a $300 discount from the regular course tuitions)
Includes Books, five days of Onboard Food & ASA Certifications
2019 ASA103-104 Schedule
May 8-16 July 9-17 Sept 7-15
May 29-Jun 6 Jul 24-Aug 1 Sept 23-Oct 1
Jun 15-23 Aug 14-22 Oct 22-30
Combined ASA101-103-104 Courses
13 Day Course & Cruise- Rock Hall to Rock Hall
Tuition $2850
plus ASA Fee of $39
(This is a $600 discount from the regular course tuitions)
Includes Books, five days of Onboard Food & ASA Certifications
2019 ASA101-103-104 Schedule
May 4-16 July 5-17 Sept 3-15
May 25-June 6 Jul 20-Aug 1 Sept 19-Oct 1
June 11-23 Aug 10-22 Oct 18-30


  • With adequate previous experience, students taking the ASA103 course may challenge ASA101 for an additional fee of $250 to cover the cost of books and ASA testing plus the $39 ASA membership fee. Students seeking to challenge ASA101 will be asked to submit a description of their experience in advance for approval by our teaching staff.

  • You may board the boat and sleep aboard the  evening before your course starting date and until the end of your course.

  • Special dates can be arranged for groups of four or more students who cannot make any of the above scheduled dates.

  • Students can receive the combined course discounts above while choosing their own class dates.  To qualify for the combined discount: (1) Register for all classes prior to the first class on one registration form.  (2) Classes that you choose are in the same calendar year.  (3) Final payment is due for all classes 60 days before the start of first class, or upon class registration if less than 60 days prior to start of first class.

ASA118 Docking Course 

Two Day Course
Tuition: $550
Includes Books & ASA Certification

2019 ASA118 Docking Schedule
Apr 30-May 1 Jun 27-28 Aug 24-25
May 2-3 Jun 29-30 Aug 31- Sept 1
May 23-24 July 18-19 Sept 16-17
Jun 8-9 Aug 3-4 Oct 5-6
Jun 24-25 Aug 8-9 Oct 15-16

Docking a large cruising boat safely and without damage can be a daunting task especially when the wind blows 20 knots. Bow sprits and marriages are often broken or severely damaged in the process. We've designed a hands-on docking practice program on Island Packet 32 foot cruising yachts to help all sailors, whether experienced or beginner, to learn the best methods for docking.



Private Docking Instruction
$1050 per day for a group of two, three or four students.
Two days are required if ASA118 Certification is desired

Due to insurance restrictions, we cannot conduct docking instruction on boats other than our own.  However, we are happy to schedule private docking instruction on one of our Island Packet 32s for two to four students in a group. Often couples schedule one day of private docking instruction with a specific focus on their needs and they find this to be sufficient.  If the group desires ASA118 certification, two back to back days must be scheduled in order to cover all of the skills and examination required for certification.  


Just Go Sailing 

 $250 per person per day

2019 Schedule
Sept 7 Sept 14 Sept 21
Board boat at 0900; no overnight accommodations

For ASA 103 and above graduates, we've added a new one-day "Just Go Sailing" opportunity to round out our sailing season and take advantage of the Fall weather in Chesapeake Bay.  The emphasis will be on enjoying a day of sailing as well as practicing and refreshing your skills before the long winter's hibernation under the guidance of one of our exceptional instructors.  We will be aboard S/V NAVIGATOR, our Island Packet IP40 ocean sailing vessel. Four sailors maximum per class. ASA111 Certification included.

Request Additional Information

Online Course Registration


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Copyright The Maryland School of Sailing & Seamanship, Inc., All rights reserved.
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