Course 102
Become a Sailor in One Weekend
Prerequisite: None
Boat: Rainbow 24
Days: Sat. - Sun.
Cost: $395 Register Now


Course 102 is by far our most popular course. Conveniently scheduled over a weekend, this introductory course strikes the perfect balance between intensive instruction and relaxed fun on the water. Taught on our famous Rainbow sloops, 102 is the perfect way to start a sailing career.

Students often wonder if you really can learn to sail in a weekend. The answer to that question is a resounding “yes”! The basics of sailing are really quite simple and can be mastered by nearly everyone in two days. Once the basics are mastered, you can practice and refine your skills for a lifetime and never know everything there is to learn. This open-endedness makes sailing an ideal lifetime sport. Whether you learn as a child or as an adult, you can practice for a lifetime and there will always be another challenge to overcome or another technique to master.

Course 102 presents the bare minimum of theory to help you understand what is going on in the boat. You will be sailing during that first session. Building on the introduction, Course 102 provides the basics of sailing vocabulary, principles of sailing, sail trim, steering with a tiller and rules of the road. All of this information is presented in a safe, non-threatening way as you sail your Rainbow under the watchful eye of your on-board instructor.

At the end of the weekend you will be ready to begin your sailing career. The best follow-up to our course is to sail. Sail with friends, crew on a racing boat, rent a Rainbow from us, charter or buy a boat, but the more you sail, the more you will be amazed at how much you learned in your weekend course.

Course 103
ASA Course 101
Three-day New Sailor’s Mini Holiday
Prerequisite: None
Boat: Rainbow 24
Days: Mon. - Wed.
Cost: $525Register Now


An even better way to learn to sail is to take our Course 103. The first two days cover the same introductory content as our famous weekend introductory course, with the addition of a third day of supervised sailing. The additional sailing time helps reinforce your new sailing skills and affords more time ashore to explore the Annapolis area.

Course 103 is a favorite for combining with overnight accommodations into one of our convenient learning vacation packages.

Course 105
ASA Course 101
Five-day New Sailor’s Vacation Course
Prerequisite: As with Course 102, there are no formal prerequisites for these introductory courses.
Boat: Rainbow 24
Days: Mon. - Fri.
Cost: $695Register Now


This course is the all-time favorite of students and instructors alike. Similar to Course 103, but providing three full days of supervised sailing with no instructor aboard, this course comes close to being the ideal learning experience on the water. Combined with one of our accommodation packages, a week sailing in Annapolis is the ideal vacation.

Course 105 is the only beginner’s course we recommend for students interested in either ASA or U.S. Sailing’s Basic Keelboat Certification.

Course 104
Learn to Sail on a Hunter 36
Prerequisite: None
Boat: Hunter 36
Days: Sat. - Sun.
Cost: $525 Register Now


Course 104 is an introductory course designed for beginners with no prior sailing experience, but who do not want to learn on a small keelboat. The course content of 102 has been adapted to a larger cruising boat. This course is especially useful for first time sailors starting out on a cruising boat or beginners who will be crewing on larger boats. Classroom time is kept to a bare minimum and hands-on sailing is emphasized. The focus of Course 104 is on basic sailing skills. The small class size and low student to instructor ratio ensures maximum learning and an enjoyable first sailing experience.

Course 132
Become a Sailor in One Weekend (Advanced)
Prerequisite: Previous sailing or power boating experience.
Boat: Hunter 36
Days: Sat. - Sun.
Cost: $525Register Now


Course 132 covers the same content as 102 but is designed for people with previous sailing or boating experience. This course is taught entirely on board a cruising auxiliary and can be tailored exactly to the needs of the student. Many adults, taking up sailing again after learning as children, find this course the perfect refresher to re-awaken long dormant skills.

Course 217
ASA Course 103
Five-day Sailing Vacation Course
Prerequisite: Courses 217 require a minimum of two people per boat. At least one person should have completed course 102, 103, 104 or 105, or have equivalent small boat sailing experience.
Boat: Hunter 36
Days: Mon. - Fri.
Cost: $2,900 / boat*


For many recreational sailors the ultimate sailing vacation is a live-aboard cruise. Our flotilla cruises (a flotilla is a group of boats cruising together) offer the best introduction to cruising available for families and couples. Designed for sailors with some experience, our flotillas offer a five-day tour of some of the best cruising areas on the Bay. We provide the boat and the experience and local knowledge of an on-board instructor. Students provide their own bedding, food and enthusiasm. At the end of each day’s sail the instructor moves aboard a lead boat for the night, leaving the students with the privacy of their own boat. The usual cruise plan affords the experience of anchoring out two nights and spending two nights at marinas. Many families find this experience so rewarding they return summer after summer for an unforgettable vacation together.
* You may bring up to 6 students for the one tuition. You provide provisions and linens.

Click here for more course information (WORD DOC)

Course 222
Weekend Introduction to Cruising
Prerequisite: Students should have some sailing background and some general knowledge of boats
Boat: Hunter 36
Days: Sat. - Sun.
Cost: $550 / person*


This course is a shortened, weekend version of our five-day cruising course.
Students should have some sailing background and some general knowledge of boats. In two days and one night aboard, students can sample the joys and challenges of living and cruising on a sailboat. Many peaceful and attractive anchorages are attainable in a one-day sail from Annapolis and Course 222 seeks to take maximum advantage of this fact. Fully provisioned and equipped boats and friendly, knowledgeable instructors make Course 222 a popular weekend course.

Click here for more course information (WORD DOC)

Note: Students may book as singles, but we may require a minimum enrollment to run cruising courses.
* Price includes all provisions and linens.

Course 225
ASA Course 103
Bay Country Cruising Course
Prerequisite: Students should have some sailing background and some general knowledge of boats
Boat: Hunter 36
Days: Mon. - Fri.
Cost: $1640 / person*


Our Bay Country Cruising Course is designed for experienced small boat sailors who want to experience the cruising lifestyle. For one low tuition cost we provide it all: the boat, provisions, bedding and the round-the-clock services of an on board instructor. While this may sound like a luxury vacation, it is really a very intense learning situation. Students experience all aspects of cruising, from planning the itinerary, meal planning and shopping, to navigation and chart reading. Many of our students use this course to “put it all together” after taking lower level courses. This course is a tremendous confidence builder and a perfect transition from daysailing to cruising.

Each course is different and the instructor and students decide where they wish to go and whether marina hopping or anchoring in quiet coves is the plan. In the course of the five days and four nights aboard, students will experience all aspects of cruising, from choosing the sail plan for the day to engine checks; from cooking on board to anchoring safely and securely in a protected cove while a thunderstorm roars overhead.

Many students use this course to qualify for either ASA or U.S. Sailing's Basic Cruising Certification.
* Price includes all provisions and linens.

Click here for more course information (WORD DOC)

Note: Students may book as singles, but we may require a minimum enrollment to run cruising courses.

Course 313
Preparation for Handling a Cruising Auxiliary
Prerequisite: Several years of small boat sailing experience and good basic sailing skills.
Boat: Hunter 36
Days: Sat. - Sun.
Cost: $525Register Now


The focus of Course 313 is on the things that make a cruising boat more complex than a daysailer. Issues like size and maneuverability, electrical and engine systems and all other systems needed for even a weekend aboard dominate this weekend course. Experienced small boat sailors “moving up” will find this information invaluable.

Course 322
Coastal Navigation and Piloting
Prerequisite: Good boating skills, including familiarity with the basic use of a nautical chart.
Boat: Hunter 36
Days: Sat. - Sun.
Cost: $525Register Now


Course 322 presents a perfect balance of theory and practice. Students will review the basic concepts, assumptions and conventions of coastal navigation. Chart reading, plotting dead reckoning courses and the impact of electronic aids to navigation will all be thoroughly explored. At least half the class time will be spent underway, putting the skills taught in the classroom into practical application.

Course 335
ASA Course 104
Preparation for Bareboat Chartering
Prerequisite: Course 225 or a strong sailing background with some cruising experience.
Boat: Hunter 36
Days: Mon. - Fri.
Cost: $1045Register Now


Most new sailors seem to have a plan, either immediate or long term, to bareboat charter in some exotic location such as the Caribbean or the South seas. Course 335 can be a major step in realizing that dream. This course is for sailors with big boat experience who are looking forward to chartering. The mix of theory and practice concentrates on docking under power, basic navigation, engine checks and basic troubleshooting— areas that plague fledgling charterers. What to look for on taking command of a chartered boat, how to organize a crew, and some basic emergency steps to take when things don’t work out quite as planned are also touched upon.

Students are graded on a specific list of skills. This grading sheet is kept on file so that potential charter companies can call us and check your references at any time. Having such a third party source of information on your sailing resumé can go a long way toward helping to secure that first charter.

Course 335 may be used to qualify for either ASA or U.S. Sailing’s Bareboat Cruising Certification.season.

Please contact us toll free at
800.638.9192 or (410) 267-7205

Email: info@annapolissailing.com

>> Register Online Now! <<


We Make Sailing Fun!