Starboard Sailing Classes
All Classes
All of our classes are American Sailing Association (ASA) certified. This ensures you are getting quality certified sailing instruction recognized around the world. Our instructors are US Coast Guard licensed Captains and certified by the ASA. The quiet, well protected waters of Middle River are perfect for beginning sailors while just a short sail from the greater Chesapeake Bay for practicing your advanced sailing skills.
Training Vessels
Starboard Sailing only uses cruising sailboats similar to what are chartered all over the world. These boats have large comfortable cockpits and cabins. Clean and well maintained, these boats are fully equipped with wheel steering, inboard diesel engines and electronics.
Basic Sailing and Coastal Cruising (ASA 101/103)
If you are looking for an in-depth (four days) basic sailing class, this is the one for you. Want to buy a boat? Want to charter a cruiser? The Basic Sailing and Coastal Cruising class will take you from a sailing novice to a competent skipper. This course covers the basics such as sailing theory, terminology, and rigging the boat. You then progress to boat systems, navigation and regulations. You will learn tacking, jibing, how to trim the sails, steer a course, read the wind and waves, and dock the vessel. You will literally “learn the ropes” while under the direct supervision of your patient captain.
Course fee: $1350
Coastal Cruising (ASA 103)
This is our three-day intermediate sailing course for those who are previously certified sailors or have some experience sailing smaller watercraft. You will learn sail trim techniques, seamanship, navigation strategies, weather, diesel engine operation and systems. You will practice safe anchoring, mooring and docking. You will gain experience with sailing maneuvers such as reefing, heaving to and multiple man overboard techniques.
Course fee: $950
Coastal Cruising and Bareboat Chartering (ASA 103/104/IPC)
Coastal Cruising and Bareboat Chartering is designed to introduce you to handling a larger cruising yacht and preparing you for chartering a boat for an extended vacation cruise. Our course includes the ASA International Proficiency Certificate (IPC) that is required by many European charter companies for skippering their boats. You will spend 4 days and 3 nights aboard the boat pulling into secluded anchorages or marinas after the day’s sail. You and your crewmates will provision the boat for the cruise as well as planning and navigating to the next day’s destination. During your trip, you will learn coastal navigation, boat systems, electronics, and meteorology. Advanced sailing skills you will acquire include anchoring, mooring, docking, sail trim, and heavy weather sailing.
Course fee: $1750
Bareboat Chartering (ASA 104/IPC)
Bareboat Chartering is for experienced sailors wanting the certification to charter a cruising sailboat anywhere in the world. Our course includes the ASA International Proficiency Certificate (IPC) that is required by many European charter companies. This extensive course is 3.5 days and 3 nights aboard the training vessel, dropping anchor or tying up to a slip each evening. The crew will learn to provision and plan the extended trip. You will learn how to operate all of the boat systems including the marine electronics.
Course fee: $1250
Cruising Catamaran and Bareboat Chartering (ASA 104/114/IPC)
Cruising Catamaran and Bareboat Chartering is a 3.5 day, 3 night, learning adventure aboard a cruising catamaran. If you ever dreamed of chartering a catamaran for your family and friends, you can do it! This class teaches the special features, systems and sailing characteristics of today’s cruising cats. You will hone your skills at sailing, motoring, navigation and seamanship aboard a late model multihull. Our course also includes the ASA International Proficiency Certificate (IPC) that is required by many European charter companies.
Course fee: $2050
Cruising Catamaran (ASA 114)
This is a cruise and learn, live-aboard voyage on a full-size catamaran. ASA114 Cruising Catamaran is a 3 day, 2 night, cruise. You will learn the special features, systems and sailing characteristics of today’s cruising catamarans. You will hone your skills at sailing, motoring, anchoring and docking aboard a late model multihull.
Course fee: $1650
Advanced Coastal Cruising and Navigation (ASA 105/106)
This is a comprehensive class focusing on higher level sailing, navigation and seamanship skills. This voyage is 5 days, 4 nights of long-distance sailing and navigation training. You will be keeping watch at the helm on a night passage to destinations unknown.
Our navigation class teaches both traditional and electronic navigation. The navigation certification includes calculating and applying charting, dead reckoning, deviation, current and leeway to your voyage. Your navigation training is applied on the water, as you learn.
Course fee: $1950
Docking (ASA 118)
Ask any sailor and they will tell you that docking is the most stressful maneuver in sailing. In our docking class, you will learn many new techniques to reduce the stress level of leaving and arriving in the slip. You will practice bow in, stern to, spring out as well as parallel docking. This one-day class is offered as a skipper’s private instruction or as the ASA 118 docking endorsement.
Course fee: $450
Book a Class
Check available dates to book a class today. Follow the link below!

“I want to thank you for such a thorough and enjoyable 3-day class. Your patient, knowledgeable, and encouraging instruction increased my confidence in being a skillful crew member and skipper. I enjoyed my time with you and I’m thrilled to now be a member of the American Sailing Association thanks to your expert guidance!”
— Carolyn B.