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ASA, US-Sailing & Other Certified Sailing Schools in Maryland

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ASA & US-Sailing Certified Schools at Annapolis, Havre de Grace, Rock Hall, Baltimore, Grasonville, Solomons, St. Michaels, and Tracey's Landing  in Maryland..

USCG Captain's License Online

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MARINERS LEARNING SYSTEM (MLS) ONLINE- USCG Approved Online Captain's and Masters License Study Packages, Home Study Guides & FCC Online Tests - Located in Pennington NJ, Mariners Learning System provides U.S. Coast Guard Certified Licensing Courses with their flexible online training. Auxiliary Sailing & Towing endorsements are also available.

NauticEd Online Sailing Education

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Take online theory sailing courses with NauticEdwith two free sailing courses and sailing resume, and then use the skilled in-house sailing instructors from the NauticEd affiliated sailing schools in the U.S., Canada, Europe, Australia & around the world to gain practical sailing experience and confidence. Once you pass the courses and practical training, you'll be awarded with a NauticEd Sailing Certification with Verified Practical Competency. Yacht Charter Companies worldwide accept and acknowledge the NauticEd Sailing Certification. Read more..

Annapolis Sailing School - Annapolis MD

annapolis sailing school

Established in 1959, Annapolis Sailing School is one of the oldest sailing school in the country and offers a whole range of courses and programs inclusing ASA certification programs for people of all ages. The schools instruction, known as the Annapolis Way, maximizes hands-on, on-the-water instruction, while providing students the necessary amount of theory. This allows students to learn skills physically while also giving students the theoretical basis to continue to learn on their own. The boat used, The Rainbow 24’ which is the best boat around for basic sailing instruction. The Annapolis Sailing School, in coordination with famous boat designers Sparkman & Stephens, built it specifically for that purpose.

Basic Courses

  • The Basic Sailor (Module A & B)
  • Basic Sailor Certified - ASA 101 (Modules A, B & C)
  • The Basic Sailor Certified - Accelerated - ASA 101
  • The Complete Sailor (Modules A, B, C, D & E)

Cruising Courses

  • The Advanced Sailor Certified ASA 101 & 103
  • Cruising Boat Basics
  • Cruising Boat Handling
  • Discover Cruising
  • Basic Coastal Cruising - Daytime - ASA 103
  • Basic Coastal Cruising - Overnight - ASA 103
  • Bareboat Cruising Certification - ASA 104
  • The Skipper - ASA 103 & 104


Other Programs

  • Evening Sail
  • Boat Rentals

Baysail School & Yacht Charters - Havre de Grace MD

bay sail school

Located at Havre de Grace MD, Baysail School & Yacht Charters offers professional sailing instruction as well as a selection of recent model yachts for charter. BaySail has been repeatedly honored by the American Sailing Association (ASA) as a School of the Year. From beginner through Bareboat Charter Certification and navigation, BaySail offers a full range of ASA certified courses designed to enhance your skills and love of sailing. The school is very close to Philadelphia and Baltimore. BaySail also offers SailTime, a fractional sailing membership that’s the newest way to sail the Chesapeake Bay.

ASA Courses

  • 1-Day Introduction to Sailing
  • Basic Sailing Course - (101)
  • Basic Coastal Cruising (Learn To Charter Course) - (103)
  • Bareboat Chartering Certification Course - (104)
  • Bare Boat And Catamaran Combo Course (104 - 114)
  • Five-Day Combo Course - (103 & 104)
  • Coastal Navigation Course - (105)
  • Advanced Coastal Cruising - (106)
  • Docking Course - (118)


Other Courses

  • Customized Sailing Courses
  • Women Only Classes (101 & 103)
  • Private Instruction

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Blown Away Sailing - Rock Hall MD

blown away sailing

Located at the historic Rock Hall MD, Blown Away Sailing offers ASA programs and certifications form introductory sailing to advances courses. The school is at the Haven Harbor Marina which is also a resort destination. . In addition to a full array of marine services, Haven Harbor offers lodging at the High Tide Inn and a restaurant and bar is serves up tasty fare on the weekends. All of the Captains are licensed by the United States Coast Guard and certified by the American Sailing Association.

ASA & Other Courses

  • Intro to Sailing
  • Private Instructions
  • ASA 101, 103, 104, 105, 106

Cruise Annapolis - Annapolis MD

cruise annapolis

Located at the historic maritime quarter of Annapolis MD, Cruise Annapolis is a chartere management company and also offers ASA sailing courses and c certification. For charters, you can experience the best new sailing yachts from Jeanneau and catamarans from Fountaine Pajot. The Chesapeake Bay is well-known as an outstanding waterway for cruising. Protected waters, great anchorages, gorgeous natural scenery, bountiful seafood, unique, historic towns and villages, and a forgiving bottom make the Chesapeake an excellent choice for sailors, novice and expert alike.

ASA & Other Programs

  • Learn to Sail
  • Catamaran Courses
  • Private or Group Instruction
  • Yacht Charters

Delmarva Sailing School & Charters - Rock Hall MD

delmarva sailing school charters

Located at Rock Hall MD, Delmarva Sailing School & Charters is an American Sailing Association affiliated sailing school and a charterer of premier sailboats. The school teaches and certifies the students to ASA standards, and offers the entire series of ASA sailing classes for inland, near coastal, and ocean water, from beginner to advanced level. Delmarva Sailing School & Charters sailing classes are all taught in a live aboard approach, where the student is totally immersed into learning how to sail. During classes students typically visit locations like Annapolis, Saint Michaels, Galesville, the Magothy River, the Rhode River, Solomons Island or other destinations as they learn to sail.

ASA Courses

  • ASA 101, 103, 104, 105, 106, 107, 108, 114, 118, 119
  • ASA 101 Challenge
  • Practice Sail Program
  • Home Study

mls boat captain

J World Annapolis - Annapolis MD

j world annapolis

Established in 1992, J World Annapolis has been providing the very best in coaching and instruction to new and experienced sailors from around the world. J World prides itself on being known as the performance sailing school, where you learn much more than the basics of sailing. The instructors are standouts within the sailing instruction community, with years of training and sailing experience. J World’s Fleet of J Boats provides the ultimate classroom environment. They are fast, responsive, and a blast to sail providing you with vital feedback after adjustment. Their design allows students to easily transfer their new skills to other boats of any size.

US Sailing Certifications

  • Basic Keelboat
  • Basic Cruising
  • Bareboat Cruising
  • Coastal Navigation
  • Coastal Passage Making
  • Celestial Navigation
  • Offshore Passage Making

Sailing Fundamentals

  • TrySail - 3 Hour Group Lesson
  • Sailing Fundamentals 2-Day 
  • Basic Keelboat / Sailing Fundamentals 5-Day
  • Basic Keelboat / Sailing Fundamentals 3-Weekend

Performance Sailing

  • Performance Sailing 2-Day
  • Performance Sailing 5-Day
  • Performance Sailing 3-Weekend


  • Introduction to Racing 5-Day
  • Advanced Racing 5-Day
  • Introduction to Racing 2-Weekend
  • Spinnaker & Race Boat Handling
  • Crew Training
  • Thursday Night Racing


Big Boat Racing

  • Big Boat Racing Week
  • Annapolis to Newport Race
  • Newport to Annapolis Passage
  • ARC Bahamas

Cruising / Liveaboard

  • Basic Cruising/3-Day
  • Bareboat Cruising/5-Day Liveaboard
  • Cruising Boat Handling
  • Coastal Passagemaking/4-Day Liveaboard

Other Facilities

  • Private Instruction
  • Chartering

Mid-Atlantic Sailing School - Baltimore MD

mid atlantics sailing school

Established in 2014, Mid-Atlantic Sailing School is located at Baltimore MD and offers American Sailing Association (ASA) Sailing Lessons at the ASA Certified Baltimore Sailing School located in Downtown Baltimore. The school is affiliated with the Narragansett Sailing School, which is based in Narragansett Bay, Rhode Island.

ASA Courses

  • ASA101 Basic Sailing
  • ASA103 Basic Cruising
  • ASA104 Intermediate Cruising
  • ASA105 Coastal Navigation
  • ASA106 Advanced Coastal Cruising

Maryland School of Sailing & Seamanship - Rock Hall MD

maryland school of sailing

Maryland School of Sailing offers a full range of courses from Basic Sailing lessons through Ocean Training Cruises on Island Packet yachts in Chesapeake Bay, Virgin Islands and the Atlantic Ocean between Norfolk, Bermuda and the Caribbean. The school also teaches Docking Practice classes and live online Coastal Navigation and Celestial Navigation classes. Students can earn certification from the American Sailing Association (ASA) The school is located near Rock Hall MD on the Eastern Shore of Chesapeake Bay.

ASA Courses

  • ASA 101, 103 & 104
  • Online Coastal Navigation 2018 (ASA105)
  • DVD Coastal Navigation Lectures (ASA105)
  • Online Celestial Nav 2018 (ASA107)
  • Online Electronic Navigation 2018
  • Coastal Navigation Home Study (ASA105)
  • Celestial Navigation Home Study (ASA107)
  • Optional Challenge Exam (ASA105 or ASA107)
  • ASA118 Docking Course


Other Courses

  • Introduction to Sailing
  • Private Docking Instruction
  • Combined Courses
  • DELMARVA Circumnavigation
  • Ocean Training Cruises
  • Private and Custom Classes

R&R Charters and Sail School - Grasonville MD

RR charters and sail school

Located at Grasonville MD, R&R Charters & Sail School offers basic to advanced sailing courses on the school’s Hunter 28 and Beneteau Oceanis 41 boats. Each student will enjoy a personal learning experience, as they master the knowledge and skills to feel confident in their sailing abilities. The maximum of four students per boat gives all students the greatest amount of boat handling experience on the water.

ASA Courses

  • ASA 101, 103, 104, 105, 106, 107, 118, 119, 120
  • ASA Challenge Classes
  • Become a Sail Instructor


Other Programs

  • State Safe Boater Certification
  • USCG License (Navigation Rules, Piloting/Plotting, Deck General)

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Sail Solomons - Solomons MD

sail solomons

Sail Solomons is an ASA-Affiliate sailing school and offers ASA certification courses, taught in a live-aboard environment to fully immerse you in the cruising experience. ASA certification is recognized internationally and you can begin to charter the globe. The school also has a full complement of tailored and private instruction, including marine systems and electronic navigation. Sail Solomons was recognized as the ASA Outstanding School for 2008 and 2009. Also the instructors were awarded ASA Outstanding Instructor for 2007 and 2009. Sail Solomon offers top quality sailing instruction and luxury yacht charters on the Chesapeake Bay, Caribbean, and Mediterranean. The experienced Captains provide instruction, charters, deliveries and marine consulting.

ASA Courses

  • ASA 101, 103, 104, 105, 106, 114, 118, 119


Other Courses & Programs

  • Introduction to Sailing
  • Learn to Sail
  • Sailing Tune-Up
  • Private Instruction
  • Upgrade to a Larger Boat Course
  • Instruction for Couples to Sail Safely in Harmony
  • Electronic Navigation Courses
  • Systems Courses
  • Yacht Charters
  • Sailing Club
  • Yacht Delivery & Consultancy

Sailing Academy at the Inn at Perry Cabin - St. Michaels MD

inn perry cabin sailing academy

Whether you’re looking for a relaxed introduction to reef sailing or you want to zip through your American Sailing Association certificates, the Sailing Academy offers expert tuition for you. Whichever course you choose, the Sailing Academy will be a highlight to your stay at Inn at Perry Cabin by Belmond. Step straight from the manicured lawns of the Inn to the moorings on the Miles River.

ASA & Other Courses

  • Learn to Sail in a Weekend
  • Learn to Sail Basic Keelboat
  • Learn to Sail Basic Keelboat & Cruising

The Sailing Academy - Tracey's Landing MD

the sailing academy maryland

Located at Tracey's Landing MD The Sailing Academy (formerly known as Capitol Sailboat Club) offers sailing and Bluewater cruising classes to participants including basic and advanced ASA courses. Although the academy is not a boat rental facility, the school makes the boats available to students and can be chartered for a day, or join the Sailboat Club to have regular access to the fleet. As you progress, you can move up to larger boats. The Sailing Academy was started by cruising sailors and is cruising focused. The Sailing Academy is centrally located on the western shore of the Chesapeake Bay at Herrington Harbor Marina.

ASA & Other Courses

  • One Session Try-Sailing
  • Fundamental Power Course (Six lessons which are conducted on the water, plus one online seminar)
  • Sailing Basics- Start Here
  • ASA 101, 103, 104

You may also read: Online Sailing Certifications & RYA Skipper Theory