Michelle Gregg
Sep 8, 2025
My husband and I took the basic keelboat course over the weekend. It was amazing. I am new to sailing and Captain John was so patient and explained things over and over. I appreciated the hands on aspect of learning. We didn’t sit in a classroom very long at all. We were in the sailboat actually sailing almost immediately. We are in the process of buying a sailboat and Captain John made everything he taught applicable to the experiences we would have on our new boat. We found the course to be so helpful we are signing up for more courses.
Sydney Swan
Jul 6, 2026
Best Place Ever !The Staff are welcoming and friendly. The yachts were all in great working shape and seemingly very well cared for.
Jonathan Tagg
Jul 4, 2026
Sailtime was a great experience, and our teacher Karen was incredibly patient and competent. We loved our class and look forward to the next one in July!
Judd Mendelson
Jun 29, 2026
took the asa 101 sailing course. great experience. knowledgeable instructor
Jeffrey Davis
May 4, 2026
Capt Tom was great in his role as instructor - fully knowledgeable and experienced, while very keen to meet each of us at our individual level of interest and skill. The boat was in excellent condition, and safety was prioritized. The course was quite good for anyone preparing to charter / own a catamaran.
Matt Waters
Dec 29, 2025
Jennie and husband (John?) were exceptionally interesting (having traveled the world) and knowledgeable (having worked at and with multiple global sailing/charter companies).My wife and two daughters did the basic 101 sailing school and spend about 3 hours out on Willoughby Bay, located just off of the Hampton Roads Bridge Tunnel (headed East on Interstate 64 from Hampton towards Norfolk).We went into the session with no idea what to expect (we won tickets at an auction) and came away with a confidence and basic know-how-to-sail confidence. We were so pleased that we are looking at possibly joining the SailTime Membership, my daughter is investigating sailing jobs in the states and Europe.I would highly encourage SailTime VA to local-area residents and others who may be visiting. Also located right under their offices is a great seafood restaurant with around 15 tables tops, that you should plan on sticking around for after your sailing adventure.Cheers,MW
Mrs. Gregg
Sep 25, 2025
Captain John is the best! He is very knowledgeable and patient.
Tyler Heerwagen
Sep 21, 2025
Great source for Sailing Training. Good collection of boats to learn and sail on and good selection of instructors and staff. Good sailing grounds as well. Quick access to open water with consistent winds. Recommend!
Michelle Gregg
Sep 8, 2025
My husband and I took the basic keelboat course over the weekend. It was amazing. I am new to sailing and Captain John was so patient and explained things over and over. I appreciated the hands on aspect of learning. We didn’t sit in a classroom very long at all. We were in the sailboat actually sailing almost immediately. We are in the process of buying a sailboat and Captain John made everything he taught applicable to the experiences we would have on our new boat. We found the course to be so helpful we are signing up for more courses.
Sydney Swan
Jul 6, 2026
Best Place Ever !The Staff are welcoming and friendly. The yachts were all in great working shape and seemingly very well cared for.
Experience the confidence to set sail on the open water during a relaxed excursion with gorgeous Chesapeake Bay as your backdrop. Located conveniently in Norfolk, VA, Norfolk Sailing is an esteemed local provider of sailing experiences and group outings on the water.
Under the guidance of an experienced instructor, you and your group can learn the ins and outs of coastal navigation. Rest assured that our certified instructors know how to maintain a safe and relaxed setting that puts the beauty of the bay on full display!
Our Norfolk sailing charters cater to both novices and seasoned sailors. Sailing experiences can range from tame and passive to an action-packed cruise. Our renowned sailing lessons are ideal for those ready to master the art of sailing!
Master the art of sailing with personalized private instruction in Norfolk, Virginia. Whether you're a novice eager to learn the basics or an experienced sailor looking to refine your skills, our tailored sessions are designed to meet your individual needs. Enjoy the flexibility of learning on our boat or yours, with expert guidance from our seasoned instructors. Located at Willoughby Marina, our private instruction offers a unique opportunity to navigate the beautiful waters of the Chesapeake Bay. Gain confidence and competence as you learn essential boating skills in a supportive and engaging environment. Our instructors are committed to providing a comprehensive learning experience that is both educational and enjoyable. Book your private instruction today and embark on a journey to becoming a proficient sailor. With our expert guidance, you'll be navigating the waters with ease and confidence in no time.
Experience a delightful 3-hour charter, available during the day or at sunset, aboard our luxury catamaran on the Chesapeake Bay. Relax and enjoy the serene waters with family and friends, or celebrate a special occasion in style. This private charter offers a unique way to explore Norfolk, VA, while enjoying a leisurely cruise. Your voyage will be guided by a US Coast Guard-certified Captain and a professional deckhand.
The IQC 201: Basic Keelboat Instructor Qualification Clinic is the first step in becoming a certified sailing instructor with the American Sailing Association. This clinic is designed to equip you with the skills and knowledge necessary to teach the ASA 101 Basic Keelboat course. Over two days at the Willoughby Marina, you will undergo rigorous training and evaluation to ensure you meet the high standards required for certification. Join us in Norfolk, VA, and take the first step towards a rewarding career in sailing instruction.
The ASA 202 is a one-day clinic designed to verify your ASA 102 Basic Keelboat Sailing 2 Instructor qualification. Your competency will be compared with the ASA’s internationally recognized Standards. This is not a course of instruction as such. While you will gain valuable knowledge from your experience in the Clinic, your competence as a sailor and a teacher is presumed; you are attending to become certified to instruct.
The IQC 203: Basic Coastal Cruising Instructor Qualification Clinic is an essential step for aspiring sailing instructors. This clinic is part of the ASA keelboat training system and certifies individuals to teach the ASA 103, Basic Coastal Cruising course. Participants will be evaluated on their knowledge, skills, and teaching abilities, ensuring they meet the high standards required for ASA certification.
The IQC 204: Bareboat Cruising Instructor Qualification Clinic is an intensive one-day program designed to certify individuals to teach the ASA 104, Bareboat Cruising course. This clinic is part of the ASA keelboat training system and focuses on evaluating the candidate's knowledge, skills, and teaching abilities. Participants will undergo rigorous assessments, including a written examination, oral examination, and on-the-water skills demonstration, all conducted by a certified ASA Instructor Evaluator.
The IQC 205: Coastal Navigation Instructor Qualification Clinic is a comprehensive one-day program designed to certify individuals to teach the ASA 105, Coastal Navigation course. This clinic is the fourth instructor-level clinic in the ASA keelboat training system, focusing on classroom-based learning without on-the-water evaluations. Participants will be evaluated on their knowledge, skills, and teaching abilities, ensuring they meet the high standards required for ASA instructor certification.
The IQC 206: Advanced Coastal Cruising Instructor Qualification Clinic is a specialized program designed for aspiring sailing instructors. This clinic is part of the ASA keelboat training system and focuses on certifying individuals to teach the ASA 106, Advanced Coastal Cruising course. Participants will gain the skills necessary to instruct others in advanced coastal cruising, including night-time sailing techniques.
The IQC 214: Cruising Catamaran Instructor Qualification Clinic is a comprehensive one-day program designed for aspiring sailing instructors. This clinic certifies candidates to teach the ASA 114, Cruising Catamaran course, ensuring they possess the necessary skills and knowledge to instruct others effectively. Participants will undergo rigorous evaluations to demonstrate their proficiency in both theoretical and practical aspects of catamaran sailing.
The IQC 216: Dinghy Endorsement Instructor Qualification Clinic is a one-day intensive program designed for aspiring sailing instructors. This clinic evaluates your knowledge, skills, and ability to teach the ASA 116 Dinghy Endorsement course. Participants will undergo rigorous assessments, including a written examination, oral examination, and on-the-water skills demonstration, all under the guidance of a certified ASA Instructor Evaluator.
The IQC 217: Basic Celestial Navigation Endorsement Instructor Qualification is a comprehensive one-day clinic designed to certify individuals for teaching the ASA 117 Basic Celestial Navigation Endorsement course. This clinic evaluates the candidate’s knowledge, skills, and ability to teach ASA classes, ensuring they meet the high standards required for ASA instructor certification. Participants will undergo a rigorous evaluation process, including a written examination, oral examination, and demonstration of on-the-water skills.
The IQC 218: Docking Endorsement Instructor Qualification Clinic is a one-day intensive program designed for aspiring sailing instructors. This clinic certifies individuals to teach the ASA 118 Docking Endorsement course, focusing on evaluating candidates' knowledge, skills, and teaching abilities. Participants will undergo rigorous assessments to ensure they meet the high standards required for ASA instructor certification.
The Marine Weather Endorsement Instructor Qualification Clinic is a comprehensive 3-day program designed to certify individuals for teaching the ASA 119 Marine Weather Endorsement course. This clinic evaluates the candidate's knowledge, skills, and ability to teach ASA classes, ensuring a high standard of instruction. Participants will undergo rigorous assessments, including written and oral examinations, as well as on-the-water skill demonstrations.
Embark on a thrilling journey with our ASA 101: Basic Keelboat course, designed for both novice and experienced sailors. This two-day course will teach you how to sail a 22-foot boat in light to moderate winds and sea conditions, ensuring you gain confidence and skills to navigate familiar waters without supervision. Our certified instructors provide personalized attention, ensuring a comprehensive learning experience. This course is taught over 2 consecutive days. Located at the Willoughby Marina in Norfolk, VA, this course offers an immersive sailing experience on the stunning Chesapeake Bay. You'll learn essential sailing techniques, safety protocols, and gain hands-on experience that will prepare you for independent sailing adventures. Join us for this popular course and become part of the vibrant sailing community. Whether you're looking to start a new hobby or enhance your sailing skills, the ASA 101: Basic Keelboat course is the perfect opportunity to set sail with confidence.
The ASA 103: Basic Coastal Cruising course is designed for those who want to enhance their sailing skills and experience the thrill of coastal cruising. Over two days, participants will learn to sail a 30-50 foot boat in coastal waters, gaining the confidence and skills needed to act as skipper or crew. This course is perfect for those looking to expand their sailing knowledge and enjoy the beauty of the open sea.
Learn how to safely and efficiently dock an auxiliary powered sailboat under almost any condition with the ASA 118: Docking Course. This course is designed to provide you with the essential skills and knowledge needed to handle a single inboard or outboard engine sailboat. Gain confidence in your docking abilities through hands-on practice and expert instruction at Willoughby Marina.
Embark on a journey to master the art of celestial navigation with our ASA 117 Basic Celestial Navigation Endorsement course. Over two days, you'll learn to apply celestial navigation theory and practice to determine your position at sea using a sextant and Nautical Almanac. This course is designed for those who wish to enhance their sailing skills and gain confidence in navigating open waters.
The ASA 114: Cruising Catamarans course is designed for those who wish to gain advanced knowledge and skills to safely command a 30-50 foot sailing catamaran. This comprehensive course covers essential topics such as catamaran structure, performance under sail and power, boat systems, seamanship, safety, and emergency response. With a focus on practical learning, students will experience sailing in moderate to heavy winds and sea conditions, preparing them for coastal waters along the Chesapeake Bay, the Caribbean, and beyond.
Refresh your sailing skills with the ASA 111: Sailing Review Clinic in Norfolk, VA. This clinic is perfect for ASA certified sailors who need a refresher or want focused instruction in specific areas like docking and sail trim. Choose between a half-day or full-day session to suit your schedule and learning needs.
Embark on a transformative sailing journey with the ASA 103 and 104: Bareboat Charter Certification Combo. This comprehensive course is designed for aspiring sailors who wish to master the art of skippering a 30 to 50-foot boat in coastal waters. Over four days, participants will gain hands-on experience and theoretical knowledge, ensuring they are well-prepared to navigate the seas with confidence. Whether you're looking to enhance your sailing skills or pursue a new adventure, this certification combo offers the perfect blend of education and excitement.
The ASA 104: Bareboat Cruising course is designed for those who wish to learn how to skipper a sloop-rigged, auxiliary powered keelboat of approximately 30 to 50 feet in length. This course will equip you with the skills needed to confidently navigate coastal waters during the day. By the end of the course, you will be able to handle a keelboat with an inboard diesel engine, making you ready for your own bareboat adventures.
Master the art of coastal navigation with our ASA 105 course, designed for both power and sail enthusiasts. This comprehensive course covers all the essential navigational theory needed to safely guide a sailing vessel through coastal or inland waters. With no prerequisites required, this course is perfect for those looking to deepen their understanding of nautical charts and compass reading.
Embark on a comprehensive sailing journey with our ASA 101 to 104: Novice to Bareboat Certification Combo. This course is designed for those who wish to transition from a novice sailor to a competent bareboat skipper. Over five days, you'll receive both classroom instruction and hands-on experience aboard a 36′ sailboat, ensuring you gain the skills and confidence needed to navigate coastal waters safely.
Experience the thrill of sailing with our Colgate 26' Full Day Rental. Perfect for both seasoned sailors and beginners, this rental offers a full day of adventure on the beautiful Chesapeake Bay. Enjoy the freedom to explore at your own pace and discover the stunning scenery and wildlife that the bay has to offer.
ASA 106 Advanced Coastal Cruising is the ultimate course for sailors looking to take on more challenging conditions by learning the advanced techniques and seamanship required to navigate coastal waters confidently, day or night, in all weather. Whether you’re dreaming of longer passages or exploring more remote destinations, ASA 106 gives you the experience and knowledge to handle your boat like a seasoned skipper in various demanding scenarios. You’ll learn advanced sail handling, night navigation, heavy weather tactics, and emergency procedures. This course emphasizes decision-making, leadership, and boat management while cruising in variable weather and sea states. Through practical, hands-on training, you’ll navigate longer passages, perform crew-overboard drills, and manage a vessel’s systems while underway. ASA 106 prepares you for advanced cruising adventures, ensuring you’re ready for any conditions coastal cruising might throw at you.
Sailboat performance starts with exceptional design, and the Colgate 26 delivers on all fronts. Its well-balanced construction ensures speed without sacrificing safety. Our Colgate 26 is a shallow-draft version, ideal for exploring areas like the Chesapeake Bay, offering versatility without compromising comfort or performance. The Colgate 26 was designed with careful attention to critical specifications: weight, waterline and overall length, keel depth and weight, sail plan, and both standing and running rigging. These features combine to create “The Boat For All Reasons,” setting a benchmark in its class.
The Aventura 37 Catamaran offers an unparalleled sailing experience with its elegant design and spacious layout. This catamaran is perfect for those seeking a luxurious and comfortable journey on the water. With a raised helm station and ample seating, it provides excellent control and relaxation for up to 6 guests. Enjoy the sunbathing areas and the well-equipped interior, making it ideal for both short trips and extended adventures.
Personalized Sailing Adventures For Every Voyager
We offer the premier way to set sail in Norfolk, VA, for voyagers of all skill levels! If you're looking for an engaging activity in a relaxed setting that tests your skills and wit, our tours will leave you feeling like an experienced sailor.
We curate our world-class sailing adventures for every guest who steps foot on our beautiful ships. There's no need to settle for a one-size-fits-all sailing trip. When you choose us, we'll work closely with you to plan an adventure that meets your expectations.
Learn about the parts of a basic keelboat, navigational rules, vessel safety, and more during your big day on the water in Norfolk, Virginia! Our excursions are popular for field trips. If you're look...
Learn about the parts of a basic keelboat, navigational rules, vessel safety, and more during your big day on the water in Norfolk, Virginia! Our excursions are popular for field trips. If you're looking for a workplace excursion that lets employees build leadership skills and tools for conflict resolution, we offer special packages that are tailored for corporate team-building sessions. Of course, our clients can also learn to sail by signing up for basic keelboat certification and advanced coastal cruising courses with our talented, passionate team.
Chasing adventure? Glide along the waves under the vast open sky when you choose Norfolk Sailing as your guide. We offer one of the best ways to enjoy downtown Norfolk as a local or out-of-town visito...
Chasing adventure? Glide along the waves under the vast open sky when you choose Norfolk Sailing as your guide. We offer one of the best ways to enjoy downtown Norfolk as a local or out-of-town visitor. Whether you book a private charter or join one of our "mixer" events, you never quite know how your time on the water will take shape. In addition, you'll enjoy breathtaking views and unparalleled photo opportunities, making every moment on the water a chance to create unforgettable memories that you'll want to share with friends and family.
You'll end your Norfolk sailing excursion with a new appreciation for the might and majesty of the Chesapeake Bay after exiting the vessel safely. With Chesapeake Bay being home to hundreds of wildlif...
You'll end your Norfolk sailing excursion with a new appreciation for the might and majesty of the Chesapeake Bay after exiting the vessel safely. With Chesapeake Bay being home to hundreds of wildlife species, it's not uncommon for our sailing guests to spot osprey, otters, and herons in their natural habitat. Our sailing charters and courses also offer fun ways to bond with family, friends, or colleagues, creating lasting memories that you'll cherish long after your adventure on the water.
Located just 20 minutes from sunny Virginia Beach, Norfolk is a vibrant port city and naval base on Chesapeake Bay. People who visit are impressed with the walkability of downtown Norfolk. The waterfront area is home to amazing restaurants and shops curving along the Elizabeth River.
During your stay, don't miss opportunities to visit Battleship Wisconsin at Nauticus, Norfolk Botanical Garden, and Chrysler Museum of Art. You can also take a guided tour of Naval Station Norfolk, the oldest naval port in the country, where you can learn all about the city's fascinating maritime history.
Norfolk Sailing invites you to plan a relaxing time on the bay that you won't soon forget. We offer more than 20 sailing adventures catering to your personal thirst level for adventure when exploring Chesapeake Bay.
Come explore the charm of Norfolk! With its lively waterfront, interesting history, and beautiful views, there's something for everyone to enjoy. Experience it all for yourself - book your adventure today and create wonderful memories in this lovely city!
Most frequent questions and answers
July 3, 2026
Chesapeake sailing is an incredible adventure even if you have minimal experience because of the opportunity to try your skills in sheltered waters un...
Read More: Is Chesapeake Bay Good for Beginner Sailors? A Local Instructor's Honest Answer
June 2, 2026
That summertime feeling can only mean that your Norfolk Virginia vacation is getting closer. The only problem is that you haven't had much time to sit...
Read More: Planning A Norfolk Virginia Vacation This Summer? 7 Experiences You Won't Find Anywhere Else
May 6, 2026
Most Norfolk vacation guides will tell you the same thing: the best time to visit Norfolk is based on crowd levels and hotel prices. But the real answ...
Read More: Best Time To Visit Norfolk For Sailing, Dolphins, And Chesapeake Bay Adventures
