Captained Charters & Bareboat Rentals
Captained Charters
Sunset Charter
Experience the breathtaking beauty of the Chesapeake Bay with our Sunset Charter. Sail on our luxury catamaran and enjoy a serene evening with family and friends. Whether it's a special occasion or a relaxing getaway, this charter promises an unforgettable experience.
Day Charter
Experience a delightful Day-Time Charter on the Chesapeake Bay with our luxury catamaran. Relax and enjoy the serene waters with family and friends or celebrate a special occasion. This 3-hour private charter offers a unique way to explore Norfolk, VA, while indulging in a leisurely Day.
ASA 103 and 104: Bareboat Charter Certification Combo
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.
ASA 101 to 104: Novice to Bareboat Certification Combo
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.
ASA 104: Bareboat Cruising
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.
ASA 101: Basic Keelboat
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.
ASA 103: Basic Coastal Cruising
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.
IQC 204: Bareboat Cruising Instructor Qualification Clinic (1-Day)
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.
22′ Capri Bareboat
Experience the freedom of sailing with our 22′ Capri Bareboat rental. Perfect for ASA 101 graduates, this bareboat rental allows you to explore the Chesapeake Bay at your own pace. With a maximum capacity of 4 people, it's ideal for a small group adventure. Enjoy a full 6-hour sail time and chart your own course on the water.
Your Adventure on the Chesapeake Bay Starts Here
At SailTime Virginia, we make exploring the beautiful Chesapeake Bay easy and unforgettable. Whether you're planning a fun-filled day of sightseeing, a relaxing cruise, or a special event on the water, our premium boat rentals and charters provide you with the perfect vessel for the occasion. Let us help you create lasting memories—book your experience online today and set sail on your Chesapeake Bay adventure!








