SailTime Virginia Marks Two Decades of Sailing Success in the Chesapeake Bay

SailTime Virginia, located at Morningstar Marina, is proud to announce its 20th anniversary, marking two decades of providing exceptional sailing experiences and promoting the joys of being on the water in the vibrant Norfolk community. It is currently managed by Paul and Jennie Jameson who have been working in the sailing industry as a couple for over 13 years. Throughout their careers, the Jamesons have had the opportunity to work with sailors from around the world, including the Seychelles, Dubai, South Africa, the Mediterranean, the Pacific, and the Caribbean. They are both passionate about helping new and experienced sailors discover the amazing sailing adventures that await them.

ST Virginia PR 3SailTime Virginia was established in 2004, with a vision rooted in the principles of the sharing economy. It was originally developed by Wayne Diviney, current SailTime Group CFO and his daughter Kristen Diviney McGarr, SailTime Group Director of Technology and Franchise Systems. The base was purchased in 2019 by Greg Garrett, a lifelong Hampton Roads resident and real estate businessman. Recognizing the prohibitive costs associated with new sailboats and the maintenance challenges of older vessels, Greg, a sailing enthusiast from a young age, saw an opportunity to share his love of sailing with his community, making it both affordable and accessible through SailTime. “I bought the base because I believe in the sharing economy and with the excessive cost of new sailboats and the excessive maintenance of old sailboats this is going to be the future of sailing and yachting in general. I like being on the cutting edge of what is smart, economical and fun!” Garrett explains.

Over the past 20 years, SailTime Virginia has become a cornerstone of the local sailing community. Situated at the mouth of the Chesapeake Bay, the base offers members access to some of the most stunning sailing destinations, including the picturesque Cape Charles. With a diverse fleet ranging from 34 to 41 foot monohulls, and a 37-foot catamaran, SailTime Virginia caters to a wide range of sailing preferences and experiences.

The base’s location at the beautiful Morningstar Marina at Little Creek, enhances its appeal, offering a host of amenities and nearby restaurants in a charming beach community. This vibrant setting, combined with the base’s exceptional fleet and facilities, has made it a popular choice for sailing enthusiasts.

ST Virginia PR 2The success of SailTime Virginia can be attributed to its commitment to affordability and community engagement. Members enjoy access to exclusive social events, training clinics, and American Sailing Association (ASA)-certified sailing courses. 

SailTime Virginia’s ASA Sailing School is developing a nationwide reputation since it is not only training new Virginia sailors but attracting people who want to learn how to sail from other parts of the United States. Wes, a recent ASA 114 student, and another member who took the ASA 101 & 103 courses both praised SailTime Virginia’s instructors. Wes highlighted Bob Malkin’s exceptional clarity, patience, and thoroughness, noting, “Bob is the best instructor I’ve had in four ASA courses. He explained everything clearly and was calm and patient with everyone.” Meanwhile, the other member commended Matt Dunkel for his tailored teaching approach and extensive sailing knowledge: “Matt was an incredible instructor who adapted his teaching to each individual’s learning style. His thoroughness and expertise were evident, and Jennie and the team were also great to work with. We highly recommend SailTime Virginia for ASA sailing courses.

Greg Garrett’s passion for sailing began in his youth, inspired by his father. He has dedicated his life to sharing the sport he loves, fostering a thriving community of sailors. “The most challenging aspect has been navigating the complexities of maintaining and growing the base while keeping our services affordable,” Garrett notes. “But the rewards, including the joy of seeing our members enjoy sailing and developing their skills, make it all worthwhile.”

Looking ahead, SailTime Virginia aims to continue its sustainable growth, enhancing its fleet and expanding its membership. “Our goals for the upcoming year,” Garrett says, “include finding at least two  more owner members for 2025, who want to minimize the cost of sailboat ownership while enjoying carefree use of their boat. This will expand the opportunities for more people and families to regularly get out on the water for the lowest possible cost, and continue making sailing accessible and enjoyable for everyone in our community,”

For more information about SailTime Virginia and to join the celebration, visit sailtime.com/virginia or contact us at (757) 480-7245.

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Group Size
no limit

Private Instruction

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 the scenic Morningstar 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.

Duration
2 hours
Group Size
4 to 6

Fun Friday Mixer

Join us for a delightful evening on the water with our Fun Friday Mixer! This mixed charter is perfect for meeting new friends with similar interests while enjoying a refreshing 'mocktail' and lite snacks. Feel the cool evening breeze and keep an eye out for a playful dolphin pod as you sail along the beautiful Chesapeake Bay. Our friendly crew, including a steward, deck hand, bartender, and DJ, will ensure you have a memorable experience with music, games, and more.

Duration
6 hours
Group Size
Up to 6

6 Hour Private Charter

Embark on a private boat charter in Norfolk, Virginia, with SailTime Virginia. Set sail on a 6-hour private boat charter, accommodating up to 6 guests. Explore the bay, relax, and create cherished memories with family and friends. Your exclusive aquatic adventure awaits.

Duration
3 hours
Group Size
no limit

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.

Duration
3 hours
Group Size
Up to 6

Brunch Charter

Experience a delightful Brunch-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 4-hour private charter offers a unique way to explore Norfolk, VA, while indulging in a leisurely brunch.