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Broad Bay Sailing Association

Serving the sailors of the Chesapeake Bay 

A Path to Sailing

How do you get from your land-bound existence today onto the water to fulfill your dream of being a sailor and maybe someday having your own boat? Of course, there are multiple ways to get there, but there are some things you can do along the way to make it happen. 


First, you can join BBSA. This connects you to the sailors of the southern Chesapeake Bay. Then you can enjoy their company at racing, cruising, training, social and membership events. Some of the benefits of joining are listed on the Membership page.

Training: BBSA maintains a calendar of local training events, many of them hosted by BBSA or in combination with the monthly membership meeting. Training covers the gamut, from your first Boating Safety course to advanced racing techniques. 

Race Organization: Races don’t happen by themselves. They require volunteers to help set up courses, act as committee boats, and determine the race results. Volunteering to be on a committee boat is a great way to get familiar with racing rules and sailing rules of the road.

Racing: Racing is a big part of our sailing activities – many of our members participate in weekly races and distance regattas. Many boats need occasional crew or permanent crew, so this is a great way for you to get out on the water. We have a skipper-crew matching service for our weekly races. Check the Racing Calendar for upcoming race events.

Volunteer: Get involved! It’s the best way to get to know your fellow sailors and learn about sailing from them. You will also learn what goes into our events and find your own niche where you can provide much needed support. Contact the Commodore if you want to know where to start.

Event Calendar: The event calendar keeps you up to date on opportunities to participate, whether you have a boat or not. Just providing some muscle to set up potluck events is a great help. Those huge coolers filled with ice and drinks are heavy! Set-up and clean-up crews form automatically at most events, but remember they are volunteers too. A helping hand is always welcome.

Learn to Sail

Boating Safety: Did you know you need a certificate from the state of Virginia to operate a vessel with an engine exceeding 10 hp? To get this, you need to complete a boating safety course. There are online versions of this course available for free with the ability to print your own certificate when complete. Visit the state requirements page for more information and get this course under your belt.

 Sail Nauticus:  Located in downtown Norfolk, Nauticus is teaching the next generation of sailors. They also have adult   programs and boats available for members to take out for a spin on the Elizabeth River. For the beginner sailor, they offer   a US Sailing Basic Keelboat Certification course that will give you a solid foundation for sailing a small keelboat.

  ODU Sailing Camp: Youth and adult sailing camps are offered from mid-June to mid-July.

  Sail-Time: They offer both captain led training and fractional memberships of their fleet once you know what you are   doing. If you are not quite ready to commit to boat ownership, this is a great in-between phase.

Get a Little Boat: One of the best ways to learn to sail is on a small boat. It is responsive and you learn quickly which way the wind is blowing. Plus, you can’t do much damage if you make a mistake. You also learn how to right the boat when you tip over, which you will do. BBSA has Hobie and One-design Fleets if you are interested in starting small (or staying small) to hone your sailing skills.


Local chartering is another way to learn to sail, once you have the basics of boat handling and navigation in your repertoire. Charter boats are available out of Annapolis and Rock Hall Maryland. You will need to show your sailing resume if you bareboat (go without a paid captain) so be sure you keep track of your growing experience. Sailing with a captain is always a good way to try out your skills with backup available. Captains also have local knowledge that is hard to get on your own.

There are many foreign charters available if you want to head to the British Virgin Islands or the Bahamas.  These range from captained charters to bareboat options. Some charter services will send you out with a captain on board to verify your skills if your resume is a little skinny or send a captain with you for the first few days of your cruise.

Sailboat Shows

Boat shows are a great place to become familiar with the various boats available and maybe even sign up to go sailing on one them. Boat shows are also loaded with training options and seminars. There are temptations galore for both the sailor and the wannabe sailor in all the tents and booths. In the spring and fall, you can find boat shows in Annapolis. The Miami boat show takes place in the winter. The rooms get booked early, so if you want to go, plan it a year ahead.

Making Your Dream Real

There are a lot of ways to get on the water and head toward boat ownership. Some people start with buying a boat and working backwards from that. It’s probably the most challenging way to learn to sail, but it works for some.  Otherwise try some of the options listed above, and before you know it, you’ll be living your dream.

"Broad Bay Sailing Association" is a non-profit organization. Virginia Beach, VA 23454

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