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If you have additional questions, call 1-800-638-9192 and we will be happy to answer them. Annapolis Sailing School looks forward to sailing with you!

How long has the Annapolis Sailing School been in business?

We opened in Annapolis, Maryland in 1959.

When is Annapolis Sailing School in operation?

Our seasonal location in Annapolis operates April through the end of October.

Our Tampa Bay location operates year round

Is there an age limit for students?

There is no maximum age limit. Minimum ages listed below are a rough guideline and if you have a specific question, call us.

  • Beginners courses: 16 years old — Under 16 call for information.
  • Live aboard and advanced courses: 18 years old — Under 18 call for information.

How far in advance should we make reservations for courses?

Just as far ahead as possible. Some courses are booked weeks or months in advance.

Do we sail if it rains?

Yes, as long as wind and wave conditions do not create an unsafe condition.

Do I need to take a basic course or can I, based on my past experience, sign up for a more advanced course?

We strongly recommend talking with one of our staff to help you answer this question, but here are some general guidelines:

If, based on your past experience, you can rig a sloop rigged daysailer, sail away from a dock or mooring, sail for the day, return the boat, unrig it, in moderate wind conditions (10-15 m.p.h.) with someone acting as crew, then you can probably skip the beginners or basic course. However if your experience has been that of crew, not skipper, or the boat that you skippered is a board type boat or of the variety with only one sail, or it has been years since you have sailed, then one of the basic courses is probably a prerequisite to taking an advanced or cruising course.

Do you separate family members in the beginners course?

The persons listed with you on your enrollment will be in the same classroom. We recommend that family members sail on separate boats. This is only a recommendation and you may do as you wish. However, from experience, we have found that it is a quite successful method in teaching all members of the family to be skippers.

What is covered in the basic courses?

Boat nomenclature, steering, sail trimming, putting on and taking off of sails, finding wind direction, tacking and jibing maneuvers, points of sail, right of way rules (briefly), how to deal with thunderstorms, grounding and man-overboard situations and basic chart reading.

What should I be able to do once I have completed one of the basic courses?

You should be able to rig, sail away from the dock, or mooring, day sail, return to the dock or mooring and unrig up to a 24’ daysailer in light to moderate wind conditions (10-15 m.p.h.). Of course, you must have someone aboard as crew.

After I have finished the basic course, what course should I take?

This is a very individualized question and may require that you correspond directly with one of our reservationists. However, there are a few general guidelines. The array of courses offered has been designed to fit most student needs. Before you call us, ask yourself, “What do I want to be able to do after I take this course?” This sometimes will tell you what course to take. If you have doubts or need clarification, please call us on our toll-free line and our experienced staff will be glad to help you.

Can I rent a boat at Annapolis Sailing School?

The 24’ Rainbows are available for rentals by the day. Or, for one low price, a graduate of Annapolis Sailing School can join the school’s Keelboat Club and sail as much as you wish all season long. Call us toll free at 800.638.9192 for details.

Where can I stay during my visit?

Check out our list of accommodations in the area.

In addition, once you make your reservation we will provide you with instructions to access special rate accomodations for our students at the Inn at Horn Point and the Courtyard Marriott.

Helpful Information

Sailing is most fun when you are comfortable and prepared. What follows is a list of helpful hints for you to ensure a pleasant experience learning to sail.

  1. Annapolis Sailing School provides Personal Flotation Devices (PFDs) to all our students. If you have your own USCG approved PFD, feel free to bring it with you.
  2. Boat Shoes are to be worn at all times. If you do not own boat shoes, white-soled tennis shoes will suffice. Keep in mind the possibility of your feet getting wet!
  3. Annapolis Sailing School sails in rainy weather (unless notified), so be prepared with rain coats, windbreakers, etc. if the weather looks or calls for inclement conditions.
  4. Dress according to the weather. If it is cool, bring a sweater or jacket. Cotton pants are much better on a boat than denim. If the weather is hot, shorts and T-shirts are the norm.
  5. Sun Block, hats, sunglasses with straps, and lip balm are important for sailors with the extra effect of sun, wind and glare on the water.
  6. Plastic water bottles are usually a good idea. With all the sun and wind, your body will dehydrate much quicker than under normal circumstances. There is ample storage space for these and other items on board.
  7. Lunch can be purchased at one of many nearby stores or restaurants. If you choose to bring your lunch, bring it in a cooler so that you can leave it in your car.

Weather Forecast




Wind: N at 7 mph
Partly cloudy
19°F / 24°F
Mostly cloudy
32°F / 36°F
AM Clouds/PM Sun
26°F / 41°F

Current Conditions

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