Have a question?

Take a look at our frequently asked questions and their answers below!

If your question isn’t here, call 410.267.7205.

How long has the Annapolis Sailing School been in business?

We opened in Annapolis, Maryland in 1959.  The school has been run by the original owner or past instructors ever since.

When is the Annapolis Sailing School in operation?

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

Where should I stay if I'm coming from out of town?

If you’re coming from out of town, Annapolis Sailing School highly recommends staying at the Inn at Horn Point if you are a fan of bed and breakfasts. Mention that you’re a sailing school student to receive a discount! For a more standard hotel, the Country Inn & Suites is also offering a 15% discount if you use the code SMALL.

To check out our other recommendations, click here!

Is there an age limit for students?

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

  • Beginners courses on Rainbows: 16 years old — Under 16 call for information.
  • Live aboard and advanced courses on larger boats: 18 years old — Under 18 call for information.
  • We also have a kids summer camp program called KidShip Sailing. It is a five-day course during the summer. Smaller sailboats are used for that program. For more information, go to our KidShip page or give us a call.
How far in advance should we make reservations for courses?

Make reservations as far ahead as possible. Some courses are booked months in advance.

Do we sail if it rains?

Yes, as long as weather conditions do not become unsafe such as in the case of thunderstorms or high wind conditions.

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, and de-rig 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, the boat that you skippered is a dinghy 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 trim, 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 the boat, 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.

What about gratuities?

Instructors and dockhands are fairly compensated and tips are not expected, but graciously accepted.

What do I need to bring with me when I am coming to the sailing school?

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.

  • 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.
  • 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! Most importantly, make sure they are closed-toed shoes.
  • Annapolis Sailing School sails in rainy weather (unless notified), so be prepared with rain coats, windbreakers, etc. if the weather report calls for inclement conditions. Dress according to the weather. If it is cool, bring a sweater or jacket. If the weather is hot, shorts and T-shirts are the norm.
  • 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.
  • 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.
  • 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.
After I have finished the basic course, what course should I take?

This is a very individualized question however, there are a few general guidelines can help you figure that out. 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?” and check out our Course Guide for assistance. If you have doubts or need clarification, please call us and our experienced staff will be glad to help you.

Can I rent a boat at the Annapolis Sailing School?

The 24’ Rainbows are available for rentals by the day during the week and for half-day rentals on the weekend. Or, for one low price, a graduate of Annapolis Sailing School can join the school’s Keelboat Club to take part in social activities and enjoy greatly reduced rental rates.  Call us at 410.267.7205 for details.

What are the course change and cancellation policies?

The full Cancellation Policy can be found here

What is the privacy policy of the Annapolis Sailing School (scuttlebutt, LLC)?

Our privacy policy can be found here.

What is the non-discrimination policy of Annapolis Sailing School?

You can read our official non-discrimination policy by clicking here.

What are your business hours?

In Season (April-October)



Out of Season (November-March)



Are gift cards refundable?

Gift cards are good for 5 years from the purchase date. The money for a gift card is is non-refundable

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