From the Bay, From the Bay to the Blue Ridge

Learn To Sail in Winter?

By Beth Crabtree

Learn To Sail in Winter?

Yes. You. Can.

Photo by Eric Moseson

For many sailors on the Chesapeake Bay and its tributaries—that means you too, Potomac River lovers—October offered beautiful days on the water. There will no doubt be several days in November, as well, when the air is crisp and clear, fewer powerboats are on the water, and the light, fluky winds of summer have given way to steady breezes. At Halloween, most sailing programs in our area will have stopped running their on-the-water instructional programs, but that doesn’t mean you have to wait until next spring to learn how to sail. Here are a few ways for a mid-Atlantic would-be sailor to continue learning through autumn and winter.

Take a ‘Learn to Sail’ Vacation

During the winter months, some local sailing schools are in full swing with classes farther south. Sail Solomons, which runs summer classes out of Solomons Island, MD, also offers courses in the Caribbean, such as a flotilla in 2022 in Guadeloupe. Whether you’re looking at a Chesapeake-based school’s satellite program, or a school headquartered down south, such as Offshore Sailing School, look for schools recognized by the American Sailing Association or U.S. Sailing, organizations with high standards for safety and instruction.

Visit winter sailboat shows

The St. Petersburg Sail and Power Show (January 20-23, 2022) and Chicago Boat Show (January 12-16) are two such shows. (The U.S. Sailboat Show held in Annapolis in October has come and gone but worth plugging into your calendar October 13-17, 2022). Here you’ll find representatives from sailing schools and clubs who can help you get started as well as representatives from charter companies who offer learning vacations. You will also find informative, free seminars. If you’re willing to hire a captain, you could spend a weekend this fall sailing on the Chesapeake Bay, or you could charter a boat in the Caribbean for a mid-winter escape.

Private On-Water Instruction or Classroom Seminars

Many sailing schools offer private lessons, so even if their summer group sessions end in early October, they may be able to arrange private lessons on their training boats well into November. As for classroom learning, we recognize it isn’t that sexy, but the knowledge you’ll gain is invaluable, and it’s also a good opportunity to meet people in the sailing community. Schools such as J/World in Annapolis offer winter classroom courses that welcome all levels of experience.

Read Books and Tie Knots

Pick up some books and magazines about sailing. Tried and true books include “The Annapolis Book of Seamanship” (recently updated), “North Sails’ Trim Book,” “Chapman Piloting & Seamanship,” and “Sailing Fundamentals” by Gary Jobson. For Bay-specific sailing, read SpinSheet Magazine in print form or digitally at As for tying knots, go to your local boating store, purchase some line, and begin practicing knots. You’ll find step-by-step instructions in most sailing books and on many websites. See how quickly you can tie them, and then practice tying them with your eyes closed. Although it may not seem too exciting – trust us – it will be very useful on a sailboat.

Click to learn
The team at the monthly SpinSheet Magazine publishes Start Sailing Now, a new sailors guide meant to address all the questions you ever had about sailing but were afraid to ask. Find SpinSheet and Start Sailing Now in their entirety at

Beth Crabtree, a senior editor at SpinSheet, sails out of Round Bay on the Severn River in Annapolis. She pens a monthly “Start Sailing Now” column for sailors who have started as adults and gotten hooked. Find video clips of her interviewing new sailors on SpinSheet’s YouTube channel.

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