
Allowing first-time sailors to learn the basics and experience the joy of sailing in a 45-minute classroom session followed by 90 minutes on the water with American Sailing Association accredited instructors provided by Sailtime.
Learn moreMake this sailing season the best yet by investing in education.
Allowing first-time sailors to learn the basics and experience the joy of sailing in a 45-minute classroom session followed by 90 minutes on the water with American Sailing Association accredited instructors provided by Sailtime.
Learn moreApril 26, 4-6 pm & April 27, 9-11 am | Join Oakcliff for high-energy, entertaining working sessions that cover the ins and outs of competitive sailing - landing sponsors, getting on the path to the Olympics, organizing events, and more!
Learn moreThe Spring 2025 Cruisers University includes Offshore Emergency Medicine and Master Diesel Maintenance, both 3 days of intensive education. Thursday, April 24th - Saturday, April 26th.
Learn more*Schedule subject to change
11:00a - 11:45a |
An Introduction to the Rules of the Road |
Start understanding the Top 3 rules of the Road, and simple situations of who has the right of away and how to execute. Learn the basics on Sound Signal, when you can’t reach via VHF. What to do if you are not clear of their intentions? Fast start on appropriate usage of your VHF. Who is responsible? presented by Captain Deb Marlor of Simplicity Sailing |
12:00pm - 12:45pm |
Docking for Couples |
Docking can provide challenges, even for the most experienced skippers, and having a good line handler can make all the difference to a successful landing. With large doses of humor and humility, learn the key steps and some useful tricks for working together on these maneuvers. presented by Jeff Grossman & Jean Levine of Two Can Sail Yacht Sales & Service, Inc. |
1:00p - 1:45p |
Becoming an Avid Fisherwoman on a Slow Boat |
Are you looking to reel in a fresh catch every time you set sail or drop anchor? Join Nina, a seasoned sailor with over 15,000 nautical miles under her belt and seven years of sailing from the US to the South Pacific. From a novice to a passionate fisherwoman, Nina continues to hone the art of fishing while cruising. In this engaging seminar, Capt. Nina will: – Share her top educational resources for fishing newbies Don’t miss this opportunity to learn from a true expert and enhance your sailing adventures with the joy and reward of fishing. Click here to explore Nina’s fishing blogs on S/V Enjoy and get a taste of what’s in store! (https://www.enjoysailing.us/category/passaging-blogs/fishing). presented by Nina Preuss |
2:00p - 2:45p |
Celestial Navigation – There is an app for that! with Mike Novey of EZ Sextant |
Navigate in open waters without a GPS with the ‘EZ Sextant’ app. The phone’s camera is used to take sightings of the sun, moon, Venus, or Mars. The sighting results are automatically plotted on your device as running fixes, no sextant skills required. You can also use your sextant and take advantage of the built-in almanac and plotting tools. Mike will demonstrate the app and cover some celestial navigation and GPS basics. presented by Michael Novey developer of EZ Sextant |
3:00p - 4:00p |
The Everglades Challenge – An Adventure on a sailboat |
The Everglades Challenge – A firsthand account of this crazy adventure challenge as told by 11 time participant Jahn Tihansky. Join Jahn as he shares his experience and tales through video, pictures and his own words in what promises to be an entertaining and inspiring presentation. He’ll talk about how he and his partner, Jeff Linton prepared, navigated and persevered and overcame numerous obstacles to not only complete the 300 mile course aboard their beach-launch boat but also to win the overall three times. Jahn Tihansky is an Annapolis-based freelance sailing coach, marine consultant and licensed captain. He served 18 years as director of the Naval Academy’s Offshore Sailing Team, started and ran J World Sailing School in Annapolis, and has sailed aboard an incredibly wide variety of boats big and small. He continues to seek new adventures on the water whenever he can. presented by Jahn Tihansky |
4:00p - 5:00p |
Racing Discussion with Pete Boland of Sail Faster |
Join us for a dynamic discussion on how beginners can break into sailboat racing with confidence – hosted by Pete Boland, host of the popular Sailfaster Podcast, alongside top racers and experts. If you’ve ever been intimidated by sailboat racing, don’t miss this insider look at the fastest ways to get on the water! |
11:00a - 11:45a |
Basic Weather for Sailors |
This is the beginning of understanding weather and boating. Lets start with a good foundation to keep you safe on the water and avoid “drama” in your boat. Where to look, how to get the most out of your Weather apps, Weather Basics you need to know, the forecast – what to look for and tips to keep you safe on the water. Weather Basics – terms, visual aids. Weather Apps – App options and why I use them. Reviewing the Forecast – understanding the forecast, what is it telling you short term and long term. Using a Weather Routing Service – what are they, and how they work for you. presented by Captain Deb Marlor of Simplicity Sailing |
12:00p - 12:45p |
Cruising to Maine |
Are you curious about cruising to Maine? Do you have questions about spare parts, tools, and safety measures that might be needed? Have you ever wondered if lobster pots really outnumber Chesapeake crab pots, or if Maine fog is denser than pea soup? Join us for a candid presentation by Captain Cheryl Duvall as she shares highlights and a few lowlights from a recent 101-day cruise from Annapolis to Maine and back. Her image-rich slide deck features 42 destinations along the 1,820 nautical mile journey, through Long island Sound, the Cape Cod Canal, and across “Down East” Maine. She will share recommendations for anchoring, mooring, and docking between here and there. From dodging ferries near the Statue of Liberty to redefining “lobsters rolls,” her sea tales are sure to inspire your future maritime adventures. presented by Captain Cheryl Duvall |
1:00p - 1:45p |
How to Begin your Sailing Journey with Annapolis Sailing School |
presented by Annapolis Sailing School |
2:00p - 2:45p |
Line Handling & Cowboy/Cowgirl Skills |
Docking can provide challenges, even for the most experienced skippers, and having a good line handler can make all the difference to a successful landing. With large doses of humor and humility, learn the key steps and some useful tricks for being a good line handler. presented by Jeff Grossman & Jean Levine of Two Can Sail Yacht Sales & Service, Inc. |
3:00p - 4:00p |
Sailing with Kids |
Ever dream of sailing away with your family? How about just an afternoon together on the water? Bring the whole family for a casual panel discussion/Q&A with parents whose kids love sailing and learn why the sport is a fun and exciting for all ages. presented by an expert panel from SpinSheet Magazine |
11:00a-11:45a |
Cruising Comfortably for a Weekend or a Life |
What truly defines comfort for you on the water? How can you achieve it without compromise? In this thoughtfully designed course, Captain Deb provides a wealth of insights and strategies for creating a comfortable, enjoyable cruising experience. From organizational techniques to practical tips for onboard living, this course empowers sailors to optimize every aspect of life at sea. presented by Captain Deb Marlor of Simplicity Sailing |
12:00p -12:45p |
Catamarans 101 |
There are significant differences in design choices among the pride of large cruising Cats available today. These catamarans can literally be as different as a Corvette is from an RV. Explore the design & build tradeoffs, and walk through the different feature and layout choices, to help you to determine which will best match how you plan to go Catamaran cruising. presented by Jeff Grossman & Jean Levine of Two Can Sail Yacht Sales & Service, Inc.
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1:00p - 1:45p |
How do you become a (great) crew member on a race boat? |
Do you look at the sailboats finishing in front of the Eastport Bridge and think, “I wish I was out there, but I don’t know the first thing about racing?” Join lifelong racer and Annapolis Sailing School director Ian Morrison as he walks you through a typical sailboat race. He will then discuss what makes a good crew: how to read the water, where your weight needs to be and the importance of a positive attitude. presented by Ian Morrison of Annapolis Sailing School |
2:00p - 3:45p |
Racing Rules Questions & Answer session |
The Racing Rules of Sailing have been updated for 2025-2028. Learn what’s new from Bill Simon. Bill is a life long sailor and racer. For ten years he was the Race Program Director at Oakcliff Sailing where he became involved in high end racing and race official training. He retired to the Annapolis Area and remained on the Oakcliff Sailing Board for five years. Past Chair of US Sailing Judges Training and Testing Subcommittee. He is an International Judge and National Umpire. He is the Chief Judge for Eastport YC and a member of the CBYRA Area Appeals Committee. Bill is an active sailing judge and umpire in the area and nationally.
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