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ENHANCE YOUR BOATING KNOWLEDGE

Expert-led sessions covering navigation, docking, safety, and more - complimentary for all attendees

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Take your boating knowledge further at the Windy City Boat & Yacht Show. Presented by the Annapolis School of Seamanship, the Cruisers Classroom features a series of engaging discussions and panels designed to help you become a more confident and capable boater.

From navigation and docking to maintenance, safety, and the cruising lifestyle, these sessions cover essential topics for every stage of your boating journey. Whether you’re new to boating or looking to sharpen your skills, there’s something here for everyone.

Sessions take place throughout all three days of the show and are open to all attendees.

CRUISERS CLASSROOM SCHEDULE

11:00 AM

Ask A Captain

Do you ever wish you had a professional captain onboard with you, so you could ask him or herquestions about the situations that challenge you on the water? Join captains from the Annapolis School of Seamanship for a question and answer session. Come to the show and bring your questions!

Presented By: Captain John Martino, Annapolis School of Seamanship

12:30 PM

Start Boating Now

Thinking about getting into boating? There are many ways to enjoy boating from watersports to fishing to cruising. Join the pros from Annapolis School of Seamanship to get an overview of the styles and types of boats and how they fit the boating lifestyle you choose. Types of Boats, How to choice the right boat for you, Accessories and Gear, The boat buying process, Legal requirements, training and certification

Presented By: Captain John Martino, Annapolis School of Seamanship

2:00 PM

Docking De-Stressed

Is docking your vessel causing you stress and anxiety?Captain John from the Annapolis School of Seamanship show you the ropes, tricks, and techniques to make docking easy.Topics Include:

  • Situational Awareness
  • Forces
  • Line Handling
  • Communication
  • Close Quarters Maneuvering

Presented By: Captain John Martino, Annapolis School of Seamanship

3:30 PM

Anchoring & Mooring

Anchoring is an art as well as a skill. From choosing the best place to anchor to handling the ground tackle, this seminar will demystify the art of dropping the hook.

Presented By: Captain John Martino, Annapolis School of Seamanship

5:00 PM

How to Get Your Captain's License

Between the USCG requirements for sea time, physicals, applications and examinations, getting a captain’s license can seem daunting. Annapolis School of Seamanship’s expert captains will discuss the ins and outs of becoming a licensed captain. Topics Include: 

  • Types of Licenses 
  • Pre-requisites
  • Application Process
  • Using your License

Presented By: Captain John Martino, Annapolis School of Seamanship

11:00 AM

Lessons from the Chicago Mackinac Race

This one-hour interactive panel discussion offers a practical look at boating safety through the lens of the Chicago Mac Race, focusing on real-world practices used by offshore sailors. Tthe session highlights accessible, experience-based guidance for everyday boaters. It begins with an overview of the 300-mile race and offshore conditions, followed by a deep dive into the safety equipment, training, and decision-making used by race crews—emphasizing what translates directly to recreational boating. The session concludes with an interactive Q&A, grounded in recent real-life rescues off Chicago’s lakefront, and focused on helping all boaters better prepare for open-water and conditions.

Presented By: Chicago Mackinac Race

12:30 PM

Boat Buying

Curtis Stokes will discuss the proper boat buying process from A-Z or from shopping to closing. He will discuss how to find your dream boat, how to survey it and how to close on it. This seminar is packed with detail and a few war stories

Presented By: Curtis Stokes, Founder & Owner of Curtis Stokes & Associates

2:00 PM

Docking De-Stressed

Is docking your vessel causing you stress and anxiety? Captain John from the Annapolis School of Seamanship show you the ropes, tricks, and techniques to make docking easy. Topics Include:

  • Situational Awareness
  • Forces
  • Line Handling
  • Communication
  • Close Quarters Maneuvering

Presented By: Captain John Martino, Annapolis School of Seamanship

3:30 PM

Cruising the Great Loop

In this seminar, Curtis Stokes brings the Great Loop dream to vivid life. Based on his real-world experience advising countless cruisers, Curtis explores the heart of the Looper lifestyle, from what you’ll see along the way and how long it takes, to the challenges couples face and how life afloat compares to life ashore. He’ll tackle the toughest questions: time, budget, safety, community, and planning. Start preparing for the unforgettable journey of the Great Loop. Perfect for seasoned sailors and armchair dreamers alike.

Presented By: Curtis Stokes, Founder & Owner of Curtis Stokes & Associates

5:00 PM

How to Get Your Captain's License

Between the USCG requirements for sea time, physicals, applications and examinations, getting a captain’s license can seem daunting. Annapolis School of Seamanship’s expert captains will discuss the ins and outs of becoming a licensed captain. Topics Include: 

  • Types of Licenses 
  • Pre-requisites
  • Application Process
  • Using your License

Presented By: Captain John Martino, Annapolis School of Seamanship

11:00 AM

Start Boating Now

Thinking about getting into boating? There are many ways to enjoy boating from watersports to fishing to cruising. Join the pros from Annapolis School of Seamanship to get an overview of the styles and types of boats and how they fit the boating lifestyle you choose. Types of Boats, How to choice the right boat for you, Accessories and Gear, The boat buying process, Legal requirements, training and certification

Presented By: Captain John Martino, Annapolis School of Seamanship

12:30 PM

Docking De-Stressed

Is docking your vessel causing you stress and anxiety?Captain John from the Annapolis School of Seamanship show you the ropes, tricks, and techniques to make docking easy. Topics Include:

  • Situational Awareness
  • Forces
  • Line Handling
  • Communication
  • Close Quarters Maneuvering

Presented By: Captain John Martino, Annapolis School of Seamanship

02:00 PM

How to Get Your Captain's License

Between the USCG requirements for sea time, physicals, applications and examinations, getting a captain’s license can seem daunting. Annapolis School of Seamanship’s expert captains will discuss the ins and outs of becoming a licensed captain.
Topics Include:

  • Types of Licenses
  • Pre-requisites
  • Application Process
  • Using your License

Presented By: Captain John Martino, Annapolis School of Seamanship

QUICK DETAILS

At a Glance:

  • Expert-led discussions and panel sessions
  • Topics include navigation, docking, maintenance, safety, and cruising lifestyle
  • Designed for all skill levels

When:

  • June 12-14, 2026 (all three days of the show)

Access:

  • Complimentary with your show ticket
  • No registration is required.

Seating:

  • Limited to 30 attendees per session

SHOW PARTNERS