Learn to skipper a sailing catamaran

Whether you've never stepped aboard a sailboat or already have experience on the water, Waypoint's training program is designed to take you from curious beginner to confident multihull skipper.

Our curriculum focuses on the real-world skills needed to safely operate a modern cruising catamaran on Lake Michigan.

Start your sailing Journey →

Why learn on a catamaran?

Learning on the type of boat you eventually want to charter or own simply makes sense.

Instead of adapting monohull techniques later, you'll develop skills specific to cruising catamarans from day one

You’ll Learn

  • Twin-engine maneuvering

  • Catamaran docking techniques

  • Sail handling and trim

  • Weather awareness

  • Navigation

  • Anchoring

  • Boat systems

  • Crew communication

  • Trip planning

  • Safe decision-making

Your Learning Path

Explorer – Discover Sailing

Perfect for complete beginners.

No experience required.

You'll learn:

  • Basic sailing terminology

  • Safety equipment

  • Points of sail

  • Wind awareness

  • Steering fundamentals

  • Line handling

  • Crew roles

  • Enjoying a day under sail

Goal: Feel comfortable and excited about sailing.

Crew – Foundations of Seamanship

Begin developing the practical skills every skipper needs.

Topics include:

  • Knots and line handling

  • Rules of the road

  • Navigation basics

  • Weather fundamentals

  • Boat systems

  • Dock etiquette

  • Anchoring fundamentals

  • Safety procedures

Goal: Become a knowledgeable and capable crew member.

Helmsman – Catamaran Handling

This is where Waypoint becomes different.

Focus exclusively on multihulls.

Topics include:

  • Twin-engine maneuvering

  • Docking in varying wind conditions

  • Pivot turns

  • Close-quarters handling

  • Spring lines

  • Sail balance

  • Reefing

  • Crew management

  • Emergency procedures

Goal: Operate a cruising catamaran safely around the marina and under sail.

Skipper – Coastal Cruising Skills

Now students begin thinking like captains.

Topics include:

  • Voyage planning

  • Weather interpretation

  • Fuel management

  • Battery management

  • Anchoring overnight

  • Emergency planning

  • Watchkeeping

  • Guest safety

  • Provisioning

  • Decision making

Goal: Plan and execute a successful day cruise with confidence.

Waypoint Qualified – Bareboat Checkout

Everything comes together.

A Waypoint instructor joins you aboard NOVA for a practical evaluation.

You'll demonstrate your ability to:

  • Conduct a safety briefing

  • Inspect the vessel

  • Depart the dock safely

  • Maneuver under power

  • Raise, reef, and trim sails

  • Navigate effectively

  • Return and dock confidently

  • Care for the vessel throughout the day

Successful completion qualifies you to bareboat charter NOVA, subject to Waypoint's charter policies and ongoing proficiency expectations.

Continue Your Journey!

Training isn't the finish line—it's the gateway.

After completing the program, you'll have the opportunity to:

  • Bareboat charter NOVA

  • Join the Waypoint Membership Program as a skipper

  • Continue building experience through advanced clinics

  • Prepare for catamaran ownership

Start your Training →

Advanced Sailing Clinics

Continue building your confidence with hands-on workshops designed for experienced sailors, new owners, and Waypoint members. Each clinic focuses on a specific skill that helps you become a safer, more capable multihull skipper.

Featured Clinics

  • Going Aloft Safely – Proper harness use, mast climbing systems, safety procedures, and performing basic inspections and maintenance at the masthead.

  • Heavy Weather & Reefing – Sail reduction strategies, weather routing, storm preparation, and decision-making in changing conditions.

  • Advanced Docking & Close-Quarters Handling – Master spring lines, crosswind docking, tight marina maneuvers, and emergency docking techniques.

  • Anchoring & Mooring – Selecting anchorages, setting and retrieving anchors, mooring ball procedures, and overnight anchoring best practices.

  • Marine Electrical & Energy Management – Understand batteries, charging systems, solar, inverters, and power management while cruising.

  • Diesel Engine & Systems Essentials – Routine maintenance, troubleshooting common issues, and confidence operating twin diesel engines.

  • Navigation & Passage Planning – Advanced chart work, electronic navigation, weather interpretation, and planning safe Great Lakes passages.

  • Emergency Preparedness – Crew-overboard recovery, towing procedures, emergency communications, fire response, flooding, and equipment failures.

Get Advanced Clinic Updates →

Never Stop Learning

The best skippers are lifelong students. Our Advanced Clinics are designed to sharpen your skills, build confidence, and prepare you for more ambitious cruising adventures—whether you're chartering NOVA, cruising the Great Lakes, or preparing for extended voyages beyond.

Frequently Asked Questions

  • Most sailing schools end when you pass a class.

    Waypoint's program is designed around what comes next.

    Every lesson builds toward independent multihull sailing.

    Whether your goal is to charter NOVA, join the Waypoint Membership Program, or someday own your own cruising catamaran, your training has a clear purpose.

  • No. Our curriculum is designed for complete beginners as well as experienced sailors transitioning to multihulls.

  • Everyone progresses at a different pace. We focus on demonstrated competency rather than simply completing a set number of hours.

  • Our primary goal is preparing you to safely operate a cruising catamaran. As the program grows, Waypoint may incorporate nationally recognized certifications where they enhance your learning and opportunities.

  • Students who successfully complete the Waypoint Bareboat Checkout and meet our charter qualifications may become eligible to bareboat charter NOVA.

  • We offer flexible pricing based on project type and complexity. After an initial conversation, we’ll provide a transparent quote with no hidden costs.

“What I love most is the flexibility. I can go at my own pace, revisit lessons, and keep learning whenever it works for me.”

Judy Walsh. Lake Forest, IL.