Waypoint Sailing Society

Membership Designed Around Your Sailing Journey

Woman sailing on the private North Shore of Chicago at sunset.

Whether you're discovering catamarans for the first time or you're an experienced skipper looking for regular access to the water, the Waypoint Sailing Society offers a place to learn, connect, and grow.

A community built around sailing, lifelong learning, and unforgettable experiences on the Great Lakes and beyond.

Society Member

Your First Step Into the Community

Perfect for those who have discovered a passion for sailing and want to spend more time on the water.

Society Members enjoy exclusive access to Waypoint events, educational opportunities, and preferred pricing on training and private sailing experiences. It's the ideal way to become part of the community while building the skills and confidence to progress toward independent sailing.

Benefits

  • Preferred pricing on training programs

  • Preferred pricing on private sailing experiences

  • Invitations to member-only sailing events

  • Educational seminars and guest speakers

  • Seasonal social gatherings

  • Early access to select experiences and events

  • Monthly member newsletter with cruising tips and Waypoint updates

  • Access to the Waypoint community

Best for: New sailors, boating enthusiasts, future members, and aspiring owners.

Qualified Skipper

Earn the Privilege to Take the Helm

Qualified Skipper status is earned—not purchased.

After successfully completing the Waypoint Multihull Academy and demonstrating the knowledge, judgment, and boat handling skills required to safely operate NOVA, members may become eligible to bareboat charter the vessel.

This designation reflects trust, competency, and a commitment to safe seamanship.

Benefits

Everything included with Society Membership, plus:

  • Eligibility to bareboat charter NOVA

  • Priority access to charter reservations

  • Extended booking windows

  • Access to Advanced Multihull Clinics

  • Annual skipper proficiency review

  • Invitations to destination sails and flotillas

  • Opportunity to mentor newer members

Best for: Experienced sailors and graduates of the Waypoint Multihull Academy.

Executive Member

A Limited Membership for Dedicated Multihull Sailors

Executive Membership is reserved for experienced skippers who want regular access to premium multihull sailing while helping shape the future of the Waypoint community.

Membership is intentionally limited to preserve exceptional access, maintain a close-knit culture, and ensure the highest quality experience for every member.

Admission is by application and approval.

Benefits

Everything included with Qualified Skipper, plus:

  • Highest charter booking priority

  • Preferred executive charter rates

  • Complimentary annual checkout and skills review

  • Invitations to Executive-only sailing events

  • Annual strategy dinner with Waypoint leadership

  • Early access to future fleet additions

  • Invitations to exclusive flotillas and extended cruises

  • Concierge trip planning assistance

  • Priority invitations to manufacturer demonstrations and new boat previews

Best for: Experienced sailors seeking a premium, long-term relationship with Waypoint.

Founding Executive Member

Help Build the Future of Multihull Sailing on the Great Lakes

Founding Executive Membership is a one-time opportunity offered to a select group of individuals who believe in Waypoint's vision from the very beginning.

These members aren't simply joining a club—they're helping establish what we hope becomes the premier multihull sailing community on the Great Lakes.

Founding memberships will never be offered again once all positions have been filled.

Exclusive Founding Benefits

Everything included with Executive Membership, plus:

  • Permanent recognition as a Founding Executive Member

  • Founding Member pricing locked in for the life of your membership (subject to maintaining active membership)

  • First access to new vessels added to the fleet

  • Opportunity to provide input on future fleet acquisitions and member offerings

  • Recognition aboard NOVA and on the Waypoint website

  • Invitation to an annual Founders Dinner and planning session

  • Legacy status as one of the original members who helped launch the Waypoint Sailing Society

Membership is limited to preserve exclusivity and ensure every Founding Member plays a meaningful role in shaping the future of the organization.

Request Membership Information

The Waypoint Sailing Society was created for people who believe life is better under sail.

Tell us about your sailing experience, your goals, and where you see yourself in the Waypoint community.

We'll help you determine the membership that's right for you

Start your Membership Journey →

Your Questions, Answered

  • No. Society Membership is open to anyone with an interest in multihull sailing. Whether you're completely new to sailing or have years of experience, we'll help you find the membership and training path that's right for you.

  • Not at all. The Waypoint Sailing Society was created for people who want to enjoy the multihull lifestyle without the responsibilities of ownership.

  • Bareboat chartering is available only to Qualified Skippers who have demonstrated the knowledge, judgment, and boat handling skills necessary to safely operate the vessel. Members may qualify through previous experience, a successful checkout, or completion of the Waypoint Multihull Academy.

  • Great! Experienced sailors are encouraged to apply. Depending on your background, you may be eligible to complete a Waypoint checkout evaluation rather than progressing through the full training curriculum.

  • Society Membership is designed for those who want to learn, connect, and participate in the Waypoint community. Executive Membership is a limited, application-only membership for experienced sailors seeking premium access, exclusive events, and a greater role within the Waypoint Sailing Society.

  • No. Executive Membership is intentionally limited to preserve fleet availability, maintain a strong community culture, and ensure exceptional experiences for all members. Applications are reviewed based on sailing experience, goals, and alignment with Waypoint's values.

  • Yes. Our vision is to build the premier multihull sailing community on the Great Lakes. As Waypoint grows, members will enjoy access to an expanding fleet of premium sailing catamarans and new destinations.

  • Absolutely. Members enjoy access to exclusive educational seminars, dock socials, destination sails, flotillas, owner workshops, guest speakers, and seasonal gatherings designed to build both sailing skills and lasting friendships.

  • Yes. One of Waypoint's core missions is to help sailors progress from their first multihull experience to confident ownership. Through training, chartering, educational clinics, and ownership guidance, we'll help you gain the knowledge and experience needed to purchase and enjoy your own cruising catamaran.

  • Simply complete our membership application and tell us a little about yourself, your sailing experience, and your goals. We'll contact you to discuss the membership options that best fit your journey and answer any questions you may have.

  • Because we believe catamarans offer one of the most enjoyable and accessible ways to experience life on the water. By focusing exclusively on multihulls, we're able to provide specialized training, meaningful experiences, and a community centered around the unique lifestyle these boats inspire. Our goal is simple: to become the home of multihull sailing on the Great Lakes.