About Us

Thanks for joining along our journey! We are Cindy and Jeff Cunningham, and have been sailing the Great Lakes for nearly 20 years, first on our 1986 Catalina 30 and since 2015 on our 1996 Catalina 34 MKII called Respite.

Cindy is a retired high school teacher who taught government, psychology, and history for nearly 40 years. She has been sailing big boats for 20 years, often on all-women crews. She believes women learn sailing best while sailing with other women. Cindy has delivered racing boats as well as other vessels on lake’s Michigan, Huron, and Erie. She proudly captains our beautiful boat!

Jeff is a retired journalist and swimming coach, who has been sailing and racing most of his adult life. He finds exploring new ports and marinas exciting. Jeff loves to meet new people and hear their stories – both sailing and life. His job is to keep the boat afloat and running. He is by no means a master mechanic, or fiberglass repairman but enjoys keeping the boat in the best shape he can.

We have been married for 44 years... and counting!

Duncan is our 10-year-old Carin Terrier who has been sailing his entire life. He loves to explore new ports and find new ice cream shops. Duncan also loves having his picture taken with any one who will hold him.

We started our website, SailingWithDuncan.com, to document our travels. A place where we can tell the many stories of the places we travel and the people we meet. The stories as documented here are true as far as we can remember... or something like that.

Thank you for taking the time to read our stories. We hope you find them a small “Respite” from your daily life. If you choose to, please leave you comments and questions. Duncan will answer when he can!

Happy Sailing!

Cindy and Jeff 

+ Duncan!