Cindy and Jeff Cunningham have been sailing the Great Lakes for nearly 20 years, first on their 1986 Catalina 30 and since 2015 on their 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 captains the couple’s 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.

The two have been married for 44 years.

Duncan is a 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.

The Website

Sailingwithduncan.com is a website dedicated to documenting the travels of Duncan, Cindy and Jeff and telling the stories of the places they travel and the people they meet. The stories as documented here are true as far as they can remember, or as told to them.

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, Jeff, and Duncan

Urban Cycler
The three of us at the top of the cliff in Covered Portage

City Skyline
Duncan's last day on Respite

Old City Street
One happy couple.

Urban Cycler
The three of us at the top of the cliff in Covered Portage