Meet Greg & Cait Scannell of On A Boat Sailing

Today we’d like to introduce you to Greg & Cait Scannell

Hi Greg & Cait, thanks for joining us today. We’d love for you to start by introducing yourself.
Greg has been sailing since high school getting his start racing on his Neigbor’s Tartan 10 on Lake Erie. Upon moving to Chicago in 2012 he raced out Columbia Yacht Club and taught lessons there as a sailing instructor. Cait would often stare out her window at the sailboats while working at Skidmore Owings Merrill in downtown Chicago. Her wanderlust and stress from work motivated her to take lessons and as luck would have it Greg was her first instructor. The couple began racing together and in 2016 Cait decided to buy a Cruising class Jeanneau Sun Odyssey 37. Greg claimed at the time that “sailboats are a lot of work” while Cait was thinking “I know just the guy to help me.” Together they started On A Boat Sailing, a seasonal sailing charter business in 2018. In 2020 during the Covid pandemic the couple decide to embark of Americas Great Loop- a circumnavigation of the eastern United States that takes you from Chicago to the Gulf of Mexico, around Florida, up the east coast to the Hudson River and Erie Canal and back to Chicago through the Great Lakes. The trip originally was planned to sail the Caribbean but due to travel restrictions most island nations remained closed. For three months Greg and Cait cruised the Bahamas from February 2021 to April before returning to Florida and completing the loop.

I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
Lots of lessons learned along the way. We’ve seen 15’ waves and water tornadoes on Lake Michigan. Broken down at South Manitou Island in Lake Michigan and Middle Island in Lake Huron. Learned how to fix diesel engines, sew torn sails and get the boat ungrounded when stuck on a sand bar or shoal.

Things were far from normal at the October start of the loop trip since on Day 2 they had a harrowing experience in the set of locks at Brandon Road, just south of Joliet on the Des Plaines River. They entered the locks and were placed directly behind a tow vessel that was pushing nine barges.

“When the tow started to leave, it cranked up their huge engine and we were thrown off the lock wall and were spinning around inside the lock enclosure,” Larson said. “We were screaming and just trying to get the boat tied to the wall again. It was probably the most scared we have ever been on the boat.”

As you know, we’re big fans of On A Boat Sailing. For our readers who might not be as familiar what can you tell them about the brand?
A sailing charter in Chicago, IL specializing in small group outings on Lake Michigan. We have completed over 600 charters since 2018 and have hundreds of five star reviews. The perfect place to celebrate a bachelor/bachelorette party, proposal or engagement, birthday party, anniversary or just hang with friends and family on the water. World class sailing along a beautiful skyline with luxury amenities and service. We’ve been featured in many photo shoots most notably getting on the cover of the spring 2024 issue of Chicago Stye Weddings magazine.

Are there any apps, books, podcasts, blogs or other resources you think our readers should check out?
We love following other like minded sailing adventures on YouTube and Instagram. Sailing Florence, SV Delos, La Vagabond and so many more

Pricing:

• Charters starting at $300/hr

Contact Info:

• Website: https://onaboatsailing.com
• Instagram: @onaboatsailing