Chicago sailing, Detroit sailing, instruction, sailboat lessons, an innovative sailing timeshare program and more.

Professional Captains

Someone wise once said "you are known by the company you keep". Pinnacle is honored to keep company with USCG Licensed Captains that are the best in the business. Deeply skilled mariners that are highly educated with remarkable career and life experiences; and inviting personalities.

Each of our Professional Captains have had vast time at sea and undergo rigorous screening and testing by the United States Coast Guard to achieve and maintain their Master license.

Every course offered by Pinnacle Yachts is taught exclusively by these highly skilled USCG Licensed Captains. Using Pinnacle's renowned curriculum, they deliver top-quality instruction in a way that builds skill and confidence.

Our Professional Captains are also available for hire directly by Pinnacle Members to assist with operating the yacht so that the member can focus on entertaining business associates, friends and family. Pinnacle Professional Captains are wonderful people that make your yachting event truly special and help you shine as the host.

Captain BJ
USCG Licensed Master

The "Ever-Charming" Captain BJ is graceful and articulate - and one heck of a serious mariner. Few people can handle a yacht like her in any conditions due to her extensive off-shore experience. She has also instructed at Womanship, a highly regarded east coast school dedicated to teaching woman to sail. Her career as a National Account Manager to a Fortune 250 company gave her the opportunity to travel the country and expand her sailing expertise to the San Juan Islands, Chesapeake and Long Island Sound. She summers in Chicago teaching on sail and powerboats, and spends winters teaching yoga and traveling the globe. BJ holds a MA in Psychology from DePaul University

Captain Mayre
USCG Licensed Master

A consummate professional, Captain Mayre is a wonderful, patient teacher and highly skilled sailor. Her students often comment to management about their delight with her teaching. Mayre's interesting resume includes a stint as a country singer in New York City in the 70s, and most recently as an adjunct professor in writing. She lives along the southern shore of Lake Michigan with her menagerie of pets. Mayre holds a BA from Depauw University and an MBA from Harvard Business School.

Captain Pat
USCG Licensed Master

If you were in a storm on the North Atlantic in January, and could have only one person with you, you would want Captain Pat. Vastly experienced, steady, brave and an absolute gentleman. Pat led a distinguished career in law enforcement as a narcotics agent.

Captain Rich
USCG Licensed Master

Growing up on Long Island Sound, Rich was drawn to offshore sailing. It was this great enthusiasm for the sea that led him to the U.S. Coast Guard Academy and later to serve with the Coast Guard. A twenty year corporate career followed, and now in addition to his commitment to Pinnacle Yachts, Rich is a dedicated middle-school math teacher and athletic coach. He owns a fine sailboat in Chicago, vacations on his second boat in Florida, and frequently sails the blue waters of the Caribbean. Rich holds a BS in Ocean Engineering from the U.S. Coast Guard Academy, an MS in Education from Lewis University, and an MBA from Pepperdine University.

Captain Dave
USCG Licensed Master

Dave has been following his passion for connecting people with the water by working in the charter and tour boat industry for more than fifteen years. He has held USCG Captain positions with some of the most prestigious large ships in Chicago and Key West. Using his love of Chicago architecture and history, Dave is known for creating informative and memorable on-the-water experiences. He also has a reputation as very thorough and patient instructor. Dave holds a BS in Financial Management from DePaul University.

Captain Leo
USCG Licensed Master

Leo is an insightful mariner that enjoys sharing the knowledge he has amassed over his thirty-five years on the water. He has sailed extensively on both coasts, the Chesapeake, the Great Lakes, and has delivered yachts to the Caribbean via Bermuda, and has participated in six Chicago to Mackinac Island races. Leo has also owned several power and sailing yachts. He enjoys the water year-round providing sail and powerboat instruction, and captain services in the north during summer; and yacht deliveries in the south during winter. Leo holds a BA in Economics from the University of Wisconsin, Madison.

Captain Robert
USCG Licensed Master

Enjoying the wind from a yacht or on a motorcycle, Robert embraces the outdoors. After many years of powerboat ownership, he began sailing in San Francisco Bay in 1979, and then purchased his own sailboat to cruise the great lakes. He has sailed the San Juan Islands and is also a skilled sailboat racer. Robert had a distinguished career in law enforcement, which culminated as the head of the Illinois State drug enforcement program. He dedicated many years as a community leader, serving as Alderman and Mayor in the Northwest Suburbs. Robert holds a BS from DePaul University.

Captain Mitch
USCG Licensed Master

Mitch has explored the waters of Australia, New Zealand and the Philippines, has sailed both coasts of the U.S., and is an avid outdoorsman and licensed pilot. He has served as managing partner of a private equity firm and was a management consultant at major firm in Chicago. Mitch has a friendly, attentive style that fits very well with those new to sailing. He holds an undergraduate degree from the University of Illinois and an MBA from the University of Chicago.

Captain Eddie
USCG Licensed Master

A sailor and saxophone player, Captain Eddie is an artist on the water and on the stage. His love of sailing shows in the classic yacht he has beautifully restored with much skill and attention to detail. He was a highly regarded sailing instructor for the skipjack adult sailing program at Columbia Yacht Club. He has raced in many Chicago to Mackinac Island and other port-to-port races. He is also a talented saxophonist and professional bandleader playing most recently with his band "Paris Swing". Eddie holds a BA from the University of Illinois at Chicago.

Captain Larry
USCG Licensed Master

Larry is a recognized "voice of the mariner" in the development Chicago's waterway safety initiatives. He is a former president of the International Ship Masters' Association, Chicago, and was a member of the USCG Ports and Waterways Safety Assessment Taskforce for Chicago. The Chicago Riverwalk Expansion Project values Larry's participation and contributions as a caring river safety activist. For many years he has captained tour boats on Chicago's river and lakefront. An executive vice president, Larry had a very successful career in the reimaging of major global brands. He is a highly knowledge mariner, superb instructor and absolute gentlemen. Larry holds a BS from The Ohio State University in Industrial Design.

Captain Russ
USCG Licensed Master

Russ was born with a love of the water. As a boy he wandered the harbors of Chicago and built his first sailboat at age twelve. He has since honed his skills and has emerged as a highly sought-after racing and cruising skipper. Russ is an "Island Goat" with over 30 successful Chicago Mac Races to his credit. He is passionate about the importance of lifelong learning with teamwork. This attitude is manifest in his yachting, musical and distinguished civic service endeavors. Russ holds a BS in Business Administration from Western Illinois University.

Captain Pam
USCG Licensed Master

Friendly and energetic, Pam teaches yacht piloting with confidence and finesse. She is known for her ability to use varying techniques to match the unique learning needs of her students, which makes her a very popular among people new to boating. Pam is a graduate of the University of Wisconsin with Bachelor degree in Fine Art.

Captain Joe
USCG Licensed Master

A lifelong resident of Chicago, Joe has crewed and skippered on many of the elite Lake Michigan regattas including thirteen Chicago to Mackinac races with several top five finishes. He has logged over 5,000 miles on the west coast in prestigious Puerto Vallarta, Cabo San Lucas and Ensenada Mexico races. As a professional Captain, Joe fulfills a desire to share his love for boating. Joe believes "Education is an unfinished symphony. Helping others realize their potential is a persistent goal." Joe holds a BS from the University of Illinois at Chicago.

Captain Rolando
USCG Licensed Master

Captain Rolando is a teacher at heart. He serves as a charter captain and teaches powerboat and sailing classes at Pinnacle Yachts. He is also an Instructor Trainer with US Sailing, the national governing body for the sport of sailing.

Rolando is a wine enthusiast, an opera lover, and an avid scuba diver. While on land, he is a violin instructor at DePaul University and a Violin Teacher Trainer with the Suzuki Association of the Americas. Rolando holds degrees from Shenandoah Conservatory and Penn State University.

Captain Mark
USCG Licensed Master

Students commend Mark's patient and motivating style which makes becoming a safe and competent boater a pleasure. At age nineteen he worked as an amusement park skipper on a riverboat in the Wisconsin Dells. Although he enjoyed being called "captain" by his passengers, he has since grown to know the importance and responsibility of actually being one. For the last eight summers he has sailed the Great Lakes in his sloop "Speakeasy" with his wife and trusty boat dog, Java. He has also sailed the Caribbean and Croatia. With a PhD in Education from the University of Wisconsin-Madison, Mark devoted decades teaching educators to use technology in their work.

Captain Gary
USCG Licensed Master

Growing up boating on the lakes of Illinois and Wisconsin, Gary started sailing the waters of Lake Michigan in 1987. Since then he has raced in 17 Chicago Macs and sailed over 15,000 miles around the Great Lakes, West Coast and the Caribbean. He enjoys teaching both beginners and the more experienced, and does so calmly with patience, understanding that everyone learns differently. Safe enjoyment of the water is his top priority. Gary holds a BS from Southern Illinois University.

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"I just wanted to take a minute and compliment you, your team and your systems... Everyone is very professional to deal with, replies promptly and works with their Captain's vs. against. You find a way to say yes (when appropriate of course) instead of no. [Captain] Pat's a great guy and instructor. What I would give to have just 10% of his patience! I observed that the other instructors had similar relationships with their trainees. Good management, good people, good systems and a pleasure to work with. You deserve nothing but success. Job well done."

D. B.
Small Business Owner
Captain, Independence Day

Chicago sailing, Detroit sailing, instruction, sailboat lessons, an innovative sailing timeshare program and more. Sailboat instruction, lessons, sailboat timeshare program, Detroit & Chicago sailing.