Chesapeake Whalertowne

We currently have the complete Boston Whaler boat line available and are eager to help you find the perfect boat to fit your needs. Whether it is a day offshore fishing the canyons, a day waterskiing and swimming with family and friends, or searching the Chesapeake’s amazing back creeks and shallows, we have a Boston Whaler to take you there.

Tommy Ottenwaelder | Chesapeake Whalertowne


Tom “Tommy O” Ottenwaelder joined Chesapeake Whalertowne’s sales staff in October 2018 after 29 years of Active Duty service in the U.S. Coast Guard. With a Master 100GT professional captain’s license and lifetime of boating experience, Tommy O brings a unique perspective to recreational boating sales and service. He uses his experience not only to help clients find the right boat but to further guide them to a relaxed and enjoyable boating lifestyle.

Jake Boulay | Chesapeake Whalertowne


Jake Boulay has been a member of the Chesapeake Whalertowne sales team since 2015. Prior to moving into sales, Jake handled logistics and service management. During his tenure he has gained an in-depth knowledge of the Boston Whaler and Mercury Outboard brands. Jake’s lifetime of experience on the water gives him a true understanding of the best boat to fit your needs. 

Bart Hiltabidle | Chesapeake Whalertowne


Bart Hiltabidle is one of the most recognized names in the Annapolis boating community. Bart has helped shape Boston Whaler’s legacy in the Annapolis area. Whether you are in search of a 13’ Super Sport or the flagship Boston Whaler 420 Outrage, Bart has the knowledge and expertise to help narrow your search to the perfect boat. Chesapeake Whalertowne opened a new and exciting location in downtown Annapolis in 2018, featuring waterfront access and an indoor showroom at the base of Ego Alley.

Rick Boulay, Jr. | Chesapeake Whalertowne


Rick Boulay, Jr. has been a member of the Chesapeake Whalertowne sales team since 2006. Since joining the sales team, Rick has become one of the highest volume sales producers for Boston Whaler nationwide and an expert within the Boston Whaler Yacht program. Whether you are looking for brokerage services or new boat sales, Rick can help you get the boat you are looking for (or looking to sell) quickly and for the best value. Rick is the General Manager of Chesapeake Whalertowne and also a member of the Boston Whaler Design Team.