Meet our Management Team

Kathy – General Manager/OwnerKathy

Kathy has spent over 27 years working in the tourism industry. Throughout college she worked for Old Town Trolley Tours in Boston as a ticket seller and tour guide. By the time she left Old Town Trolley in 1994 she had been promoted to General Manager of Retail, overseeing six ticket/retail stores in Boston and Washington D.C. In 1995, with 10 years of experience under her belt, Kathy moved to Portland and started her own tour company “Mainely Tours” offering trolley tours of Portland as well as chartering her vehicles for transportation, weddings, etc. In the spring of 2009 Kathy and her husband Bill, who owned Eagle Island Tours, in an effort to streamline their operation and better serve the tour and charter market, began operating their trolley tours and harbor cruises under one new name, Portland Discovery Land & Sea Tours. Although Kathy spends much of her time behind the scenes working on marketing and bookkeeping for the company, she still prefers spending summer days at the Long Wharf ticket booth, meeting and greeting our customers! In her spare time Kathy enjoys travelling with Bill and their 2 kids, Nicolas & Juliana.

Bill – General Manager/OwnerBill

Captain Bill has lived in Maine all his life and has called the Greater Portland area home for the past 15 years. Bill’s interest in the water and boats began at a very young age as the son of a Merchant Marine Officer and an avid Steamboat enthusiast. “Growing up with a mariner as a father, I don’t remember ever being on a boat and not being in the wheel house. It was clear early on that one day I would be a Captain.” Bill has a passion and close connection to Casco Bay as some of his descendants lived and worked on the islands in the bay. Bill genuinely enjoys working at Portland Discovery because of all the wonderfully dedicated people he has the opportunity to work with and considers it an honor to be able to expose people from around the world to the incredible sights and diverse history of Portland and Casco Bay. When Captain Bill is not working, he enjoys spending time with his beautiful wife Kathy and their two children Nicolas and Juliana.

Jake – Office Manager Jake

Jake was raised in Windham, Maine, and though having lived in states as far away as New Mexico, was drawn back to Portland’s salt air and small city charm. He has been with Portland Discovery for 9 years, originally as ticket sales staff and now as Office Manager. He represents our company in all office operations, whether it’s a question about a Land and Sea Tour or details of a private charter. He likes working at Portland Discovery because of the great cast of employees that return to us every season, being able to help clients book memorable events and being able to show off the wonderful city of Portland to first time visitors. His spare time is spent playing frisbee golf, riding his bike, seeing live music or listening to music and reading. Call or email today and you’ll probably talk to Jake!

Chris – Captain/Maintenance ManagerChris

Chris grew up in Rhode Island sailing small boats at an early age until beginning his commercial boat career just out of High School. A graduate of Maine Maritime Academy, he has worked on vessels ranging from tugboats to research vessels and has traversed many countries and oceans. Chris settled in Portland because of its way of life and its connections to the ocean and the working waterfront. When he’s not working he’s right back out exploring Casco Bay, whether it be by sailing, rowing or surfing. He is going on his second full season with Portland Discovery as a full time captain and maintenance director and thoroughly enjoys being able to share his love of the ocean and beautiful Casco Bay with our many visitors.

Jack – Ticketing/Sales Manager Jack#2

Jack is originally from the Portland area and has held previous jobs as a lobster fisherman and owned his own landscape business for 13 years. Having travelled the world, he returned to Portland to raise a family, and his love of the outdoors and interacting with people brought him to Portland Discovery. Truly a “Jack” of all trades, he manages our ticket booths, deckhands on our boats and often makes the rounds to hotels and local businesses promoting new programs and tours as well. He enjoys talking to our diverse customer base and helping them make some great memories on their vacations. In his time off he is camping, hiking, traveling and spending time with his wife.

Covid-19 Message To Our Customers

Dear Valued Customers,

The challenges of providing a safe experience for our customers, staff, families and our community due to Covid-19 have caused us to make the very difficult decision to not operate our tours for the 2020 season. All customers who had previously booked tours or charters with us for the 2020 season will receive a full refund.

We will be back in 2021 to warmly welcome you aboard our tours. See you next year!