Our team members are all maritime professionals with experience in training advanced and novice crew. So you’ll likely have one or two seasoned captains aboard! We have sailed a combined 200,000+ nautical miles on over 50 different vessels ranging from 16′ to 530′, sail and power. We’ve delivered boats to and from the Caribbean & Bahamas, been across the Atlantic, circumnavigated Newfoundland, raced to Alaska, and lived aboard during chilly New England winters. We all have worked on sail training vessels in positions from dishwasher or deckhand to mate, engineer, chief medical officer or captain. Oh, and don’t forget the tugboats, a lobster boat, and primitive row/sail boats too!
Our instructors and crew are carefully selected from our team to ensure the best pairing for each course, drawing from the experienced professionals listed below.
We’re not just sailors trying to make a living doing what we love,
we are educators who love to sail.
Teresa Carey (Owner/Captain)
Teresa is a US Coast Guard licensed master and sailing educator with thousands of sea miles and two decades under her belt. She began sailing on the Great Lakes and has sailed the Pacific Northwest, Caribbean, and the Western Atlantic from Panama to Newfoundland. She worked for the Outward Bound sea program, where she taught seamanship and leadership to teens and adults aboard traditional vessels. Teresa has sailed schooners, sailing yachts, mega yachts, dinghies, and even a lobster boat. She has sailed offshore and coastal, both solo and with a crew. Teresa moved aboard a small sailboat in 2008 and sailed solo between Maine and the Bahamas for a few years. Teresa has spoken about leadership and sailing at national events, boat shows, Cruiser’s University, and other functions. She was the producer for One Simple QUESTion, a sailing documentary. She was the director for Hello Ocean, providing research expeditions for early career scientists and artists. During the ‘off season’ she is a science media producer, currently producing a science news podcast for Discovery Channel.
Ben Carey (Owner/Captain) @morsealphaexpeditions
Ben holds a USCG 200 ton Master and 500 ton Mate of Towing. He grew up on Long Island Sound and was drawn to the water at an early age, when he started clamming commercially. Ben has spent the last 25 years working aboard a wide variety of vessels from schooners and tall ships to tugboats and dinghies. He bought his first sailboat, Chamois, a Nor’sea 27 in 2006. A few years later he listed Chamois for sale, and met Teresa when she inquired about buying it! She didn’t buy his boat, but she did “buy the farm” 🙂 Ben then moved up to Elizabeth, a 28′ Bristol Channel Cutter, which was the boat on which he and Teresa sailed to Newfoundland and made the film One Simple Question. Since then he has crossed the Atlantic, delivered vessels to and from the Caribbean, and worked aboard tugboats. His passion for sailing and good seamanship led him to co-found Morse Alpha Expeditions, and the purchase of Rocinante. He loves sharing his passion and experience, and he also loves baking cookies!
John “Sockeye” Calogero (Captain)
John holds a USCG 100 ton Ocean Master and 200 Near Coastal Master plus a 200 ton Ocean Mate’s License. He is also a Wilderness EMT. After a scientific cruise to Greenland as a student on a 144 foot square rigged barquentine, John “Sockeye” Calogero stepped up into the role of a deckhand and a maritime educator for the first time. That was in 1983 and launched a varied career including boat building and a voyage to Saudi Arabia on a merchant vessel during Desert Shield (after Desert Storm). Since 1994 he has captained and instructed Outward Bound courses in open oar and sail boats in Washington, British Columbia, Massachusetts, Maine, Florida, and the Bahamas. In between Outward Bound courses he ran a charter boat in Alaska, delivered goods to an orphanage in the Bahamas by schooner, monitored whale watching in the Salish Sea, instructed many ASA sailing courses, and completed the Race to Alaska not once, but twice! John has sailed thousands of miles, and brings his vast knowledge and amazing patience to the Morse Alpha team.
Tara Watkins (Mate)
Tara holds a USCG Master’s License and certification as a Wilderness First Responder. With experience working with Outward Bound Schools, NOLS, and Atlantic Challenge USA, Tara brings a diverse range of expertise to her role at Morse Alpha Expeditions. She has led countless expeditions, including the 2022 Race to Alaska, where she sailed alongside fellow instructor John Calogero.
A passionate advocate for inclusivity in outdoor activities, Tara volunteers with nonprofit organizations such as Women on the Water and SEASTR, working towards the goal of creating accessible waterborne adventures for all. Tara’s teaching style emphasizes hands-on learning, safety, and fostering confidence in all participants. She’s an avid early morning swimmer – and has a knack for luring others to join her on this most sacred of morning rituals! Be warned!
Courtney Boucher (Mate)
Courtney Boucher is a USCG licensed Captain with a 100 ton Master and 200 ton Mates license. She’s enthusiastic sailor. Having grown up in Annapolis MD, she’s been around the water since day one. She’s gone on to sail schooners, pulling boats and, a variety of sailing yachts. She raced to Bermuda, sailed the Caribbean on tall ships, and knows the Chesapeake Bay like the back of her hand. She currently splits her time working for S.E.A. – Sea Education Association, sailing aboard the 134′ Brigantine Corwith Cramer, and leading expeditions with Outward Bound here on the Maine Coast and in the Florida Keys. She’s an educator through and through, and enjoys the process of watching her students grow as sailors and as leaders. Courtney is also a certified Wilderness First Responder. If we call her “Beans”, don’t be alarmed, that’s her nickname!
Olivia Lord (Mate)
Olivia holds a USCG 100 ton Near Coastal Master and 200 ton Near Coastal Mates license as well as her Wilderness First Responder Certification. A student of the sea since she was small enough to double hand an Optimist dinghy, Olivia first grew in ocean literacy on the ever-breezy Buzzards Bay on Cape Cod, MA. Since then, she has accrued time on a wide range of sailboats as a Quissett Yacht Club sailing instructor, Brown University Collegiate racer for four years, SEA Semester Assistant Scientist and Third Mate on 135’ Brigantines for six years, and Hurricane Island Outward Bound Captain and Instructor since 2021. Through Sea Education Association and Outward Bound, Olivia has accrued more than 20,000 nm underway: learning, absorbing, then teaching life and leadership in an oceanic environment in both the South Pacific and North Atlantic waters. She deeply loves the community that grows on overnight sailing expeditions, loves to share and teach all that she knows about sailing and the sea, and is an avid stargazer.