Making Every Voyage Unforgettable
We’re a small crew of seasoned captains and hosts who believe the best memories are made on the water. From sunset sails to private anchorage-hopping charters around the Bay, we make it easy for you to relax, celebrate, and explore at your own pace.
Safety, comfort, and personal connection guide everything we do. We listen to what you want, tailor each itinerary together, and handle the details—so all you need to do is show up and enjoy the breeze.
Our Team
Duncan Hood
As an ASA Senior Master Instructor Captain Hood has roamed the globe: from the warm waters of the Caribbean to the bustling coasts of China; from the Baltic shores of Poland to a surprisingly vibrant sailing community in Oklahoma.
Today, Captain Hood sails his own schooner, Adventurer. Every charter he leads is enriched by decades of teaching experience, global credentials, and a genuine passion for sharing the water with others. Whether you are a seasoned sailor or stepping aboard for the very first time, you will find a captain who knows the bay intimately, tells a great story, and takes pride in making every voyage safe, memorable, and thoroughly enjoyable.
Owner, Sr. Master Instructor & Captain
Jennifer Champion
As an ASA instructor and Navy Qualified Off Shore skipper, Jennifer got her start sailing on a small lake in Maine at a young age. From there the boats and bodies of water have grown allowing her to sail both Inland and International waters building her experience and fueling her passion for both sailing and teaching others . Jennifer is currently pursing both her USCG Masters License and the privilege of becoming an ASA Master Instructor.
Jennifer takes safety and technique very seriously because focusing on both can allow for the best experiences and the most joy while doing it. As a female skipper, it is both an honor and a mission to empower other female sailors to grow their skills and showcase their undeniable talent in this sport. She lives by the motto that a well fed crew is a happy crew and regularly whips up great meal options underway!
Operations Manager
What began as a transformative crew experience in 2009 has since evolved into nearly 700 days at sea, a USCG OUPV license, and a respected role as an advanced American Sailing instructor. From his home base in Alexandria, Virginia, Randy skippers everything from his nimble Cape Dory 25D to grand 48-foot traditional schooners, bringing a unique blend of military-grade discipline and a deep-seated passion for maritime life.
Today, Randy specializes in taking intermediate sailors out of their comfort zones and preparing them for the realities of offshore cruising. He is known for his signature calm under pressure—a trait forged in service and refined on the waves. He teaches his students to be their own leaders, methodical problem-solvers, and disciplined navigators. But it's not all checklists and crisis management; Randy is equally famous for keeping crew morale high by whipping up gourmet meals from the galley after a long day on the water.
Owner, Heritage Sails & Captain
Randy Borland
Raul Cardenal Captain
Captain Raul Cardenal brings a lifetime of ocean-loving adventure, Navy-honed leadership, and genuine sailing passion to every charter. A Miami native, Raul grew up near the water and never really left it. Whether he’s navigating a breezy afternoon sail or sharing a sunset story over the rail, he turns every trip into a memorable escape.
Along the way, Raul turned his shore leave into serious sea time. He holds a U.S. Coast Guard Operator of Uninspected Passenger Vessels (OUPV) license for near-coastal waters and is a highly credentialed American Sailing Association instructor (ASA 101 through 206, plus Docking, Cruising Catamaran, and more). He’s also a PADI Divemaster for those who like to see the water from a different angle. Fluent in English, Spanish, and some Portuguese, he makes every guest feel welcome—no matter where they’re from.
Captain
To keep up with all our adventures look us op on our socials! We would love it if you would tag us in your pics, give us a like, and follow us for more.
Ready to Plan Your Cruise?
Send us a quick note and we’ll get back to you with date options, package ideas, and friendly answers to any questions.