About us

Key West Captains is as local as it gets, but has the worldwide network in place to complete even the biggest of tasks! Our backgrounds range from 100 ton Master Captains, American Sailing Association (A.S.A)  Instructors, military veterans, corporate executives, boat builders, general contractors, college athletes, retired police officers, HVAC technicians, business owners, mechanics, sailors, power boaters and even have a teammate that has biked across the world! Like seriously! On a bicycle! With the vast majority of us living aboard our own large vessels docked at marinas right here on the island..... To say that we are living and breathing the boat life, would be an understatement. 


Whether you are looking to snorkel the reef this afternoon, schedule an overnight private charter to the Dry Tortugas next week or have your vessel moved from New York to the Bahamas next month.... This is the team to contact!!!! Call/Text (305) 209-3414

Meet The Team


Captain Brian Tober

Freelance Captain - previous charter business owner - retired corporate executive - resides on his 41' sailboat here in Key West



Captain Gregg Zahn

100 ton Master - Business Owner - Retired Wealth Management Lending Officer - resides on his 40+ foot power boat here in Key West



Konrad Mackey

1st Mate - Boat Builder - Army Veteran - Service Technician -resides on his 46' catamaran here in Key West 



Captain Paul Grande

100 ton Master - Marine Corps veteran-charter business owner-Retired Sergeant Rochester PD- resides on his 40+ foot trawler here in Key West


Captain Bridget Woods

Freelance Captain - Founder of Sun Kissed Key West - Long time Key West local


Captain Andrew Knott

100 ton Master - Yacht Broker - ASA Instructor - resides on his 46' monohull here in Key West



Captain Justin Garreaux

Freelance Captain - ASA Instructor - Computer Science - Resides on his sailboat here in Key West



Patrick Carter

1st Mate (future Captain) - Whitewater river

guide - snorkeling & fishing guide - handyman, local bartender and musician


Captain Jason Lape

Long time Key West Captain. Worldwide cyclist. Literally. All the way around.  Kayaked North America from Canada to Mexico. Appalachian trail guide. Motor cycle tour guide in Vietnam. Resides on his sailboat here in Key West

Captain Dustin Garland

50 ton Master - Business Owner - 


Captain Bryan Held

Freelance Captain - Resides on his sailboat here in Key West

Brianna Lester

1st Mate - Free Diver - Resides on her 40+ foot Hatteras here in Key West

Billy Jay

1st Mate - HVAC Technician - The guy every single one of us call when we're stumped on a boat issue -  Resides on his 40+ foot Hatteras here in Key West

Captain Nick

100 ton Master - General Contractor -

Boat Builder - Property Manager -

Resides on his sailboat here in Key West