About us
Key West Captains is as local as it gets — with a worldwide network capable of handling even the biggest tasks. Our team brings together an extraordinary range of experience:
100-Ton Master Captains | ASA Sailing Instructors | Military Veterans | Corporate Executives | Boat Builders & Mechanics | General Contractors | College Athletes | Retired Police Officers | HVAC Technicians | Business Owners | World Bicycle Traveler | Yoga Teachers | Retreat Guides | Fitness Instructors | Breathwork Facilitators | Firefighters | Free Divers | Scuba Divers | Snorkel Guides | First Responders
With the vast majority of us living aboard our own vessels at marinas right here on the island — to say we're living and breathing the boat life would be an understatement.
Whether you're looking to snorkel the reef this afternoon, schedule an overnight private charter to the Dry Tortugas next week, or move your vessel from New York to the Bahamas next month...
This is the team to contact.
Meet The Team
Captain Brian Tober
Freelance Captain - Previous Charter Business Owner - Retired Corporate Executive - Resides on his 41' Sailboat in Key West
Alexandra Ruth Smyth
First Mate - Charter Specialist - Office Manager - Retreat Guide - Fitness and Yoga Instructor - Entrepreneur - Resides on 33' Sailboat in Key West
Captain Patrick Carter
50 Ton Master - Whitewater River Guide - Snorkeling & Fishing Guide - Handyman, Local Bartender and Musician
Captain Dustin Garland
50 Ton Master - Business Owner - Key West Tree Care - Florida Native
Captain Cameron Pitzer
50 Ton Master - Sailor - Freediver - Surfer - Business Owner of Mystic Blue Sailing Adventures - Resides on 42' Sailing Catamaran here in Key West
Captain Aaron & Angie
Freelance Captain & Mate - Business Owner of Nude Charters - Reside on their 40'+ Sailing 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' Trawler in Key West
Captain Nathalie Meyers
50 Ton Master - Underwater Spearfishing Association world record holder - Underwater Photographer
Captain Andrew Knott
100 ton Master - Yacht Broker - ASA Instructor - resides on his 46' Sailboat
Captain Jason Lape
Long time Key West Captain - Worldwide cyclist - Appalachian Trail Guide - Motor Cycle Tour Guide in Vietnam
Captain Bryan Held
Freelance Captain - Resides on his Sailboat here in Key West
Brianna Lester
First Mate - Free Diver - Resides on her 40+ Foot Hatteras here in Key West
Billy Jay
First 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