On Watch Yacht Delivery & Training

On Watch Yacht Delivery & Training


Reliable, Reputable, Experienced.

Veteran Owned. Use our years of experience to build your experience!

welcome="" ownership.NEED A DELIVERY QUOTE? E-MAIL: 


welcome="" ownership.


Phone: 941-704-6206

Welcome to a PROVEN and professional way to have your yacht delivered! On Watch Yacht Delivery & Training is owned and operated by Captain Jeff Lewis. Captain Lewis is a 50 plus year experienced 100 Gross Ton Master Captain on both power and sail. As a former Customer Service Manager in the Aviation Industry, he has a background of providing superior service. His combination of business, military and maritime experience makes for an outstanding experience for our clients.

"WHY do we do what we do?"  We have a passion for boats and everything that comes with life on the water! After a lifetime of experience aboard boats, we still have a love and reverence for the ocean and the boats we love to spend special times on. We know how precious your vessel can be in your life and we can relate!

How is On Watch different? Since 2008, we provide professional service from quote to completion. We are a FULL TIME SERVICE, not part timers doing deliveries as a side job. To start, we send you a detailed quote and an open, honest assessment of your delivery or training needs. We provide you with  specific breakdown of our calculations, where all funds will be distributed throughout the delivery.

Second, we strive to calculate our delivery quote as accurately as possible based on the information about the yacht provided by the client.  This being said, we strongly suggest you provide as accurate information as possible so we can give you an accurate quote.

This calculation is based on the information available to On Watch Yacht Delivery & Training.  The configuration of your vessel and its capabilities must be accurate. ie. Folding vs fixed props, underpowered vessels, owner modifications from the standard build and design as well as mechanical failures during transit, fouled bottoms and or props, etc can negate this offer.

If we are ahead of schedule, we will credit you back and reduce the final delivery fee.

We understand some owners would like to participate in the delivery. If you are mentally and physically capable of participating, we are happy to have you along for the adventure. We can provide an offshore training package starting at $1200.00 pp.  (See Details on our Training Page)

Deliveries are not "cruises!"  We don't take a leisurely sail on your dime...we WORK on your behalf! Even if you can't join us, we will provide you regular updates of your vessel's location via e-mail using SPOT Locator & Garmin inReach technology. You will have the peace of mind knowing where your vessel is at all times. 

As a boat owner and lover, I know how you may feel entrusting your vessel to a virtual stranger. I hope to put you at ease that your vessel is in good, capable hands. My philosophy is to always act in the best interest of the owner first! Most Captains will say they will treat your boat "As my own!"  I personally disagree... I treat your vessel with the reverence as it is NOT my vessel to take undue risk with. You can rest assured your boat is in the hands of a conscientious Captain with attention to detail. I am a Captain who conducts himself as if the owner is aboard even if he is not.



A third generation sailor, Captain Lewis has owned and operated both power and sailboats since a very young age, up to and over 80 feet in length. He was established early in life as a successful racer and competitor on various class sailboats. He has built a solid reputation as a reliable, professional and trustworthy non-smoking Captain. Your yacht is in good hands when entrusted with Captain Jeff Lewis. "I'm proud to say we have a 100% successful delivery history. Each yacht has been delivered safely and securely. I treat each vessel NOT as they are my own, but with the reverence that it is NOT my vessel to take undue risk with when under my command."

Every delivery has different requirements, thus, planning is as important as the execution of the delivery. A good delivery captain should have a solid grasp as to what to expect concerning weather, vessel condition, its capabilities, and crew capabilities.

With more than 50 years of experience on various size power and sail driven boats, Captain Jeff Lewis has successfully completed dozens of trans-oceanic trips. Captain Jeff Lewis retired from the U.S. Coast Guard in 2000 with Honorable Distinction and held a "Secret" level security clearance during his entire tenure in the Coast Guard reflective of his honesty and integrity.


Captain Jeff Lewis has successfully completed many trans-oceanic deliveries on sailing and power vessels from 30' to 80' and over 100,000 offshore track miles, serving as Captain and Navigator. He is an experienced, accomplished boat handler and navigator in the Atlantic, Caribbean and Gulf of Mexico. He was honored with "Outstanding Instructor" by The American Sailing Association in 2010.  He served as a Skimmer Vessel Captain during the BP Oil Spill Clean Up Effort in 2010. He is a skilled sailor with a lifetime of more than 50 years of safe sailing and powerboat operating and heavy weather experience.

See the video below for a taste of the weather I have lots of experience in!...


>Discover Boating Certified Instructor Examiner (POWER)

>Multi Engine & Single Engine & Directed Thrust Vessels

>Close Quarters Precision Maneuvering Instructor

>Advanced Docking Instructor

>Power boating Made Easy Instructor

>Sailing Catamaran Certified Instructor

>2010 American Sailing Association, "Outstanding Sailing Instructor"

>U.S.Coast Guard Retired with Honorable Distinction

>100 Gross Ton Master Licensed

>Passagemaking Experienced

>Offshore Qualified/Experienced

>TWIC Card Holder

>First Aid & CPR Certified

>Towing Endorsement

>Sailing Endorsement

>ASA Sailing Instructor: 101, 103, 104, 114.


...An Introduction to One of Our Associate Captains

 Captain Jim Deyo has been operating boats, both power and sail, for over forty years. His early experience as a teenager was with 16 to 20 foot ski boats and small sailboats (Sunfish and Hobie Cat). After enlisting in the US Coast Guard he was designated as a Search and Rescue (SAR) Boat Coxswain operating 30, 40, and 41 foot Utility Boats, as well as a 44 foot Motor Life Boat on Chicago's Lake Michigan water front. SAR Coxswain duties included formal training in navigation, twin and single screw boat handling, search and rescue planning, extreme weather operations, and crew management. He gained larger vessel experience during Coast Guard officer candidate training. Sailing CGC Eagle, a 295-foot square rigged barque as Cadet Executive Officer, he coordinated watch schedules and held positions as Conning Officer, Quartermaster of the

Watch, and Lead Helmsman on CGC Eagle's month long cruise from Chesapeake Bay to New Orleans. Later in his Coast Guard career, Captain Jim Deyo graduated Naval Flight Training and was designated a HC-130 long range SAR Aircraft Commander. He also served 3 years in an exchange tour as a Primary Flight Instructor for the Navy. Captain Jim Deyo retired from the Coast Guard with Honorable Distinction after 21 years of service.

Outside of USCG, Captain Jim Deyo has gained extensive passage making experience aboard both power and sail driven vessels. He has owned, skippered, or crewed aboard both monohull and catamaran sailboats to 56 feet, as well as single, twin, and directed thrust propulsion powerboats to 65 feet. He regularly cruises the southern Chesapeake Bay, Albemarle and Pamlico sounds aboard his 35 foot express cruiser, as well as offshore fishes (gulf stream) the Outer Banks of North Carolina. He has been racing locally for the past eighteen years with his local yacht club and Albemarle Sound Sailing Association on his own Irwin 32, as well as crewing aboard other club member’s boats. A professionally trained aviation instructor, he leverages that experience to effectively teach boat handling concepts in a cohesive, calm, and easygoing style.


>USCG 50 Gross Ton Master Licensed
>Towing Endorsement
>Sailing Endorsement
>Discover Boating Certified Instructor (POWER) >Multi-Engine & Single Engine & Directed Thrust Vessels >Close Quarters Precision Maneuvering Instructor >Advanced Docking Instructor

>Powerboating Made Easy Instructor
>Passagemaking Experienced
>Offshore Qualified/Experienced
>U.S. Coast Guard Retired with Honorable Distinction >Transportation Workers Identification Card (TWIC) Holder >First Aid & CPR Certified

>FAA Certified Commercial Multi-engine Aircraft Pilot >FAA Certified Flight Instructor
>PADI Open Water Diver Certified 


Captain Jeff Lewis