Cruisers Coaching

the horizon is waiting..

Learn to Cruise!

You've got to start somewhere

An underwater scene featuring a diver with fins near a large sculpture of a reclining man made of rock, with two hollowed rocks at the base, and a snorkeler swimming above the sculpture, in clear blue water.
People on a boat, with one person leaning over the side and another steering, under a canopy during daytime.
Assorted raw fish and seafood including a lionfish on a wooden cutting board at a market or dock.

Learn how to harness the horizon with Relentless. Teaching new cruisers how to confidently pilot and manage their own vessel is the most rewarding part of what we do. We offer flexible options to meet your schedule and timeline.

❋ Intentional Structure

We start with the basics. It’s easy to get overwhelmed with systems onboard a cruising yacht. We are here to ease your mind and take the stress away from taking it all on alone. We are here to help you achieve your cruising dreams into new waters for you and your family.

❋ Customizable Learning

We offer flexible learning by video calls, onboard training, and in-person instruction and tutorials. Our captain services can also be contracted to make extended passages such as Bahamas Gulf Stream Crossings to assist you until you are fully confident.

❋ Expert Facilitation

Among many different facets of cruising we will cover the following plus much, much……much more:

-Piloting

-Docking

-Anchoring

-Voyage planning

-Safety and Compliance

-Vessel systems / off-grid living

-Sailing (when applicable)

-Vessel and engine maintanence

-Provisioning

-Extracuricular activities: Fishing, Diving, tender driving, etc.

❋ A Supportive Space

There’s no judgment. We all start from somewhere when it comes to different skill sets. We want you to enjoy the process of learning to cruise and experience the laid-back teaching style that we bring onboard. It’s not all running rigging and amp-hours. We want to show you how to properly unwind in unique destinations as well!

A scenic view of a turquoise bay with a sailboat and a motorboat anchored near the shore. The background features a cloudy sky and a distant strip of land with low vegetation and small trees. Foreground includes lush green shrubs and plants.
A woman in sunglasses and a bikini stands in shallow clear blue water on a beach, with a camel partially submerged in the water, and a tropical landscape with lush green trees under a bright blue sky.

A 3 day course comprised of everything you need to know to get your cruising journey started. Our private captain travels to you and your vessel to provide intensive, yet laid back, informative instruction that will sharpen your skills before you cast off the lines to paradise.

Cruiser’s Boot Camp

  • -Vessel and system familiarity

    -Piloting skills and basics

    -Cruising logistics

    -Anchoring & docking

    -Vessel care and management

  • -Provisioning

    -Sailing instruction

    -Tender/ Dingy piloting and use

    -Radio and electronics use

    -Rules of the road

    -Safety and Compliance

    -Peripheral gear instruction

    -Diesel maintenance

    -Off grid systems

    -Foul weather and storm prep

  • in the words of the famous treasure salvor Mel Fisher, Todays the Day!

    On day three we will put together everything learned during our time together. Your vessel will be taken for a full and final shake-down cruise where you display your newly found skills at the helm and around the deck.

A small inflatable boat with an outboard motor on calm water during sunset, with a colorful sky and scattered clouds in the background.
Woman in swimming goggles and swimsuit underwater holding a sun lounger.

Most insurance companies require vessel owners with minimal experience to be accompanied by professional captains for a minimum requirement of time. In addition to these parameters we provide on-board (literally) training while actively cruising or making passage from the comfort of your own vessel.

Passage with Captain’s Assistance

A small bonfire burning on a sandy beach with two dogs in the background and boats on the water, under a cloudy sky during sunset.

Ongoing Assistance and Video Chat

In addition to our onboard instructional and lessons we provide ongoing assistance throughout your cruising journey. There are always issues to arise and systems that malfunction. When its getting late and you don’t know where else to turn, we are waiting for your call and ready to help you trouble shoot or provide guidance.

  • "Captain Steve was very patient and a blast to be around. He made learning the lines of our own vessel fun in a way that it never felt overwhelming. Because of his training we were able to continue on from the Bahamas to the Lesser Antilles feeling like we were born to cruise."

    Former Customer

  • "Even as a total beginner, I never felt lost. The step-by-step structure and encouragement along the way made all the difference."

    Former Customer

  • "This has been such a worthwhile investment in our new cruising life. Relentless helped us learn what would have taken years to come by through hard fought battles and made us feel like we have been doing this our entire lives. Can't recommend this service more."

    Former Customer

Are you ready to cruise?

Learn to Cruise!