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CAREFREE BOAT CLUB
  • Home
  • Membership Pricing
  • Availability & Fleet
  • Locations
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  • Popular Destinations
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  • Shared Ownership Program

Member Training

Become a Great Boater

We provide members with individualized, hands-on training. We strive to help our members become safe, competent and confident Captains. Members train with certified Captains and our experienced dock staff until they are the best boater they can be!  In addition to being licensed by either CT or NY, all members spend 5 hours on the water with a Captain, getting hands-on experience. 
The training was excellent! [The Captain] was patient, informative and so helpful.  He made us all feel at ease and gave us plenty of time to really get a feel for the boat. 
8/28/25, Melissa S.
The training was great. . . No room for improvement. [The Captain] was informative and a pleasure to spend time with. I feel ready to get on the water. 
6/20/25, Martin L.
The training sessions were wonderful. [The Captain] was fantastic — flexible with our schedule, highly informative, and especially helpful when it came to docking, which is arguably the most challenging part of boat handling.

We took advantage of both sessions and are actually heading out tonight (weather permitting) for the twin-engine extra training with [our dockmaster].
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As a new boater. . . I can’t stress enough how helpful the training has been. Having a guide as you leave certain ports to walk through markers, routes, and best practices really makes a difference in building confidence.
7/8/25, Tanya P.
Today’s training was great. It was very informative, educational, great hands on experience and lots to continue to learn and absorb as we go. [The Captain] was fantastic and helped us make the most of our time together. We definitely left feeling confident and ready to get out on the water again!
7/29/25, Christine S.
My on the Water Training was very helpful.
-  told me all the mandatory things I need to know for safety 
-  he adapted his on the water training to my skill level and knowledge base
- he pointed out many things to be aware of an cautious of out there
- gave me a sense of the other carefree locations and the pros and cons of boating out of each
- tuned his input to how I want to enjoy the boat.
- made me feel comfortable about getting out there
6/8/25, Richard W.

Learn at Your Own Pace 

We know everyone learns differently, which is why we offer flexible ways to build and strengthen your boating skills—on your schedule.
  • Zoom Classes
    During the off-season, we host live Zoom sessions on a variety of topics designed to educate and enhance your boating knowledge.
  • YouTube Tutorials
    Our YouTube channel is filled with instructional videos and practical boating tips you can watch anytime.
  • Sea School Training
    For hands-on experience, sign up for our Sea School sessions with an experienced Captain. These focused classes give you the techniques and confidence you need to get the most out of your time on the water.
  • Dockside Practice
    Schedule one-on-one time with your dockmaster to practice key skills like docking, navigating with GPS, planning trips, and more.
Our youtube channel

Docking Fundamentals

How to Anchor

How to Navigate in a Channel

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  • Home
  • Membership Pricing
  • Availability & Fleet
  • Locations
  • Training
  • Sea School
  • Popular Destinations
  • Boats For Sale
  • More Questions?
  • Shared Ownership Program