I became a charter yacht broker the hard way; I earned it! It all started back in the late 60’s. I learned to sail at the ripe old age of 39. Making every mistake, a sailor could make. I scared the bejesus out all my friends and family. It took me a few years. Nevertheless, I finally got the hang of it.

Fortunately, for everyone concerned, my sailing skills improved enough that I earned my 100 ton U.S. Coast Guard Master’s License. 

My Master’s License enabled me to start up my Day Sail operation with a sleek 43ft sailing yacht named LAKE STREET. the US Coast Guard licensed us to carry 20 passengers.

The business was an enormous success. However much of the success was due to LAKE STREET ‘s having a monopoly. She was the only sailing vessel of its type on Lake Michigan that US Coast Guard licensed to carry up to 20 guest. All the rest of the charter yachts could only carry 6 passengers.

We catered to corporate and private with 2-3 hour sailing cruises. A highlight of these cruises was the beautiful backdrop of  Chicago’s Skyline.

Coupled with the private charters, I also offered a verity of theme charters. Such as a Monday Night Blues Cruise with live music. The Wednesday Night Beer Can Races. And on Saturday mornings I offered Sailing Lessons, and on Sunday mornings a Brunch Cruise with live music.

In a seven year period LAKE STREET entertainment over 10,000 guests. The yacht consistently had charter bookings twice a day on weekdays. On the weekends, we it was three charters a day on both Saturdays and Sundays.

Eventually I added CANAL STREET, a 25ft sailboat to my charter boat fleet. It served as a bareboat charter and was available to experienced sailors .

At this point the thought hit me that I had a captive audience while on charter. With that in mind, I started dabbling in promoting sailing vacations in the Caribbean. Hence this was the beginning of my career as a charter broker.

By the early 90’s, LAKE STREET and I were worn-out. With that in mind, I decided to focus solely on my Caribbean charter yacht brokerage. Due to a family health issue, I had to take a brief hiatus that lasted until 2018. At that point I attempted to reestablished myself in the industry by opening Charter the Caribbean. It was not an easy road back. After the two back to back hurricanes that hit the Virgin Islands in late 2017, the recovery was slow. Then along came Covid-19, which put a hold on everything.

With these events behind me, I am currently in the process of getting Charter the Caribbean back on track. I am confident with the support of a loyal client base it will happen.

I love this business and believe in what I have to offer my loyal clients. And that is, exceptional help in arranging my client’s customized sailing vacations. The luxurious fully crewed, yachts I offer are located throughout  Caribbean, Bahamas, South Florida, and New England.

It is my duty to my clients to find  them the yacht and crew that best matches their desired location, time frame, and most importantly, their budget.

For more information, contact Dennis at Charter the Caribbean at 317-745-1990 or email: charter@charterthecaribbean.com


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