How I Became a Charter Yacht Broker

It all started back in the late 60’s. when I learned to sail at the ripe old age of 39. Making every possible mistake, a sailor could make. I scared the bejesus out all my friends and family. It took me a few years. But, nevertheless, I finally got the hang of it.

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

My Day Sail Operation with LAKE STREET

The Master’s License enabled me to able to start a day sail charter operation on Chicago’s waterfront. I started the business with a boat I leased from the owner of AAA Boat Yard in Chicago. I renamed the boat LAKE STREET, after a well-known Chicago street. LAKE STREET was a sleek, but long in the tooth, 43 ft. racing sailboat. Working with the boat’s owned and the US Coast Guard I was able to attain a licensed to carry 20 passengers plus a crew of three.

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

What LAKE STREET Had to Offer Guests

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

Coupled with private charters, I also offered a variety of theme charters. On Monday nights it was a Blues Cruise with live music. On Wednesday nights, the Burnham Park Yacht Club Beer Can Races. Saturday mornings I conducted Sailing Lessons, and on Sunday mornings I offered a Brunch Cruise with again live music.

In the seven year period I operated LAKE STREET, I entertainment over 10,000 guests. The yacht consistently went out on charters twice a day during the week. And on both Saturdays and Sundays. it when out on charters three times a day.

I later added a second boat to my charter operation. It was a  25 ft. sailboat I named CANAL STREET. It served as a bareboat charter yacht and was available for experienced sailors to sail.

The Emergence of Charter of Charter the Caribbean

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

By the early 90’s, LAKE STREET and I were worn-out. It was time to switch gears. I decided to focus solely on my Caribbean charter yacht brokerage business. Back in 1992, when almost every charter yacht broker was advertising in the yachting and travel magazines of the day, I was one of the very first brokers to market my business on the Internet.

Had a Few Set Backs Along the Way

Due to a family health issue, I took a brief hiatus from the business that lasted until 2018. At that point I attempted to reestablished myself in the industry by opening a new brokerage I named, Charter the Caribbean. It was not an easy road back. After the two back to back hurricanes the Virgin Islands in late 2017, recovery was slow. Then along came Covid-19, which put a hold on everything.

Renewed Dedication to Charter the Caribbean

With these events now 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, believe in what I have to offer my loyal clients is the best possible vacation anyone could ever dream of. My years of experience as a charter boat captain has taught me how to be sure my clients are entertained well on a charter boat. Also, in my arsenal of experience are at least 20 yacht charters I have personally done in such places as South Florida, the Bahamas, and the Caribbean. From these charters I have gained a wealth of local knowledge to be shared with my clients.

What is my Goal? 

My goal is to go that extra mile when arranging my client’s customized sailing vacations. The yachts I work with, in many cases, I’ve previously been aboard or have known their crews for a while.

These yachts are luxurious, superbly maintained, and fully crewed with professional captains and  well trained chefs. The yachts are located throughout  Caribbean, Bahamas, South Florida, and New England. In addition to the locations mentioned, I am currently in the process of establishing Charter the Caribbean in the Mediterranean charter yacht market.

A Pledge to My Clients

I see it as 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:


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