Bob Challie

Bob Chaille786-234-4652

Bob Chaille is a native Floridian born and raised in Miami Florida. His passion for boating began as a child on his Father’s Sport fishing yacht fishing the waters of Coastal South Florida. After graduating from Miami Dade University, Bob enjoyed a career with the Miami Dade Police Department with his favorite assignment as a tactical officer on the SWAT Team.

He obtained his Commercial pilot’s license and spent time piloting fixed wing and helicopters in the corporate sector. His retirement from law enforcement offered him more time on the water and he moved to Stuart, Florida where he resides with his wife and two dogs.

Bob enjoys camping, fishing, boating and traveling the country in a motorhome. Bob offers a wide array of knowledge about all varieties of power boats from center consoles to large sport yachts.

His honesty and integrity along with a pleasant personality, outstanding customer service will guarantee your experience with him will be a pleasant and fun endeavor. Bob also serves his community in various organizations and is a state certified Guardian ad Litem for the Nineteenth Judicial Circuit.

Some of his affiliations are with the United States Power Squadron, United States Coast Guard Auxiliary, Kiwanis Club, United Way, Captains for Clean Water and various other civic and environmental groups.

Bob also holds a USCG Master Captains License and is a member of the International Yacht Broker Association where he attends professional training seminars.


Fellow Boaters
I can heartily recommend Bob Chaille as a Broker for your firm and especially for the sale of your boat.

Bob has the uncanny ability to prescreen potential customers to eliminate “Tire Kickers” from serious potential buyers making his service invaluable to fellow sellers. This skill saved me time and reduced my apprehension and stress in selling my yacht.

He remained very helpful with finding the qualified buyer and throughout all phases of the sales process never leaving me wondering what to expect next. My boat had been on the market for about three years and I engaged several brokers from other firms without success in selling. It was not until Bob was engaged that positive showings began to happen. Immediately Bob became thoroughly familiar with my vessel, which was very useful during showings and discussions with potential clients. I was present during the showing with the eventual buyer and was so impressed with Bob being a consummate professional along with demonstrating his amazing people skills. Not only did he find the correct buyer but was able to educate them as to realistic expectations with buyer a thirty-year-old yacht regardless of how well it has been maintained that it will not meet the expectations of a new vessel.
Overall Bob is very personable and knowledgeable Broker and is a credit and valuable asset to any Yacht Brokerage Firm or clients who use his services. I am happy to serve as a reference for Bob Chaille if needed.

Bill Gelpke
Member and Instructor United States Coast Guard Auxiliary for 36 years
Member United States Power Squadron for 51 years
Member Marine Trawler Owners Association MTOA for 19 years
Port Captain for MTOA Jensen Beach, Florida
Former member Boston Yacht Club, Marblehead, Massachusetts
Former member Saints & Sinners Yacht Club
Former member Crossroads Cruising Club
Member of BoatUS for 43 years

Bob Chaille is a great low-pressure broker, yet he always conducts business in a professional manner and does what he says he will do. Today that is rare to find, especially in the sales industry. When problems came up he offered multiple solutions; all of them useful & above board & proper. He finds solutions, yet still offers other suggestions as well. As my time frame changed for the closing &/or walk thru due to unforeseen problems, Bob continued to solve issues & coordinate solutions even though he had left on vacation and was out-of-town. If I ever sell my Sailboat, “Dream Chaser”, or buy another, Bob Chaille is the only Broker I would call. I would never hesitate to recommend him to other friends & sailors. Not only is he a great Yacht Broker he has become a great FRIEND TOO!

Troy Cain, Retired U.S. Army Cpt., N.A.S., Key West, Florida

I just wanted to drop a thank you to you for your hard work on getting my deal done. You and your company were very professional. Diane and I are very happy with our new boat. Any business we can send your way I will and feel free to use us as references anytime.

Again thank you, Ray and Diane Snow, Scituate, Massachusetts


I wanted to write and thank you for all your assistance completing my recent boat purchase while I was overseas. When I first contacted you about your listing, I was simply looking for basic information about the vessel, with the intent to engage a “buyer’s” broker to represent me. After a short conversation and a couple follow-up emails on the first day, I no longer felt it was necessary to have separate representation from the seller. You came across as a very honest, straight-shooting yacht broker. All this, having never met you in person!

Now that I am the proud new owner of that boat, I can say I have never been happier than with the service I’ve received through you! Your honesty, easy-going personality, prompt follow-through, and personal code of ethics has been such a wonderful surprise over some of my past experiences. Good on Ya’, Bob and thank you so very much!

Vincent Shrigley, MAJ, USAF, Ret. USCG Master 50T, ASA Instructor Marsh Harbor, Bahamas


I Thought I would drop you a note and say thanks for all the effort you put forth on the sale of our vessel. We appreciated the time you spent with the marketing and sale of the product. It is hard work to get sellers and buyers together and your ability to bring it all together was great. We could tell you were more interested in the relationship of the owners and their best interest rather than the sale. This is appreciated as this is not the case most of the time. The sale of the product sometimes overrides the process and your company clearly does not allow that to take place. You made it clear that if we were not happy, no sale needed to take place.

Brig and Linda Burgess, Palm City, Florida

Bob…..Check arrived in the mail today. Thank you very much for your professional, attentive, helpful, and personable service during the sale. And we did much better than anticipated. Should you be asked for a reference by another seller, I would be happy to explain my good experience.

Richard Lewis, Tappahannock, Virginia


I apologize for not getting this to you sooner, for the job you did on selling my boat it should have been immediate and I want to cover a few things that stood out to me that set you apart from other brokers I have worked with.

First of all, you did not let the size of my boat be an issue when you took on the listing. You understood that it would most likely need to be shipped and it was never a question that you could find the right buyer that would be willing to take on that effort. A 50-foot yacht on a landlocked lake is quite an undertaking.

Second, you set clear expectations from the beginning in regard to a realistic listing price and expected sale price. This is very important because it allows me to financially plan for the proceeds in a meaningful way.

Third, you vetted prospects in a way that eliminated the typical emotional roller coaster that comes with selling a large asset. Knowing that every potential buyer that looked at my boat could reasonably buy it if they chose, took out any inclination I may have had about my time being wasted. I really appreciate that.

And finally, you were there 100% of the time for questions, concerns, solutions, or just to talk. You are a pure professional in every manner and I will absolutely be calling you when the day comes for my next boat purchase.

Thank you,

Robert Ortega, Lake Lanier, Georgia

Dear Bob,
Just a quick “thank you” for your invaluable assistance in helping me sell my 370 Cruisers Yachts. I had originally advertised this vessel on “Boat Trader” and after six months with only one bona fide call I decided to give you a try and WOW it was the best thing I did.
We provided you with the same write-up and picture’s that we used for “Boat Trader” and within 45 days after listing with you, we had two showings along with two offers.
You helped facilitate terms and conditions that were acceptable to both us and the buyers. You were there for the sea trial and always a call away to help answer any questions we or the buyers had successfully.

I would recommend you to any buyers or sellers without hesitation.

Best Regards,
Captain Howard Anderson U.S.C.G. 100 Ton Master, Naples, Florida

Hi Bob,
Suzanne and I wanted to send a note of appreciation for your great work in helping us purchase our boat. We knew right away that you were the right broker to help in our search, and you guided us smoothly through the process from day one and were thereafter delivery too. Best of all you really listened to our concerns and kept us informed through the entire transaction. Thanks for a job well done Bob. We’re telling all our boating friends about the high quality work you do for buyers and sellers alike.
Best regards,
Captain James McNamee Unlimited Ship Master, USMM

Featured Yachts for Sale by Robert Chaille

Click on the photo to see more details

Ft. Pierce, FL
36 Carver 2005
Cabin Cruiser

View all yachts for sale.