Who We Are

Our top rated captains and first mates are your expert guides on fun-filled sailing adventures

Captain Kelly Callahan

Captain Kelly Callahan

Captain Kelly Callahan knows the shores of Southwest Florida like the back of his hand. A native Floridian and sailing since the age of five, he has over 40 years of experience navigating the Florida waterways and the Gulf of Mexico. Captain Kelly’s certification by the United States Coast Guard assures you of a safe, enjoyable and relaxing cruising experience.

Besides his sailing credentials and expertise, Captain Kelly has been in the service industry for many years. His warm, friendly nature and genuine interest in pleasing his customers have been key to building a thriving and successful business. Captain Kelly is known as a positive and fun guy with a great sense of humor. It is not uncommon for his customers to become his lifelong friends. He will put your mind at ease, entertain you with his jokes and show you a great time.

Captain Stephen Adney

Stephen Adney

Captain Stephen has always had a passion for water. Learning to sail at a young age he raced numerous small boats and has sailed in small lakes, Lake Michigan, as well as the Atlantic Ocean.   After obtaining his USCG 100 ton Captains License with a sailing and towing endorsement he began working in Chicago operating taxi and tour boats.  Captain Stephen recently completed American Sailing Association Instructor Courses.  He is qualified to teach Basic Keelboat, Basic Coastal Cruising, Bareboat Chartering, and Coastal Navigation.  As well as being a professional mariner, Captain Stephen is also a PADI Divemaster and has logged hundreds of dives around the world.

Safety is important to Captain Stephen and he is always mindful of the well being of passengers.  He wants his passengers to have fun in a safe manner.  As a USCG licensed Captain he is subject to random drug testing and has a zero-tolerance policy to drugs on board.

Captain Stephen wants you to join him for a sail. You can be as involved or uninvolved as you wish.  He’d like you to take the helm and steer or trim the sails.  Let him know what you want to do and he’ll do everything possible to accommodate you.  

Captain Dave Durham

Captain Dave

Captain Dave Durham grew up in Kentucky and has always enjoyed fishing, boating and water skiing. He spent most of his adult career as a banker, graduating from the University of Kentucky and the Kentucky school of banking. Dave eventually relocated to South Florida, starting a management placement company based in downtown Naples. He has a passion for photography, the outdoors, and most of all the ocean. He has lived in Florida for 37 years and has navigated the water’s from Tampa Bay to Key West for all of them. Dave has spent the last 17 years living on the beautiful Isles of Capri and refurbishing his 37-foot sailboat. He enjoys taking guests out, showing them the beautiful waters, wildlife and ecosystem of the Naples, Marco Island, and the Ten Thousand Islands.

“It just never gets old seeing the smiles on the faces of the young as well as the older guest when a pod of dolphin play in our wake, or a stingray breaches the surface of the water, or a friendly sea turtle passes by. It is truly fun sharing these experiences with our guests.” 

Capt. Dave holds a USCG Master Captain license and is CPR and First Aid certified.

Captain Jerry Beno

Jerry Beno

Captain Jerry got the boat bug at an early age, having some of his best childhood memories on his uncle’s boats in Michigan. He bought his first Sea Ray powerboat at age 20, and has owned a Hunter sailboat and two award winning antique wooden boats. He became an avid sailor and bareboat charter captain in Lake Michigan, Chicago, taking sailing trips to Michigan, Wisconsin, the Bahamas, and many charter trips through the Chicago River, Navy Pier, and along the lovely Chicago skyline. After relocating to Florida, he has since created memorable experiences with hundreds of guests on charters in the Florida Gulf coast throughout Naples, Fort Meyers, Marco Island, and the Isles of Capri. He has a good pulse on his charter groups, recognizing social cues to ensure he is providing the best experience according to the mood of the group. He’s very friendly and communicative on how to tailor the boat trip to your interests- whether touring the gorgeous mansions in Naples to the natural preserve mangrove islands near Marco Island. Most guests have become friends with Captain Jerry and wish they could sail longer!

Captain Benjamin Avery

Benjamin Avery

Captain Benjamin will ensure your experience makes you feel like a real local as he tells you about this beautiful area of SW Florida. After moving to Naples from his home town in North Carolina, Captain Benjamin made it a point to seek out the hidden gems of beaches along our glorious coast. Here he discovered his passion for life on the water. Captain Benjamin’s enthusiasm spreads like a wildfire, making every guest fall in love with the water the same way he did. With 6+ years of experience, Captain Benjamin provides an entertaining cruise that not only guarantees guests feeling safe, but leaves them with beaming smiles from ear to ear!

Captain Daniel Short

Daniel Short

Captain Dan grew up in Northwest Indiana with a love for all activities related to the water. His introduction to sail began by hanging out on docks at marinas on and around the Great Lakes volunteering to clean boats in exchange for sailing lessons and crew positions. He is a Marine Corps veteran who earned a Combat Action Ribbon serving with 2d Recon Battalion in the Middle East. After being honorably discharged from the Marine Corps, Captain Dan attended The Ocean Corporation in Houston and worked offshore as a commercial diver for Global Divers and Contractors. He fell in love with Florida while enjoying a bareboat charter in Islamorada and moved to Naples in 2010. Captain Dan has owned and renovated several sailboats and fishing vessels throughout his life and currently owns a Catalina 42 MK II that he keeps in Fort Lauderdale so his family can spend time together in the Florida Keys and the Bahamas. “I have enjoyed working for several of the outstanding charter companies southwest Florida has to offer, but Cools Beans is by far the most rewarding because the focus is on building lasting relationships and making lasting friendships while sharing the wonders of the paradise we live in.” Captain Dan holds a USCG Master Captain license and is CPR and First Aid certified and teaches at Palmetto Elementary School in Naples.

First Mate Sharon Callahan

Sharon Callahan

As First Mate, Sharon’s job is to make sure your cruising experience is fun and memorable. Along with booking reservations for our cruises, she is running the business end of Cool Beans Cruises. Her favorite part of her job is coming out for an occasional sail to meet our wonderful guests. Sharon is also a service oriented individual with 30 years experience in the commercial real estate industry. Along with Captain Kelly, Sharon has the natural ability to make you feel welcome and at ease.

You can be sure that when you leave your cruise on “Cool Beans,” you will be back to sail with us again soon. Book your private Naples and Marco Island Florida cruise today.