For nearly 20 years, Sharon and Kelly Callahan have owned and operated Cool Beans Cruises, their catamaran business based just outside Marco Island. The business serves both Marco Island and greater Naples area. Their journey began with a shared love, for each other and for life on the water. When Sharon met Kelly, she fell in love with the him and the boating lifestyle that would become the foundation of their future.
In 2006, the couple purchased their first boat, and by 2007, Cool Beans Cruises officially set sail. What began as a passion project quickly became a beloved local business built on partnership, trust, and a love for creating meaningful experiences.
Our top rated captains and first mates are your expert guides on fun-filled sailing and pontooning adventures
Captain Kelly
Captain Dave
Captain Jerry
Captain Patrick
Captain Cedric
Captain Margot
Sharon Callahan
Captain Kelly
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 Dave
Born and raised in Kentucky, Captain Dave grew up with a love for fishing, boating, and water skiing. After a successful career in banking and business management, his lifelong passion for the ocean led him to South Florida—where he has spent the last 37 years navigating the coastal waters from Tampa Bay down to Key West.
For the past 17 years, Dave has called the beautiful Isles of Capri home, where he personally lovingly restored his 37-foot sailboat. Nothing brings him more joy than taking guests out to explore the pristine waters and wildlife of Naples, Marco Island, and the Ten Thousand Islands.
“It never gets old seeing the smiles on our guests’ faces—young and old alike—when a pod of dolphins plays in our wake, a stingray breaches, or a sea turtle glides past. Sharing these moments is what it’s all about.” — Capt. Dave
Qualifications & Local Expertise:
- USCG Licensed Master Captain (CPR & First Aid Certified)
- 37+ Years navigating South Florida’s waterways
- Specialties: Eco-tours, wildlife spotting, and local history across Naples & the Ten Thousand Islands
Captain Jerry
Captain Jerry caught the boating bug early, building some of his best childhood memories on his uncle’s boats in Michigan. By age 20, he bought his first Sea Ray powerboat and has since owned a Hunter sailboat and two award-winning antique wooden vessels.
After years as an avid sailor and bareboat charter captain navigating Lake Michigan, the Chicago skyline, and the Bahamas, Jerry brought his expertise south to Florida. Today, he crafts unforgettable charter experiences across Naples, Fort Myers, Marco Island, and the Isles of Capri. Known for his warm personality and intuitive hospitality, Jerry excels at reading the room—tailoring every excursion whether your group wants to tour Naples’ waterfront mansions or quietly explore pristine mangrove preserves.
“Every group brings a different energy. My goal is to listen, communicate, and customize the trip so it’s exactly what you dreamed of—whether that’s laid-back relaxation or an exciting eco-adventure.” — Capt. Jerry
Qualifications & Local Expertise
- Licensed Charter Captain with decades of maritime experience
- Versatile Navigator: Experienced in everything from classic wooden boats to modern sailboats and powerboats
- Tailored Experiences: Custom itineraries spanning Naples, Marco Island, and the Gulf Coast
Captain Patrick
Captain Patrick has been at the helm since 1970, when his very first voyage on the Great Lakes sparked a lifelong passion for international sailing. Over the decades, he has captained sailing catamarans through Greece, Croatia, the British Virgin Islands, and New York City—even completing a 3,902-nautical-mile nonstop Atlantic delivery of a 114-foot luxury sailing yacht from Antigua to Spain.
An avid competitive racer, Patrick spent years campaigning a Star Boat across top venues from Chesapeake Bay to Tampa Bay. Beyond his world travel, Patrick brings decades of elite instructional and safety leadership to Cool Beans Cruises, having served as lead sailing instructor at the City Island Yacht Club in NYC and being named “Big Brother of the Year” by the United Way in Tampa Bay.
“After sailing all over the globe, there’s still nothing quite like the natural beauty of Marco Island. I love helping guests relax, learn, and take in these incredible waters.” — Capt. Patrick
Qualifications & World-Class Expertise
- USCG 100-Ton Master Captain (CPR & First Aid Certified)
- ASA Certified Sailing Instructor since 1986 (American Sailing Association)
- Safety Certified: Red Cross Advanced Lifesaving, Water Safety Instructor & PADI Advanced Open Water Diver
- International Proficiency Certificate with 50+ years of global blue-water seamanship
- Education: B.A. from Saint Leo University | MBA from St. Cloud State University
Captain Cedric
Captain Cedric’s passion for the sea and nature began in his home country of South Africa before he brought his love for the outdoors to Southwest Florida 30 years ago.
A staple in the local boating community, Cedric spent years running his own ecological tour business, Fantasea Boat Tours, and served as head captain on the Marco Island Princess before joining the Cool Beans family. Whether he’s pointing out native bird species or guiding you through quiet coastal waterways, Cedric’s deep ecological knowledge and infectious enthusiasm turn every private pontoon excursion into an unforgettable day in paradise.
“Southwest Florida’s coastal ecosystem is truly one-of-a-kind. I love showing guests the hidden beauty of our waters—your first trip with us definitely won’t be your last!” — Capt. Cedric
Qualifications & Local Expertise
- USCG 100-Ton Master Captain (CPR & First Aid Certified)
- 30+ Years exploring and navigating Southwest Florida’s waters
- Master Eco-Guide: Former founder of Fantasea Boat Tours & former Head Captain of the Marco Island Princess
- Specialties: Private pontoon charters, local wildlife identification, and coastal ecology
Captain Margot
An Isles of Capri local, Captain Margot is a true nature enthusiast who can usually be found on the water—whether she’s boating, kayaking, paddleboarding, or jet skiing in search of local wildlife. After more than 20 years as a magazine publisher behind a desk and in city traffic, Margot traded corporate life for her true passion: the Gulf waters and coastal conservation.
Having captained boats for family and friends for over two years across Ft. Lauderdale and the Isles of Capri, getting her official Master Captain’s license was the very first milestone she tackled after retiring from publishing. A dedicated volunteer with the South Florida Wildlife Center and an active mangrove clean-up advocate, Margot brings a genuine love for local wildlife and eco-preservation to every charter.
“Stepping away from the computer and onto the boat was the best decision I ever made. Entertaining guests and sharing my passion for our local wildlife and conservation is truly a dream come true.” — Capt. Margot
Qualifications & Local Expertise
- USCG Licensed Captain (CPR & First Aid Certified)
- Dedicated Conservationist: Active local mangrove restoration advocate & former wildlife volunteer
- 20+ Years boating experience across Ft. Lauderdale and the Isles of Capri
- Specialties: Wildlife spotting, local eco-conservation, and eco-tours across Marco Island and Naples waters
Sharon Callahan
As First Mate and Operations Manager, Sharon is the welcoming force both on land and on the water. Beyond keeping Cool Beans Cruises running smoothly behind the scenes and managing reservations, Sharon brings 30 years of top-tier commercial real estate experience to our team—meaning exceptional service, clear communication, and attention to detail come naturally to her.
While she keeps the business in shipshape, Sharon’s favorite part of her job is stepping aboard for a sail to meet our guests. Working alongside the crew, her natural warmth and hospitality ensure you feel relaxed, welcome, and right at home from the moment you step onto the deck.
“From your very first booking call to the moment we dock, our goal is to make your cruise effortless, fun, and completely unforgettable. We love seeing our guests leave as lifelong friends!” — Sharon
Role & Expertise
- First Mate & Guest Hospitality: Dedicated to making your time on board relaxed, safe, and fun
- Operations & Booking Manager: Seamlessly managing reservations and charter logistics
- 30+ Years Professional Experience: Bringing elite customer service and business management background to Cool Beans Cruises
- Specialties: Guest relations, personalized charter planning, and local trip recommendations