Cruise Naples & Marco Island, Explore Nature, Relax, Sunbathe . . .
Who We Are

Let our Captains and First Mate be Your Expert Guides on a Fun-Filled Sailing Adventure

Captain Kelly Callahan is passionate, qualified and fun to be around . . .

Captain Kelly CallahanCaptain 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.

Meet Captain Josh

Captain Josh EricksonBorn and raised in Hudson, Wisconsin, Captain Josh Erickson spent his childhood along the shores of the beautiful St. Croix River and Boundary Waters Canoe Area Wilderness of Northern Minnesota. He has a deep passion for environmental stewardship which led him to Florida where he attended Florida Gulf Coast University and earned degrees in Environmental Studies and Biology. Captain Josh also holds a 100 ton, USCG Master license and is a wilderness first responder. His previous nautical experience includes leading educational tours through The Rookery Bay Estuarine Research Reserve, The Ten Thousand Island National Wildlife Refuge, Everglades National Park, Big Cypress National Preserve, The Dry Tortugas National Park and the Nepali Coast of Kauai, Hawaii. His ambition to explore the unknown brought him to the far reaches of East Asia and several island nations throughout the Pacific. When he’s not sailing, Captain Josh enjoys kayaking, fishing, diving and planning his next adventure.

Meet Captain Gerard “Gerry” O’Neil

Captain Gerard “Gerry” O’Neil started sailing as a teenager in Long Island Sound and Newport/Block Island areas. Since moving to Chicago in 1988, he has been an avid racer, winning numerous regattas and participating in National and World Championships in locations across the country including Lake Michigan, Charleston SC, Annapolis MD, and Key West. He has also participated in multiple Newport to Bermuda ocean races and the 2016 Conch Republic Cup race to Cuba. Gerry especially loves sharing his passion for sailing through teaching. He has trained many crews on-the-water and presented several seminars on sail trim and racing strategy and tactics. Gerry met Susan, his wife of 25 years, while racing. She was the competition and since have competed together and against each other, in addition to raising two wonderful boys who also sail.

Meet First Mate Sharon Callahan . . .

First Mate Sharon on Cool BeansAs 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.

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Catamaran Cruises around Naples and Marco Island for Fun, Adventure, Special Events and Vacation Memories to Treasure for a Lifetime!