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Cool Beans Cruises

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377 Capri Blvd.
Isles of Capri
Naples, Florida 34113


Contact Person:
Kelly Callahan


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Cool Beans Cruises - Welcome
Charter Our "Cool Beans" Private Catamaran and Experience the Ultimate in Fun and Relaxation as you Cruise Naples and Marco Island, Florida.
Packages & Pricing

Your enjoyment and comfort is our mission
Whatever is your sailing pleasure, we go the extra mile to make it happen. Whether your interests are nature, relaxation, shelling or sightseeing, our goal is to bring your vision to life aboard the "Cool Beans" Catamaran. Complimentary tasty treats and refreshments are included. There is also a clean restroom and shower onboard. 

Sailing Excursions for Southwest Florida tourists and local residents
Book your own private charter cruise aboard the Cool Beans Catamaran and have the time of your life. Your sailing adventure among family and friends is an excursion you'll be talking about for years to come. Of course, you're invited to come back for more cruising fun, again and again. 

Sailing the Naples and Marco Island, Florida region
Some of the most beautiful beaches and unspoiled coastal waters of the Gulf of Mexico are right here in Naples Florida and Marco Island. Majestic sunsets over the Gulf are breathtaking. Your fun-filled private sailing excursion in this region will leave you smiling, rejuvenated and totally satisfied. 

Cool Beans Cruises - Our Boats
Expect Fun & Relaxation Aboard our Cool Beans Naples and Marco Island Catamaran Sail Excursions. Set Sail Onboard one of our 2 Beautiful Catamarans

Our Newest addition, a 42 ft. Catamaran , Cool Beans will accommodate up to (*) 20 Guests  (*) In most instances we will limit the number of guests to 12 – 14 with the exception of a Private Charter.

Our 33 ft. Catamaran, Cool Beans II will accommodate up to 6 Guests

More About Our Boats
You Ultimate Charter Sailing begins on one of these Immaculate COOL BEANS Catamaran Sailing Vessels.

Our fleet consists of two (42-foot and 33-foot) Catamaran Sailboats
Our boats can accommodate 2 to 20 guests for a comfortable and enjoyable sailing experience. Both boats are fully equipped with the following features:

- Comfortable bow seating for sightseeing and sunbathing
- Spacious front/bow seating with drop down ladder for easy on/off to the beach.
- Roomy head room
- Separate shower and restroom
- Saloon provides protection from the elements
- Comfortable dinette seating
- A unique combined cockpit & saloon that allows for comfortable outside & inside seating

Sailing adventures for nature, shelling, sunsets, sightseeing

Our cruising packages and agenda are designed with you in mind. Whether your interests are nature, sunsets, swimming, shelling or sightseeing, we offer you a fun-filled cruising adventure.

Nature enthusiasts delight in the abundant sights and sounds of sea life, wildlife and tropical vegetation along the shores of Naples and Marco Island. Watch dolphins leaping before your eyes and manatees swimming among mangrove-dense coastal waters of the Gulf of Mexico. Get a close up view of ospreys, eagles, herons and other birds native to Southwest Florida in their natural habitat. Our excursions include visits to unspoiled Naples and Marco Island beaches where you may explore, swim and collect shells. Naples beaches have been voted among the top 10 beaches in the U.S. by National Geographic Traveler and The Travel Channel.

Spectacular sunsets along the Gulf of Mexico are some of the most beautiful to behold. On our Champagne Sunset Cruise, we depart two hours prior to sunset. This allows you time to relax, sip champagne and fully enjoy the majestic sky as the sun sets along the coastal skyline.

When sightseeing is your pleasure, you will want to take note of sprawling mansions of the rich and famous as we sail along the coastal waterways of Naples and Marco Island.

Our cruises make lasting memories
We take pride in delivering an experience that is fun, safe and comfortable. We're attuned to all of your needs including refreshments, a private shower and clean restroom.

Taking small groups on our "Cool Beans" boat allows us to really get to know our guests. We have fun together, treating them like members of our own family. In fact, many have become our lifelong friends.

Cool Beans Cruises - Who We Are
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 30 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 is lifelong friends. He will put your mind at ease, entertain you with his jokes and show you a great time.

Sharon Callahn
Captain Kelly may think he’s the boss, but First Mate Sharon knows better! As First Mate, her job is to make sure your cruising experience is fun and memorable. Sharon is a successful entrepreneur who runs a commercial real estate business when she is not swabbing the deck or carrying bags of ice to the boat. Along with Captain Kelly, she has an inherent 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 see Captain Kelly and First Mate Sharon again. Book your private Naples and Marco Island Florida cruise today.

Learn more Cool Beans Cruises

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