Love, Laughter & Life on the Water

Local businesses are at the heart of Marco Island, and the small business owners behind them play a major role in making the island such a special place to visit. With Valentine’s Day right around the corner and couples planning romantic experiences, Cool Beans Cruises delivers not only unforgettable moments on the water, but also a love story that’s just as charming as the sunsets they sail into.

From Island Romance to a Dream Afloat

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.

Why Cool Beans Cruises Are One of a Kind

The Callahans launched Cool Beans Cruises with a simple goal: to provide high-quality boating experiences with exceptional service. The business began with intimate six-passenger catamarans, added a second vessel, and eventually expanded to include a spacious 20-passenger catamaran.

Today, Cool Beans Cruises include everything from private pontoon rentals and private day sailing adventures to champagne sunset cruises. Whether guests are celebrating a special occasion or simply soaking in the beauty of Southwest Florida, there’s an experience designed to make every moment feel special.

A One-of-a-Kind Setting, From Preserve to Open Sea

What truly sets Cool Beans Cruises apart is its location. Their marina sits directly on Rookery Bay, a breathtaking nature preserve. Within ten minutes of departure, guests are out on the Gulf of Mexico, where sails are raised and true sailing begins across open waters.

Thoughtful Details, Memorable Moments

Attention to detail drives everything Cool Beans Cruises does. Sharon Callahan’s team stays personally involved in each guest’s experience, and she takes pride in the care her team provides. As a result, couples often choose their boats for life’s most meaningful moments.

In addition, Cool Beans Cruises maintains spotless vessels and hires personable captains who create a warm, welcoming atmosphere. From the moment guests step aboard, the team greets them with genuine hospitality. Because of this hands-on approach, every cruise feels both effortless and deeply personal.

Above all, the company’s foundation rests on love, partnership, and a shared passion for the water. Together, those values reflect what travelers seek when visiting Marco Island: romance, authenticity, and unforgettable scenery. Whether you’re planning a Valentine’s Day date, celebrating a milestone, or simply exploring the Gulf, a sail with Sharon and Kelly Callahan offers more than a cruise. Instead, it invites you into a love story, one sunset at a time.