Craft the perfect Key West experience!
We have a Certain Set of Skills
Is your Group up for the Challenge?
Years of chartering boats provides adventure and flexibility for your large group. We can accommodate family-friendly floating weddings, birthdays, anniversaries, and reunions. Our guides also specialize in bachelor/bachelorette parties. If your company would like to host a corporate event by sea, we’ve got you covered. We know all the best restaurants that cater. We can recommend who delivers flowers and designs custom cakes. If you need a singer/songwriter on board? We know a guy. Barefoot Billy’s waterfront venues are at three world-class Key West beach resorts. Our concierges are more than happy to arrange every aspect of your island experience.
If you can dream it, we can do it.
Enjoy a private meal with an unforgettable view. Stage the photo that will nominate you as talk of the town back home. Fancy restaurant dinners pale in comparison to a sushi lunch on the water or sandwiches on the beach. Bring your own groceries, order from Thai Island Restaurant on the dock, or have your charter catered by any of our local restaurants. Fresh Key West Pinks are among the sweetest, most succulent shrimp on Earth. Simple wine, cheese, and fruit plates are always best served alongside sounds of the ocean and sand beneath your feet. Every drink is a little bit colder, the sun just a little warmer, and your smile perhaps a little bigger when it’s attending your own Private Island Picnic.
Leave your troubles behind and embark on a culinary adventure. Leisurely cruise into the perfect position to catch our famous sunset. We’ll pop the cork on your bottle of champagne. You’ll select from makimono sushi, crab rangoons, meats, cheeses, & other sweet pastries. Domestic and imported beer, red and white wine, seltzers and soft drinks toast your view. Bring some friends and make some new ones. These are two hours of your Key West visit you’ll never forget.
Snap that perfect photo for your family’s next holiday card. After departing Garrison Bight your crew will navigate toward the Historic Seaport. Wave at jealous onlookers at Mallory Square and Fort Zachary Taylor. As you turn the Southernmost corner of the island look to the South and inhale. Only 90 miles of fresh, salt air and open ocean separate you and the island nation of Cuba. Raise your glass and say goodbye to another trip around the sun.
The Classic Key West Cruise on Barefoot Billy’s Boats capture that nostalgic feeling at sea. Romantic ocean breezes flow across the bow. Gentle waves lap against the hull. Exotic marriage ceremonies, exciting bachelorette parties, or solemn celebrations of life all find just the right niche floating on the ocean. Wear your Sunday best or string together that South Beach Bikini. There’s sun and fun for everyone on the calm waters surrounding Key West.
The 45-foot Corinthian accommodates up to 49 passengers with plenty of space for groups of more than six passengers. Bench seating along the deck provides relief from the warmth of the sun and our open bow becomes the perfect place to soak in some rays. Whether you provide your own catering or allow us to serve you, your private event is guaranteed to be memorable.
The Atlantic Bottlenose Dolphin is one of the most intelligent animals on planet Earth. They are also the most playful! They love to swim alongside and behind the wake of the boat and often will jump out of the water to get a better look at us. Their hearing has a range ten times higher than humans and Dolphin breathe air just like we do. They use a blowhole on top of their head in front of their dorsal fin and are much better at holding their breath than we are. Dolphins love leaping out of the water. Bring your family or pod of friends and we’ll see if we can’t school you a little about our favorite friends in the sea.
Imagine your family and friends relaxing in the middle of the ocean. A short ride from Key West lie these pristine, sandy time capsules. Battered by weather over centuries these mangrove sanctuaries refortify themselves after every storm. “Boca Grande”, “Snipes Point”, “Marvin Key”, and “Woman Key” are hidden treasures accessible only by small watercraft. Your tax dollars preserve these isolated pieces of paradise. It’s about time you laid eyes on your investment.
Float on comfy foam lily pads surrounded by the Florida Straits or Gulf of Mexico. Snorkel and sneak a peek at colorful aquatic life. Sunbathe on the bow of the boat. Read a book under an umbrella with a gentle current tickling your toes? This is the Florida Keys’ signature experience and the ultimate way to relax and rejuvenate.
Snorkeling is the safest and easiest way to engage all the underwater life in our oceans. The Keys are the best place in North America to check out what’s swimming below the waterline. In fact, our water is warmer than Hawaii’s year-round. We can head out to the Florida Great Barrier Reef in our National Marine Sanctuary or any of numerous coral heads. You’ve never seen so many vibrant colors in one place! Watch parrotfish crunch on coral while you spend some time with Nemo (clownfish), Dory (Royal Blue Tang), and countless other species. You’ll notice your hair, skin, and entire body feel refreshed after a nourishing swim in the sea. Ponce DeLeon came down here looking for the Fountain of Youth. After you go snorkeling in The Florida Keys you’ll agree he found it!