This day typically lasts about eight hours (or can be 4) from the time you leave the marina to the time you get back and may include fueling time. There is no chance to forget anything as you will go out on the same yacht for the ... More

Enjoy the day hanging out on our 30 ft Double Deck Slide Boat. Have full access to all of our water toys. Relax and listen to music in the shade. Barbecue lunch or dinner and watch the sunset. Swim off the Slide Boat or relax on o... More

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon sun and cool off in the bright aqua waters of the Keys as you snorkel and explore Florida's a... More

Looking for a simple easy way to elope in Key West - look no further - our professional photographers are also officiants and so they provide a combo - they marry you then photograph this lifetime moment. Our professional will mee... More

This trip takes you and your party, (Up to 26 Guests), on a private sunset sail to enjoy wines from around the world and a variety of beers. You will be sailing on a 65-foot schooner while watching the sunset into the ocean. There... More

The Experience: Don't miss your chance to experience a luxury charter in the Florida Keys, versatile enough for any on-water activity you can envision. Whether you're interested in snorkeling, light tackle fishing, sandbar hopping... More

Experience the best of both worlds with our Island Fishing Tour, exclusively offered by Cowboy Cowgirl Sportfishing Charters. Unlike typical fishing charters, this unique excursion combines thrilling fishing action with serene isl... More

Discover the unparalleled joy of exploring Key West waters aboard this center console! Our fleet boasts the newest, most luxurious vessels, fully equipped with top-tier upgrades for your comfort and convenience. Nestled within our... More

Rent your own private yacht and savor the beautiful Key West sunset away from the crowds. Do it all on a luxury catamaran reserved just for you! Dolphin watch, jump off of the bows of the boat, sail along the Key West coastline, a... More

Embark on a voyage of discovery with our Eco Adventure Charter in Key West. Immerse yourself in the pristine beauty of our marine ecosystem as we explore secluded mangrove forests, vibrant coral reefs, and hidden coves teeming wit... More

Join us on a 2-hour walking tour through the dark and untold stories of Key West. Our tour will begin at St. Paul’s Episcopal Church, where we will share stories of its haunted past and the intriguing legend of Robert the Doll. ... More

This day typically lasts about four hours (or can be 8) from the time you leave the marina to the time you get back and may include fueling time. There is no chance to forget anything as you will go out on the same yacht for the o... More

Book your Private Departure Transfer from Marathon / Islamorada /Key Largo to Fort Lauderdale Airport (FLL). Don't go through all the hassle of waiting in a long taxi or shared shuttles queues and use our private, door to door ai... More

This 1-hour boat ride/loop starts at the Spanish Harbor Bridge and goes up to the Bahia Honda Bridge and the Seven Mile Bridge. We’ll cruise up the bay side and back down the ocean side (or vice versa). Learn the history of the ... More

Book your Private Transfer from Key West Int Airport (EYW) to Key West Cruise Port. Don't go through all the hassle of waiting in a long taxi or shared shuttle queues and use our private, door-to-door airport/port transfer. You... More

Experience the charm of Key West from a unique perspective with our Harbor Cruise. About Set sail from historic seaports and meander through picturesque harbors, where colorful sailboats and historic landmarks line the waterfront... More

This day typically lasts about eight hours (or can be 4) from the time you leave the marina to the time you get back and may include fueling time. There is no chance to forget anything as you will go out on the same yacht for the ... More

Key West is famous as mainland America's Caribbean resort town. Here, time slows down as the island vibes take over. But there is more to this island than umbrella drinks and warm breezes. Key West has an incredible history, fro... More

Book your Private Transfer from Key West city hotels or any address to Key West Cruise Port. Don't go through all the hassle of waiting in a long taxi or shared shuttles queues and use our private, door-to-door city/port transfer... More

Join us for an immersive walking tour of the Key West Historic District, where each step reveals captivating stories and hidden gems. We’ll explore iconic buildings with unique histories, uncovering tales of colorful figures who... More