Sail on a comfortable Catalina 42 with a wing keel then go snorkeling from the easy access open transom.

Meet Captain Clay Mills - USCG 50 Ton

Sailpony Charters is led by a captain whose life has been shaped by the sea for more than five decades. His sailing experience began in 1972 along the California coast and the Channel Islands, where he lived aboard a 40-foot wooden sailing sloop with his father. Those formative years—anchoring at Anacapa and Santa Cruz Islands and learning seamanship through daily life afloat—laid the foundation for a lifelong career under sail. In 1981, he began working for a charter sailing club, regularly sailing to the Channel Islands. By 1984, he owned and sailed a 30-foot Blanchard sloop in Long Island, New York, navigating Long Island Sound and the Hudson River. Following service in the U.S. Army, he attended a one-year boatbuilding school in Washington State while sailing throughout Puget Sound, combining hands-on construction knowledge with practical offshore experience. His career then expanded into the Caribbean, where he built, delivered, raced, and sailed large catamarans throughout the U.S. Virgin Islands, British Virgin Islands, and beyond. He delivered Gold Coast Yacht Catamarans to destinations throughout the Caribbean and the Bahamas, helped build and operate a charter catamaran in Puerto La Cruz, Venezuela, crewed aboard the large trimaran Wanderlust, and captained private and crewed charters aboard vessels including a Morgan 50. Among his most meaningful voyages was helping to build and sail a traditional dugout canoe in Dominica, followed by a journey deep into the Orinoco River system from Venezuela to Guyana, reconnecting Dominican Carib Indians with their ancestral roots. Returning to the United States, he managed a sailing club in Redondo Beach, California, teaching ASA sailing courses and leading voyages throughout Southern California and to Catalina and the northern Channel Islands. He later moved to the San Francisco Bay Area, where he taught U.S. Sailing courses out of Sausalito, managed and lived aboard a 75-foot schooner, sailed a Pearson Ariel, sold boats for McGrath Yachts, and repaired, restored, and delivered vessels along the California coast from San Diego to San Francisco. In Marblehead, Massachusetts, he restored multiple fishing and sailing vessels before restoring a 30-foot sloop and sailing from New England to Hilton Head, South Carolina, and onward to Key West, Florida. For seven years, he served as a Scouting America captain at Sea Base in Islamorada, leading sailing, fishing, and snorkeling expeditions throughout the Florida Keys, from Key West to Key Largo. During this time, he also captained private charters throughout the Lower Keys, including voyages to Dry Tortugas and Marathon. Most recently, he purchased and restored a Catalina 42 in North Lake Champlain, Vermont, and sailed her back to Key West—bringing together inland waters, offshore passages, and decades of accumulated seamanship. Sailpony Charters reflects a lifetime of global sailing, vessel restoration, instruction, and exploration. Every charter is guided by deep experience, calm professionalism, and a genuine respect for the sea—offering guests not just a sail, but a connection to the true craft of sailing.

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