Later, while walking through Placencia, I noticed that there were islands for sale. Suddenly the phrase came to me: Pickleball Island. The idea was simple, ridiculous, and perfect all at once: a Caribbean island built around pickleball, beach parties, friendship, music, food, and fun. When I said it out loud, Tom’s eyes got huge. He understood it immediately.

Over the next several days, we sailed to Tom and Lisa’s favorite islands. One island was owned by a husband, wife, and their 13-year-old daughter who had built an entire island life from scratch. Sailors could tie up to a mooring ball, radio in for dinner, and the husband would greet them with his favorite rum drink. Whatever his wife prepared that night was dinner.

Seeing that family, meeting the Swedish couple who built the Placencia Yacht Club, and discovering the world of sailors from Europe, Canada, and the United States who come down for months at a time opened my eyes. There was a whole lifestyle built around friendship, adventure, beaches, music, food, rum drinks, and community.

When I got home, the practical truth was obvious: building an actual private island would require millions for power, water, courts, bungalows, staff, food service, and everything else. So the idea evolved. Instead of building an island from scratch, we would create intimate Caribbean resort takeovers for like-minded couples.