Sailing into the famous marina of Horta on the island on Faial is the quintessential yachting experience. This maritime town has been a mid-Atlantic steppingstone for sailors since the Age of Discovery, and today it’s a pitstop for international regattas like Les Sables-Les Açores-Les Sables. Check out the colorful wall on the marina’s breakwater – seafaring superstition states that sailors should paint a message on it to ensure divine protection for their crossing. Take a whale-watching trip or go hiking at Caldeira, a two-kilometer-wide and 400-meter-deep volcanic cone. And don’t miss the opportunity to visit Pete’s Café Sport, which is overflowing with yachting memorabilia – and merry sailors – from around the globe. This charming café opened in 1918 and is world famous among the sailing community.