Enynyl alcohols, which can be conveniently prepared, are packed with functionalities useful for many transformations given the appropriate conditions. During the course of this research concerning the reactivity of enynyl alcohols, we devised a convenient protocol to conduct hydrobromination reaction of terminal alkynes, without the need for gaseous hydrogen bromide, to give access to various 2-bromo-1-alkenes in moderate to excellent yields and in excellent selectivity. The vinylic bromides thus obtained readily underwent Sonogashira cross-coupling reaction to give rise to the required enynyl alcohols. A variety of enynyl alcohols were prepared and studied for their reactivity under various conditions, namely Lewis acid-promoted and electrophilic halogen-promoted conditions. In particular, we found that 2-alkynyl-2-propen-1-ols could readily undergo an intramolecular oxymetalation in the presence of gold or platinum catalysts to give 2-substituted-4-methylfurans. In addition, 2-alkynyl-2-propen-1- substituted-1-ols could also readily undergo an ICl-promoted reaction to conveniently and efficiently yield 2,5-disubstituted-3-iodo-4-chloromethylfuran derivatives. The latter reaction is found to be widely applicable to a variety of secondary enynyl alcohols and can provide structurally-diverse furans in moderate to excellent yields.