Hostal Nicolas de Ovando
Cuidad Colonial, Calle Las Damas, Santo Domingo 10210, Dominican Republic
A Historic Night's Sleep Situated on Las Damas, the first paved street in the New World, Hostal Nicolas de Ovando is one of the most historic places you can sleep in the Western Hemisphere. The hotel incorporates three houses and patios built in 1502 for Santo Domingo's founder and governor, Nicolas de Ovando. The 5-star property is listed as a UNESCO World Heritage Site, and its numerous colonial courtyards, fountains and gardens are the perfect place to snack on organic Dominican chocolate or to smoke an authentic cigar. There's also a pool, albeit the view overlooks a street and a semi-noisy cruise dock so it's not always ideal.