The Gallery Inn, Puerto Rico
Owned by the same couple for decades, the historic Gallery Inn is run like an informal B&B -- guests are greeted by name, much of what the restaurant serves is grown in the garden, and no two rooms are the same (though they do share lots of Spanish-style charm). Also like a B&B, the hotel lacks amenities such as TVs and a fitness center. The property's main draws include the convenient Old San Juan location, ocean views from the wine deck, and the artsy, laid-back feel. The innkeepers are both artists, and it's evident they put thought into every detail of the restoration -- expect beautiful old-world details like brick floors, wood beam ceilings, rich rugs, sculptures, and antique knickknacks.