Puerto Rico’s 500-year-old capital is a history buff’s dream come true. The Spanish settled this harbor as a New World home base, and that influence is still evident, from the fortress walls lining the coastline to the rainbow of colonial buildings along narrow streets. Venture further out from the old town and nature unfolds. You can scale high into the jungled mountains of El Yunque Forest, or keep to the foothills on a riverside horseback ride. If despacito is more your speed, pick a pristine beach and recline with codfish fritter and rum drink in hand. San Juan cruises give you the perfect outpost to dial up or dial down your vacation.

You’ll find Bridgetown strikes a fine mix of island warmth and English heritage. Stately colonial buildings intermingle with colorful wooden homes, open-air markets, and catch-of-the-day cafes. Outside of the bustle of “Town,” as the locals call it, Barbados is a new kind of paradise in any direction. Cruise to Barbados and head towards the shore for pink-and-white-sand beaches that stretch on endlessly and crystal clear turquoise waters. Or stick to the center of the island, you’ll find rolling hills and valleys, sugarcane fields and historic plantations. You can even travel underground to discover limestone caves with their own waterfalls.