The Challenges of Doing Business in CubaRelations are thawing, but entrepreneurs should tread carefully.

This article is part of ourTrends 2016coverage.

Fewer than 100 miles of ocean separate the U.S. and Cuba, but the nations have spent the last five decades in different worlds. Ever since John F. Kennedy signed Presidential Proclamation 3447 on Feb. 3, 1962, declaring "an embargo upon all trade" in response to Cuba nationalizing U.S.-owned Cuban oil refineries without compensation, Americans have been effectively blocked from doing business in the country.