Since we're talking about Cuba, don't expect everything to be perfectly clear:
U.S. citizens need approval from the Treasury Department to spend money in Cuba. Since the end of the Eisenhower administration, most business transactions with Cuba are banned and punishable with hefty fines or even jail time. Cuba remains the only country in the world off-limits to U.S. tourists.
That said, it's recently become much easier for Americans to legally visit the island just 90 miles off the coast of the U.S. for reasons other than tourism.
In January 2015, President Barack Obama expanded the categories of authorized travel to Cuba.
U.S. citizens can legally travel to Cuba if they are engaging in 12 categories of activities such as professional research, participating in an athletic event, performing in a concert, working on a humanitarian project or taking part in educational activities.
Previously many of these activities required applying for a specific license and maneuvering a labyrinth of government bureaucracy. Now many U.S. citizens can essentially "self license" if they believe their travel to Cuba meets the legal requirements.
The new Cuba policy allows thousands more Americans -- but not everyone -- to visit Cuba for the first time. The Treasury Department has answered frequently asked questions about the relaxed policy online (pdf).
Americans are still not allowed to visit Cuba for the purposes of tourism.
Travelers should be able to show their visit helped the Cuban people or had an educational component to it.
Soaking up rays on the beach and sipping mojitos doesn't cut it. That said, there doesn't appear to be much of an effort by U.S. government officials to determine who did or didn't hit the beach or go nightclub hopping in Cuba.
Travel companies are busy developing additional "people-to-people" offerings to meet the demand spurred by the elimination of much of the formal traveler licensing process.
U.S. cruise lines such as Carnival have even proposed bringing boatloads of Americans for educational tours and several ferry operators have proposed re-establishing regular service between Florida and Cuba.
Still wary of CIA plots against the island, Cuban officials are studying the avalanche of U.S. proposals carefully.
Until recently, U.S. travelers with licenses or going illegally often had to fly via a third country and were often at the mercy of the unpredictable flight schedules and creaky Russian airplanes of Cubana Airlines, the badly run state airliner.
Now there are multiple daily flights from Miami and more flights being added from destinations such as Tampa, New York and Orlando operated by major carriers including American and JetBlue.
However, seats still must be booked through third-party charter companies as airlines won't be able to sell tickets to Cuba directly until the United States and Cuba negotiate a new civil aviation agreement.
While the flight from Miami to Havana only takes 45 minutes, it's recommended to check in four hours before departure time.
Expect to spend a lot of time in various lines behind people bringing suitcases full of car parts, flatscreen TVs and spandex to needy relatives on the island.
Cuba is really not ready to receive a huge influx of visitors, particularly from the United States.
There are not enough good hotels, and infrastructure is in terrible shape. U.S. credit cards still aren't accepted in Cuba and forget about overseas roaming on your U.S. cell phone.
You will most likely be taking a vacation from the Internet, too. Apart from hotels and a few dozen Cuban government "hot spots," there is very little connectivity in Cuba.
Netflix may be available here now but in reality you won't be catching up on your favorite shows.
Critics of Obama's new policy toward Cuba say any increase in trade will ultimately flow into the coffers of the Cuban government.
While it's hard to cut the Cuban government out of the equation, there are ways to make sure your stay benefits Cuba's growing number of small entrepreneurs.
For starters, stay in a "casa particular" or private home rather than a government-run hotel.
Airbnb.com has a large listing of casas to choose from. Renting from Cubans provides a more unique, genuine experience than hotel stays and at a fraction of the price.
After four years of living in Cuba, it's very rare these days that I eat at a government restaurant.
Instead, the dining scene in Cuba revolves around "paladars," the privately owned restaurants that despite Cuba's many shortages are increasingly sophisticated and creative.
Bowing to private industry, the Cuban government has said it is planning on closing many of the state's inefficient, drab eateries.
Under the new regulations, U.S. visitors to Cuba can legally bring $100 of Cuba's coveted cigars home with them.
The problem is most boxes of Cuban cigars in state-run stores sell for much more than $100, with a box of premium Cohiba cigars usually going for over $400.
You can of course buy cigars (most likely fakes) for much less from the throng of black market sellers who stake out hotels pestering tourists. But those contraband smokes typically don't come with receipts.
Frequent travelers to Cuba say that they have brought back a box or two to the United States without experiencing any issues.
While traveling to Cuba is still a hassle and legally murky, many U.S. travelers think now is the time to come.
Cuba is experiencing a boom in visitors from the United States and from other countries, who want to see Cuba before the island becomes too "Americanized."
That's probably a long way off from happening since the Cuban government is resisting any major changes to the island's political system and state-controlled economy.
And there's always the possibility that the next U.S. president could roll back many of the changes enacted by Obama.
Still, a visitor coming to Cuba will witness a long misunderstood island in the midst of an exciting and long-awaited transition.
Patrick Oppmann is CNN's Havana-based correspondent. Follow him on Twitter @CNN_Oppmann or see his pictures of life in Cuba on Instagram @cubareporter.