There are two ways for U.S. citizens to visit Cuba: 
the legal way, and the not-so-legal way.

Internet Access in Cuba

Is a Third-World Fiasco

However you get to Cuba, you’ll discover two things: First, Cuba is a quaint little island caught in a time warp of the 1950s, and perhaps, the most "unwired" Internet plot of land in the entire world. Sure, hotels and many companies have Internet service used to run their business. But if you’re looking for the Cuban variation of the Starbucks Internet café, better forget it. For that matter, you might just as well leave your laptop at home, since you’ll find virtually no service.

Most Cubans do not have authorized access to the Wide World Web, although many can access international e-mail and a more limited government-controlled intranet at government jobs and schools.

A Cuban hotspot is the Capitolio, Cuban's now defunct capitol building.

Internet service in Cuba is restricted and all of those offering services are either state-owned, or they are private foreign owned firms who have a special license to operate in Cuba. For those who have authorization to obtain internet service the cost is about U.S. $300 per month, by means of a regular telephone modem. For corporations the fee oscillates between $600 and $800, plus an additional fee is levied based on bandwidth used.

Of course, that makes trading stocks online a difficult, but not impossible, chore. I stayed in Old Havana and Internet service was rarer than new car showrooms. Yes, you’ll find the Internet on dialups in many hotel lobbies, and in a few government buildings like the train station. That means I had to plan carefully.

Since you have to buy blocks of time, a half-hour, or an hour, in advance, I arranged it so that I would get on the Net a half-hour before the market opened and a half-hour into the trading day. I could scout out promising trades before the market open, and make my trades during the meatiest part of the trading day. If I could buy additional time, I would. If I couldn't, I'd set sell stops and be on my way. If you're a decent trader, you can get away with that, but of course, you'll never earn top-dollar that way because you won't be able to follow the rhythm of the day and cash in when it's the best time to do so.

Vintage cars are everywhere in Cuba, but most are what we would politely call "junkers." And worse yet, I'm old enough to identify every one of the heaps in this picture.

In Cuba, of course, that's about all the Internet service you'll find. Hotel dialup. There is no such thing as in-room hotel Internet service, high speed Wi-Fi cafes and restaurants, Kinko-like retailers, or anything that smacks of broadband.

Varadero is typical of most “resort” cities I visited. There are few "Internet cafes" and access through the hotel is that same old, take-a-number routine that I grew to detest. I want you to picture a busload of kids from, say, Internet-savvy South Korea, piling into a hotel lobby or café with Internet service and every one of these kids wants to send an email to the folks back home. Better order lunch and dinner now because it’s going to be a long wait. 

Moreover, you may be promised Internet service at your hotel, only to find the system down and collecting cobwebs. Most tourists get so fed up they check for messages by phone. It’s not only faster, but more reliable. And---it almost less expensive.

Getting To Cuba

As I said before, there's two ways to get to Cuba, legally and illegally. Contrary to popular belief, however, U.S. law does not prohibit US citizens from visiting Cuba. But, the Feds go out of their way to make it difficult for you to travel there.

First, the U.S. bans most U.S. carriers from flying into Cuba or using U.S. airspace to get there. Get this: you can fly from most any city in the U.S. to Miami, but making the short hop from Miami to Cuba will likely involve a long swim.

Moreover, tourism is "sorta" banned by the Trading With the Enemy Act, which prohibits US citizens from spending money there. So, unless you intend to camp under a bridge and beg for food on the steps of the Capitolio, you’re going to have some explaining to do with Customs. And of course, U.S. dollars are useless on the island. The Cuban convertible peso is the going currency. Or the Euro which must be converted to pesos.

The Illegal Way to Visit Cuba

Of course, there are many other ways to get to Cuba and skirt U.S. laws. And if I had to do it all over again, I’d probably choose the illegal way. Why? Because there’s a lot less bureaucratic nonsense to put up with and your flight accommodations will be a lot nicer.

The Cubans, after all,  have no restrictions on US tourists. On the contrary; they welcome U.S. visitors and their money with open arms. And more than 100,000 U.S. citizens flock to Cuba every year; only about 20% do so legally, while the rest slipped in through third countries.  

And that's easy: simply board a U.S. air carrier and fly to Canada or Mexico or virtually anywhere else in the world, and then book a flight from that country into Castro’s heartland. Or better yet, use one of the many travel agents like USA Cuba Travel to book a tour.

Cuba's tourism boom is fueling an increase in traffic on the 40 airlines that service Cuba. Charters account for about 90 percent of arrivals.

I snapped this beautiful Cuban model at the Hotel National de Cuba where I stayed in Havana. It's a terrific hotel. I highly recommend it.

Leading international carriers have regular scheduled service from Europe, Canada, and Central and South America, and more are being added. If you want flexibility, choose your airline carefully—some are notoriously accommodating; others are not.

The Legal Way to Visit Cuba

There is, of course, a legal way to get to Cuba. And that's what I did. To do so, you’ll need a license from the U.S. Office of Foreign Assets Control (OFAC), US Department of the Treasury, (Washington, D.C. 20200).

Here's a laundry list of folks who can visit legally: Journalists and supporting broadcasting or technical personnel, government travelers on official business, members of international organizations of which the U.S. is also a member (traveling on official business),  full-time professionals whose travel transactions are directly related to research in their professional areas, and other travelers who have received specific licenses from OFAC prior to going.

But here's the kicker: When you enter Cuba "illegally," you fly a carrier like Air Canada. You'll board a sleek, modern jet and you'll deplane at Havana Jose Marti International Airport, where the glitterati land.

But when you fly legally from Miami International, you'll wait in line at least FOUR HOURS while they process the locals returning to Cuba.

Here's the kind of noisy charter aircraft you'll get flying legally to Cuba from Miami. The only blessing? A short flight.

Then you'll board a twin-prop, puddle-jumper of an aircraft, and deplane in a featureless, oversized hangar in Havana where you'll do battle with completely unsympathetic customs agents. And would you believe that it cost me more than TWICE as much to fly the 90 miles from Miami to Havana than it did to fly the 1800 miles from Minneapolis to Miami.  No more. The next time I plan adventure travel to stock trade in Cuba, I'd  fly Minneapolis to the Bahamas, and then to Cuba.

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