Welcome to Cuba: New Ways to Visit the Island Legally

After taking more than 100 cruises, I am well acquainted with the Caribbean, but the region's largest island, Cuba, is virtually invisible to me. Because I have no personal knowledge of the place, its a black hole in my Caribbean universe.

The official U.S. policy to ignore Cuba was invoked in 1961. Perhaps I know so little about Cuba because that is just the way certain people wanted it.

Policy changes by President Obama has the Treasury Department once again granting people-to-people licenses, which greatly expand opportunities for U.S. travelers looking to visit Cuba.

A few years ago there was talk about opening up Cuba to American cruise ships, but the idea was largely shot down by some experts claiming Cuba couldnt handle it. I find that ridiculous: two U.K. cruise lines already include Havana on their itineraries and Cuba is home to many all-inclusive resorts that attract thousands of Canadians and Europeans each year.

For decades Havana was the crown jewel of Caribbean tourism--especially during the Prohibition Era in the U.S. Many aspects of Havana's glory days still exist largely unchanged, although you rarely hear about it. But is Havana really ready for unbridled U.S. tourism? Lets put it this way: Cuba could handle the tourists, but things there would certainly change quickly.

There is no place in the world like Cuba anymore. The island is much the same as it was in 1960, and while it is inevitable that Cuba will open up someday, it will probably lose some of its charms.

That's why I want to see Cuba as it exists now. And for the first time in eight years, I have a chance to visit the country legally as an American tourist; no stipulations, as long as I go with the right tour conductor.

Tom Popper, owner of the travel company Insight Cuba, just received a special U.S. Treasury Department people to people dispensation to take American tourists directly to Cuba. Popper started Insight Cuba in 1999 and operated tours through 2003, until the State Department put his license on hiatus. Last January he was allowed to reapply and was granted official clearance as of June 28.

To qualify, Popper had to design a program to bring Americans into contact with Cuban culture. Insight Cuba now offers six different itineraries ranging four to nine days in length that all begin in Havana. The trips visit childrens schools, museums and venues that feature distinctly-Cuban music and art. From there, some tours go overland to various places of interest throughout the Caribbeans largest island.

Prices for the packages include transportation on the island, hotels, meals and all tours. It also includes the Letter of Authorization to visit Cuba that the company must issue to you in the name of the U.S. State Department. The tours start with a 35-minute flight from Miami to Havana. Accommodations include four- and five-star hotels, some of which were places renown during the American Prohibition era, like El Presidente Hotel and Hotel Nacional.

The six different itineraries vary from a Weekend in Havana to seven-night adventures. One package takes travelers through Havana and then to colonial Trinidad amidst the coffee plantations in the Sierra del Escambray Mountains. Another seven-night tour starts in Havana and then takes participants to the Pinar del Ri� region where farmers grow tobacco for Cuban cigars.

Most tours include a meeting with the Committee for the Defense of the Revolution, a 50-year-old organization that promotes social welfare and community relations in neighborhoods throughout Cuba. The Cubans are surprisingly open to political discussions, and all points of view are considered.

After this serious meeting, guests will attend a neighborhood block party to eat, drink and talk with the locals. Mixing with the people--without government intervention--is the beauty of the Insight Cuba cultural program.

If you have seen the documentary The Buena Vista Social Club, you know Cubas music heritage runs rich and deep. The eight-day Havana Jazz Experience (organized in conjunction with JazzTimes Magazine) offers different musical experiences daily, with evening visits to Havanas famous jazz nightclubs. You'll visit Egrem, Havanas largest record label, and then spend an evening at La Zorra y el Cuervo jazz club. You'll see the favorite haunts of Hemingway, enjoy a private jazz concert in the afternoon, and visit the famous Jazz Caf� at night. The tour also includes a visit to the Cuban Music Institute, followed by an evening at the world-famous Tropicana Cabaret. The next day features a private music and dance workshop, followed by a two-hour All Things Salsa rhythm workshop, then dinner and music at the Hotel Nacional. The last day provides a percussion workshop in the morning followed by a lecture at the Museum of Music. Popper says these music itineraries often turn into impromptu jam sessions between the locals and Americans.

More politically-minded travelers may choose the Bay of Pigs itinerary. It starts with four days in Havana before traveling to the Zapata Peninsula to visit the Playa Gir�n battle site, including a museum depicting the events from the Cuban perspective.

The more artistic-minded may opt for the Pinar del Ri� itinerary, which visits an orphanage, a school for deaf and blind children, a community project to promote art and music (Callej�n de Hammel) and the Copellia Ice Cream Emporium.

For more detailed information on these various Cuban itineraries from Insight Cuba, click here or call 800-450 CUBA (2882).

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I started writing about stock market investing for Motley Fool in 1995, but previously I worked aboard cruise ships. I co-founded the CruiseMates.com cruise travel guide on the Internet in New York City in 1999. CruiseMates was acquired by Internet Brands in 2006. Once CEO, I am now the editor of CruiseMates