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The Current Prices Charged for a Trip to Cuba Show that Neither the U.S. Tour Industry Nor the Cuban Government Has Yet Gotten Serious About American Travel to That Island

Tours to Cuba, offered by the nation's best-known tour operators, continue to be priced at outrageous levels, confirming that both the Cuban authorities and the U.S. tour operators, have yet to negotiate realistic terms for expanding the number of Americans going there.  The latest outrage is offered by the well-known "", whose very name used to  describe a policy of inexpensive tour opportunities.  Starting in February of 2016, CheapCaribbean will be offering an eight-day tour of Cuba from Miami, costing a starting price of $5,500 per person, based on two persons traveling together.  Should Cheap Caribbean change its name?
Such absurdities as a starting price of $5,500 for what it is a one-week tour, confirm the advice we've often given here.  If you wish to enjoy a look at the authentic life of Cuba, at decent prices, you will simply book a normal airfare to Havana from where you live, via one of the airlines going there via Kingston, Jamaica, the Bahamas, or Cancun.  And then you will go for your accommodations to either, or to any number of Cuban real estate sources, renting a room (a "casa particular") in the apartment of a Havana resident.
Will the room you receive often lack normal creature comforts?  Of course it will.  It will not compare to the usual amenities you expect.  But it will place unpretentious visitors in an apartment of the sort occupied by average Cubans, and it will not require any unusual hardships on your part.  It will simply be slightly less comfortable than usual, but supplying a normal night's sleep.
                                       Photo by Bryan Ledgard/Flickr
As for your meals, and payment for your room, you will simply change your money at a "Cadeca" (a Cuban change bureau), exchanging either dollars or, better yet, Euros into "convertible pesos".  Cadecas are found at the Havana airport or at any number of locations in town.  Or you will change your money at the BFI Bank in Havana, using the proceeds to buy your restaurant meals.  (As a side note, Mastercard is currently claiming that its U.S. credit cards are now regularly accepted throughout Cuba; check before going). 
That course of conduct is currently the best procedure available to intelligent Americans wanting to experience Cuba.  When a company called Cheap Caribbean (for heaven's sake)  asks $5,500 per person, based on two persons booking (a total of $11,000), a do-it-yourself trip is the only realistic alternative.  Fly, let's say, to Jamaica, and change planes for the short hop to Havana.  And stay, during your time in Havana, in the apartment of a normal Cuban.
If, contrary to my advice, you insist on joining an organized tour to Cuba, your best bet will be the one-week variety offered by Road Scholar (, the former Elderhostel, for $3,895 per person based on two persons traveling together, still an outsized amount for arrangements of that sort.  It is the lowest such price known to me--but still an overpriced figure for an experience that is best had on your own.
Again, go independently--and make use of one of those "casas particulares".