Just today a relative contacted me about how to go about booking one of those newly available flights from the US to Havana.  Last week the President of the US changed limits on Cuban cigars and rum. This morning, my Skift newsfeed had news of Trip Advisor being granted a license to sell Cuba travel.  So getting to Cuba for mojitos and the beach should be easy peasy, right? Not so fast! Real people are running into real troubles trying to turn their dreams of visiting Cuba into reality.  We went in 2015 with Insight Cuba, and I posted about it here, but here is my updated advice based on the latest news!

It is still a bit complicated to travel to Cuba, but getting more "open" every day! Unfortunately, it's not easy to just "book a flight" to Havana yet. As my cousin found out, when he tried booking a flight, the airlines refer you back to the US government for the "official" rules. And those seem to say you can travel so long as you are still traveling for one of the "approved" reasons.  But reading this doesn't help you book the flight, so you are back to square one. 

This is the official FAQ from the US Dept of Treasury https://www.treasury.gov/resource-center/sanctions/Programs/Documents/cuba_faqs_new.pdf

 

Even if you manage to find a travel agent who can book your flight, there is the matter of putting together an itinerary on the ground that will satisfy the US governments requirements. (No one checks this before or during your trip...but US officials could ask for your trip's purpose at anytime in the future, so I always travel with my paperwork in my passport, even though no one has ever asked to see it.)
The hard part of planning your own trip is few of the people or non governmental organizations in Cuba are on the internet yet, so it is very difficult to arrange these activities on your own. If you have a relative or contact through your place of business, place of worship or NGO where you already volunteer, this might be easier. Trip Advisor may make it easier, but as stated in the Skift article, that's not ready for roll out just yet. 

I think you if you are ready to travel this winter, it may be best to arrange a trip through some kind of outfitter or tour group. We decided to go with a small group and did not regret it. Group dynamics can be interesting, we met some interesting people in our group... a TV writer, civil servants, doctors, lawyers, entrepreneurs, professional athletes, even a bus driver who moonlights as a jazz pianist; every one of them fascinating to talk to and experience the trip with because of their unique outlooks on life. But even more importantly, were the fascinating people we met in Cuba and the activities arranged by Insight experts. We met artists and musicians and children in local schools. Our local guide was quite open about sharing the joys and challenges of her life in Cuba. Our daughter got to play saxophone with a young jazz band in the same underground jazz club where Dizzy Gillespie played pre embargo, which was an experience she won't soon forget!

We used Insight Cuba, you can see more about our experience on our blog here: 
http://www.goseeittravel.com/travel-blog?category=Cuba

Editor Note: Since posting this Carnival Corp has decided to suspend the service of Fathom Cruise line. However, several other cruise lines are introducing service to Havana, including the Royal Caribbean Corp announcement in early December, that a few of their branded ships will be making port of call stops in Havana this spring.  The advice about cruising to Cuba still holds true! I would add though that recent news stories also report greater food shortages for the people of Cuba due to increased tourism, so considering a cruise which provides food for it's own guests, may alleviate some of that, if it's a concern to you. 

Other resources for easily planned trips are the Fathom cruise line which is a service oriented specialty cruise run by Carnival. The advantage is a relaxing vacation on the ship on the way to and from Cuba.  The disadvantage is that you are not fully immersed in the country by staying there. Until the power cuts off and the jazz band keeps playing in the dark (as happened to us) you can't say you've really experienced what the country is all about. 

Another small group tour designed for active retirees is focused on culture is Overseas Adventure Travel 

Younger people might find a trip run through a group like Intrepid which focuses on a younger demographic.

If your heart is set on just going independently (no groups) try Wendy Perrin's WOW site for an outfitter that will organize a tour for you.  The advantage to that is with no other travelers to accommodate, and you can customize your itinerary to your specific interests. 

Lastly...the good news! Trip Advisor has been granted licenses to sell travel direct to consumer- this will probably end up being the cheapest option, once it's available! It might still be a little while and my experience planning Trip Advisor trips, is it will require a lot of leg work and probably not provide high touch customer service that the smaller specialized travel providers can provide in the planning or booking process. 

Right now, just because things are changing so fast, I'd still recommend a small group trip or check out Wendy Perrins WOW site for a destination expert to plan an independent trip. If you decide to wait to "book on your own" with Trip Advisor- let me know! I'll want to do a "Goseeit" people interview with you to see how it went to share with our readers!