The adventure actually started almost a year before, at the end of the trip to Guatemala and Costa Rica in 2015, when John Gressett asked me, “what do we do for an encore?”  We were pretty happy with the way our first trip had come together and we knew that many of the participants were eager to go somewhere else the next year.  “What about Cuba?”  I’m not sure which of us said it, but it was definitely on my mind over the next few months as we searched for another interesting “Adventure” destination and relations with Cuba began to thaw.

At EAA, John ran into Jim Parker who was actively promoting the idea of trips to Cuba and by August we started to work out a deal.  While Jim is a great guy, I was a little nervous about some of the practical issues to getting a large group of planes in and out of Cuba without any problems and the insurance question was a continuing nag as we tried to cross the T’s and dot the I’s on what the trip would look like.  How many days? Where do we stay? Will the Cuban’s allow us to land in Havana and then fly to Varadero or do we go to Varadero first and then Havana?  Is 100LL available (and safe to use) at both airports?  Cuban visas?  Cuban landing permits?  What currency should we have?  The questions were literally endless, and while helpful, Jim at times seemed just a little vague on many of these details.  As it turned out, the Cuban’s were also being vague on the details and kept changing the plan during the months leading up to the trip.  It was definitely good that Jim was working with the Cuban’s, because I’m not sure the trip would have survived if either John or I had had to deal with the uncertainty.

What finally convinced me that we could and should do this trip was the accidental dinner pairing at Migration 13 in Dallas.  At the final dinner, I sat down next to two couples and introduced myself and before you know it we are talking about the trip they and Jim Parker had just completed to…Cuba!  They gave us a lot of information about how their trip had gone (both the good and not so good), and how well Jim had navigated the authorities and arranged the trip on relative short notice (they flew over in August and were the first two Cirri to land in Havana).  Their experience gave me enough confidence that Jim could actually pull this off and we weren’t all going to get shot at or worse have our planes confiscated and sent to Cuba jail.

Evidentially there were many COPA members that felt the same way, as our registration process lasted a record 6 minutes to get all 15 planes signed up and we ended up with nearly 20 waitlisted for the trip.  Once we had pulled the trigger, now the real work started.  We had to make sure that Jim Parker could actually put together a trip we would all remember the rest of lives for good reasons, not bad.

Over the ensuing weeks, hundreds of little decisions got made, spreadsheets built and several calls were held with the group to assure them things were well organized and to make sure they had done their own pre-trip planning.  Key tasks that each person had to do were to make sure their passports were up to date and wouldn’t expire in the 6 months following the trip, apply for, receive and affix the Customs and Border Protection sticker for their plane for 2016, setup an eAPIS account and learn how to do the filings for each leg of the trip that crossed a US border in either direction.  And what turned out to be the most difficult for some was to get the appropriate Cuban endorsement on their insurance policy.  Mine turned out to be somewhat enigmatic:


Ultimately, one of our group was denied, John Gressett’s plane belongs to a club and with its more complicated issues, he couldn’t get the underwriter to make the exception even though the previous year he had flown the plane through Central America and as far south as Costa Rica.  Instead of losing John on the trip, we organized a work around for Beth and John that involved leaving the plane in Key West and hitching rides with other pilots for just the Cuban segment, but picking the plane up and flying it down to Puerto Rico.  Having John’s experience and organizational skills along made things much easier.

As the trip took shape, we settled on the following itinerary:

Feb 4 – Arrive at Tamiami Airport (KTMB) and gather for a group send off dinner

Feb 5 – Fly from KTMB to KEYW then land and then pickup clearance to Havana

Feb 5 – Tour Havana by bus and stay at the Memories Miramar Hotel (2 Nights)

Feb 6 – Tour Havana by bus and old cars, dinner show – Buena Vista Social Club

Feb 7 – Transfer by bus to MUHA and fly short segment to MUVR (Varadero)

Feb 7 – Transfer by Bus to lunch at Dupont Resort then to Iberostar Varadero Hotel and Resort (2 Nights)

Feb 8 – Beach or Sky Diving in the morning and a trip to a local farm for lunch then dinner at the hotel

Feb 9 – Transfer to MUVR to depart for Vieques Island via Bahamas lunch and fuel stop (W Hotel – 4 nights)

Feb 10 – Local flying during the day, Bioluminescent Kayaking (Bio Bay) plus dinner in town

Feb 11 – San Juan side trip, tour of Vieques or at leisure – group dinner at the Tin Box

Feb 12 – St Martin side trip, final group farewell dinner at W Hotel

Feb 13 – Depart for the US or other locations

The entire trip was virtually all inclusive of most meals and hotels for the 9 nights including all visas, handling at all airports and landing fees and most tours.  The only major outside expenses were fuel purchases and 3 dinners while on Vieques.  Total fee paid to COPA was kept under $8,000 per plane (double occupancy) and we stayed within our budget.

Our biggest concern, as it always is with these trips, are planning for any contingencies.  Bad weather, broken planes, someone gets sick or has an accident are all things the organizers have to worry about and have at least a plan should things come up.  We encourage everyone to purchase trip insurance in advance of departure to handle most of the sickness or accident scenarios.  Broken planes were covered by working with the Advanced Aircraft at KTMB, the local Cirrus Service Center, to make sure that they would be able to help us in or out of Cuba with parts or repairs should they be needed.  Several planes that had excess weight capacity brought spare tires and other basic parts to cover the more likely issues.   Weather we would deal with as it presented itself and while it turned out to be somewhat challenging, we avoided any major delays or changes to the trip schedule though the initial departure of February 4th saw a major cold front with associated thunderstorms drape itself across central Florida, preventing at least one plane from making the first send off dinner.

John Gressett has written an excellent set of articles that will appear in the next two issues of COPA Pilot talking about the actual trip, so I won’t duplicate that here.  However, I did want to include a few more pictures from the trip that the magazine wouldn’t have room to publish.

Lastly, we asked ourselves again at the end of this trip what we could do next year to top Cuba and so far I haven’t come up with anything.  I will be leading another adventure trip back to Churchill MB to see the Polar Bears and Beluga Whales from August 20-25 that will be posted on COPA soon, but we are still thinking about next winter and hoping we can again find an excuse to leave Wisconsin for warmer weather.

Arrival at MUHA (Havana)

Gloria and Jim Ratley with Beth and John Gressett - Revolutionary Square, Havana Cuba

Classic Cars

Walking Tour of Old Town with our Guide

Cigar Rolling

Dancing at the Buena Vista Social Club

Dinner at a “Private” Restaurant

Tour of Famous Cuban Artist, Jose Fuster’s, Home and Work Shop

Cuban Orchestra Free Concert

Example of Havana Architecture in Good Repair

Havana Street in Disrepair

Old Castle in Havana’s Waterfront

Havana’s Harbor

Varadero – DuPont Resort and Golf Course

DuPont Resort – Bar and Lounge

Varadero Beach – Sky Divers

Chris Baines Enjoying a Natural Coconut Drink on a Cuban Farm


Boat at Vieques Island

Cirri Lined Up at Vieques Airport (TJVQ)

Lunch at Cap Juluca Resort – Anguilla (British) - A short flight from Vieques

Getting Ready for Kayaking at Bio Bay

Bio Bay at Vieques - (Not my picture – hard to get a good shot)

Bananas – A Dinner Option in Esperanza on Vieques Island

Vieques Tour

Arecibo Observatory Seen from Cirrus on the Way Home