Havana, Cuba – Your Bucket List Incentive Destination?

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We recently operated a dealer incentive program to Havana, Cuba and what an amazing experience it was. It was honestly one of the best, but most challenging programs we’ve ever operated.

Had we known what a roller coaster ride it would be to get to the finish line we may have ended up in Mexico or some other been there done that destination. But in our never-ending struggle to raise the bar, keep it fresh, unique and exciting, we stuck it out even after Trump announced he was going to get tough with Cuba in April of 2017. In reality, the only change was limiting individual travel and not being able stay at hotels owned or operated by the military wing of the Cuba government. The good news was that it really was more of a warning and groups who booked the new and fabulous Kempinski hotel were grandfathered in – whew!

I must say however, that Trump did have some valid points with the way the one party Cuban system has operated over the past 50 + years and there really is a need to make substantial changes to the political and economic landscape. But that’s a whole other therapy session.

Here are some of the highlights and challenges you’ll face if you think Cuba is on your incentive program bucket list.

  • Stay at the new Kempinski if you can. Located in the heart of Havana, the hotel is competitive with any 4 or 5 star on the planet. Great space, amazing roof top pool, great bar, oversized rooms, good Internet, and all the amenities any high-end client would expect. The service is a little lacking at times but an easy fix with a wad of CUC pesos. Remember – they all make $40 per month so a $5 tip goes a long way and provides the much needed motivation.
  • Another option is the Parque Central hotel located across the street from the Kempinski. Kind of an upscale Best Western but hey – you’re in Cuba! It also has a nice roof top pool, larger rooms and great bar area but in a desperate need of a full renovation. All part of the experience I guess. There’s also a Sheraton and Melia hotel, but they’re outside the downtown area and I would highly recommend staying in the heart of the city.


  • We held our welcome reception at the Kempinski’s rooftop terrace. The F&B manager, the A/V guy and the cigar rollers didn’t seem to grasp the concept of the start time and we were still setting up as guests arrived. UGH. Not even $20 pesos per guy could get them to move faster but we scrambled and pulled it off – barely. The guests were so enamored with the view of bustling downtown Havana that they hardly noticed. The band showed up an hour early and just started playing. Uh – how about a drink and some food and then you play when the guests arrive (in my best Spanglish) – they were more than eager to oblige.




  • On Day 2 we offered optional activities, which we actually made up during our site inspection.The Havana Vice tour – which consisted of a cigar factory tour and rum tasting. The cigar factory epitomized the confluence of communism and capitalism at it’s finest. We were greeted by this huge poster of Fidel Castro and Caesar Chavez having a good laugh together as though they were the Cuban version of Dean Martin and Jerry Lewis (see picture) After seeing the incredible poverty one had to ask – “What’s so funny?”

Our English-speaking guide led us around the factory floor and we watched what had to be 500 people rolling the worlds finest cigars.

Of course, the rollers offered to sell us cigars right from their stations which many people took advantage of. 10 Cigars for $20 pesos – a steal and a great way to promote capitalism and democracy!! We should have made this our CSR! At one point our “Minder” intervened and said we can’t buy cigars from that guy- oh but you can buy directly from mi amigo – this guy. Ahh – the joy of budding capitalism.

  • Other tours included the Ernest Hemingway pub-crawl, an amazing art gallery tour, old Havana walking tour, vintage car tour and a getting cultured tour complete with a ballet performance at the newly renovated Gran Teatro. As you walk around old Havana on Obispo Street there’s live music emanating from every bar. You feel like you’re in some sort of a communist Nashville but with beaches. The mojitos are cheap and the bands are great and it’s almost impossible not to get caught up in the authentic vibe of this blossoming city.


  • On night two we hosted dine arounds all over the city. The restaurants for the most part are great if not unique. I ended up at one of the hippest spots in the City called La Guardia. Our van pulled up on what seemed to be a condemned building. “This is it,” our DMC guide yelled as we all looked at each other as if this was some sort of evil plan to capture and torture the American spies. As we entered the building we then climbed a steep marble staircase to the 2nd floor only to be greeted by laundry hanging on clothes lines strapped between two massive pillars in what was once a grand ballroom in a private residence. We continued up the next set of stairs and finally entered a packed roof top restaurant in full swing as the DJ blasted Daft Punk and other assorted techno hits. We had a great meal with good service and enjoyed a rum aperitif on the roof top terrace with an amazing view of a hot Havana night.


  • After the dine arounds we all headed to the Tropicana Show. They sit you down, give you your mandatory personal bottle of rum, bottle of coca cola, and wish you luck. The show includes a cast of thousands and provides great entertainment value as guests are transported back in time to a 1958 Ricky Ricardo extravaganza where the band plays a difference version of the same song for 2 hours. It was awesome!!


  • Day three was more of the same tours but later that day we hired 40 vintage cars to take our guests over to the old La Davina Pastora fortress for a private dinner. It really was the highlight of the program. I had stumbled across a band playing earlier that day on our walking tour and hired them on the spot to play during our departure from the hotel.

  • Later that night we managed to get the entire group in to see the Buena Vista Social Club and everyone danced and drank copious amounts of rum. When in Rome……..


  • The last night we held the final night dinner at the newly renovated Grand Teatro. We were in the Grand Ballroom that was decadently adorned with marble floors, chandeliers and open-air windows that faced the city’s new Capital Building. This night was by far our most challenging as we were informed that the venue didn’t have staff to set up the stage. Wait What?! How about every guy gets $20? That turned out to be the quick fix. Someone also forgot the white wine and the food was cold but the whole managing expectations thing paid off and the guests muscled through it and ended up dancing to a great 15-piece Havana big band that rocked the house.

At the end of the program everyone was ecstatic simply based on the opportunity to experience such a unique and vibrant city but more importantly, an amazing culture of talented, aspiring and honest people who are getting a good taste of finally being rewarded for hard work and ingenuity.

Event Connections Group is an event management company specializing in creating first class travel incentive programs, customer events and sales meetings for a variety of clients.

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