I went to Havana for a long weekend with InsightCuba back at the start of 2017. Overall, I thought the trip was poorly planned and disorganized and while some of that can be chalked up to the nature of traveling in Cuba (and the fact that we visited over the New Year's Eve holiday weekend), some of it is without a doubt the fault of InsightCuba.
As my father Mark H noted, the itinerary we received just days before departure bore little resemblance to the schedule that was actually followed. I had done a lot of pre-departure reading about Cuban culture and was prepared to go with the flow as far as things being closed or changed at the last minute in Cuba, but there were changes to the itinerary even before we left the US, when they switched the meeting time for departure to the Miami airport from 3:30 to 4:30 am. That wouldn't have been such a big deal, except the hotel forgot to switch our wake-up call so we lost sleep unnecessarily. On a related note, the hotel they chose in Miami (https://www.yelp.com/biz/pullman-miami-airport-hotel-miami) was awful. The hotel in Havana, the Melia Cohiba, was perfectly satisfactory, although I would have loved to have stayed at the legendary Hotel Nacional (which we did at least get to visit on the tour).
Our itinerary was arts- and music-heavy to begin with, but after a cigar factory visit and a visit to a Cuban grocery store were cancelled, there was essentially nothing on the agenda that wasn't related to the fine arts. I enjoy art and particularly enjoyed getting to hear Cuban jazz, but it was overload and the itinerary really could have benefited from more diversity (history, sports, etc. were not covered in any meaningful way).
One of the biggest disappointments to me was a "walking tour" of Old Havana that consisted of visiting just two of Old Havana's four central plazas and standing around in a circle while our guide droned on endlessly. At the time, I thought perhaps this was just the nature of walking tours, but a few weeks later I did a walking tour in New Orleans and was pleasantly surprised when we actually *walked*.
One day my father and I ditched the tour group right after lunch (they were going to see still more art studios) and spent the afternoon walking all over Havana by ourselves. It was by far my favorite part of our trip, which is not what you hope for when you've spent a lot of money for a guided tour.
Our guides were friendly, but honestly not very helpful. Our itinerary had one night free to dine on our own at one of Havana's paladares (privately owned restaurants). InsightCuba had given us a list in advance of recommend paladares and told us they would make reservations for us once we were in Cuba. I was nervous about this, because our paladar night was January 1, which is an even bigger holiday in Cuba than it is in the US, but they assured me it would be no problem. Of course then we get to Cuba and the guides announce that they've been calling around and they can't reservations anywhere because of the holiday, so they suggest we just join them for a group dinner at a place they'd booked (which, based on the quality of the rest of the meals InsightCuba arranged, was probably absolutely terrible). I had the (brilliant, if I do say so myself) idea to ask the concierge at the Melia Cohiba for help and, lo and behold, she was able to get us a reservation at L'Atelier, a paladar on InsightCuba's list that was just blocks from the hotel (and that turned out to be delicious). It reflects very poorly on the company that a hotel concierge could get us a dinner reservation when the tour guides couldn't.
I also agree with my father's criticisms of the quality of the meals. I understand the nature of a group tour is that choice is fairly limited and Cuba is not known for having great food, but most of the restaurants we visited (with the exception of El Aljibe and the paladar) were frankly awful, and the options for those who don't eat pork or beef were basically non-existent. At one restaurant I was served a piece of bread with a few cucumber slices on it - no spread, no other veggies, no nothing. Even at El Aljibe, where we enjoyed wonderful roasted chicken, the vegetarians in our group were offered nothing except rice and beans. Come on, I know that Cuban cuisine is not veg-friendly, but rice and beans is not a meal, especially for the price paid for a tour like this.
It's also worth noting that I became ill from the food in Havana and I did not eat or drink anything except at the restaurants InsightCuba brought us to and a paladar they recommended. I have a strong stomach and have traveled in rural Southeast Asia without becoming ill, so I was surprised and disappointed that I got sick here.
Some photos from my trip can be seen here (note that many were taken while we were exploring on our own, so don't assume you will see all these things w/InsightCuba): https://destinationsanddesserts.com/2017/02/01/havana/ read more