It's been almost 10 years since we went to Cuba. Our company was Cross Cultural Solutions. Our 'culture' was the International Jazz Festival in Havana.

I'm so not a 'package tourist', but, this seemed to be our only option to get there legally.

It was a great company, we stayed in Old Havana at what was then the Golden Tulip, I think it might be an Iberostar now. Once again wouldn't have been my choice on where to stay, too large and impersonal.

We had tours arranged every day and different choices of music venues every night.

We went to Cuba with Insight last December and were there for New Years Eve. that is the very busiest time of the year. I also wonder how things will be due to the hurricane since some areas were destroyed. We found the trip educational, the hotels they had us at were not good at all but we were not there to stay in a fancy hotel. We were at the Nationale in Havana and it had lovely public rooms but the hotel rooms were early 1960's and marginally clean. Other hotels were not good at all. Meals were just ok. We were in a group on 2 busses of 15 each. One guide was exceptional and the other terrible. We felt it was overpriced, but we wanted the experience and we were glad we went.

That's disappointing. I was hoping Insight would be excellent. Will start looking closely at other tour groups. They all seem to be overpriced. I would like to go in from Canada or Cancun but friends are nervous about us doing it. Anyone done Lonely planet or road scholar?

If you go in illegally, and enter and leave through the same country, you're going to have extra passport stamps for that country. Even though Cuba doesn't stamp your passport, if a sharp eyed Immigration official spots those stamps, you could have a lot of explaining to do.

I've been to Cuba legally twice, most recently, last April, and will return this April. I go with a very small photography group and if you have an interest in serious photography, I would suggest that you look at photography groups. They stay small and are more flexible than the larger agenda-focused groups.

I have stayed in various hotels in Havana, and other than the top three (Iberostar, Saratoga, and Melia Cohiba ) you will not find hotels that meet what you would consider a 4 star/luxury hotel in the US. However, that is not what you go to Cuba for. I have stayed at the Iberostor (previously Golden Tulip/Parque Central) and loved it. The location simply cannot be beat. I have also stayed at many of what Cuba calls "4 star" (US 2-3 star) and they were fine to awful. Note: plumbing is not Cuban's strong suit, so you need to take a shower when you can, not when you want to. The most important thing is hotel location so that you can walk to Old Havana. You should call Insight and specifically ask them what hotels they are using. I know they used to have a luxury option, but I don't see it on their site anymore.

Food in Cuba is marginal unless you go to good paladars--of which there are many these days--and they are great fun.

Don't go illegally if you have the option to go legally. it's not worth the stress.

Bottom line--I just love Havana and can't wait to get back. They have great mojitos that make up for the (mostly bad) food and the people are wonderful.

Here are some photos to make you fall in love with the place. There are other great (and many better) albums in this Cuba forum. Go and have fun. You'll be able to say you were in Cuba "before it "opened". It is changing rapidly. The difference from eight years ago to last April was astonishing. Go now. Have fun. It's changing fast.

https://www.facebook.com/media/set/?set=a.10150894989862959.478118.589287958&type=1&l=8e38cf7c50

Oh, and last thing. All tours to Cuba are expensive. Cuba is an expensive place to visit--the hotels are all US prices as is the food. The flights from Miami are $500-600 round trip for a 45 minute flight. No competition in airlines is not a good thing for passengers, but they are making hay while the sun shines--and the flights are always packed without an empty seat.

Insight Tours did not get their recertification to offer Cuba tours.
Roadscholar offers an excellent tour and did get recertified.

SusieQQ, you are incorrect about Insight. They did get their recertification. So did most other companies that were in the pipeline.

BostonHarbor, I returned yesterday from a RoadScholar tour with some people who were enrolled on an Insight tour and switched by Insight because they did not have their certification. There was also an article in the NYTimes listing Insight as one of those that did not get the certifcation.
Perhaps they got it just recently.