Read this post if you're hoping to make it to Cuba before the next permanent ban.
For the past couple years I've made it a point to try to go out of the country at least once...so twice thus far (first Peru, now Cuba). Going to Cuba was a pretty arbitrary decision and it wasn't very high on my "must visit" list. A couple co-workers and I were talking about wanting to take a trip and Cuba came up as a viable option. What started off as a half joking "Yeah, sure let's go!" ended up being a group of eight people ranging family members to lose acquaintances and everything in between (i.e. co workers, roommates, boyfriends, friends).
I knew traveling with so many people would be challenging but everyone was flexible, had a great attitude throughout. We had one person who was a planning champion and knew exactly what she wanted to do during our time there.
Note: If you're traveling anywhere in a large group, this is THE ideal situation. One or two people need to be deeply invested in everyone having a good time and the planning process and everyone else needs to have as few opinions as possible and be down for whatever.
We were there for six days total and spent time in: Havana, Vinales, Varadero, Cienfuegos, Trinidad, and Playa de Este. Our Airbnb was in Havana so we did day trips out to Vinales (tobacco farms & horseback riding), Varadero, and Playa de Este. We spent one night in Trinidad and covered Cienfuegos on our way down.
The whole crew in Viñales, tobacco farm, horseback riding through the farm:
I won't get into a timeline of how we spent our time but just a list of the hits, misses, and other unsolicited advice.
Trinidad & Cienfuegos I was on the fence about making the 4 hour drive to the southern coast of Cuba and almost skipped out on it since it meant spending a night down there as well. But, I can't emphasize this enough, it was by far one of my favorite parts of the trip! Trinidad was the most picturesque town and our tour guide was incredibly informative and open to answering our questions. The Disco Ayala, a disco club inside a real/natural cave, was absolutely worth it even though we had to take a legit hike to get to the entrance. If you go to Cuba, extend your trip two days if necessary and go check out Trinidad.
Tour Guides Our super champion planner set us up with a tour company that found us a tour guide in every city we visited. Again, I was hesitant at first but since I was in the "have few opinions as possible" party and was doing nothing to help plan the trip I went along with it. This was also very helpful because we had someone explaining to us (in great English) the significance of what we were seeing and historical insights that we wouldn't have gotten otherwise. They were also all kind enough to add some color commentary of their own so it was great to hear local perspective on some of the current turmoil.
Accommodations I usually prefer to stay in hostel style housing to meet other travelers and be frugal but since we were such a big group staying for an extended period of time and spending time away in Trinidad it made sense to opt for an Airbnb. This also worked out in our favor. One of the girls in our group was a native Spanish speaker and we were able to hit it off with our hosts right away. It also helped that they were a young couple who were open to spending time with us! One night they took us to a concert their close friend was singing in and was the best night out we had. We would have never gone to a random local concert if it hadn't been for them!
Our Airbnb, impromptu dance lessons from our hosts, and the concert we went to:
Travel within Cuba If you're going in a large group (I'd say more than 4 people) and plan to travel to different parts of the country, hire a driver for the entire duration of your trip. I was skeptical about the cost v. benefit but it ended up being much cheaper in the long run and way more fun. Our driver Yuni was basically our body guard for the trip and was looking out for us everywhere we went. He had great intel on where to eat, go dancing, and best spots to hang out. His wife came along with us one day and she was much chattier and answered a lot of our questions about how the locals feel about Fidel, Americans, and of course Trump.
Moral of the story is don't let me plan a trip because I tend to be skeptical of all the things that end up being really beneficial. Ha. Just kidding....kind of!
Don't Venmo someone with the description "Cuba" you will get flagged and the payment will not go through right away. This is true even if you're getting brunch at a place called Cuba in New York City (yes, it's a real place, yes it's really good, but no it's not really Cuban food)
Cuba Libre - Cuba's deadly version of the Rum & Coke. Don't over do it with the Cuba Libres, it will haunt you. Thanks to this trip I'm now on my quest to find my drink of choice.
Be sure to check out the Havana flee market. I'm not big on souvenirs but they had some really great artwork by local artists. We learned that all the vendors used to be free standers on the streets of Havana but were forced to come together in this one location by the government. I also had the most eerily accurate tarot card reading done by a woman who practices Santeria, everything that woman said to me still gives me the chills!
Picture of my tarot card reading! It was all in Spanish so my friend was there translating for me.