I've been to Cuba twice, (1993 and 2019), and my wife's been three times. We just went this past Easter and stayed four days. Our family of four went, along with a cousin and a friend.
We flew from Orlando to Havana and it could not have been easier. We flew Jet Blue, which is about an hour flight and encountered no issues. In fact, we had no issues the whole trip. We stayed at an Air BnB that my kids arranged and we got our visas at the Jet Blue check-in at the Orlando airport. We arranged to get some Euros from our bank here in Florida before we left so we wouldn't get charged the extra ten percent using US dollars. At the airport in Havana, we exchanged some of the Euros for CUCs, which we also did a couple days later at a local bank/money exchange place in Old Havana.
I always ask to get my passport stamped and I did it in 1993 as well as this last trip. I want proof that I've been there. (We were journalists in the 90s so that wasn't an issue but found it not to be an issue on this year's trip either.) We used taxis sparingly but walked mostly while in Old Havana. There was internet at the place we stayed but I opted not to even bring my mobile phone on this trip. My wife and I enjoyed a four day break from being online. We were also surprised at how many restaurants were now all over as opposed to when we were there in 1993.
We had a very nice time and family trip, and enjoyed Cuba and its people. I guess I somewhat resemble Hemingway now in older age as that became my nickname from a number of Cubans as we walked around. I got a chuckle out of it. About a week before we left home, an announcement was made from the US that some travel restrictions were coming. Apparently it pertained mainly to US tourists coming by cruise ship and the one visa option. The visa option we used was the one dealing with care for the Cuban people, which is still allowed as of this post. (People-to-people is not.)
Being a native Floridian and hearing about my grandparents going there in the 40s and 50s, I've always been intrigued with Cuba. I definitely recommend visiting there, especially before there's a McDonald's and Starbucks on every corner. By the way, we tried to check on doing a day trip to a beach and cavern, (Saturn), but found that they didn't allow diving in Saturn and we could not arrange sensible transportion from Havana to these combined dive/snorkel sites. When we were there in 1993, we mostly stayed in Varadero, which made it much easier. (We flew there from Toronto back then with no issues.)