Cuba

Rick does not do tours in Cuba. However, Road Scholar has several Cuba tours. I was on one in 2013 and thought it was wonderful. The people are so kind and welcoming.

Our trip to Cuba ranks among our favorites! We went with a local university group which was a great option.

I took a tour like this one with Go Ahead Tours. It was educational and enjoyable. This was in 2017, before Trump reimposed some of the restrictions Obama had lifted, but from the description it still looks a lot like my experience. I've traveled with Road Scholar to other places, and I'm sure they would do a good job in Cuba as well.

Travelling independently to Cuba is probably more difficult now than pre-Trump. You may need to go via Canada or Mexico. Your credit and debit cards won't work in Cuba. I'm not sure whether you can exchange US currency there for Cuban Convertible Pesos (CUCs), the money used in the tourist industry there. I had Euros left over from previous trips, which I could easily exchange for CUCs.

You'll find more about Cuba using the search function above, under the "Beyond Europe" part of this forum. As noted above, Rick Steves doesn't have a tour to Cuba. He does have a video that would be worth watching, though it may now be dated re the rules.

Like Mary Beth I used Road Scholar to go to Cuba, albeit more than 10 years ago. It was packaged as a cultural exchange and it was suggested to bring school supplies for one of our visits, for example. The guide, from the government, was really informative but also carefully shepherded us from curated stop to curated stop. We stayed in two 5 star hotels.
A family friend with family still there had a much more authentic experience!
So, based on what you hope to see/learn/experience, that might guide your options.
I went to Little Havana in Miami beforehand, and that was a really excellent choice, especially the military museum tour/Bay of Pigs.

Was a guest of the film school there in 2012.

One of my favorite trips ever.

The clean streets as in no garbage anywhere was impressive.

The smiles that greeted us everywhere were memorable.

Had been advised to take baseball cards to share with the children. Did so and one young boy in his school uniform smiled so proudly with joy that I snapped a photo. Submitted it to The LA Times and it was published in their travel photo section.

Take Kleenex packets to use as toilet tissue. Take a coin purse. Sturdy shoes or sandals.

If you decide to explore travel with Road Scholar, I suggest you join two Facebook sites. One is Women of Road Scholar and the other is Friends of Road Scholar. There are a number of people on both who have done one of the Cuba tours.

We did Road Scholar’s 2-week tour the length of the island in 2019. The furthest from Havana, in Guantanamo province, many people on the street asked us for pens and skin cream. If you go t the eastern end, try to take little bottles of skin cream and pens.

Adding...not meaning to imply that other forum members' experiences with Road Scholar are not valid. Just indicating there may be folks on there who have gone this year.

Are you planning to travel independently or hoping to find a good tour?

Pam makes a good point about recent experience being more relevant than, say, my response based on a trip from a decade ago! It's not intended as a review or recommendation for Road Scholar but based on the US regulations if you fly from the US, your visit needs to fall into at least one of twelve categories along with other restrictions, so it's not as easy as planning a typical tourist trip.
Road Scholar, at least at that time, handled some of these technicalities, and I am not a Spanish speaker.

Planning on traveling with my son (who speaks Spanish). I’ve heard a lot of good things about Road Scholar but hoping to do this trip independently…

Thanks to everyone for your input. Very helpful!

I recommend Cuban Adventures to tour Cuba. They are an Australian run company, but they use local guides, stay at local Airbnbs, and eat at local private restaurants, which keeps their costs down, compared with staying at hotels with a foreign guide. They are also a small group tour, even smaller than RS, at 16 people.

I did their 8 day tour (most popular),; they wen to Havana, Vinales, Cienfuegos, Trinidad, and Santa Clara. We had a mixture of Canadians, Americans, Australians, British, compared to RS, which is mostly American. Their tours are also legal for Americans, and will make not mention of Cuba on payments or records.