US citizens trip to Cuba

You do not need to use a company.

Many people have travelled independently under the OFAC general licenses.

There are some reports here and on Trip Advisor.

I've met (literally) countless Americans travelling independently. It has been happening for years.

Cheers,
Terry

I've done it during every one of my 60 plus trips since 1993. Not especially a difficult thing to do.
Trap

HI IrishGalShoes.
I went for a brief first trip in September. I speak English and Portuguese, not Spanish. I traveled by taxi, car with driver, and Viazul bus. I stayed in casas particulares, making my own arrangements on CubaJunky. It was not any harder or more complicated than anywhere else in the world. Remember that the rest of the world has been traveling there for years, backpackers to resort visitors.
Getting the tourist card for the Cuban government and checking the "reason for travel" box on the form for the US government were not complicated (airline has a the party agency to arrange) and neither government's border process in either direction was any challenge. US officials just said Welcome Home.
If you want to plan your own trip, go for it.

N25 is correct. We have also been to Cuba over 60 times since 1998. We never used any tour guides and if we were traveling outside Habana we just rented a car. Outside of Habana, traffic is very light which makes driving easy. We always had a good road maps and we found Cubans along the road very helpful when we got confused or lost. We always stopped before dark and asked for directions to a nice casa particular. We visited every province except Isla de Juvenitud(Isle of Pines). Only danger is from European drivers going over 150 km/hour on the Autopista. We believe these nuts are Italians. Watch you rear-view mirror and move to the right when you see their cars coming up fast. Have fun in Cuba, it is a nice country, but very different from everyehere else. Cubans have almost no money.

N25 is correct. We have also been to Cuba over 60 times since 1998. We never used any tour guides and if we were traveling outside Habana we just rented a car. Outside of Habana, traffic is very light which makes driving easy. We always had a good road maps and we found Cubans along the road very helpful when we got confused or lost. We always stopped before dark and asked for directions to a nice casa particular. We visited every province except Isla de Juvenitud(Isle of Pines). Only danger is from European drivers going over 150 km/hour on the Autopista. We believe these nuts are Italians. Watch you rear-view mirror and move to the right when you see their cars coming up fast. Have fun in Cuba, it is a nice country, but very different from everyehere else. Cubans have almost no money.

By casas do you mean people's homes? Or hotels? We were thinking of spending a few days in Havana, 1 or 2 in Trinadad, a few days in beach area. Should I book hotels all beforehand or just the Havana one & ask for recommendations for the other spots once we're there? Thank you SO much for your help!!

HI IrishGalShoes.
I went for a brief first trip in September. I speak English and Portuguese, not Spanish. I traveled by taxi, car with driver, and Viazul bus. I stayed in casas particulares, making my own arrangements on CubaJunky. It was not any harder or more complicated than anywhere else in the world. Remember that the rest of the world has been traveling there for years, backpackers to resort visitors.
Getting the tourist card for the Cuban government and checking the "reason for travel" box on the form for the US government were not complicated (airline has a the party agency to arrange) and neither government's border process in either direction was any challenge. US officials just said Welcome Home.
If you want to plan your own trip, go for it.

By casas do you mean people's homes? Or hotels? We were thinking of spending a few days in Havana, 1 or 2 in Trinadad, a few days in beach area. Should I book hotels all beforehand or just the Havana one & ask for recommendations for the other spots once we're there? You said you just went in Sept- Are you American? Any issues proving your trip fell under 12 general license? Thank you SO much for your help!!