Depends on how much you are willing to pay for the convenience of not having to do the planning. Really it's not that hard. Maybe you are unaccustomed to planning your other trips though.
What parts of Cuba are you hoping to see and in what time frame? Have you looked at a guidebook? What are your interests? Which airport do you intend to fly into? Do you speak any Spanish?
A casa particular on CubaJunky runs about 25-30CUC/night.
Viazul bus is not difficult to book once in Cuba, and taxis also take private parties and groups from town to town.
You can hire a guide for the day in Havana for example. And taxis for day trips.
A good guidebook (maybe Lonely Planet) can tell you about sights, but the trip is really about experiences.
IMO the Lonely Planet's Thorn Tree Cuba forum has the best informed posters who have been traveling to Cuba, some for decades, and some of whom also post on TA.