I'm seeing some good fares to Sao Paulo the week after Christmas.
We already have a Brazil visa from our previous trip (Rio, Iguacu).

Do you think Sao Paulo is a good vacation destination for a couple from NYC area.
Are there any fabulous places to go not far from Sao Paulo?

Personally I am not a big fan of SP. It seems to have all the negatives of NYC, but (unlike NYC) none of the culture a world class city of its size should. But if you want to eat well, and go clubbing without hearing much of a unique Brazilian sound, go for it. The exchange rate is very good, and yes, you can find some good fares.
There's a whole coastline within a couple of hours of the city that is heavily used by residents of this sprawling metropolis. On my first visit, there was a great headline photo of people sitting on top of their stopped cars in a weekend traffic jam trying to get to the beach.
I wouls choose to spend my city time in Rio and Salvador, with more unique Brazilian culture and music, and Brazilian food, just a short flight away. There are low key beach destinations close to each of them, like Ilha Grande or Morro do São Paulo.

I live in São Paulo and i can say its not a good destination to someone from NYC.
I would suggest you FLORIANOPOLIS if you like big cities with beautifull beaches (its WAY more beautifull then Rio de Janeiro).
If you are looking for a different vacation, just try BONITO (MS). Its just out of this world!

Better to go to Buenos Aires than Florianopolis if you fancy a place chock full of Argentinos.
Bonito is best combined with a trip to the Pantanal. As a single destination for a foreign visitor, it is a lot of expense and effort for value. Time consuming too, unless you take a small plane, expensive.
OP could also consider the Colonial towns in the mountains of Minas Gerais, if thinking of a non-beach destination.

Hi, I am also seeing better options for flying into Sao Paulo rather than Rio de Janeiro. Is it easy to get from Sao Paulo to Rio? What would be the best way? (Don't think we would not be driving there)!
Thanks.

Hi, I am also seeing better options for flying into Sao Paulo rather than Rio de Janeiro. Is it easy to get from Sao Paulo to Rio? Would a flight be the best way? Would it be worth staying a night in Sao Paulo or just booking a flight a couple of hours after we get there?
Thanks.

Flying between the two cities is the way to go, although make sure that you leave enough time between flights if you are on two separate tickets. Also note that there are more than one airport in São Paulo.

@excited_confused--
You can take the bus (about 6 hours) or fly between S.P. and Rio.The "better options" would really have to reflect the additional air fare and travel time to actually be "better". If you want to go to Rio, fly to Rio, not S.P.
As mentioned, S.P. Is not particularly touristic, and IMO there are too many other interesting places to spend your time, but you may need to relax after the long international flight. Where else do you plan to visit?
For any flights within Brazil, the fares go up sharply the closer to departure, so buying on arrival at an airport guarantees the highest fare possible (if that is what you meant).
Domestic airlines are TAM, GOL, Azul, and Avianca.