
About 300 kilometres and four-and-a-half to five-and-a-half hours — over the Serra do Mar, down to the sea, then north along the coast into Paraty.
The best route drops you out of São Paulo onto the modern Rodovia dos Tamoios, down the mountain to Caraguatatuba, and then north on the coastal BR-101 through Ubatuba and across the state line into Paraty. It trades a little time for a lot of ocean.
Leave São Paulo on the Rodovia Ayrton Senna / Carvalho Pinto heading toward São José dos Campos, then take the Rodovia dos Tamoios — recently modernised with tunnels through the Serra do Mar — down to the coast at Caraguatatuba. From there, join the BR-101 (Rio–Santos) heading north through Ubatuba, cross into Rio de Janeiro state, and continue to Paraty.
The Tamoios descent is dramatic and, in the older open sections, can be foggy or slow behind trucks; the newer tunnel stretch is fast and easy. Once you're on the coast road north of Ubatuba, it's the same beautiful, curvy Costa Verde highway that runs all the way to Rio.

Plan for 4.5 to 5.5 hours door to door, including a stop. The variable is the Serra do Mar: on a clear weekday the Tamoios flies; on a foggy morning or a holiday weekend the descent and the coast road both slow down. Summer weekends see heavy beach traffic around Ubatuba — leave early.
Expect tolls on the São Paulo highways and the Tamoios, plus a plaza or two on the Rio–Santos. An automatic tag (Sem Parar, ConectCar) makes life easier, but cash works. Fill the tank before the mountain descent and top up in Ubatuba if you're low — the prettiest stretch has fewer stations.
As on the Rio side, this is a winding coastal road with speed cameras. Keep to the limits, don't overtake on blind curves, and avoid the mountain sections at night or in fog.
Arriving from the south, you'll reach Paraty from the Ubatuba side. Head for the hill above the bay — Cantinho do Marinheiro — drop the car, and walk down into the old town when you're ready.
Pick your chalet and check live dates on Airbnb, or message Bianca first — she'll help you plan transfers, tours, and the little details.