These 14 days are designed to show you one of the richest strips of coastline in Brazil, including a day and a night in each of the two big cities to top things off. This is a very well-rounded trip that gives you a look at the big cities (including the famous sights of Rio de Janeiro), two large tropical islands, some of the best and most sparkling beaches on the coast, and an old, colonial Brazil via an 18th-century historical town. You’ll need a rental car to complete this journey, and much of the driving takes place in the afternoons, when you can get some wonderful scenic views along the coastal highway.

DAY 1
Arrive in São Paulo, check into your hotel, then take a tour of the downtown area, including Sala São Paulo, the Pinacoteca, and the Mercado Municipal. Enjoy dinner out in Jardins, Pinheiros, or Vila Madalena.

DAY 2
Treat yourself to early-morning shopping in Brás, then rent a car and make your way out of the city along the Rio–Santos coastal highway just after lunch. Drive up the coast to Cambury or Maresias for the afternoon and evening (about 3–4 hours driving).

DAY 3
Lounge the morning away on the beaches of Cambury and Maresias, then drive to São Sebastião and take the ferryboat to Ilhabela. Check into your hotel in the village, then explore the island for the rest of the day by car.

DAY 4
Indulge in snorkeling, sunbathing, or hiking on the island until late afternoon. Then you’re off to Ubatuba, three hours up the coast. Arrive in Ubatuba around nightfall. Stay in the Centro or Toninhas. Take an evening stroll along the boardwalk in the Centro.

DAY 5
Explore Praia do Cedro, Praia Grande, Praia do Lázaro, and Praia Domingas Dias during the day. Enjoy dinner in town in Ubatuba or at the pier in Saco de Ribeira.

DAY 6
Drive up the coast to explore Prumirim, Puruba, and the island of Couves (boat trip from Prumirim). Break out the snorkeling equipment for these spots.

DAY 7
Spend the morning driving up the coast to Paraty (3 hours) and catch the inland tour of the waterfalls and fazendas. Then drive up to the northern beaches (Praia Grande or Iriguaçu) or south to Paraty-Mirim for the rest of the day (about thirty minutes drive). Head back to the Centro Histórico for the evening.

DAY 8
Take a full-day boat excursion. Spend the afternoon and evening in the Centro Histórico. Go shopping.

DAY 9
Hike to Praia do Sonho in the morning, then spend the afternoon exploring the village and beaches of Trindade. Eat dinner in Trindade or Paraty.

DAY 10
Get up early (around 4:30 a.m.) for a drive to Mangaratíba to catch the 9 a.m. ferryboat across to Ilha Grande (leave your car at the port with the parking service). If you miss the boat, catch a private schooner in Mangaratíba or south in Angra dos Reis. When you arrive on the island, briefly explore the village of Abraão, then catch a boat tour out to Saco do Céu and surrounding beaches.

DAY 11
Hike to Lopes Mendes, stopping at all of the fabulous beaches along the way. Take your time going out there, as you’ll be taking the boat taxi back to the village for the evening.

DAY 12
Hike to the Feiticeira waterfall then back to the village for a late lunch. Catch the 5:30 p.m. ferry back to Mangaratíba. Drive to Rio de Janeiro (4 hours) and return your car.

DAY 13
Take a city tour of Rio. Spend the evening out in Ipanema or Leblon.

DAY 14
Enjoy a morning stroll along the boardwalk from Copacabana to Leblon, then head to the airport for your flight home.