I would recommend that your brother take the following itinerary which runs via the old IC1 national road to Lisbon and has no tolls except in crossing the Tagus at Lisbon. (Provided by google maps:)
Note there is a 90km speed limit on much of this route.
Link to map here:
http://maps.google.com/maps?f=d&source=s_d&saddr=Acesso+ao+Porto+Comercial+de+Portim%C3%A3o&daddr=A22+to:Lisboa,+Portugal&geocode=FaJ_NgIdVNR9_w%3BFVCzNgIdfCSB_w%3B&hl=en&mra=ls&via=1&dirflg=t&doflg=ptk&sll=37.926868,-9.030762&sspn=2.045127,4.938354&ie=UTF8&ll=37.918201,-8.695679&spn=2.045367,4.938354&z=8
Driving directions to Lisbon, Portugal - 300 km – about 4 hours 34 mins Via A22 -
1. Head southeast on Acesso ao Porto Comercial de Portimão 0.3 km
2. At the roundabout, take the 1st exit 0.4 km
3. Turn left at Av. Rio Arade 0.2 km
4. At the roundabout, take the 1st exit onto Av. das Comunidades Lusíadas 0.3 km
5. Slight right at Av. Eng. Francisco Bívar 0.1 km
6. Turn right to stay on Av. Eng. Francisco Bívar 0.4 km
7. At the roundabout, take the 1st exit 0.3 km
8. At the roundabout, take the 3rd exit onto R. Jaime Pahinha 0.4 km
9. Take the ramp onto Av. V6 Go through 1 roundabout 1.5 km
10. Slight right to merge onto Av. Paul Harris 0.2 km
11. Slight left to stay on Av. Paul Harris 25 m
12. Slight right to stay on Av. Paul Harris 0.6 km
13. Slight right to stay on Av. Paul Harris 0.1 km
14. At the roundabout, take the 2nd exit onto Estr. EN124 0.8 km
15. At the roundabout, take the 2nd exit and stay on Estr. EN124 0.5 km
16. Continue on Estr. Nacional 124/N124 Continue to follow N124 Go through 2 roundabouts 2.1 km
17. At the roundabout, take the 2nd exit onto A22 Acessos 0.3 km
18. Merge onto A22 via the ramp to Faro/A2/Lisboa 26.4 km
19. Take exit 9 toward Lisboa/Ourique 0.2 km
20. Merge onto IC1 Go through 1 roundabout 197 km
21. Continue on N10/N5 Continue to follow N10 18.4 km
22. Slight right at Av. Antero de Quental/N10 (signs for Setùbal) 1.0 km
23. Turn left at Estr. de Palmela/N10/N252 0.3 km
24. Slight right at Variante da Várzea Go through 1 roundabout 1.5 km
25. At the roundabout, take the 1st exit onto Estr. São Luís da Serra/N10 Continue to follow N10 22.9 km
26. Take the ramp onto N10 2.9 km
27. Continue on Av. Primeiro de Dezembro de 1640 0.4 km
28. Take the ramp on the left to Lisboa/Sesimbra/Almada/Setúbal 0.5 km
29. Keep left at the fork, follow signs for Sesimbra/N378 0.3 km
30. Keep left at the fork, follow signs for Lisboa/A2/Almada and merge onto A2 9.1 km
31. Continue on IP7 Toll road 4.6 km
32. Take the exit toward Praça Comércio/Belém/Alcântara 1.0 km
33. Slight right at Praça Gen. Domingos de Oliveira 0.2 km
34. Turn right at R. João de Oliveira Miguéns 0.2 km
35. Turn left at Av. 24 de Julho 0.3 km
36. Turn left at Av. 24 de Julho/N6 Continue to follow Av. 24 de Julho 2.4 km
37. Slight left at Cais do Sodré 0.2 km
38. Continue on Av. da Ribeira das Naus 0.6 km
39. Turn left at Praça do Comércio 12 m
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