Hello: We will be a group of 6 friends, in our 60's and very active, traveling to Portugal for 6 weeks in October. Our trip will include Porto, wine areas, Lisbon, down to Cabo de sao Vicente, and interesting points in between. We will mostly be traveling by trains or buses. Except if we need to hire a driver or a guide to take us inland if we necessary. Can anyone recommend a reasonable priced B&B or Hotel in or around Lisbon and Porto close to transportation, that would accommodate our group? Also any recommendations on guides that could take our group to wine areas or day trips when necessary. Thank you for any and all recommendations.
Hotels look at booking.com
This website will give you some ideas of who to contact for wine tours in and around Oporto.
http://www.portoturismo.pt/
and on LP here is another guide to information you are seeking: http://www.lonelyplanet.com/portugal/the-north/porto/things-to-do/top-things-to-do-in-porto

For scenery you can do a day trip to Sintra (by commuter train), then by Scotturb bus 403 (http://www.scotturb.com/Default.aspx?tabid=153&language=pt-PT&id=403) to Cabo da Roca, walk near Cabo da Roca (there are several longer and shorter hikes along the cliffs and between villages), continue by bus 403 to Cascais, then either walk along the seaside promenade to Estoril and take a commuter train to Lisbon from there or just take the train from Cascais.
Another option is Sesimbra, an hour by TST bus 207 (http://www.tsuldotejo.pt/ver_horario.php?fx=207_Ida_20130601_20301231_lineScheds.svg.png) from either Praca Espanha or Alcantara in Lisbon. In Sesimbra you can relax on the beach, walk up the castle or walk along the coast westwards. If you are adventurous, it is possible to walk along small paths up to Cabo Espichel, 14 kms to the west. From Cabo Espichel or nearby Azoia you can catch a bus back to Sesimbra.
In my opinion it doesn't make much sense to go to Porto if you have just 5 days in Lisbon. Plenty to see in Lisbon and around and Porto would need at least 2 days to do it justice.
Not so far from Porto, you can also find winery, the Vinho Verde wine (green wine), on Minho Region, northen Portugal. Have a nice trip in Portugal, enjoy it.

There is so much to explore between Porto and Lisbon. In my opinion, one of the best regions would be the Silvercoast, where you'll find Óbidos, Peniche, Caldas da Rainha, Alcobaça, Rio Maior and it's Salinas!
It's a must see, if you wish to have accommodation in the region look for West Holidays.

Hi i´m from portugal and i live in Lousã, i recomend you to visit sintra it´s wonderfull!!! To travel in portugal i think train is cheaper than bus. There are many beautifull places to visit in Portugal in my area for example you can visit the old stone villages and do one of the many trails between the villages.
http://www.youtube.com/watch?v=GlBgrkRjGjE Lousã
http://www.youtube.com/watch?v=Q_qaQICXCW8 Sintra
http://www.youtube.com/watch?v=OecMdZubGjk Porto