What is the best anonymous web surfing program for less than $100.00 a
year? I'm looking for something that prevents ISPs and administrators
from seeing where I'm at currently and where I've been recently. The
program doesn't have to have all the bells and whistles but it does
need to do these 2 things really well!

Hi! Thanks for the question.

One way to answer the question is to look at product reviews of
anonymous web surfing tools from professional publications.

The constant products on the list are 

Anonymizer - $29.95 to $99.95

and 

Zero Knowledge from Freedom - $59.95
http://www.zeroknowledge.com/
http://www.zeroknowledge.com/privacy/default.asp

The links to the different reviews are presented below.

"Cat's Clicks: Surf and Email Anonymously"
http://www.techtv.com/callforhelp/catsclicks/story/0,24330,2211,00.html

"Anonymous Browsing"
http://www.pcmag.com/print_article/0,3048,a=12633,00.asp

"Privacy Watch"
http://www.pcworld.com/features/article/0,aid,17819,00.asp

"Surf the Web by Proxy"
http://webveil.com/matrix.html

"Carnivore: How Much Bite Behind the Bark?"
http://www.computerworld.com/managementtopics/management/outsourcing/story/0,10801,48051,00.html

Search terms used:   
"anonymous web search" reviews
  
I hope these links would help you in your research. Before rating this
answer, please ask for a clarification if you have a question or if
you would need further information.
  
Thanks for visiting us.  
  
Regards,  
Easterangel-ga  
Google Answers Researcher

Hi,

I don't know if it's the best or not, but give a try to anonymizer at
http://www.anonymizer.com/

Regards
Bio

I have subscribed to Anonymizer, in the past, but currently I am a
subscriber to SafeProxy Gold, and I am very satisfied. Unlike
Anonymizer, the service is capable of handling https sites, and it can
(at the user's option) permit Javascript to run (this, of course,
lessens security, but there are times when it is desirable.) The
handling of cookies (also at the user's option) is very well done, and
the cookies that are stored on the remote server are easy to view.
Unlike Anonymizer, which has fairly frequent outages and slowdowns,
this service is very reliable and very fast.

SafeProxy Gold is a terrific bargain at $29.95 per year.

http://www.safeproxy.org/gold.html

SafeProxy also has a free anonymizing proxy with some pop-up ads, and
no support for https sites:

http://www.safeproxy.org/use.html

Don't know if it's of any use to you but... to send email anonymously
try http://anony.co.uk or http://www.manicmail.net.