I think you are thinking about this the wrong way. People become caffeine tolerant quickly, but tolerance goes away pretty quickly too. You would get more benefit out of the opposite approach - spending most of your time without caffeine, but drinking a cup of coffee rarely, when you really need it. You would effectively be caffeine naive most of the time, with brief breaks for caffeine use, and this never develop much of a tolerance. If it's been a long time since that first cup of coffee that you don't remember it, trust me, the effects of caffeine on a caffeine-naive brain are incredible.

I know I once read a study that says you can get back to caffeine naive in two weeks if you go cold turkey, but I can't find anything on it again for the life of me. I do remember distinctly that going cold turkey is a bad plan, as the withdrawal effects are pretty unpleasant - slowly lowering your dose is better.

On a more practical level, it is certainly possible to have relatively little caffeine, such that you aren't noticeably impaired on zero caffeine, while still having some caffeine. The average coffee drinker is far beyond this point. I would try to lower your daily dose over the course of a month or so until you are consuming less than a cup of coffee a day - ideally, a lot less, like no cups of coffee. Try substituting tea (herbal or otherwise) if you need something hot to drink to help kill the craving - herbal tea has no caffeine, black tea has about 1/4 of the caffeine per cup, and if you add cream and sugar the taste will be familiar.

EDIT: VincentYu's comment above is interesting in light of this. I am not going to perform my own meta analysis on this, but there are a great deal of studies that find that caffeine tolerance and caffeine withdrawal are real things - a quick Google Scholar search for "caffeine tolerance" will find them.

I am now very interested in a large study on this without the possible conflict of interest. Also, I find it odd that they choose to not include studies before 1992.

where when you're not on caffeine you're below baseline and caffeine just brings you back to normal

This is a hypothesized explanation for the acute performance-enhancing effects of caffeine that fits well with the Algernon argument, but it is not a conclusive result of the literature. For instance, the following recent review disputes that.

Einöther SJL, Giesbrecht T (2013). Caffeine as an attention enhancer: reviewing existing assumptions. Psychopharmacology, 225:251–74.

Abstract (emphasis mine):

Rationale: Despite the large number of studies on the behavioural effects of caffeine, an unequivocal conclusion had not been reached. In this review, we seek to disentangle a number of questions.

Objective: Whereas there is a general consensus that caffeine can improve performance on simple tasks, it is not clear whether complex tasks are also affected, or if caffeine affects performance of the three attention networks (alerting, orienting and executive control). Other questions being raised in this review are whether effects are more pronounced for higher levels of caffeine, are influenced by habitual caffeine use and whether there [sic] effects are due to withdrawal reversal.

Method: Literature review of double-blind placebo controlled studies that assessed acute effects of caffeine on attention tasks in healthy adult volunteers.

Results: Caffeine improves performance on simple and complex attention tasks, and affects the alerting, and executive control networks. Furthermore, there is inconclusive evidence on dose-related performance effects of caffeine, or the influence of habitual caffeine consumption on the performance effects of caffeine. Finally, caffeine’s effects cannot be attributed to withdrawal reversal.

Conclusions: Evidence shows that caffeine has clear beneficial effects on attention, and that the effects are even more widespread than previously assumed.

The authors' conclusions:

• Caffeine improves performance on both simple and complex attention tasks.
• Caffeine improves alerting, executive control and potentially also orienting.
• There is inconclusive evidence on dose-related performance effects of caffeine.
• There is inconclusive evidence on the influence of habitual caffeine consumption on the performance effects of caffeine.
• Caffeine’s effects cannot be attributed to withdrawal reversal.

Note the following conflict of interest:

The authors are employees of Unilever, which markets tea and tea-based beverages.