Found an old list I put up on another forum of some of the jump maps I used to play and on which I learnt to rocket jump on. Some are aimed at demo for those who like that sort of thing.
Also this is a pretty good guide for a solly:
http://www.youtube.com/watch?v=bkqrRY4SZzYThere is a bit of info on the standard etc of each to get a better idea of what to expect - some of these may now be hard to find but in general they are available on gamebanana.com
1. jump_adventure A very good jump map with a progressing difficulty from novice to expert.
2. rj_rocketeer Basic rocket-jumps and a good start for beginners.
3. jump_rush An rj map for beginners.
4. jump_impact An rj map with a progressing difficulty from easy to moderate.
4.5. jump_impact_beta2 Same as jump_impact, but with harder jumps.
5. jump_skip An entertaining and not too hard map to practice speed (skip) jumping.
6. jump_propel_fixed_v2 A good map with moderate difficulty. Newer version is now available with all jumps fixed and passable.
7. rj_rocketeer_advanced Moderate to expert rocket-jumps.
8. jump_tholos Moderate to expert difficulty.
9. jump_pagoda Map for expert rocketjumpers.
10. jump_bob_fixed It?s a demo map, but can be done with soldier.
11. jump_dystopia12. jump_yucca A map for expert soldiers.
13. jump_revenge A map for Demoman, but the Beginner Course and some of the jumps on Expert Course can be done by Soldier. Beginner Course is actually pretty good for new soldiers.
14. jump_hobo A fun map. Can be done both by Demo and Soldier.
15. jump_noob_a1a A very challenging map both for Demo and Soldier. Only one jump is impossible for Soldier.
16. jump_muffin_b3 A demo/soldier map. Jumps on expert course take some practice to beat.
17. jump_housebeta Another demo/soldier map. The map focuses mainly on pogo skills.
18. jump_lite_a0 A very good map with easy to moderate jumps.
19. jump_hobo2