Well MJay, I recommend that they be played in this order:
Classic, 2, Legends, Caravans, Odyssey, Unlikely Heroes.

Each game is unique in its own way.  For example:
-Classic is 90% trading, so makes gameplay quite relaxing.
-2 takes place in the Carribean, and relies on mostly battle-oriented missions.
-Legends is based on Arabian Nights, and draws you into a fanciful world of wonder, intrigue, and mystery.  This game has the best story line, I believe.
-Caravans takes you onto the historic Silk Road, and uses camels instead of ships.  I think this own has the most realistic gameplay, from an historic stand point.
-Unlikely Heroes is merely Legends with differen characters, goods, and story.  But don't let that fool you, it's still lots of fun.  (It's last on the list only because the game is so close to Legends that I don't want you to become bored with the style of gameplay too quickly).

I hope this helps.  Enjoy!

Totally agree with Matthias720. These are some fun games. Unlikely Heros was the hardest to complete I kept getting blown apart. But take your time and build up the flying fleet and have lots of cannons and spells. Loads of fun. Love Ivory.

So, I've never played these.  Should I jump into Classic, or would Legends be better?  Not even sure I'll like it...how different is the online play?

I don't like downloading the demos... I hate having extra stuff on my computer.  If I download the demo, it's because I'm going to buy the game.  That's why I was hoping the web version would give me enough of a taste of the game to see if I wanted to buy it.

Thanks for the answer tho.  I'll probably check the web version out.