Hobbits in Valinor?

[Sardy]

This evening I started reading The Hobbit to my 5-year old son. His first reading, my own beyond count.

Early in An Unexpected Party, I came upon a passage that made me pause. While certainly, The Hobbit is a more whimsical tale, written by a more lighthearted Tolkien and set in a not fully realized Middle-earth, nevertheless, it is part of the cannon. If nothing else, it's inconsistencies with later work make for wonderful discussion and speculation. That said, here's the passage that is the subject of this thread:

"Gandalf, Gandalf! Good gracious me! Not the wandering wizard that gave Old Took a pair of magic diamond studs that fastened themselves and never came undone till ordered? Not the fellow who used to tell such wonderful tales at parties, about dragons and goblins and giants and the rescue of princesses and the unexpected luck of widows' sons? Not the man that used to make such particularly excellent fireworks! ... Not the Gandalf who was responsible for so many quiet lads and lasses going off into the Blue for mad adventures? Anything from climbing trees to visiting elves---or sailing ships, sailing to other shores!

Hobbits sailing ships to other shores? So many young Hobbit boys and girls off into the Blue?

When and why would Gandalf have had reason to send any Hobbits sailing to distant shores? To Valinor?