When to reach out to vendors?

If you need to do tastings or viewings or meetings, I'd schedule them all at once while you are out there and just explain you need to do them early. We plan on meeting with...

Florist: 3 months out

Hair & Makeup Trial: 1 month out

DJ: Call 2 months out & send them our list of songs

Caterer: Already met with, will confirm menu 1 month out and final head count 1 week out

Linen & China Rental: Go to showroom 4 months out & pick rentals, then let caterer know

Videographer: Meeting with 4 months out

Photographer: Know her pretty well, don't have to meet with her. I'll email her about a month out to let her know some information about the day of.

Baker: Doing tastings 7 months out, after that won't contact until 1 month out to confirm delivery

A month out, I'm going to email all vendors with a day of schedule & our coordinators contact information.

With 5.5 months you have plenty of time. We kept in touch with our DJ and our photographer regularly as we had questions, but with everyone else - florist, bakery, etc. - we honestly didn't even talk to them after signing our contracts until about 2-3 weeks ahead of time. If they had questions, they reached out to us.

If you're already planning to be in the area at a certain time, it's never a bad idea to drop them a note to say "hey, we will be in there area - would there be any reason for us to stop by?" but I wouldn't worry too much about it at this point. Just reach out to them when you have questions, and they will do the same for you. Once it gets down to about a month, reach out again and ask about any remaining balances, deadlines, etc.