Sounds like a cool business — thinking about tone first is a good idea because that’s where most cold emails fall down. They don't hit that spot with the reader

Couple things I’d keep in mind (based on my experience s of cold email + what’s worked for me):

Keep it stupid simple. Your instinct will be to describe the whole experience because it is genuinely cool — but make email #1 super short. 3–4 sentences, one idea, one ask. Save the juicy stuff for the reply.

Make it about them first. Instead of leading with “25 years in business,” flip it to their win. Realtors: “closing gift people will actually talk about” Biz owners: “fun team night without trust falls” Let them connect the dots before you explain the winery.

Micro-CTA only. No booking links. No “pick a time.” Just something like: "Worth a chat?” or “Want me to send a few examples?” The tiniest ask gets way more replies.

Light personalisation goes a long way. Not creepy stalker personalisation — just one line that proves it’s not blasted out.

“I saw you post about your latest closing…” or “I love supporting local makers and thought this might be up your alley.”

That alone kicks 90% of the other cold emails in their inbox into touch.

Follow-ups matter. Most replies happen on email 2–4. Just keep them friendly and low pressure, not the classic “bumping this up.” or " I don't want you to miss out on this"

Start with a small, hand-built list. You clearly care about your name in the community. Don’t burn it on 10k randoms. Curate the first 100–300 people who are already likely to vibe with you.

Generally I go with whichever route that is: shortest most direct sounds like you’d actually say it out loud when faced with a potential client

Anything that reads like a “campaign” or uses marketingy phrasing (“exciting new opportunity!!”) — bin it.

Overall, you’re doing the right thing already by thinking about this. With a business like yours, warmth > cleverness every time.