It's a Saturday in July, right in the middle of dinner service, and your phone buzzes for the fourth time in ten minutes. Different guests, same three questions. What time can we check in, where do we park, and what's the wifi password.
None of it is hard to answer, and that's the frustrating part. Each text pulls someone off the floor, breaks their focus, and by the time you've replied to one, another has landed. The questions are predictable, which is exactly why you can get ahead of them.
The fix is a single message that goes out automatically two or three days before each guest arrives, tied to their reservation, answering the things they were going to ask anyway. Set it up once and it runs quietly in the background all season.
Start with the questions you already answer ten times a week
You know these by heart. Before you write a word, jot down every day-of question you can remember fielding over the last month. The list is shorter than it feels in the moment.
For most inns and B&Bs it comes down to a handful:
- Check-in time, and what to do if they're early. Most of the friction lives here. Tell them the time, then tell them what happens if they roll in at noon.
- Parking. Where it is, how many spots, and whether the street is fine overnight.
- The wifi password. Put it right in the note so nobody has to ask at the door.
- The address and a landmark. GPS gets confused on some of these back roads, so a "turn at the white church" line saves a phone call.
- How far to the beach, and whether they need a sticker or pass. A lot of towns require one, and guests would rather know before they're standing at the gate.
- Check-out time and where to leave the key.
Tie it to your booking software so it sends itself
The whole point is that you set this up once and never think about it again. Most booking systems (the software that holds your reservations and calendar) can send a scheduled message on their own, triggered off the arrival date on each booking.
Look for a setting named something like "scheduled messages," "guest messaging," or "automated emails." You write the message once, drop in a couple of merge fields (little placeholders like the guest's first name and arrival date that fill themselves in per reservation), and set it to send a few days out. From then on, every new booking gets the note without you lifting a finger.
Two or three days before arrival is the sweet spot. Send it too early and they've forgotten it by the time they pack; too late and they've already texted you. Email is fine for most of this, though a short text message tends to actually get read, so use whichever channel your guests already reply to.
Keep it short, and keep it human
There's a temptation to cram everything into this note. Fight it. A wall of text about your cancellation policy and the history of the house is a message people skim once and forget.
Aim for something a guest can read on their phone at a red light. A warm line up top, the practical answers in a short list, and a sign-off with your name and number. That's the whole thing.
A short note also reads like a person wrote it, because a person more or less did. Guests reply to those. They'll tell you they're running late, or that it's their anniversary, and now you know something useful before they walk in.
Here's the shape of one that works:
Hi Sarah, we're looking forward to having you Thursday. Check-in is any time after 3. If you get here early, park in the lot behind the inn and come say hi, we'll stash your bags. Wifi is "HarborView," password "lighthouse2024." We're a ten minute walk to the beach, and the town lot takes cards. Any questions before then, just call. See you soon, Meg, 617-555-0100.
Add two or three honest local tips, not a brochure
This is where a pre-arrival note earns its keep. A couple of genuine tips make guests feel looked after before they've even arrived, and they quietly cut down on the "where should we eat" questions too.
Think about what a first-timer wouldn't know. The breakfast spot that isn't obvious from the main road, the fact that the beach lot fills by nine on a July Saturday so it's worth going early, or that the ice cream place stays open past Labor Day but the mini golf doesn't. Small, true, useful.
Keep them current. If the clam shack everyone loves is closed on Tuesdays once the season winds down, say so, or you'll hear about the wasted trip. Tips that were right in July go stale by October, so give them a look when the season flips.
Honesty here matters more than polish. If you're tempted to have a tool draft these tips for you, be careful. AI is good at smoothing out your wording, but it doesn't know your town, and it will happily invent a restaurant or a scenic overlook that doesn't exist. Feed it your real tips and let it tidy the sentence. Never let it make up the facts.
Worth doing this week
You don't need to redesign anything. You need one message, written once, pointed at the right trigger.
- Spend ten minutes listing the questions you actually get asked in the two days before arrival.
- Draft one short note that answers them, in your own voice, with your name and number at the bottom.
- Find the scheduled-message or automated-email setting in your booking system and set it to send two or three days before check-in.
- Add two honest local tips, and update them when the seasons turn.
- Send yourself a test reservation and read the note on your phone. If it feels long, cut it.
Do that once and your front desk gets its evenings back. If you'd rather have someone wire it into your booking system and tune the wording for you, that's the kind of quiet, unglamorous automation we set up for Massachusetts inns all the time.