A simple rhythm covers almost every situation. Five points of contact, each with a job.
1. When the booking is confirmed
Ideally automatic. Confirm what they have booked, welcome them, and give the practical basics. This is where most repeat questions get prevented.
2. Two or three days before arrival
The one most hosts skip, and the one guests appreciate most. Send directions with a landmark, check-in time, and your number for the day.
By this point they have flights booked and are thinking about logistics. A message now lands exactly when it is useful.
3. Arrival day
A short note that you are ready for them, or confirming where to meet. If anything has changed, this is the moment to say so, not when they are standing outside.
4. Once during the stay
A brief check that everything is fine, on the first morning for a longer stay. This is the highest-value message you send.
A guest with a small problem will usually not raise it unprompted. They will put up with it and mention it in the review. Asking gives you the chance to fix something while it is still fixable, and a fixed problem often produces a better review than no problem at all.
Once is enough. Daily messages feel like being watched.
5. After checkout
Thank them, and mention that a review helps. Reviews can be left within 30 days of completion and appear within 72 hours.
For activities and rentals
Compress the same pattern: confirmation, a reminder the day before with meeting point and what to bring, and a thank you afterwards. For rentals, add a note about return time and condition.
What not to do
Do not message constantly, do not push for a positive review in exchange for anything, and do not use messaging to move a booking off the platform.