For tour operators

How to answer trip questions at night with saved replies

Write your five most-asked answers once, keep them a tap away, and let your inbox send them for you after hours.

Time
One evening for Good, 20 minutes each after that
Cost
Free with tools you have
Works with
Gmail, Outlook, iPhone, or any inbox
Skill
Copy and paste, then a few settings

A trip question that lands after the last tour ends usually wants the same few answers. Is Saturday open? How many seats are left? What should I bring? Can we book a private group? You know every answer by heart, and typing them fresh at 10pm after a long day on the trail is a lot to ask of anyone.

Quick answers stand out in this trade. One practitioner write-up of a mystery-shopping test of 960 multi-day tour operators reports that 11% replied within an hour, and 26% took five or more days or never replied. The study behind it isn't published in full, so read it as a rough picture rather than a hard number.

There are three levels here. Each one is a fine place to be, and each one builds on the one before.

  1. GoodFive answers, written tonightWrite answers to your top five questions in one sitting and keep them in your phone's notes. Copy, fill in the guest and date, send.Your part: one evening, then a minute per question.Start here
  2. GreatSaved where you replyThe same five answers saved as templates in Gmail or Outlook, and as shortcuts on your iPhone for texts and DMs.Your part: about 20 minutes once.Save them in your app
  3. BestYour inbox answers after hoursAn automatic reply goes out the moment a question lands at night, with your common answers and your booking link. You follow up in the morning.Your part: about 20 minutes once, then the morning replies.Step-by-step setup

Rather we set it up for you?

Boldwright can do this one for you. We write your five answers in your voice, save them where you reply, and set up the after-hours reply, in a week or less.

Have Boldwright set it up

$297 setup, then $70 a month once you've seen it work. No contract. Cancel by text.

Step 1

Your five answers

Start from these and change the words until they sound like you. Put your details in once and they fill in. Nothing here leaves your browser.

Not sure which five? Scroll your sent mail and messages from the last month and count what people ask most. For most tour operators it's these.

Is this date open?

Answer first, link second. Most people asking about a date want a yes and a way to book.

That date is full

A full date can still turn into a booking. Offer the next dates and the waitlist together.

Private or group trip

Ask for the two things you need to quote. Price it once you know the size.

What's included and what to bring

Fill the square brackets once per trip and keep one copy for each trip.

Checking in after two days

Short and easy to ignore politely. Busy people often mean to book and forget.

Keep blanks easy to spot. When you save these, write blanks in capitals, like GUEST, TRIP and DATE. A blank left in will jump out before you send.

Good

Write answers to your top five questions tonight

One sitting tonight, and every evening after gets shorter. This works in any inbox and on any phone.

  • Write answers to your top five questions tonight. Copy the five from Step 1 into a note on your phone and rewrite each in your own words.
  • Title each note by the question, like "Date open" or "Group trip", and pin the note so it's one tap away.
  • Keep your dates and open seats next to it. A short list of trip, date, seats open and price is enough. If your booking system shows live seat counts, use that instead.
  • When a question lands, copy, fill, send. Swap in the guest, trip and date, check the seats, and send. Aim for a minute or two.

Great

Save your answers where you reply

Saved replies drop into a message in a couple of taps. Pick where most of your questions land. If they come from several places, set up email and the iPhone shortcuts both.

GmailBuilt in

Any Gmail or Google Workspace account. Templates only work in Gmail on a computer. For your phone, use the iPhone shortcuts below.

  1. On your computer, open Gmail. At the top right, click Settings, then See all settings.
  2. At the top, click Advanced. Next to Templates, click Enable, then at the bottom click Save Changes.
  3. Click Compose and paste one of your five answers. At the bottom of the compose window, click More options, then Templates, then Save draft as template, then Save as new template. Name it, like "Date open".
  4. Repeat for each answer.
  5. To use one, reply to the question, click More options, then Templates, and pick it under Insert template. Fill in the details and click Send.

Google warns a deleted template can't be recovered. Keep a copy of your wording in your notes.

Checked against Gmail help docs, November 2026.

OutlookBuilt in

A qualifying Microsoft 365 subscription. Works in new Outlook, classic Outlook and Outlook on the web. If My Templates is missing, your organization may have add-ins turned off.

  1. From the Home ribbon, select New, then Mail.
  2. From the Message tab of the ribbon, select My Templates. A task pane opens.
  3. Select +Template. In the Title field, enter a name, like "Date open". In the field below it, paste your answer.
  4. Select Save. Repeat for each answer.
  5. To use one, open My Templates from the Message tab while replying and pick it. Fill in the details and send.

My Templates holds short text with basic styling. That suits trip answers well.

Checked against Outlook help docs, November 2026.

iPhone text replacementPartly built in

Free on any iPhone. Works in Messages, Mail, Instagram and any app with a keyboard. The catch: one shortcut per answer, and you edit the blanks by hand.

  1. In the Settings app, tap General, then Keyboard, then Text Replacement.
  2. Tap the Add button.
  3. Enter your phrase and shortcut. Paste one answer as the phrase, and pick a shortcut you'd never type by accident, like ;open or ;full.
  4. Tap Save. Repeat for each answer.
  5. To use one, type the shortcut in any reply box and your full answer drops in.

Checked against iPhone text replacement help docs, November 2026.

Best

Let your inbox answer after hours

This is the version that asks the least of you at night. When a question lands after hours, your inbox sends a reply right away with your common answers and your booking link. You pick up the real conversation in the morning.

Write one after-hours reply first: a line saying you're off the trail for the night and will answer in the morning, your answers to the two questions you get most, and your booking link. Then set it up in the inbox you use.

Jump to your app

GmailBuilt in

Templates turned on (see Great) and your after-hours reply saved as a template. Gmail on a computer.

  1. In the search box at the top, click Show search options.
  2. Enter what your trip questions have in common, such as the address your website form sends from.
  3. Optional: click Search to check it finds the right emails, then click Show search options again.
  4. Click Create filter.
  5. Check the box next to Send template, then choose your after-hours reply. Click Create filter.

A Gmail filter answers at any hour, day or night. Write the reply so it reads well either way, for example "Thanks for asking. Here are quick answers, and I'll write back personally soon."

Checked against Gmail help docs, November 2026.

New OutlookBuilt in

A Microsoft 365 or Exchange account. Microsoft notes automatic replies are not supported for Gmail, Yahoo or other POP or IMAP accounts.

  1. On the View tab, select View settings.
  2. Select Accounts, then Automatic Replies.
  3. Turn the Automatic replies toggle on and paste your after-hours reply.
  4. Select Send replies only during a time period, and enter start and end times.
  5. Select Send replies only to contacts if you'd rather only people in your Contacts get it. When you're done, select Save.

Microsoft warns that replying to everyone outside your organization also answers newsletters and junk. Test it with a message from another address first.

Checked against New Outlook help docs, November 2026.

Step 2

Check it worked

  • Send each saved answer to yourself with a test name, trip and date. Read it on your phone.
  • Tap the booking link. It should open your booking page, not your homepage.
  • If you set up Best, send a question from another address after hours and check the reply arrives.
  • After two weeks, notice which answer gets the most bookings. Keep that wording.

If something's off

Common snags

I don't see Templates in Gmail

Turn them on first: Settings, See all settings, Advanced, Enable next to Templates, then Save Changes. They only work in Gmail on a computer.

My Templates is missing in Outlook

Your organization may have add-ins turned off. Ask whoever runs your Microsoft account.

Won't saved answers sound robotic?

Not if they started as your own words. Add one personal line when the guest mentions something, like a birthday or a first trip.

I sent one with a blank still in it

It happens. Write blanks in capitals like GUEST and DATE, and read the first line before you send.

Want trip questions answered while you sleep?

We're a small, new shop in Denver. We'll write your answers in your voice, save them where you reply, and set up the after-hours reply with your booking link. You read the morning replies and get back to guiding.

Talk to Boldwright

Starter package: set up in a week or less. $297 setup, then $70 a month once you've seen it work. No contract. Cancel by text.