Overview
SquadTrip can automatically post messages in your Group Chat at key moments during your trip planning journey. Milestones celebrate progress and keep travelers engaged, while welcome messages greet new travelers when they join the chat.
What Are Milestones?
Milestones are automated messages posted to your Group Chat when your trip reaches specific moments. They help build excitement and keep the group engaged as the trip date approaches.
Available Milestone Triggers
Milestone | When It Fires | Example Use |
First Booking | Meant to fire when the first traveler books -- this trigger is not currently posting automatically, so post it yourself when your first booking lands | "We have our first traveler! The adventure begins!" |
60 Days Out | 60 days before the trip start date -- not currently posting automatically (see the note below the table) | "Just 2 months to go! Time to start packing lists" |
30 Days Out | 30 days before the trip start date -- not currently posting automatically (see the note below the table) | "One month away! Make sure your passport is current" |
7 Days Out | 7 days before the trip start date -- not currently posting automatically (see the note below the table) | "One week! Final reminders and packing tips..." |
Day After Trip | The day after the trip ends -- not currently posting automatically (see the note below the table) | "What an amazing trip! Share your favorite memories" |
Setting Up Milestones
Open the trip and click Edit Trip
Open Group Chat (Group Chat must be enabled)
Expand the Milestones panel
For each milestone trigger, you can:
Enable or disable the milestone
Customize the message text that gets posted
Save your changes
SquadTrip is designed to post your custom message (or a built-in default if you left the box blank) to the Group Chat at about 9 AM Eastern when the milestone date arrives. Note: the timed milestones are not currently posting automatically -- our team is looking into it. Until then, post the message in the chat yourself on the day (you can copy your saved text from this page).
Welcome Messages
Welcome messages greet travelers the first time they open the Group Chat -- as a "Welcome from [organizer]" banner with your photo -- and are also emailed to new bookers about three hours after they book.
How It Works
A new traveler books your trip and joins the Group Chat
SquadTrip shows your welcome message as a banner at the top of the chat until the traveler dismisses it, and emails it about three hours after booking
The banner shows your name and photo with the greeting you've written (a default greeting is used if you leave it blank)
Setting Up Welcome Messages
Open the trip, click Edit Trip, then Group Chat
Find the welcome message box under the Group Chat toggle (there is no separate on/off switch -- the greeting shows whenever Group Chat is enabled)
Write your custom greeting — something warm and informative works best
Save your changes
Welcome Message Tips
Include practical info: "Welcome! Check the pinned messages for our trip itinerary"
Keep it brief but friendly
Mention any important group rules or etiquette
Point new travelers to key resources (FAQ, itinerary, packing list)
Best Practices
Don't over-message — the 5 milestone triggers are spaced out intentionally to avoid spam
Make milestones actionable — instead of just "30 days away!", add a call to action like "Make sure your travel insurance is sorted"
Use the Day After Trip milestone to collect feedback, share photo albums, or promote your next trip
Welcome messages set the tone — a warm, organized first impression makes travelers feel confident about the trip
Example Milestone Messages
First Booking:
"Our first traveler just signed up! The countdown to paradise begins. Who's next?"
30 Days Out:
"30 days until takeoff! Quick checklist: passport valid? Travel insurance? Sunscreen packed? Drop any questions below!"
Day After Trip:
"What. A. Trip. Drop your favorite photos and memories below! And if you loved it, stay tuned for our next adventure..."
Troubleshooting
Problem | Solution |
Milestone message did not post on the expected date | Milestone messages (First Booking and the timed ones) are not currently posting automatically, so post the message in the chat yourself on the day. Group Chat must also be enabled and shown on the trip page, and the milestone toggle on, for a milestone to be eligible. |
Welcome message not appearing for new travelers | Confirm Group Chat is enabled for the trip. The banner appears the first time the traveler opens the chat, and the welcome email goes out about three hours after booking (skipped if they have already seen the banner). |
Milestone message posted with default text instead of my custom message | Make sure you clicked Save Changes after editing. Open Edit Trip → Group Chat, re-enter your custom text, and click Save Changes. The next milestone will use the updated message. |
I want to change a milestone message after it already posted | Posted messages cannot be edited retroactively. Update your milestone text in settings so future triggers use the new wording. You can always post a manual follow-up message in the chat. |
Frequently Asked Questions
Q: Can I add custom milestone triggers beyond the five default options? A: No. SquadTrip currently supports five milestone triggers: First Booking, 60 Days Out, 30 Days Out, 7 Days Out, and Day After Trip. These are timed to key moments in the trip planning cycle and cannot be customized to different dates.
Q: Do milestone messages appear as coming from me or from SquadTrip? A: Milestone messages are posted under your organizer account but styled as automated system messages in the Group Chat. They are visually distinct from regular user messages so travelers know they are automated announcements rather than personal messages from the organizer.
Q: Will a welcome message fire if I add a traveler manually instead of them booking online? A: Yes. The welcome banner appears the first time any chat member opens the Group Chat, regardless of how they were added, and the welcome email is sent about three hours after their booking is recorded.
Q: Can I disable milestones for one trip but keep them on for another? A: Yes. Milestone and welcome message settings are configured per trip on the Edit Trip → Group Chat page. You can enable milestones on your group vacation trip while keeping them disabled on a smaller private trip, or vice versa.
Related Articles
Contact: [email protected]