Most Popular
Sail Pro
Unlimited trips, 500 travelers per trip, and the full SMS automation toolkit — built for anyone who organizes seriously.
Save 18%
$6.58/mo
$79/yr, billed annually
Unlimited active trips
500 travelers per trip
Smart itinerary ingestion
SMS polls & RSVPs
Task delegation
Proactive SMS reminders
Itinerary broadcasts
Every Pro feature, in depth
Seven tools that cut the friction between you and a flawless trip.
Sail Pro
Unlimited trips, bigger groups.
Run as many active trips as you need and host up to five hundred travelers on a single trip. Add people by phone number and keep large rosters under control from the same workspace.
- No cap on active trips (Free: 1)
- 500 travelers per trip (Free: 10)
- Bulk invite by phone number
Sail Pro
Smart itinerary creation.
Drop in a Google Doc, spreadsheet, or long group-chat paste. Sail parses the messy details into a clean, structured itinerary you can edit like any other trip.
Sail Pro
SMS polls & RSVPs.
Run votes for restaurants, activities, or dates and collect yes/no/maybe for each event — all over SMS. Travelers reply from their messaging app and tallies update live in your dashboard.
Sail Pro
Task delegation.
Assign booking confirmations, shared packing, and other to-dos to specific travelers. They get and complete tasks by SMS, and you see status in one place.
Sail Pro
Proactive SMS reminders.
Nudge travelers before key moments so departures, reservations, and meetups don't slip. Reminders go out over SMS without anyone installing an app.
Sail Pro
Itinerary broadcasts.
Push a single update — schedule change, new attachment, or day-of note — to everyone on the trip at once. When you need reliable reach across the whole group, one tap covers everyone.
Free vs Pro
Everything on Free, plus everything above.
Pro builds on Free — your existing trips and data carry over. You keep the itinerary builder, document uploads, and org tools you already use.
Ready to upgrade?
Start with Pro today. Cancel anytime, no questions asked.
