Trippy by Often · AI travel hacking

Trippy

Find hacks to get your dream hotels at steal rates: Trippy checked thousands of date and room combinations before you booked, then kept watching the price after.

Trippy in use: the pre-booking cheatsheet (recreated from public posts)

gotrippy.ai: pick a place, a month and how many nights

Deals people found by shifting their dates

Agentic rebooking: it tracks the price after you book and rebooks when it drops

The AI cheatsheet: flexible dates, the cheapest combination

How it worked

Before you book: it searched thousands of hotel, date and room combinations and showed the cheapest way to do the same trip.
After you book: agentic rebooking watched the price and rebooked you when it dropped, up to the free-cancellation date.
Planning: an AI trip builder for the whole itinerary.

Where it came from

Trippy was the travel-hacking AI from Often, a travel startup in Mumbai.

What I learned

In travel, whoever controls the supply wins. And people barely use a travel app, so it never becomes a habit, and word of mouth has to spread extremely fast.

~1,200trips powered
₹3.2 crsaved by travellers, per gotrippy.ai
up to 70%saved after booking by auto-rebook, per gotrippy.ai

Visit gotrippy.ai ↗Often, the company Back to the desktop

Screenshots are of the live gotrippy.ai (Nov 2026). The site’s own hero video is a stock clip, so it isn’t shown here.