What If Your Next Holiday Planned Itself Around You?

Published on: 08/24/2026

By Laksh Sharma & Tanishk Shively

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What If Your Next Holiday Planned Itself Around You?

Travel is still one of the internet’s most fragmented consumer journeys: π’…π’Šπ’”π’„π’π’—π’†π’“π’š 𝒂𝒄𝒓𝒐𝒔𝒔 π’”π’π’„π’Šπ’‚π’ 𝒇𝒆𝒆𝒅𝒔, π’ƒπ’π’π’Œπ’Šπ’π’ˆπ’” 𝒂𝒄𝒓𝒐𝒔𝒔 π’‘π’π’‚π’•π’‡π’π’“π’Žπ’”, 𝒆𝒏𝒅𝒍𝒆𝒔𝒔 π’„π’π’Žπ’‘π’‚π’“π’Šπ’”π’π’, 𝒂𝒏𝒅 𝒔𝒖𝒑𝒑𝒐𝒓𝒕 𝒕𝒉𝒂𝒕 𝒐𝒇𝒕𝒆𝒏 π’…π’Šπ’”π’‚π’‘π’‘π’†π’‚π’“π’” 𝒐𝒏𝒄𝒆 𝒕𝒉𝒆 π’•π’“π’Šπ’‘ π’ƒπ’†π’ˆπ’Šπ’π’”.

AI is starting to change that.

In this newsletter, we look at:
✈️ How incumbents like Booking.com, Expedia, MakeMyTrip and ixigo are embedding AI into existing travel journeys.

🧭 The new AI-native models emerging across concierges, vertical specialists, B2B operating layers and agentic travel.

🧠 Why context, trust and execution could become the real differentiators in travel.

🏝️ How our portfolio company 30 Sundays is building one version of this future.

The next battle in travel may come down to who understands the traveller best, and who can turn that understanding into action.

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