Sunday Video: How I Use AI to Plan Every Trip (It Changed Everything About How I Travel)
👉 Sunday Mini Lesson Video

Watch the full walkthrough — including how I use these prompts for trips with my husband and the solo trips I’ve taken on my own.

This week’s topic is one I’ve genuinely been looking forward to building.

I plan trips for my husband and me — up North, longer journeys, wherever we decide to go. I’ve also traveled on my own at different points. And in both configurations, the planning used to carry a specific kind of weight that I don’t think gets talked about enough.

It wasn’t that I didn’t know how to plan a trip. It’s that the research never quite felt complete. The logistics required assembling information from a dozen different sources that never fully agreed with each other. And the what-if thinking — what if something goes wrong, what if the itinerary is too ambitious, what if I’ve missed something important — had a way of turning an exciting idea into an overwhelming project before a single booking was made.

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What changed

AI didn’t make me a better traveler. It made the planning feel proportionate to the trip — which is all I ever wanted.

The destination research that used to take an afternoon now takes twenty minutes and gives me a picture of a place that’s actually tailored to how we travel. The itinerary that used to be built from a combination of travel guides and guesswork is now built around our actual pace, our actual interests, and our actual constraints. The logistics layer that I always found most draining is now one conversation.

And the what-if thinking that used to keep trips from being planned? It’s now a prompt. I think through the contingencies before I leave so that if something does go wrong, I already know my first move.

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The 4 prompts from this week’s Sunday video

All four are ready to use today. Fill in the brackets with your specific situation and paste into any AI tool.

📌 Prompt 1 — Destination Research

“I’m thinking about visiting [destination — city, region, or country] and I want to understand whether it’s the right fit for our trip. Here’s who we are as travelers: [describe your travel style, pace, interests, physical considerations, budget range, time of year]. Please give me: (1) An honest picture of what this destination is like for travelers like us — what we’ll love, what might not work, and what most travel guides don’t mention, (2) The best time of year to go and why, (3) The neighborhoods or areas that would suit us best and why, (4) Three things to do that match our interests specifically, (5) One thing most visitors do that we should probably skip. Be specific and honest rather than promotional.”

Use for: any destination you’re considering — gets you a tailored picture, not a generic travel blog

📌 Prompt 2 — Itinerary Builder

“I’m planning a [number] day trip to [destination] and I need a realistic itinerary that fits how we actually travel. Here’s what you need to know about us: [describe your travel style, pace, physical considerations, interests, must-sees, and things to avoid]. Here are our practical constraints: [arrival and departure times, accommodation location, transportation available, budget range]. Please build a day-by-day itinerary that: accounts for realistic travel times between locations, builds in rest time appropriate for our pace, groups nearby things together so we’re not backtracking, and leaves [specific time — afternoons / mornings / one full day] unscheduled. Flag anything that needs advance booking.”

Use for: building an itinerary around how you actually travel — not how a travel guide assumes you travel

📌 Prompt 3 — Practical Logistics

“I’m traveling to [destination] on [dates] and I need help with the practical logistics layer of this trip. Please help me with: (1) Getting from [arrival point] to [accommodation] — the best options for travelers like us [describe who you are], (2) Getting around once we’re there — what transportation works best for our pace and itinerary, (3) What I need to know before I arrive that most people find out the hard way — local customs, tipping, neighborhoods to be aware of, anything that will make the trip smoother, (4) A packing list specific to this destination, this time of year, and our activities — not a generic list, (5) Any advance bookings or reservations I should make now before they sell out.”

Use for: the logistics layer — getting there, getting around, and what to know before you arrive

📌 Prompt 4 — What-If Safety Net

“I want to build a simple what-if safety net for my trip to [destination] so I’m prepared for the most likely disruptions without over-planning. Please help me: (1) Identify the three most common things that go wrong on trips like this — flight disruptions, health issues, lost items, booking problems — and give me the first step for each, (2) Give me the key phone numbers and contacts I should have saved before I leave — local emergency services, nearest hospital or clinic, my accommodation, my airline, (3) Tell me what travel insurance typically covers for this type of trip and what it doesn’t, (4) Create a one-page emergency reference document I could share with someone at home so they know how to reach me and what to do if they can’t, (5) Tell me the three most important things to photograph or document before I leave home.”

Use for: contingency planning — traveling with a what-if plan is a completely different experience

🎬 Watch the full Sunday video for the complete walkthrough of all four prompts in action.

👉 Sunday Mini Lesson Video

Now I want to hear from you: Where is the trip on your list? A destination, a region, even just a direction. Hit reply and tell me — your answer might become the example in Wednesday’s post. 🐾

— Debbie
AI Puppy Playbook · aipuppyplaybook.com

The trips I would have planned differently 🐾