6 browser tabs, 3 evenings, and Connie still didn't have an itinerary

Today's Tip: Building a Custom Trip Itinerary

The best travel agent I've ever found charges nothing… has no office… and put together a five-day Savannah itinerary in 90 seconds that would have taken a full weekend with guidebooks and Google.

Let me explain…

Connie Matsuda is a 66-year-old retired pharmacist in Portland, Oregon. She and her husband Ray have been planning a 40th anniversary trip to Savannah, Georgia for over a year. Classic Connie… she had a stack of guidebooks on the kitchen counter, a folder of bookmarked websites, and six browser tabs open every evening after dinner.

After three nights of comparing hotels, reading restaurant reviews, and cross-referencing walking tour schedules with Ray's knee problems… she still didn't have a plan. She had research. Piles of it. But no actual itinerary.

Then her daughter showed her something. She opened Gemini, typed in everything about the trip — dates, budget, what they like to do, Ray's bad knee, how fast they like to move — and hit enter.

Ninety seconds later, Connie had a complete day-by-day plan. Breakfast spots near their hotel. Walking tours scheduled in the morning when it's cooler. A riverboat dinner cruise on their anniversary night. Rest breaks built into every afternoon. Two restaurant options for each evening — one upscale, one casual — so they could decide based on how they felt that day.

Connie stared at the screen for a full minute. "It's not that it was perfect," she told me. "It's that it gave me a finished plan to react to… instead of a blank page to fill."

That's the shift. And it works for any trip… whether you're visiting grandkids in Denver, spending a long weekend at the coast, or finally taking that bucket-list vacation you've been putting off.

Here's the exact prompt that makes it happen…

When Connie ran this prompt with her Savannah details, Gemini came back with something incredible. It put the Owens-Thomas House on Day 1 — because it has elevator access for Ray's knee. It scheduled Forsyth Park for the morning on Day 2, before the afternoon heat. And for their anniversary on November 10th, it suggested a sunset riverboat dinner on the Savannah River.

Was every detail perfect? No. One restaurant it suggested had closed six months ago. But that's a two-minute website check to fix… not a three-evening research project. She swapped in a different spot and moved on.

And that's the key insight… you're not asking AI to book your trip. You're asking it to build the first draft. You still make every decision. You still call the restaurant. You still check the hours. But you start from a complete, structured plan instead of a blank page and a pile of bookmarks.

Now, I know what you're thinking… "But how can AI know what I'll actually enjoy? It's never been to Savannah. It doesn't know me."

And you're right — it doesn't know you personally. But here's what it CAN do… it can organize hundreds of options into a structured day-by-day plan in 90 seconds, filtered by your budget, your mobility needs, and your interests. That's work that used to take you an entire weekend. And if a suggestion doesn't sound right? You swap it out. You're editing a finished document… not writing one from scratch. That's a huge difference.

Here's what I'd do today. Open Gemini at gemini.google.com — or Claude or Grok, they all handle this well — take that prompt above, and swap in YOUR trip details. Your destination. Your dates. Your budget. Your knees, your tastes, your pace.

Give it 90 seconds. Then read what comes back and start editing. You'll have a better itinerary in five minutes than most people build in five evenings.

★ Quick Wins

Skill Builder: Teaching AI Your Preferences

Here's something most people never think to do with AI… tell it about yourself. Not buried in a question as an afterthought. But as a dedicated opening message that shapes every answer it gives you.

Think about it this way. If you walked into a travel agency and the agent knew nothing about you — your budget, your pace, your bad back, your food allergies — every recommendation would be generic. "Here are the top 10 things to do in Savannah." Not very helpful. But if that agent knew you prefer quiet mornings, seafood over steak, and can't walk more than 30 minutes without resting… suddenly every suggestion fits your life.

AI works the same way. The more you tell it about yourself up front, the less generic the answers become. And here's the beautiful part… you only have to write your preferences once. Then you save them and paste them at the start of any new conversation.

I call this your "About Me" prompt. It's a short paragraph — maybe 8 to 10 sentences — that covers who you are, what you care about, and how you like answers delivered. You paste it at the top of a new chat, then type your question below it. The AI uses your preferences to shape everything it says back to you.

Here's an example you can customize and save…

The trick is to write this once and reuse it everywhere. Save it in your phone's Notes app, in a Google Doc, or even on an index card you keep next to your computer. Every AI conversation you start with your "About Me" prompt will be dramatically more useful than one that starts cold.

You'll be surprised how much better the answers get when the AI knows who it's talking to. It's the difference between a stranger guessing what you want… and an assistant who already knows.