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Plan a trip

Your assistant drafts a day by day plan and a packing list from where you are going and what you like.

Suggested tools

You can set these up yourself. Get the app, follow the steps, then copy the prompt.

• TripIt

  Free. TripIt Pro is optional at $49 per year.

  An app that turns your flight and hotel confirmation emails into one trip plan.

  Download for iPhoneDownload for AndroidOpen the website

  1. Make a free TripIt account with your email.
  2. Forward each confirmation email to plans@tripit.com. TripIt builds the trip.
  3. Open the trip, tap the share icon, and send it by text to your assistant. A screenshot also works.
  4. Ask your assistant to fit the day by day plan to those times.

  Copy this prompt and give it to your assistant

  • I just got TripIt and I want you to plan my trip around my bookings. Walk me through it one step at a time and wait for me after each step: I forward each confirmation email to plans@tripit.com, open the trip, tap the share icon and send it here, or send a screenshot. Then fit the day by day plan to those times and tell me what I still need to book.

    Copy

  Your assistant does not book, pay or change a reservation, and it does not get flight delay alerts.

• Google Maps saved lists

  Free

  Save the places you want to visit in one list on the map.

  Download for iPhoneDownload for AndroidOpen the website

  1. Ask your assistant for the plan, then search each place in Google Maps.
  2. Tap Save and put the place in a new list for the trip.
  3. To show your assistant the list, tap You, tap More next to the list, then Share list.
  4. Text the link to your assistant. If it cannot open the link, send a screenshot of the list.

  Copy this prompt and give it to your assistant

  • I want to save the places for my trip in Google Maps and plan the days with you. Walk me through it one step at a time and wait for me after each step: I save each place to a new list, tap You, More next to the list, Share list, and paste the link here. If you cannot open it, I send a screenshot. Then put the places in an order that saves driving, by day, and tell me which ones to check for hours or tickets.

    Copy

  Your assistant cannot add places to your Google Maps. Hours and prices it gives can be out of date.

What to text

• Help me plan a 3 day trip to San Antonio with 2 kids. We like food and easy walks. Keep the cost low.

  Copy

• Give me a top 3 for each morning and each afternoon.

  Copy

• Make a packing list for 3 days in hot weather with kids.

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• We land at 2 in the afternoon on Friday and leave Sunday at 6. Fit the plan to that.

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• What should I check or book before we go?

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Steps

1. Text where, how many days, who is going, and what you like.
2. Tell it your limits: money, walking, nap times, when you arrive and leave.
3. Ask for a plan day by day. Ask it to change what does not fit.
4. Check hours, prices and tickets on each place's own website. It can be wrong or out of date.
5. Ask for a packing list and a list of things to book.
6. You do the booking yourself.

Example conversation

Make it stick

• Give it your real limits. "Two kids, low cost, done by 7" gets a better plan than "plan a trip."
• Keep the plan in one conversation and change it as you go.