Unsure Where to go Next? Let AI Track Your Bucket List

After traveling to many new and familiar locations this year, my husband and I have no more vacations planned for the remainder of 2026. On our most recent flight home this led to one obvious question: Where are we going next?

We have so many places we want to go to, with many having their own factors that would impact travel plans. Is there a preferred time of year to travel to this location? Could the trip be taken in a weekend or do we need a week or more of travel time? Are some destinations a priority over others?

With these factors in mind, we turned to Claude and Notion to develop a tracking system.

Step 1: Have a Conversation with AI

Below is an example of the prompt I fed to AI to generate the first step of our new tracking system:

Assume you are a travel planner. The goal is to create a Notion database of places [my partner/friend] and I want to visit. This list should have a ranking system so we can prioritize when we go to each place based on schedule, availability, price, etc. The list should categorize trips as long weekends OR longer trips. Ask me some questions to get a better understanding. When we're done, I'll ask you to generate a role, task, context, constraints and deliverable.

Step 2: Answer the Questions

Your AI platform will have questions for you to narrow down your preferences. Here are examples of the multiple-choice questions it asked us:

• How should the ranking work?
• Which factors matter most?
• Where does a long weekend end and a longer trip begin?
• How should price be tracked?
• Who will add and edit places?

Step 3: Share Your Destinations and Your Limitations

We provided AI with a list of our desired destinations. For us, this included NYC (a long weekend trip) and Japan ( an extended trip) with several options in between.

Our limitations were also shared. We mentioned our PTO allowances and also added our home airport.

Step 4: Let the AI Propose Tiers, Then Adjust

Ask the AI to propose Must / Want / Someday tiers based on your priority order. It should explain each choice ("cheap flight, only 1–2 PTO days" or "needs 10+ PTO days, so save it for a year you can stack it on a holiday"). Then move anything that doesn't feel right. You know your wish list better than the AI does.

Step 5: Ask for a Prompt

Once the plan is settled, ask the AI to write it up as an RTCCD prompt. That's a structured prompt with five parts:

• Role: who the AI should act as
• Task: what it should build
• Context: the background it needs (who you are, PTO, home airport, priorities)
• Constraints: the rules it must follow (tier names, field types, what not to add)
• Deliverable: exactly what you get at the end

This turns a long back-and-forth conversation into one clean, reusable set of instructions.

Step 6: Build Your Tracker in Notion

Create a new full-page database called "Travel Wishlist" and add properties. Here are examples of the ones we included:

Tier, Trip Type, Est. Cost, Best Season, PTO Days, Partner’s Pull, Visited, Notes

Then add four views:

By tier, long weekends, longer trips, been there

Then:

Double check AIs work. It is creating a draft document for you to edit to your own wishes.

Also, be sure to revisit the list every few months. Update your planned travel and add new destinations that have come on your radar. Your PTO accrual may also increase annually, so be sure to change this as needed too.

Bonus Tip: Skip the Homework and Hand Claude This Article

Everything above takes maybe an hour. If you'd rather spend that hour browsing flights, there's a shortcut: give Claude this post and let it do the setup for you.

Copy the link to this article, open Claude, and paste in something like this:

Read this article: https://emilyruthweir.com/blog/ai-travel-bucket-list. Use the same process to build me a travel wishlist in Notion. Ask me the step 2 questions one at a time. Then sort my destinations into Must / Want / Someday tiers, write me an RTCCD prompt I can reuse, and create the Travel Wishlist database with the same properties and views.

Claude reads the post, picks up all 6 steps, and starts asking you the questions (where you fly out of, how much PTO you've got, whether Japan is a Must or a Someday). You still give the answers. Claude handles the structure.

Two things help this go smoothly:

• Connect Notion first. Turn on the Notion connector in Claude's settings and it can build the database for you. Without it, you just get instructions for clicking through it yourself.
• Have a backup if the link won't open. If Claude can't open the URL, copy the article text and paste it in.

The step 6 rule still applies: it's a draft. Check the tiers and cost estimates before you book anything.