How We Evaluate an Itinerary Generator Before Travelers See It
A generated itinerary can be fluent, on-brand and impossible. Here is the protocol we run before any of them reach a traveler.
Field Notes · Strategy & Trust
The point of AI in an advisory business isn't fewer decisions by people. It's better ones, made sooner, with the busywork already done.

At 8:50 on a Monday, an advisor opens a thread. It holds fourteen emails between a couple planning a fortieth-anniversary trip and a colleague who has since moved on. Somewhere in there are a shellfish allergy, a firm opinion about rental cars and a half-promise of a private dinner. The AI’s draft proposal arrives forty seconds later.
There are two ways this can go wrong. She can distrust the draft and rewrite all of it, in which case the AI saved her nothing. Or she can skim it, see that it looks right, and send it, and the shellfish allergy mentioned once in message nine is gone.
“Draft, don’t decide” is the principle we design around for the ground between those two failures. It’s simple to say and harder to build than it sounds.
A draft is a proposed action with four properties:
A decision is the moment something leaves the building: money moves, a supplier receives a request, or a traveler is told something. The line between drafting and deciding is the most important boundary in any AI-assisted workflow. Most of the design work is about putting it in the right place.
Two questions settle who holds the pen.
Together they make four zones:
Here’s how common advisory tasks fall:
| Task | AI’s role | Why |
|---|---|---|
| Summarize a long client thread | Decides | Internal and easily corrected |
| Tag stated preferences in the CRM | Decides; the client can view and edit | Low stakes, but it’s the client’s data |
| Write the first proposal | Drafts | Taste, relationship and money all in play |
| Place a free 24-hour supplier hold | Decides within rules | Costs nothing and expires on its own |
| Send a routine pre-trip reminder | Decides, with a 30-minute cancel window | Low stakes, but awkward to unsend |
| Reply to a supplier about a rate mismatch | Drafts | Money and a relationship |
| Re-plan a day after a closure | Drafts | Reversible until the traveler is told |
| Describe a room or trail as accessible | Drafts, with the measurements attached | Safety and trust; a person confirms fit |
| Pay a non-refundable deposit | Informs | Money, and irreversible |
| Weather or safety go/no-go | Informs | Belongs to the guide or operations lead |
Most of the value sits in the third zone. That’s where the hours are, and it’s where the design has to be good.
People over-trust automated suggestions, especially ones that are usually right. Researchers call this automation bias. Operators call it “I didn’t think I needed to check.” It produces an uncomfortable fact: a draft that’s right 97% of the time is more dangerous than one that’s right 70% of the time, because nobody reads the 97% draft carefully.
Better models make the problem worse. It has to be solved in the workflow. Five countermeasures work:
The reviewer’s first thirty seconds should go to the things only a person can check, so the top of the draft looks like this, before any narrative:
Draft proposal — anniversary trip, seven nights, northern New Mexico
Why this shape: Two bases instead of three. The clients said in message 4 that they “hate packing up.”
Assumptions: No driving after dark (inferred from message 11, please confirm). Private dinner on night five (offered by a colleague in message 9, not yet booked).
Check these: (1) Shellfish allergy applied to all three hosted dinners. (2) The casita rate comes from a supplier sheet dated six weeks ago. (3) The pottery studio confirms by email only, and hasn’t confirmed yet.
Question for the clients: Would they trade the balloon flight for a slow start on day three?
The polished itinerary comes after this block. A draft that opens with beautiful prose and hides its assumptions in the middle is built to be approved, not reviewed.
“Human in the loop” usually means a person checks the machine. It should also mean the machine checks the person, without the authority to overrule them.
Advisors edit under pressure, and edits break things. An advisor swaps night three to a lovely inn an hour farther north and doesn’t notice that the next morning’s balloon flight now needs a 4:50 AM departure. Another moves a dinner to 7:30 PM, after the restaurant’s last seating for parties of six. Neither is a judgment error. Both are the kind of constraint check software does well and tired people do badly.
So every edit should trigger the same checks the original draft passed: opening windows, drive times, holds that no longer match, dietary notes that didn’t carry over. The result appears as a quiet warning beside the edit, never as a block. The advisor can override it with one click and a short reason. Those reasons are useful data. They show where your constraints are wrong, out of date or too strict.
You can’t manage a human-in-the-loop system by asking whether people like it. Measure it:
| Metric | What it tells you | Warning sign |
|---|---|---|
| Unedited send rate | Draft quality, and reviewer attention | Rising quickly while review time falls |
| Fact edits per proposal | How well drafts are grounded | Not falling over time |
| Taste edits per proposal | Advisors are still advising | Falling toward zero |
| Median review time | Whether people actually read | Shorter than the time it takes to read |
| Escaped errors | Mistakes that reach a traveler | Any upward trend |
| Override reasons | Where the model misreads clients | The same reason keeps recurring |
The pairing that matters is fact edits and taste edits. Fact edits mean the draft got something wrong, and they should fall as grounding improves. Taste edits mean an advisor applied judgment the model doesn’t have, such as knowing this couple will prefer the small inn to the larger resort. Those should hold steady. If taste edits vanish, either the model has become a perfect copy of your advisors’ judgment, which is unlikely, or your advisors have stopped reading.
In one pilot with a boutique agency, the median time from inquiry to first proposal fell from about two working days to the same day. About a third of proposals still went out unedited, and taste edits held steady, which we read as a healthy loop.
We build every product on this matrix. In Nova’s Itinerary Studio, a proposal stays a draft until an advisor sends it, with the assumptions block on top and every supplier fact linked to its source. The supplier holds placed by our booking workflow automation are free, time-limited and logged. Anything that costs money waits for a person.
For travel advisors and agencies, the matrix is also a client-facing promise. You can tell clients plainly what software does for them and what a person always decides. Writing that promise down, along with what the system may and may not do with a traveler’s preferences, is a core part of our responsible AI and traveler data governance work, and it runs through our approach to every engagement.
Tasks can earn more autonomy, but it should be earned slowly and lost quickly. Before promoting a task, check that:
List twenty things your team does in a typical week, from summarizing threads to paying deposits. For each one, answer the two questions about stakes and reversibility, place it in a zone, and compare that with what your tools do today.
The mismatches are your roadmap. Some will be tasks where software is deciding something a person should own. Just as often, they’ll be tasks where a person is still doing work a good draft could have done in forty seconds.
Questions
Not if the draft is designed for review. The savings come from everything before the decision: reading the thread, checking availability, assembling options and writing a first version. A well-built draft turns a two-hour task into a fifteen-minute review focused on the few claims that genuinely need a person.
Anything irreversible with real stakes: paying non-refundable deposits, telling a traveler that a place suits their access or health needs, weather and safety go/no-go calls, and anything that involves a traveler's health information. AI can inform those decisions. A person should make them.
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