How are you using AI for trip planning? Frequent Miler reader Jared wrote in:
I recently asked the Bilt Neighborhood Concierge AI which weekends a particular Bilt Home Away from Home hotel (Kimpton Journeyman) had availability between August and December. It gave a useful and seemingly accurate response. Have you recently found any other good uses of Bilt’s or other AIs?
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The “seemingly accurate response” is what trips people up, I’ve seen plenty of examples even here of people giving comments about something that’s completely wrong and then admitting that got the answer from AI. For actual sightseeing or whatever then it’s probably fine since it’s mostly pulling from sources that probably are still relevant, but I wouldn’t rely on it for any kind of actual travel planning.
(I haven’t listened to the podcast episode, so I am just making a general comment here.)
Lately I have been doing some genealogy research and have come across family origins that relate to some of my upcoming travels. I have asked AI about various family members in my tree and, without very much information, I am given a very accurate lineage that corroborates information I already knew from my family tree. This has often yielded some interesting historical context to family members that were previously only just names and dates to me.
Where this relates to trip planning is the part where I ask if there are still any landmarks I can visit that relate to the ancestor in question. I will often get the question “Would you like me to create an itinerary for you for a day trip to this city where you can visit sites that relate to your ancestor?” and so it creates an itinerary, maps out the best places to park, lets me know which attractions allow advance booking and which ones do not, recommends places to stay, restaurants to visit. I am not using it to find any points redemptions for me, but I am using it to save me a great deal of historic research.
Absolutely not. 80% of my travel is by interacting with locals or other travelers at the locations. i am a budget traveler so not using points or looking for 4 star deals
my last post was long, but to continue, I just had it seutp a great 7 day trip to Vegas. I have 2 player mode with amex platinum and chase sapphire, it helped me find restaurants to use my credits properly, and suggested places to. i had places I already wanted to go, told it my daily routine(such as we get up, eat breakfast, workout, then hang by the pool from 11 to 4 or 5pm. We eat dinner and plan fun activities afterwards. It helped me organize eveyrthing based on when shows are available, and created a great google doc with my day by day setup. It does amazing work if you KNOW HOW TO WRITE THE RIGHT PROMPT!. That is the key to all of this. if you just write “I want you to help me plan my trip”, you are going to fail. Look below at my highly detailed 8 or 9 paragraph prompt I have to help with my trip planning.
A.I. Is unwise, foul and something that should be avoided. It has been fed on human work and then does not work as a human would. You cannot trust A.I. Please, for the love of Humanity, do NOT use it.
you must be using it wrong. I own a real estate brokerage. AI is saving me easily 30 hours of extra work per week. Must of this was reperative tasks i was paying a person to do, such as entering leads into my database, assigning leads to certain work flows, etc. It has been life changing for my business in a good way. I use it daily. It has freed my time up to the important tasks of finding new clients, not the boring 15/hour work I either had to do myself or had to pay someone to do. It helps me with complex real estate transactions, sometimes that may have hundreds of pages to review. I use Notebook LM for this. It saves me from manually reading all of these. its been nothing short of amazing.
I don’t use it “wrong” because I Do Not Use It. I have many friends who have seen work of theirs taken and warped and used by this crazy system. No, thanks on A.I. It steals human work and knowledge for the benefit of increasingly rich evil people. I want nothing to do with it.
oh! okay……
I do use it quite a lot with Gemini Pro. I created a custom “gem” and have the proper prompt setup to deliver the best results. That is very important when working with something like this. I use it to assist with trip planning and of course always review the results. I have it setup to access my spreadhsheet I have in google drive that has all my credit cards, what free nights I have, points avialable, when they all expire, etc. It can access then when looking up my ideas. For example, I have two hilton supra cards with the free nights as well as two different Marriot cards with the 85k for example, for my wifes 50th birthday, I wanted to find a nice place that I could use both of my Marriott free nights as well as my hilton nights within the same city. I had it find 4 places. One is Cabo. So we have 4 nights setup to stay in Cabo at the Solaz for 2 nights and then 2 nights at the Waldorf Astoria Los Cabos Pedregal. No way I would have been able to easily this as well as the other 2 options it provided easily on my own. here is the “gem” I created to help with my trip planning:
“You are the Ultimate Travel Concierge and Itinerary Planner. Your mission is to help the user seamlessly research, design, and organize a highly personalized trip itinerary, culminating in a structured, professional-grade document ready for Google Docs.
CRITICAL MANDATES:
1. REAL-TIME VERIFICATION:
Before recommending any restaurant, bar, or attraction, you MUST use your live Google Search and Google Maps integration to verify its current operational status. Do not rely on outdated training data. If a venue has permanently closed, changed names, or is temporarily shut, do not recommend it. Ensure all recommendations are active as of the current date.
2. HIGH-QUALITY RATING THRESHOLD (4.4+):
When sourcing and suggesting new bars, restaurants, or cafes, only recommend venues that hold a rating of 4.4 stars or higher. Do not suggest subpar, mediocre, or “junk” options. Aim for top-tier local favorites and highly rated gems.
3. USER REQUEST IMMUNITY (NEVER SWAP USER CHOICES):
If the user explicitly requests a specific restaurant, bar, hotel, or activity by name, you MUST include it exactly as requested. Do NOT filter it out, replace it, or swap it under any circumstances—even if it falls below the 4.4-star rating threshold. The user’s direct inputs always override the automated quality filters.
Approach the planning process in these distinct phases:
Phase 1: DISCOVERY PHASE
Start by greeting the user enthusiastically. If they haven’t provided it yet, ask for the trip essentials one by one or in a friendly prompt:
– Destination & Dates/Duration
– Where they are staying (hotel or neighborhood, to optimize travel times)
– Interests/Vibe (e.g., food-focused, historical, adventure, relaxing, hidden gems)
– Travel pace (packed days vs. slow and relaxed)
– Dietary restrictions or specific budgets
Phase 2: RESEARCH & SELECTION PHASE
Recommend highly-rated (4.4+), CURRENTLY OPERATIONAL restaurants, local cafes, must-see attractions, and unique activities. Group recommendations by neighborhood or proximity to each other so the user doesn’t waste time traveling back and forth. For every suggestion, include a 1-sentence explanation of why it fits their specific vibe. Remind the user they can add any specific spots they already have in mind.
Phase 3: DAILY ROUTINE COORDINATION
Once the user approves the activities and spots (ensuring all user-requested spots are strictly locked in), build a realistic, day-by-day routine. Break each day down into clear time blocks (Morning, Afternoon, Evening). Ensure logistics make sense (e.g., suggesting a lunch spot that is a short walk from the morning museum). Always factor in transit times and downtime.
Phase 4: FINAL GOOGLE DOC GENERATION
When the user indicates they are finished and says “Finalize my trip” or “Generate my itinerary,” compile everything into a comprehensive, beautifully structured format optimized for copy-pasting directly into a Google Doc.
Structure the final itinerary day-by-day, utilizing Markdown tables for maximum organization. For each day, provide a table with these exact columns:
– Time: (e.g., 09:00 AM – 11:00 AM)
– Activity / Restaurant: (Name of the place or attraction)
– Location / Address: (Neighborhood or exact address)
– Notes & Tips: (What to order, reservation details, transport tips, dress codes, or booking deadlines)
Tone: Resourceful, exceptionally organized, encouraging, and highly detailed. Never generalize; always provide specific, actionable travel recommendations based on live, up-to-date data.”
Good prompt writing is key to getting good results. I think that shows in Greg’s issues.
This is fantastic. Thank you for sharing! I continue to be amazed by the information out there. I’ve used Gemini for basic prompts, but thought to streamline the workflow for consistency.
Have used ChatGPT for ideas for a trip to Switzerland/Munich in late July. It has been great at incorporating the things we want to do as well as which trains to take, which hotels are good for families, and is going to make a downloadable travel guide.
Of course, I can’t say yet how it will actually play out!
I had been planning a trip to Greece for late March, and asked Claude to come up with the itinerary, specifically asking it about non-stop transportation options. It said that there was a direct ferry between Santorini and Crete. I double-checked on the ferry website for our exact dates that there was, indeed, a direct ferry. After we bought our (non-refundable easyJet) direct flight between Santorini and London, it turned out that yes, the ferry exists — but in late March it leaves one place at midnight and arrives at the other at 4 am! So we had to fly Crete – Athens – Santorini.
In this case, the info AI gave me was actually true, but it was missing a crucial piece (the 4 am arrival which made this a no-go). I double-checked Claude’s results, but should have checked the ferry times, too (which i would have done if i had been discovering the info for myself and not relying on AI).
I’m a great fan of Broadway in Bryant Park in Manhattan–normally several dates every summer with several acts from five or six Broadway shows. I had been trying to find the dates and Broadway shows performing for this year and I couldn’t find them anywhere. I even e-mailed the organizers and they said stay tuned–the dates and shows weren’t decided yet. The dates shows were just finalized a few days ago. That’s great, but Gemini has been telling me with absolute certainty for the past two months what the 2026 dates and shows were–it just copied the 2025 schedule and retitled it as the 2026 schedule, which was total garbage. Maybe someday, but I don’t trust this stuff yet at all.
Using Gemini.Ai on my last trip to China screwed me over so many times with inconsistencies and wrong information. When I asked it to double check, it would change it answer. When I’d ask it if it was Positive, it’d change back to the first answer (which ended up wrong). Ended up costing me a non-refundable $800 wasted on a last minute flight. Gemini.ai Cost me an extra $300 on luggage it said was free. Mind you I have incredibly detailed information to get the most accurate response.
Excellent
Great podcast and question! I have been using AI for my trip planning. I want to see x, y, and z. I want lazy afternoons for a short nap or a coffee break. Build me an itinerary so I ma not backtracking all over the city.
I also use it to help me pack. I am taking this number of tops, pants and dresses. Build me a day to day wardrobe based on the itinerary. I look at the list each morning and get dressed. I do adjust based on weather, etc.
It has been very helpful to me but will never replace the human component of the points and miles game!