Planning Key West, a Kiplinger writer found a simple 'two-day itinerary' prompt gave generic tourist picks. Adding details such as 'focus on water activities, include a ghost tour, build in hotel breaks, no breakfast' produced plans that felt like hers, though everything still needed checking.
Create a [NUMBER]-day itinerary for [DESTINATION]. The atmosphere I want: [E.G. RELAXED, OUTDOORSY]. Must include: [E.G. A GHOST TOUR]. Focus on: [E.G. WATER ACTIVITIES]. Build in: [E.G. AN AFTERNOON BREAK AT THE HOTEL]. Skip: [E.G. BREAKFAST PLANS, BUSY NIGHTLIFE]. Avoid the obvious top-ten list where you can and tell me why each pick suits me.
Replace the [PLACEHOLDERS] with your own details before you send it.
How to try it
- Start with a simple prompt, then notice what feels generic.
- Rewrite it with your mood, must-dos, don’t-wants and pace.
- Fact-check each suggestion and use dedicated booking tools for flights and prices.
More travel use cases
Plan a group holiday for grandparents and children with Perplexity
One traveller used Perplexity Labs to plan a full itinerary for a party of six, including older relatives and children, for a summer trip. All that was left for her was turning up to the spa on time.
Plan a [NUMBER]-day trip to [DESTINATION] in [MONTH] for [NUMBER] people: [AGES, INCLUDING ANY OLDER RELATIVES AND CHILDREN]. Mobility needs: [DETAILS]. Mix gentle and active days, include rest time each afternoon, suggest family-friendly places to eat, and give a rough daily budget. Link to sources for opening times and prices.
Find the food locals actually eat with Perplexity
His mum had spent weeks fighting with generic tourist guides for a Curaçao trip, so one traveller spent five minutes with Perplexity and got an itinerary with food tips drawn from locals' posts on Reddit. She was delighted.
I'm visiting [DESTINATION] for [NUMBER] days. Skip the generic tourist lists. Using recent discussions from locals and frequent visitors (for example Reddit and local forums), recommend places to eat and dishes I should try, plus things to do that locals rate. Include the source for each tip and note anything that may have closed.
Gather holiday research into one notebook with NotebookLM
In a Hacker News thread on everyday AI tools, one user said they use NotebookLM to explore sources in bulk and to prepare holidays.
Using only the sources in this notebook, create a short trip briefing for [DESTINATION]: top things to see, practical tips (transport, money, opening days), food to try and anything my sources disagree on. Cite which source each point comes from.
Reference: Kiplinger