Prompts Matter - Treat AI like a Concierge

How can I leverage AI to get more out of it? Get better at prompting!

Think about how you plan trips. In the not so old days, we were used to breaking it down into Google searches or outsourcing it to a travel agent. Stay with me here. This is just an example since we have sites like Travelocity and Expedia, that do this for you. But if we did an experiment with an LLM like ChatGPT, you can use your AI more effectively depending on your prompting skills. Let's try a couple of prompts.

Good

Using AI like Google to find sites that have travel deals. A prompt might be:

Who has the best prices for flights to Orlando?

Who has the best prices for flights to Orlando? 10 seconds to write and about a minute to respond.

This did what you'd expect, it provided options for 3 airlines with travel times but actually didn't provide prices?!? How many more of these will you have to do to get to the real result you're looking for?

Better

Using AI to find the best prices on Tuesday afternoon excluding airlines you don

Find me a flight out of Philadelphia on Tuesday afternoon to Orlando. Only inclu

stop flights and exclude Spirit Airlines. My budget is $500 for the flight.

30 seconds to write and about 2 minutes to respond.

Find me a flight out of Philadelphia on Tuesday afternoon to Orlando. Only include non stop flights and exclude Spirit Airlines. My budget is $500 for the flight.

Created a great chart with departure times and flight duration. Perfect if you are planning on staying with relatives that will pick you up at the airport, but what if you're looking for more?

Best

Using AI to plan your trip whole trip similar to the way you would ask a Conierge or travel agent.

This prompt took longer to write than it did for Grok to generate an amazing result.

Generate an itinerary for my trip to Orlando the week of December first. I will leave on Sunday the 30th and need to be back Friday night. I prefer either American Airlines or Southwest as my airline. Show me the cheapest nonstop flight from PHL to MCO. Include a spacious rental car from either alamo or enterprise. I would like to pick that car up at the airport. I want the hotel to be either hilton or marriott and be close to Disney world. Relative Price will be the deciding factor for each of these requests so include the prices in the response.

Grok provided a complete itinerary for the trip. It provided multiple options and dug in on figuring out where at Disney I might want to go and which days. Check out the results below -

Trip Itinerary: Orlando (Disney World Focus) - November 30 to December 5, 2025

Your trip spans from Sunday, November 30 (departure from PHL) to Friday, December 5 (return to PHL), covering 5 nights in Orlando. This itinerary assumes a primary focus on Disney World, with time for parks, relaxation, and light exploration. I've prioritized your preferences: American Airlines or Southwest for flights (cheapest nonstop option selected), Alamo or Enterprise for a spacious rental car (SUV/minivan class for roominess, pickup at MCO), and Hilton or Marriott for the hotel (close to Disney World, with the cheapest relative option chosen). All selections are based on relative pricing from current data—flights around $80–$160 roundtrip, rentals $200–$300 for 5 days, hotels $500–$1,000 for 5 nights. Prices include estimates for taxes/fees but can fluctuate; book soon as early December is off-peak but demand rises near holidays. Total estimated cost for transportation and lodging: ~$850 (excluding park tickets, food, etc.).

Flight: Cheapest Nonstop Roundtrip (Southwest Airlines)

Southwest offers the best relative prices among your preferred airlines (typically $60–$80 one-way vs. American's $80–$140), with perks like 2 free checked bags. Based on schedules and recent fares for similar dates:

• Outbound: PHL to MCO on Nov 30, e.g., WN 2496 departing ~1:05 PM, arriving ~3:40 PM (2h 35m).

• Return: MCO to PHL on Dec 5, e.g., WN 1902 departing ~6:35 PM, arriving ~9:15 PM (2h 40m).

• Price: ~$120 roundtrip (including taxes; under $500 budget). American alternatives start at ~$160 roundtrip but are higher. Book via Southwest.com for real-time confirmation.

Rental Car: Spacious Option (Alamo Minivan)

Alamo edges out Enterprise on relative pricing (~$43/day vs. $45–$50/day for similar vehicles) and has strong reviews for ease at MCO. Pickup/drop-off at the airport (Level 1, no shuttle needed for on-site counters).

• Vehicle: Minivan (e.g., Dodge Grand Caravan or similar; seats 7+, spacious for luggage/gear).

• Dates: Pickup Nov 30 (post-arrival), return Dec 5 (pre-departure).

• Price: ~$215 for 5 days (including taxes/base fees; add ~$50 for insurance if needed). Enterprise equivalent (e.g., at MCO counter) would be ~$225–$250 for a similar minivan—slightly higher but comparable service. Book via Alamo.com.

Hotel: Cheapest Near Disney (Fairfield by Marriott Inn & Suites at Flamingo Crossings)

Marriott properties are generally cheaper than Hiltons near Disney (~$100/night vs. $200+), with Fairfield offering the best value (close to Western Entrance, ~10-min drive to parks). It includes free parking, pool, breakfast, and shuttle options to Disney (book in advance).

• Location: 13351 State Rd 535, Orlando (near Magic Kingdom/Animal Kingdom; easy access via I-4).

• Dates: Check-in Nov 30, check-out Dec 5 (5 nights).

• Price: ~$500 total (~$100/night including taxes; pet-friendly if needed). Hilton alternatives (e.g., Hilton Orlando Buena Vista Palace) start at ~$1,000+ for 5 nights—nicer amenities but double the cost. If you prefer Hilton, switch to that for ~$230/night. Book via Marriott.com.

Day-by-Day Itinerary

This is a relaxed plan for a family/group trip, assuming 4 Disney park days (buy multi-day tickets ~$400–$500/person via Disney.com). Adjust for weather (mild ~70°F) or energy levels. Total drive time minimal with hotel proximity.

• Day 1: Sunday, Nov 30 – Arrival & Settle In Fly PHL to MCO (~$60 one-way). Pick up Alamo minivan at airport (~15-min process). Drive ~20 min to hotel, check in. Afternoon: Explore Disney Springs (free shopping/dining area, 10-min drive). Evening: Relax at hotel pool or grab dinner nearby. (Drive: ~15 miles total.)

• Day 2: Monday, Dec 1 – Magic Kingdom Head to Magic Kingdom (~10-min drive). Focus on classics like Space Mountain, Pirates of the Caribbean. Use Genie+ (~$20/person) for shorter lines. Evening fireworks. Return to hotel. (Drive: ~20 miles roundtrip.)

• Day 3: Tuesday, Dec 2 – Epcot Drive to Epcot (~15-min). Enjoy World Showcase, Guardians of the Galaxy ride. Sample international food. If interested, add Disney's Hollywood Studios nearby. (Drive: ~25 miles roundtrip.)

• Day 4: Wednesday, Dec 3 – Animal Kingdom & Relaxation Visit Animal Kingdom (~10-min drive) for Avatar rides, safari. Afternoon: Return to hotel for pool time or visit a non-Disney spot like Gatorland (~20-min drive, optional). (Drive: ~20 miles roundtrip.)

• Day 5: Thursday, Dec 4 – Hollywood Studios or Free Day Go to Hollywood Studios (~15-min) for Star Wars/ Toy Story Land. Or use as a rest day: Shop at outlets or relax. Evening: Disney Springs again. (Drive: ~25 miles if park.)

• Day 6: Friday, Dec 5 – Departure Morning: Quick hotel checkout, optional last-minute Disney if time. Drive ~20 min to MCO, drop off car. Fly MCO to PHL (~$60 one-way, evening flight). (Drive: ~10 miles.)

Additional Tips & Costs

• Total Estimated Costs: Flights $120, Rental $215, Hotel $500 = ~$835. Add Disney tickets (~$400+/person), gas (~$50), food (~$300 for basics), and parking (~$25/day at parks if not using shuttle).

• Transportation Notes: Use hotel shuttle for parks to save on parking/gas. Minivan fits groups comfortably.

• Customizations: If you want more non-Disney (e.g., Universal, ~20-min drive), swap a park day. For upgrades (e.g., larger suite), prices rise ~20%.

• Booking Advice: Confirm all via official sites (Southwest, Alamo, Marriott) for latest availability/prices. Early Dec is low-crowd, but book fast. If details change (e.g., group size), let me know for refinements!

The moral of the story, the next time you want to use AI, think about it and write a longer prompt. By giving the AI more parameters and just giving it a couple of bumpers to suggest only your favorites or avoid the big pitfalls, you will be able to complete more work in a shorter period of time with FANTASTIC results.