How to plan a trip with AI

Trip planning is one of the most underrated AI use cases. In 30 minutes you can have a day-by-day itinerary, restaurant picks, a packing list, and a list of questions to ask your travel companions. The trick is using AI for the structure and verifying the specifics yourself.

The starter prompt

Copy and adapt:

"Help me plan a [number] day trip to [destination] in [month/season]. Travelers: [who, ages, interests]. Pace: [relaxed / packed]. Budget: [budget level]. We are interested in [food / hiking / art / history / etc.]. We want to avoid [crowds / chain restaurants / etc.]. Give me a day-by-day itinerary with morning, afternoon, and evening suggestions. Include a few restaurant ideas per day. Note anything that requires reservations."

Example: real trip plan

Prompt:

"Help me plan a 5-day trip to the Oregon Coast in October. Two travelers, ages 65 and 67, both walk well. Pace: relaxed, no more than 2 hours of driving per day. Budget: mid-range, $200-300 per night for lodging. We love seafood, lighthouses, and coastal hikes. We want to avoid touristy spots. Day-by-day itinerary with restaurant ideas. Note anything that needs reservations."

AI gives back something like:

Day 1: Fly into Portland, drive to Cannon Beach. Lunch at Pelican Brewing. Visit Haystack Rock. Stay at Stephanie Inn (reservations needed 2+ months ahead).

Day 2: Cannon Beach to Pacific City via Tillamook (cheese factory). Drive a scenic loop. Sunset at Cape Kiwanda. Dinner at the Pelican Pub.

[continues for 5 days]

From there, iterate. "Day 3 has too much driving. Swap." "We don't like cheese factory tours; replace with something else."

Step by step: a working trip planning session

Step 1: The high-level pass

Use the starter prompt. Don't worry about details yet. Read the itinerary; flag anything that sounds wrong.

Step 2: Refine the pace

• "Day 2 is too packed. Cut the museum."
• "We don't like waking up early. Push everything by an hour."
• "Add a rest day on day 4."

Step 3: Refine the food

• "Suggest restaurants that aren't tourist traps. Where would locals eat?"
• "More casual breakfast spots. Less hotel restaurants."
• "We're vegetarian; rewrite all the food suggestions."
• "Find a restaurant that does live music on Friday night."

Step 4: Add logistics

• "What time does each thing on day 2 typically open?"
• "Which of these need reservations?"
• "What's the cheapest way to get from [A] to [B]?"
• "Make a list of everything I need to book in advance."

Step 5: Get a packing list

"Based on this October Oregon Coast trip, give me a complete packing list for two people. Include weather-appropriate layers, anything specific to the activities, and items I might forget."

Step 6: Verify the specifics

This is the most important step. AI is good at suggesting; AI is bad at current operating hours and prices. Before you commit:

• Google each restaurant. Confirm it's still open.
• Check official sites for park / museum hours.
• Confirm any tours mentioned still operate.
• Verify lodging availability and prices.

Trip planning prompts worth saving

For a specific scenario

• "Plan a 3-day weekend trip to Carmel for two seniors who love walking, coffee, and bookstores."
• "Help me plan a multi-generational trip to San Diego for 8 people, ages 6 to 75. Pool time, beach, and one big activity per day."
• "Plan a solo 4-day trip to New Mexico in November. I'm 60, interested in food, art, and quiet hikes. Budget: under $1,500."

For decisions

• "Help me decide between flying to Maui or San Diego in March. We have 5 days. Budget $4,000. Pros and cons of each."
• "Is it worth renting a car in Honolulu for 3 days, or should I use Uber and tours?"
• "Compare staying in downtown Seattle vs Bainbridge Island for a weekend trip."

For pre-trip prep

• "What time of year is best to visit Big Sur to avoid crowds but still have good weather?"
• "What do most first-time visitors to Italy regret not knowing?"
• "What is reasonable to expect to spend per day in Mexico City for a couple staying at mid-range hotels?"

During the trip

• "It's raining in Portland. Replace my outdoor plans for the afternoon with indoor options."
• "We're tired tonight; suggest somewhere casual within walking distance of our hotel [paste hotel name]."
• "My flight got delayed 5 hours; what should we do at LAX?"

Asking AI about specific destinations

• "What is the best neighborhood to stay in for first-time visitors to Lisbon?"
• "How crowded is Yosemite in July? What weekdays / hours avoid the worst crowds?"
• "What are the rules for renting an RV in Iceland?"
• "How do I get from Rome to the Amalfi Coast without renting a car?"

What AI does best for travel

• Day-by-day itineraries with realistic pace
• Comparing two destinations or routes
• Restaurant recommendations matched to your interests
• Packing lists tailored to climate and activities
• Translating phrases ("How do I say 'I'm allergic to nuts' in Italian?")
• Currency conversion explanations
• Cultural tips ("What do I need to know about tipping in Japan?")

What AI is bad at for travel

• Current prices and hours. Always verify.
• Restaurants that closed. A restaurant from 2022 may still be in AI's memory. Google it.
• Real reviews. AI summarizes from old data. Check recent reviews on Google or Yelp.
• Booking. Most AIs can't actually book hotels or restaurants. Use real sites.
• Specific addresses or directions. Use Google Maps. AI can be wrong.
• Weather forecasts. Look at weather.com or NOAA for actual forecasts.

Combine AI with real travel tools

• Google Maps: save AI-suggested places to a list. Plan routes between them.
• Google Flights: compare prices for the dates AI recommends.
• Airbnb / hotel sites: for actual reservations.
• OpenTable / Resy: reserve the restaurants AI recommends.
• Wikiloc / AllTrails: verify hikes AI suggests are real and currently open.
• Perplexity: verify specifics with sources.

Beware AI scams in travel

Fake travel websites are getting more sophisticated thanks to AI. Watch out for:

• "Hotel booking" sites that don't actually book anything
• "AI travel agents" that aren't real travel agents
• Phony tour operators with AI-generated reviews
• Fake "official park ticket" sites that mimic real ones

Always book directly through the operator's official site or an established booking platform.

5 things to try first

1. Pick a trip you're considering. Ask ChatGPT to plan a 3-day version of it.
2. For a trip already booked, ask AI: "Here is my itinerary [paste]. What would you add or change?"
3. Have AI build a packing list for your next trip.
4. Ask "What do tourists most often miss in [city]?" for somewhere you've been before.
5. Try Perplexity for a specific question: "What is the current entry fee for Hearst Castle?"