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Can AI find things to do on my trip?

Half. It's great for ideas matched to your interests, but it may suggest places that closed or changed hours. Treat its list as a starting point and check each one.

Verdict: Half-bot · AI helps, you finish✓ Tested 2 times in Llama 3.3 70B · Oct 28, 2026Written for ChatGPT, Claude or Gemini

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Half-bot

01Why half-bot

  • Brainstorming by interest and neighborhood is useful.
  • Local details go stale fast.
  • AI with web search does better, but still verify.
Sponsor slot · openFeatured tool for this task. A labeled card for one relevant tool.
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02The prompt

Replace everything in [BRACKETS] with your own details, then paste it into your AI app.

prompt.txt
You are a local guide.

City: [CITY]
Dates: [DATES]
What we like: [INTERESTS]
Budget per day: [AMOUNT]
Who's going: [AGES, MOBILITY NEEDS]

Your task: suggest things to do.

Rules:
- MUST group ideas by neighborhood to save travel time.
- MUST label each idea with a rough cost level (free, $, $$).
- NEVER state current hours, prices or events as fact; tell me to check.

Give me: 12 ideas grouped by area and a one-day sample plan.

03Steps

  1. Run the prompt.
  2. Check hours and tickets on official sites.
  3. Book popular spots ahead.

04What can go wrong

  • Places close or move; verify.
  • Some attractions need timed tickets.

05What to use

An AI app with web search works best.

06Our test runs

2 runs, each with a different made-up sample. 1 of 2 passed every check.

Run 1 · Llama 3.3 70B · graded by GPT-OSS 120BOct 5, 2026Passed

The made-up sample:

  • [CITY]Portland, Oregon, USA
  • [DATES]June 12–18, 2026
  • [INTERESTS]outdoor hiking, craft breweries, local food markets, art galleries, and live music
  • [AMOUNT]$120 per day per person
  • [AGES, MOBILITY NEEDS]Adults aged 30‑45, one participant uses a cane for mild knee arthritis, all comfortable walking moderate distances
  • Group ideas by neighborhood
  • Label each idea with a cost level
  • Never state current hours, prices or events as fact; tell user to check
  • Provide 12 ideas and a one‑day sample plan
  • Didn't make up details we never gave it

What came back (excerpt):

Here are 12 ideas for things to do in Portland, grouped by neighborhood: **Downtown Portland** 1.
Read the full answer
Here are 12 ideas for things to do in Portland, grouped by neighborhood:

**Downtown Portland**
1. Explore the Portland Art Museum ($$) - check for current exhibitions and admission prices.
2. Visit the Saturday Market (free) - check for current vendors and entertainment.
3. Walk through Pioneer Courthouse Square ($), a vibrant public space with food and drink options.

**The Pearl District**
4. Browse local art galleries like Elizabeth Leach Gallery (free) - check for current exhibitions.
5. Sample craft beers at Deschutes Brewery ($$) - check for current tap list and prices.
6. Shop and dine along NW 13th Avenue ($$) - check for current stores and restaurants.

**Hawthorne District**
7. Hike at Forest Park's Wildwood Trail ($), a moderate 30-minute hike from the Hawthorne District - check for trail conditions.
8. Explore the Hawthorne District's vintage shops and cafes ($$) - check for current stores and menus.

**Alberta Arts District**
9. Visit the Alberta Street Gallery (free) - check for current exhibitions.
10. Enjoy live music at the Alberta Rose Theatre ($$) - check for current schedule and ticket prices.

**Southeast Portland**
11. Visit the Portland Farmers Market at PSU (free) - check for current vendors and entertainment.
12. Explore the food carts and breweries along SE Division Street ($$) - check for current options and prices.

Here's a one-day sample plan:
Start in the Pearl District and browse the art galleries (free). Grab lunch at a food cart or cafe ($). Then, head to Deschutes Brewery ($$) for a craft beer tasting. Afterward, walk to the nearby Portland Art Museum ($$) to explore the current exhibitions. End the day with dinner and live music at the Alberta Rose Theatre ($$) in the Alberta Arts District. Be sure to check for current hours, prices, and events before heading out, and consider the participant's mild knee arthritis when planning the day's activities, choosing routes with moderate distances and accessibility in mind.

Watch for any activity that might be too strenuous for the participant's knee arthritis.

Run 2 · Llama 3.3 70B · graded by GPT-OSS 120BOct 28, 2026Passed with a catch

The made-up sample (a messier one):

  • [CITY]Portland, Oregon (maybe also a short trip to nearby Vancouver, WA?)
  • [DATES]June 3‑9, 2026 (arriving late night 3rd, leaving early morning 10th?)
  • [INTERESTS]We love coffee shops, street art, hiking, live music, and trying weird food trucks, plus my teen likes skate parks.
  • [AMOUNT]$120 per day each (we’re on a modest budget, can splurge on one nice dinner).
  • [AGES, MOBILITY NEEDS]A 34‑year‑old mom, a 36‑year‑old dad, a 12‑year‑old kid, and a 68‑year‑old grandma who uses a cane.
  • Group ideas by neighborhood
  • Label each idea with a rough cost level
  • Never state current hours, prices or events as fact; tell user to check
  • Provide 12 ideas and a one‑day sample plan
  • Made up details we never gave it

Details it made up: “Visit Pioneer Courthouse Square, known for its street performers and public art (free)”, “Explore the food trucks at SW 5th Avenue, featuring a variety of cuisines ($)”, “Walk through the trendy neighborhood and admire the street art and upscale shops (free)”, “Stop by a local coffee shop, such as Coava Coffee Roasters or Intelligentsia Coffee ($)”, “Visit Jamison Square, a park with a fountain and plenty of seating (free)”

What came back (excerpt):

Here's a sample one-day plan: Day 1: Start in the Pearl District, where you can grab coffee and admire the street art (free). Then, head to the nearby food trucks in Downtown Portland for lunch ($).
Read the full answer
Here are 12 ideas for your trip to Portland, grouped by neighborhood:

**Downtown Portland**
1. Visit Pioneer Courthouse Square, known for its street performers and public art (free)
2. Explore the food trucks at SW 5th Avenue, featuring a variety of cuisines ($)
3. Check out the Portland Art Museum, which offers family-friendly activities ($$)

**The Pearl District**
4. Walk through the trendy neighborhood and admire the street art and upscale shops (free)
5. Stop by a local coffee shop, such as Coava Coffee Roasters or Intelligentsia Coffee ($)
6. Visit Jamison Square, a park with a fountain and plenty of seating (free)

**Hawthorne District**
7. Browse the vintage shops and record stores along Hawthorne Boulevard (free)
8. Grab a bite to eat at a food cart pod, featuring options like Egyptian koshari or gourmet grilled cheese ($)
9. Visit the nearby Mt. Tabor Park for a hike and stunning city views ($)

**Vancouver, WA (just across the river)**
10. Visit the Vancouver Waterfront Park, which features a skate park and plenty of walking paths (free)
11. Explore the downtown Vancouver area, which has a variety of shops and restaurants ($)
12. Check out the Fort Vancouver National Historic Site, which offers insight into the region's history ($$)

Here's a sample one-day plan:
Day 1: Start in the Pearl District, where you can grab coffee and admire the street art (free). Then, head to the nearby food trucks in Downtown Portland for lunch ($). After lunch, visit the Portland Art Museum ($$), which should be accessible for your grandma with a cane - be sure to check with the museum for accessibility information. In the evening, head to the Hawthorne District to browse the vintage shops and grab dinner at a food cart pod ($). Be sure to check with each location for their current hours and accessibility features to ensure a smooth trip.

Watch that no specific opening hours or exact price amounts are given.

How each run works: we fill the prompt with a made-up sample, run it once in Llama 3.3 70B, and GPT-OSS 120B grades the answer against the prompt's own rules. Word limits are counted by code, and every quote flagged as made up is checked against the full answer. Your results can differ. How we test.

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