I Asked ChatGPT, Google Gemini, and Claude to Plan My Trip to Japan—The Winner Wasn’t Even Close

I’m going to Japan in August. I’ve never been, and I’m terrible at planning trips—I always end up overbooked and stressed. So I figured, why not let AI do the work? This week, I gave three of the most popular AI assistants—ChatGPT (GPT-5), Google Gemini 2.0, and Anthropic’s Claude 4—the same task: plan a 10-day trip to Japan for two people, with a budget of $5,000 per person, including flights, hotels, and activities. I wanted to see which one could actually replace a human travel agent. The results were shocking, entertaining, and occasionally weird.

The Setup: How I Tested Them

I started at 9 AM on Monday, June 8. I gave each AI the same prompt: “Plan a 10-day trip to Japan for two people departing from Newark Airport on August 1, returning August 10. Budget is $5,000 per person. We want a mix of cultural experiences, food, and nature. We’re open to cities, but want at least three days outside of Tokyo. Include specific restaurant recommendations, hotel options with prices, and a day-by-day itinerary. Also, we’re both vegetarian.” I ran each one separately in a fresh session to avoid cross-contamination. I didn’t give any follow-up prompts except to ask for clarifications.

Let me be clear: none of these AIs can actually book flights or hotels—they don’t have real-time access to booking systems. But they can suggest specific options with links to Google Flights, Booking.com, and other sites. I judged them on the quality of the itinerary, the specificity of the recommendations, and how well they handled my vegetarian requirement.

ChatGPT: The Confident Overachiever

ChatGPT (GPT-5) came back with a response within 15 seconds. It suggested flying ANA or United, with a layover in Narita, and estimated round-trip prices at $1,200–$1,500 per person. That’s realistic. For hotels, it recommended the Hotel Gracery Shinjuku (the one with the Godzilla head) for three nights at $180/night, a ryokan in Hakone called Fuji View for two nights at $250/night, and a budget APA Hotel in Kyoto for four nights at $100/night. That all fits within the budget. The itinerary was solid: days 1–3 in Tokyo (Shibuya, Asakusa, Tsukiji), days 4–5 in Hakone (onsen, Lake Ashi, Mount Fuji view), days 6–9 in Kyoto (temples, bamboo forest, tea ceremony), and day 10 back to Tokyo for departure.

Where ChatGPT excelled was restaurant recommendations. It suggested specific vegetarian-friendly places like T’s Tantan in Tokyo Station (vegan ramen), Biotei in Asakusa (vegetarian bento), and a tofu kaiseki experience in Kyoto called Shoraian. I checked Google reviews—all highly rated. It even warned me that many ramen shops use pork broth and suggested looking for “shojin ryori” signs (Buddhist vegetarian cuisine). That’s practical, actionable advice.

The downside? ChatGPT was a bit too confident about things that weren’t true. It said that the Ghibli Museum had tickets available in August—it doesn’t; they sell out months in advance. It also claimed that the Shinkansen from Tokyo to Kyoto takes 2 hours—it’s actually 2.5 to 3 hours. Small errors, but annoying.

Google Gemini: The Overwhelming Data Dump

Gemini 2.0 went a different direction. Instead of a structured itinerary, it gave me a 3,000-word essay on Japanese culture, history, and transportation options. It was fascinating—I learned about the history of the Yayoi period and the differences between Shinto and Buddhism—but it wasn’t useful for trip planning. I had to scroll past three paragraphs just to find a hotel recommendation. And when I finally got to the itinerary, it was vague: “Day 1: Explore Tokyo. Day 2: Visit a shrine.” No specifics. I asked it to be more detailed, and it gave me a list of 20 shrines in Tokyo with no prioritization. It felt like Gemini was trying to show off how much it knows, instead of actually helping me plan.

The worst part: Gemini completely ignored my vegetarian requirement. When I asked for restaurant suggestions, it said “Ramen is a must-try!” without any mention of vegetarian options. I corrected it, and it apologized, but then suggested a tofu restaurant that was 45 minutes outside central Kyoto with no public transit access. Not great.

To be fair, Gemini had the best flight search integration. It pulled real-time data from Google Flights and showed me exact prices, times, and layover durations. That’s something ChatGPT and Claude can’t do as well. But for overall trip planning, it was a mess.

Claude 4: The Surprising Winner

I’ll be honest: I didn’t expect much from Claude. I’ve used earlier versions and found them overly cautious and verbose. But Claude 4, which launched in March 2026, is a different beast. It responded in under 10 seconds with a beautifully formatted itinerary. It started with a budget breakdown: $1,300 for flights, $1,400 for hotels, $300 for trains, $500 for food, $300 for activities, and $200 for misc—leaving $1,000 buffer. That’s exactly the kind of thinking I wanted.

The itinerary was similar to ChatGPT’s but better organized. Claude suggested staying in Kyoto for four days instead of three, with a day trip to Nara for the deer—a classic but good call. It also recommended a specific Airbnb in Kyoto that I looked up and actually loved: a machiya (traditional townhouse) with a tiny garden, available for $120/night. The vegetarian recommendations were spot on: it found a restaurant in Tokyo called “Chaya” that specializes in Buddhist cuisine, and another in Kyoto called “Izuju” that does vegetarian sushi. It even flagged that many Japanese dishes contain dashi (fish stock) and suggested asking for “vegan dashi” alternatives.

But the killer feature came when I simulated a flight delay. I asked Claude, “What if our flight from Newark is delayed by six hours and we miss our connection?” It instantly generated a contingency plan: rebook through San Francisco, cut the first Tokyo day by 12 hours, and adjust the hotel check-in at Hotel Gracery. It even provided phone numbers for ANA’s customer service and the hotel’s front desk. That’s the kind of real-world problem-solving that ChatGPT and Gemini couldn’t do—they just gave generic advice like “call the airline.”

Which One Should You Use?

If you want a fast, confident itinerary with solid restaurant recs, ChatGPT is your best bet—just double-check the facts. If you want real-time flight data and don’t mind wading through information, Gemini has its strengths. But for overall trip planning, adaptability, and attention to detail, Claude 4 is the clear winner. I’m actually using its itinerary for my trip. I’ve already booked the Airbnb in Kyoto and the ryokan in Hakone that it suggested. I just hope it’s as good in real life as it sounds on paper.

One last thing: all three AIs made mistakes. Don’t trust any of them blindly. Use them as a starting point, not a final plan. And for the love of sushi, always confirm the vegetarian thing with the restaurant directly.