How I Used AI To Plan My Vacation To Japan

As a tech consultant, I’m always looking for new ways to put AI to work. But today, I want to talk about something beyond the usual business applications – how I used Claude, an AI assistant, to plan my family’s Japan adventure. It saved me a load of time.

You might be thinking, “Wait, you used AI for travel planning?” Most of us default to the usual suspects: TripAdvisor, travel blogs, and those massive Google Docs we share with family members.

Instead of jumping between dozens of browser tabs and trying to piece together the perfect itinerary, I simply had a conversation with Claude about what my family and I wanted to experience in Japan.

The magic wasn’t just in getting suggestions – it was in the back-and-forth dialogue that helped refine our plans. When I mentioned we wanted to experience both traditional and modern Japan, Claude didn’t just spit out a generic list of tourist spots. Instead, it helped craft daily itineraries that made sense geographically and culturally. For example, when Claude suggested pairing a morning visit to the serene Meiji Shrine with an afternoon in electric Akihabara, it also explained how these contrasts would give us a deeper understanding of Japan’s cultural evolution.

AI adapted plans on the fly. When I mentioned concerns about travel times between locations or specific dining preferences, Claude would instantly recalculate routes and suggest alternatives. No more spending hours on Google Maps trying to figure out if my ambitious plans were actually feasible.

As someone who works with technology daily, I’ve seen plenty of AI use cases, but this experience reminded me why I love this field. It’s not about replacing human judgment – it’s about enhancing it and speeding it up. Claude didn’t plan my trip for me; it planned it with me, taking my preferences, concerns, and family dynamics into account every step of the way.

Be specific about your interests and constraints. The more context you provide, the more personalized your itinerary becomes. And don’t be afraid to ask for adjustments – that’s where AI really shines, iterating and refining plans until they’re just right.

Online Travel Sites

Reagan National Airport

Online travel booking is easier than ever. And for us lucky folk in Washington DC with three airports (Dulles, Reagan, and BWI) there are flights everywhere and lots of deals. Below are some useful travel sites.

Travel Reservations

Travelocity – early leader in online reservations with roots back to CompuServe and AOL. Now known for the gnome commercials.

Orbitz – developed by airlines in response to Expedia and Travelocity.

ITA – uses the search system that powers Orbitz, but allows far more complex trips.

Priceline – offers standard purchases or allows you to name your own price for flights, hotels, and car rentals. Pitchman is now William Shatner.

Expedia – started by Microsoft, bought by Ticketmaster, now independent.

Hotwire – owned by Expedia. Unique in that you purchase hotels based on location and star rating. You only find out the name of your hotel after the purchase.

Kayak – travel search aggregator. Kayak does not directly sell tickets, but links to all the sites that do and makes a small amount of money on click throughs.

Bing Travel– recently renamed from Forecast.com, now owned by Microsoft. This site has flight price trends and predictions to help you decide if you should buy or wait for a better fare. It’s not perfect has helped me on a couple of occasions with suggestions to wait for a better price.

Special Airlines

JetBlue and Southwest airlines are not part of the above travel reservation sites. You can only book with them directly.

Other Resources

The Savvy Traveler Blog – deals and news by Rudy Maxa who often discusses travel on WAMU’s Kojo Nnamdi Show on NPR in DC.

Flyertalk – forum for frequent flyers to discuss deals and reward programs. This is where serious deal seekers go to discuss optimizing their points and airline status.

Liftopia – discount ski lift tickets and ski hotel deals.

TripBuzz – find local activities.

Have other travel resource recommendations? Email me to let me know.

6/12/16 UPDATES: Updated ITA Link and added TripBuzz, thanks to Phoebe.