I Let AI Plan Our Weekend Getaway to Nashville—Here’s What Happened

What if you could have a personal travel planner that never gets tired, never forgets a detail, and delivers a full itinerary in seconds? That’s exactly what I set out to test when I let AI plan a three-day trip to Nashville, Tennessee, for Ed and me.

We’ve been wanting to visit Music City for a while—Ed’s a huge country music fan, and I’m always up for a great food adventure. The catch? We travel on a budget, and our eating preferences don’t always match up. I lean toward classic Southern comfort food, while Ed’s a vegetarian, which can sometimes make picking restaurants a challenge.

Would AI get it right? Could it create a trip that fits our style, keeps us on budget, and makes the most of our time? There was only one way to find out.

Step 1: Asking AI to Plan Our Trip

To start, I asked AI to create a three-day itinerary for a trip to downtown Nashville in April 2025. Here’s the exact prompt I used:

I want you to create a travel itinerary for a three-day trip to downtown Nashville, TN, in April 2025. The itinerary should be well-balanced, including must-see attractions, hidden gems, great local food spots, and some flexibility for relaxation. Assume we love country music, are budget travelers, and that one of us is a Southern foodie while the other is a vegetarian. Provide a detailed schedule for each day, with time estimates, transportation options, and alternative activities in case of bad weather. Also, include practical AI-powered travel tips, such as how to use AI for real-time navigation, translation, and finding last-minute reservations. The goal is to see how useful AI is at planning a trip from start to finish.

Within seconds, AI gave me a full itinerary—down to meal recommendations, alternative rainy-day activities, and even how long it would take to walk between locations.

At first glance, it looked pretty solid. It had all the must-see music landmarks (like the Country Music Hall of Fame and Ryman Auditorium), some hidden gems (like Marathon Village and the Musicians Hall of Fame), and plenty of food stops that seemed to fit both our tastes.

But would it hold up in real life?

Step 2: Reviewing the AI Itinerary—Does It Actually Work?

Here’s what AI suggested:

Day 1: Honky-Tonks, History & Southern Eats

📍 Breakfast at Biscuit Love (The Gulch)—a popular Nashville staple known for bonuts (biscuit donuts) and hearty breakfast plates.
📍 Country Music Hall of Fame and Hatch Show Print—a must for Ed, and Hatch Show Print is a cool bonus—it’s where many legendary country posters were designed.
📍 Lunch at Assembly Food Hall—a big food court with options for both of us (Prince’s Hot Chicken for me, a veggie taco spot for Ed).
📍 Johnny Cash Museum and Ryman Auditorium Tour—Ryman is known as the “Mother Church of Country Music.”
📍 Evening: Honky-Tonk Bar Hopping on Broadway—Tootsie’s Orchid Lounge, Robert’s Western World, and The Stage, all with free live music.
📍 Late-Night Snack: The Diner—a solid 24/7 option after a night of music.

My Thoughts:
🔹 This day was packed. AI stacked too many museum visits back-to-back, which could be overwhelming. I’d swap the Johnny Cash Museum for later and maybe add a mid-afternoon break.
🔹 Food choices looked great, but I’d need to check wait times at Biscuit Love (it gets crazy busy).
🔹 I loved that AI suggested free activities like Riverfront Park and the Pedestrian Bridge for sunset views.

Day 2: Exploring Beyond Broadway

📍 Breakfast at Dose Coffee—a lesser-known coffee spot close to Centennial Park.
📍 Centennial Park and The Parthenon—A full-scale replica of the Greek Parthenon? In Tennessee? Absolutely.
📍 Lunch at Edley’s BBQ—more local than the tourist-heavy Peg Leg Porker. Plus, they offer a meatless taco for Ed.
📍 Musicians Hall of Fame or National Museum of African American Music—a choice between hidden-gem music history or interactive exhibits on R&B, soul, and gospel.
📍 Dinner at The Southern Steak & Oyster—a good mix of seafood, steak, and veggie-friendly options.
📍 Evening Show: Bluebird Café (if we can get in) or 3rd & Lindsley (more realistic).

My Thoughts:
🔹 AI adjusted well for a more relaxed pace.
🔹 I loved that it included backup options for shows, knowing Bluebird Café sells out fast.
🔹 Food was spot-on—I get BBQ, and Ed has a real meal instead of just side dishes.

Day 3: Last-Minute Shopping & Farewell

📍 Breakfast at Elliston Place Soda Shop—a classic Southern diner.
📍 Shopping at Marathon Village—vintage shops, a whiskey distillery, and local artists.
📍 Lunch at Sunflower Café—a vegetarian Southern café—before heading to the airport.

My Thoughts:
🔹 Perfect slow morning before flying out.
🔹 Sunflower Café is a fantastic veggie-friendly find—I’d never heard of it before.
🔹 AI recommended getting to the airport 2 hours early, which is smart.

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Step 3: Final Verdict—Would I Let AI Plan Another Trip?

✅ What AI Did Well:
✔ Found hidden gems I wouldn’t have known about.
✔ Suggested realistic, budget-friendly options for meals and activities.
✔ Included backup plans for sold-out situations.
✔ Helped me optimize the flow of each day to maximize time.

❌ What AI Missed:
✘ Didn’t account for restaurant wait times—I’d need to tweak reservations myself.
✘ Some walking distances were off, requiring Uber/Lyft in a few places.
✘ Overloaded Day 1 with back-to-back museums, which needed a slight rearrangement.

Would I Use AI Again for Travel?

Absolutely! But I’d use it as a starting point, then refine it. AI is fast, efficient, and finds things I wouldn’t have thought of, but human judgment is still needed to make sure the schedule actually flows well.

If you want to try this for yourself, I put together a free guide:

Download “The Ultimate AI-Powered Weekend Getaway Planner” → here.

It includes the exact AI prompts I used, a step-by-step guide to tweaking your itinerary, and real-world AI travel hacks to make your next trip stress-free.

So, what do you think? Would you let AI plan your next trip? Let me know in the comments! 🎸🎶