Using AI to Plan Activities for a Last-Minute Family Trip to Miami: A Case Study

There’s a certain thrill in booking a last-minute trip—especially when you’re escaping the bitter cold of a New York winter. But spontaneity comes with its own set of challenges: finding the right activities, narrowing down dining options, and making sure everything fits seamlessly into a limited window of time.

This year, my family is heading to Miami for a quick getaway from February 15 to 19. We’re prioritizing outdoor activities, family-friendly experiences, and great food—but with only a few days to plan, I wanted to see how AI could streamline the process.

Spoiler alert: it worked. But not without some back-and-forth to refine the results. Let’s walk through how AI transformed broad, open-ended ideas into a concrete itinerary in just a few minutes.

Step 1: The Initial Ask

The process started with a simple idea:

“We’re taking a trip to Miami and I wanted to use AI to get suggestions about what we could do while we’re down there. Why not write a blog post about how to use AI to help plan activities for a trip that others can use?”

From there, I laid out the details: we’d be staying at two different hotels—MB Hotel by Wyndham (Feb 15-17) and Hyatt House Miami Airport (Feb 17-19). I’d be heading home on the 17th, leaving my wife and daughter to enjoy the last two days without me. We needed kid-friendly activities, family-friendly restaurants at different price points, and an easy way to get around without relying too much on public transportation. Since we walk a lot, anything within a mile or so was fair game.

The AI responded with a round of general ideas, but I immediately saw room for refinement. I find it's easiest to ask the AI if there's any questions it has for me that would be helpful. Then I add my own refinements, but the back and forth also helps get the ideas flowing.

Step 2: Refining the Search

AI can work best when given specific parameters, so I started narrowing things down:

1. Outdoor activities should be the priority. The whole point of the trip was to escape the dreary winter back home.

2. Dining suggestions should be split into budget categories, with a note on what each restaurant is known for.

3. Public transportation is okay, but not when we have luggage.

4. We need rainy-day backups. Miami weather can be unpredictable, and I didn’t want to be caught without options.

5. AI’s role is to help refine, not just list things. I wanted this to be a real case study in how AI improves decision-making, not just spits out search results. Google could do that and doesn't require it's own article.

That’s when things started getting good.

Step 3: Dining—From Broad to Useful

AI’s first attempt at restaurant recommendations was decent but too general. I needed more specificity and quality control—no tourist traps, just well-reviewed places that actually fit our needs.

So I adjusted the request:

“Give me 5 or so well-reviewed lunch spots near each hotel (budget & mid-range) and 3-5 well-reviewed dinner options at each price point. Also, my wife isn’t big on seafood, so make sure every place has something for her.”

The AI came back with a much stronger list. Here’s a quick preview:

Miami Beach (Near MB Hotel)

Lunch:

• La Sandwicherie – Fresh sandwiches & salads 🥖

• Oh! Mexico – Authentic Mexican 🌮

• Hosteria Romana – Cozy Italian with great pasta 🍝

• Little Niko Pizzeria – Pizza & gelato 🍕

• Tapelia Spanish Cuisine – Spanish food with solid non-seafood options 🍖

Dinner:

• Pane e Vino – Handmade pasta 🍝

• Santorini by Giorgios – Greek flavors with meat & veg options 🇬🇷

• Yardbird Southern Table & Bar – Southern comfort food 🍗

• Byblos – Eastern Mediterranean, stylish setting 🍢

• Planta South Beach – Upscale plant-based dining 🌱

I'd be lying if I said I understood all of the emojis but this was exactly the level of detail I needed researched, but with concise results. I didn’t have to sift through reviews or read each menu to find out whether each place had something for everyone. AI had already done that heavy lifting.

Step 4: Activities—Balancing Walkability & Weather

With dining locked in, it was time to focus on what we’d actually do. The AI’s first batch of suggestions included a mix of beaches, parks, and museums. But again, some tweaks were necessary:

“Let’s prioritize outdoor activities near each hotel, but also add rainy-day backups based on the Miami forecast.”

The AI pulled up a 5-day forecast and noted some rain on the 18th. With that in mind, it refined the list:

Outdoor Must-Do’s:

• Miami Beach Boardwalk – Scenic oceanfront stroll

• South Pointe Park – Beautiful park with a playground & views

• Lummus Park – Iconic beach area for relaxing & people-watching

Rainy Day Plans (Feb 18)

• Phillip & Patricia Frost Museum of Science – Aquarium, planetarium, and interactive exhibits 🦈🔭

• Miami Children’s Museum – Engaging exhibits for kids 🎨

The process was fluid and interactive—I asked, AI adjusted, and within minutes, I had a set of recommendations tailored for my family.

Step 5: The Final Rundown

With everything laid out, I asked for a concise summary I could share with my wife. In seconds, AI generated this streamlined trip rundown, ensuring we had clear choices without information overload.

Final Thoughts: How AI Helped Streamline Travel Planning

This entire process—from broad brainstorming to a polished itinerary—took only a few minutes. AI didn’t just find information; it refined it, making the overwhelming task of last-minute travel planning far more manageable.

Here’s why this worked so well:

✅ Efficiency: AI processed vast amounts of data instantly, presenting only the most relevant results. ✅ Personalization: Every recommendation aligned with my family's preferences and needs. If it didn't, I'd mention how and have it try again. ✅ Adaptability: AI factored in real-world variables like weather and walkability. ✅ Comprehensive Insights: From dining to logistics, it covered everything we needed.

This experience proved that AI isn’t just for SEO marketers—it’s a powerful tool for compiling and sifting through real world options. The key is interactivity: the more I refined my requests, the better the results became.

So, next time you’re planning a trip? Try using AI to cut through the noise and get straight to the good stuff. It’s like having a personal travel assistant—minus the hefty price tag.

Now, time to pack for Miami. ☀️😎