We Took a 4-Day Family Trip to Surfside, Miami and AI Planned the Whole Thing (Here’s the Itinerary)
I want to be honest about something: I love to travel but I hate planning travel. The researching, the tab-opening, the trying to figure out if a restaurant is actually good or just has good Instagram… it’s a part-time job I never signed up for. And don’t even THINK about telling me I should just let my husband do the planning LOL!
So when we decided on a family trip to Surfside, Florida this year, I did something I should have been doing for years. I handed the whole planning job to AI and just showed up to edit.
Here’s what the process looked like and the actual itinerary we used.
How I started
I opened ChatGPT and gave it everything it needed to know in one message:
“I’m planning a 4-day family trip to Surfside, Miami, Florida. We have two boys, ages _ and _. We love being on the beach, good food (adults like seafood and Cuban food, kids are picky but will eat pizza, tacos, and chicken fingers), and some low-key cultural stuff but not a packed schedule. We’re staying in Surfside. Give me a day-by-day itinerary with specific restaurant recommendations, things to do, and any tips for the area.”
What came back was a full 4-day plan. I went through it, looked things up to verify they were real and still operating, made swaps where I had personal preferences, and ended up with a trip we actually used.
The actual itinerary:
Day 1 — Arrival + Settle In Arrive, check in, walk to the beach. Surfside Beach itself is the move. It’s a small, calm stretch that’s much less crowded than South Beach and genuinely great for little kids. Low-key dinner close to wherever you’re staying. We grabbed food from a local spot rather than a sit-down on arrival night, because we all know kids are always a disaster after travel.
Day 2 — Beach Day + Bal Harbour Morning on the beach. Surfside Beach, build sandcastles, let the kids destroy themselves. Afternoon, walk or drive 5 minutes to Bal Harbour Shops if you want to browse (it’s beautiful even if you’re not shopping, totally outdoor and walkable). Dinner: there are solid Cuban food options in Miami Beach nearby — arroz con pollo, plantains, the works.
Day 3 — Wynwood + Lunch This is the cultural day. Wynwood Walls is worth the drive from Surfside (about 25–30 minutes). It’s a massive outdoor street art district and genuinely cool even with kids. Go in the morning before it gets hot. There are food halls and casual lunch spots right in the neighborhood. Afternoon, head back and do an easy beach sunset.
Day 4 — Morning Beach + Departure Last morning beach time before checkout. We grabbed pastries and coffee and sat by the water. Low-key. Perfect.
The restaurant strategy
I asked ChatGPT specifically: “Give me 5–6 restaurant options near Surfside that work for a family with picky young kids, where adults can also eat really well. Include one Cuban, one seafood, and make sure they have something kid-friendly on the menu.”
I then took that list and cross-referenced it on Google Maps reviews before booking. I don’t just take AI’s restaurant picks at face value… I verify them. A restaurant that was great when the model was trained might have new ownership now, or closed. Always double-check before you make a reservation.
What AI saved me
Probably three or four hours of tab research. The kind where you open 15 different “best restaurants in Surfside” articles and they all say different things and none of them are from this year. Instead I had a curated starting point I could edit, rather than a blank page I had to fill.
AI trip planning isn’t magic. You still have to show up and make it yours. But as a starting point, it is wildly better than nothing, and it takes 15 minutes instead of an afternoon.
The prompt I’d give you to steal: “Plan a [#]-day family trip to [destination]. We have [kids’ ages]. We love [activities/food preferences]. We’re staying in [area]. Give me a day-by-day itinerary with specific recommendations.”
Go. Book the trip. You’ve been putting it off.
Want to start using AI but don’t know where to begin? Download my free AI 101 Guide for Non-Techy Moms — it covers the tools, the prompts, and exactly how to get started today. Zero tech background required. 👇 grab your free copy here