How nice of him, Right?
My wife and I are both retired and the winters are looong here in Massachusetts. We try and get away someplace warm every year.
Last year we spent a week in Key Largo. The year prior, we had spent all of January down south. We drove so that our dog Rosco could join us and we spent time in Savannah, GA, Charleston, SC, Bradenton, FL, and St. Augustine, FL.
We had a great time, but January can be chilly. A few days, we needed to wear all of our clothes at once, layering-up to fight the chill.
So the following year, I searched out places in the Keys and found a nice quiet resort in Key Largo where it was sunny and 80 every day.
Again, this year, I want to be warm.
Grok
I’ve written before about how helpful Grok has been, but he really outdid himself here. I started with a question about the Caribbean:
I’m looking for a 5-7 night carribean winter vacation spot – direct flight from boston, adults only or at least quiet, lots of dining choices, activities, beach front
Grok came back with 3 options, 2 of which were in places I would consider somewhat less-safe. So I replied:
also looking for safety. I’ve heard the dominican and jamaica can be dangerous.
Grok is Patient
He did quite a bit of work on the first request. I got 3 paragraphs like this one

and then I got a table comparing all 3 options on each of the criteria I’d mentioned. He put some effort in!
If Grok were a travel agent and I asked the follow-up about safety, I probably would have gotten a big sigh and an “OK…let me look again.”
Not Grok, He was happy to keep searching.
Context
Grok also remembers the context of our discussion. I don’t need to ask my original question about the Caribbean, I just ask about safety and he remembers we’re discussing the Carribean.
This is helpful, because I had lots of follow-ups. I asked for hidden-gems that were discounted. I asked about nearby golf courses, and about hiking. If I had to re-type the whole schpeil about Carribean, warm weather, quiet…over and over, my fingers would fall off – both of the ones I type with.
Attention Span
And here’s where Grok really wins.
I may check the first one or 2 hits in Google. And even with that, I’ll skim.
Not Grok. He reads every word on all relevant websites.
With each question I ask, Grok shows me the number of websites he’s checking. I can watch the count go up.
With most responses he provides a table to make comparison easier. like this one.

Grok Doesn’t Get Offended
I can tell him I don’t like something. Or find me a better rate, or that flight doesn’t seem to be non-stop – what gives?
And he’s not right all the time. Those prices in the table above were way low for January. I told him so.
Wrap Up
I continue to be impressed with Grok. I also used ChatGPT, and was impressed as well.
It’s nice to have someone (thing?) who is willing to do the legwork and summarize for me. It’s also great that I can ask unlimited follow-ups and I don’t catch any flak.
AI isn’t perfect. I still went to the travel sites, compared and booked on my own, but Grok provided lots of great suggestions and helped me narrow my search.
So in a few weeks, we’ll be off to Grand Cayman. Can’t wait.
ps. Grok also provided the beach pic for this post.


What about Rosco….. Does he get to go as well?
Sadly, Rosco will be at the pet hotel near home. No beach-time for him.