One of the many immediate uses for AI is in the world of travel and travel planning. My own first experience with AI occurred when a friend who worked in IT lead me through a demonstration of ChatGPT showing me how he had already used it to plan a two-week vacation, right down to picking out what clothes they should pack because of the expected weather. Interesting. Here is my own contribution to the world of AI-generated travel content.
AI and Travel Converge
I have noticed recently that lots of folks have been reading the five-part series I posted last year comparing wintering in the Algarve and Portugal and the Costa del Sol in Spain. It seems that lots of retirees are beginning to start looking for information about these European destinations for their own winter getaways early this year.
About three years ago, after several great stays in Spain, I began to wonder if there were other destinations in Europe that might be great winter getaway choices as well. I was thinking the Greek islands, or Crete, most of which I imagined to be further south than the Costa del Sol.
That thinking was laid to rest when I discovered that Tarifa, just on the other side of Gibraltar, was the most southerly point in continental Europe. This got me rethinking my consideration of the islands. I was so intrigued that I found a map showing latitude and added my own demarcation line from Tarifa straight across the Mediterranean. As it turns out, the islands of Crete and Cyprus are only slightly further south than the Costa del Sol. And the Greek islands don’t really come in to play at all.
The first image below, from Google Maps ,shows the location of Tarifa, and the second image shows you the little latitude map I marked up. Clicking on the first image will bring up the enlarged carrousel images.
So, I abandoned the idea of an alternate destination for us. We seemed to be in the European sweet spot already. That was until recently.
I have been working on a presentation for a talk I will be giving to a community group in another city after I get back from Europe in October; looking at my little latitude map got me thinking that although other destinations probably wouldn’t be of interest to us mainly because the flight time would be about double what we currently enjoy. However, other interesting locations may well be of interest to other retirees. And a detailed comparative analysis of those locations may be a benefit to some of you.
I wasn’t terribly excited about the idea of doing a lot of data gathering about other destinations since I wasn’t personally interested in them; so, I decide that ] I was going to assign the project to the AI Chatbot ChatGPT. I was thinking good things about its abilities after it picked all the winners in the Open championship golf pool that was organized by my golf associates. That was the last post before this one if you are interested in reading about that AI experience.
My Use of Chat GPT
Before we get to the result of ChatGPT’s most recent effort, I think I will do a little explaining about the specifics of how I used it. And, about how thoroughly ChatGPT drilled down into the project. Once you start reading the content under the horizontal line below this section, all the words are ChatGPT’s. The only time I interject is where there will be a red line and a quote from me… either a prompt I gave my special new friend, or where I felt it was necessary to inject a bit of information.
FYI, when you assign any AI agent to do some work, you begin the process by asking it a question. In AI world, these questions are referred to as “prompts”.
I’d like to think you can follow along with what ChatGPT’s intention was here and perhaps even enjoy what appears to be its original thinking. I say original thinking because after using it many times I have found that it frequently takes off on a tangent and comes up with some novel ideas about how to fulfill the assignment completely on its own. A good example of that will be the “Snowbird Value Index” that you will read about shortly. It has been my experience that AI chatbots tend to give you way more information that than you asked for, or relevant ideas you didn’t know you needed.
I have not really done any editing of what ChatGPT had to say here, other than I left out some occasional sentences or contributions that were totally redundant to what it had already said.
You should also know that the graphic title image you see here was completely created by ChatGPT without any real input from me about what I wanted to see or how it should look. All I did was tell it that I needed a title image and that it should reflect what the piece was about.
This was the prompt I provided:
“I now need you to produce a title image for this blog post that reflects the purpose of the post”
In its report ChatGPT labelled my prompts as the “User” speaker and its own responses as “ChatGPT”, so it reads as a bit of a conversation – albeit, a mostly one-sided conversation. Additionally, it provided its own title for the project as well.
Here we go…
Wintering in Europe – Cost Comparison and Snowbird Value Index
User
We are thinking about wintering in Europe for February and March. I need you to rank European countries along the lines of how much it will cost us to live in each. You can choose the criteria, but certainly amongst that would be the cost for a short-term rental, grocery prices, public transportation cost, restaurant costs. Rank them from least expensive to most expensive.
ChatGPT
Since you’re planning to spend two full months in one location, I would place the greatest emphasis on the following factors:
- 40% – Short-term apartment rental
- 25% – Groceries
- 15% – Restaurants and cafés
- 10% – Public transportation
- 10% – Miscellaneous daily costs
These categories account for the vast majority of day-to-day expenses for Canadian snowbirds.
Overall Cost Ranking (Least Expensive to Most Expensive)
| Rank | Country | Estimated Monthly Cost (CAD) |
| 1 | Bulgaria | $2,200–2,700 |
| 2 | Romania | $2,300–2,900 |
| 3 | Albania | $2,400–3,000 |
| 4 | North Macedonia | $2,500–3,100 |
| 5 | Montenegro | $2,700–3,300 |
| 6 | Portugal | $3,000–3,700 |
| 7 | Spain | $3,100–3,800 |
| 8 | Greece | $3,200–3,900 |
| 9 | Croatia | $3,300–4,100 |
| 10 | Malta | $3,400–4,200 |
| 11 | Italy | $3,700–4,600 |
| 12 | Cyprus | $3,800–4,700 |
| 13 | France | $4,100–5,200 |
| 14 | Germany | $4,200–5,300 |
| 15 | Belgium | $4,300–5,500 |
| 16 | Austria | $4,400–5,600 |
| 17 | Ireland | $5,000–6,500 |
| 18 | Netherlands | $5,100–6,600 |
| 19 | Switzerland | $6,000–8,000+ |
| 20 | Iceland | $6,500–8,500+ |
Best Value Destinations
If I were balancing cost, climate, healthcare, ease of getting around without a car, English spoken, and overall enjoyment for a Canadian couple, I’d rank them:
- Spain (especially the Costa del Sol)
- Portugal (especially the Algarve)
- Greece (Crete or Rhodes)
- Southern Italy
- Montenegro
- Croatia
- Bulgaria
Given your previous questions about Europe, another country I’d encourage you to consider is Montenegro. It combines Adriatic scenery reminiscent of Croatia with prices that are often 20–30% lower, making it an increasingly popular destination for longer winter stays.
I’ve put together another map showing you where the countries ChatGPT is suggesting can be found.
ChatGPT
If you’re interested, I can also prepare a “Snowbird Value Index” ranking these countries not just by cost, but by factors like winter weather, walkability, healthcare, airport access from Canada, English proficiency, and overall quality of life for a two-month stay. That often paints a different—and more useful—picture than cost alone.
User
Sure, go ahead and provide your Snowbird Value Index.
ChatGPT
Since I know you’re looking at this as a Canadian couple escaping winter for two months, I think a simple cost ranking doesn’t tell the whole story. Instead, I created what I call a Snowbird Value Index.
Snowbird Value Index
I scored each country (out of 100) using the factors that I think matter most for a February–March stay:
| Category | Weight |
| Winter climate | 25% |
| Cost of living | 20% |
| Short-term rental availability | 15% |
| Public transportation | 10% |
| Healthcare | 10% |
| Walkability | 5% |
| English spoken | 5% |
| Ease of flights from Canada | 5% |
| Overall lifestyle | 5% |
Snowbird Value Index:
|
I interject here simply because ChatGPT does not always provide short introductions about why it’s providing additional information. Here it has clearly chosen to provide the details related to, “the weather”, the first factor it considered when developing its Snowbird Index. Definitely useful.
Winter Weather Comparison
| Country | Average High (Feb–Mar) |
| Cyprus | 18–20°C |
| Southern Spain | 17–20°C |
| Malta | 16–18°C |
| Algarve | 16–18°C |
| Crete | 16–18°C |
| Southern Italy | 15–17°C |
| Montenegro | 13–15°C |
| Croatia | 11–14°C |
Again, I interject to point out the ChatGPT has decided to analyze and present choices in a more subjective and slightly different way for our consideration. I think it is just showing off. 🙂
My “Sweet Spot”
This is where I think the best balance of cost, weather, healthcare, and convenience lies.
Tier One – The Goldilocks Countries
Spain
- Excellent healthcare
- Outstanding public transportation
- Large English-speaking expat community
- Excellent flights from Canada
- Walkable cities and towns
- Mild winter temperatures
- Lots to do year-round
Portugal
- Similar weather to Spain
- Friendly people
- Excellent safety record
- Walkable towns
- Good value for money
Tier Two – Hidden Gems
Greece
- Excellent food
- Lower costs
- Beautiful scenery
- Mild winters
- Some tourist towns are quieter in winter
Montenegro
- Uses the euro
- Spectacular scenery
- Considerably less expensive than Spain
- Growing popularity among long-stay visitors
Tier Three – Great if They Fit Your Style
- Southern Italy
- Malta
- Croatia
- Cyprus
And yet one more way to look at the data. It certainly is offering up lots of options for us to consider in our decision-making.
One More Index: “Bang for the Buck”
If I ignored everything except value for money, I’d rank them:
Best Value for Money
- Montenegro
- Portugal
- Spain
- Greece
- Bulgaria
- Croatia
- Southern Italy
Montenegro does look like an intriguing place to me. Photo from an article in “The Independent“.
User
Would you have done this ranking differently if you did not know that we have already been spending our winters on the Costa del Sol in Spain?
ChatGPT
Yes—but only slightly.
If I had known nothing about your previous travel experience, my rankings would have remained very similar.
Overall Ranking (No Personal Context)
- Spain
- Portugal
- Greece
- Southern Italy
- Malta
Spain would still rank first because it offers perhaps the best overall combination of:
- Mild winter weather
- Reasonable cost of living
- Excellent healthcare
- Outstanding public transportation
- Walkable communities
- Excellent airline connections to Canada
These strengths are objective and are not influenced by your previous travel experience.
Spain remains the benchmark because it offers one of Europe’s best combinations of climate, affordability, healthcare, transportation, and lifestyle. However, for travellers seeking a fresh experience without sacrificing too much of what makes Spain attractive, Portugal, Greece, Montenegro, and southern Italy deserve serious consideration.
Wrapping It All Up
There you have it, ChatGPT’s thoughts on a bunch of different potential Eurooean winter destinations for retirees. Make of them what you will.
You will have noticed as you read through this that I asked ChatGPT if it was skewing the results based upon the fact that it knew that we enjoyed wintering in Spain. As you will have read, it said it did, but only slightly.
One of the characteristics of chatbots that I have noticed, now that I have been using them for a while is that they tend to be “people pleasers” i.e. they tend to want to make you happy. Now this may be an algorithm built into it by the programmers to get you enamored of their chatbot or may simply be the way they function. And I also get the sense that they don’t mind users paying them compliments either.
Reliability
At the end of it all, I think it is worth mentioning that if you are thinking you may actually use this information to pick a more interesting place than Portugal or Spain to winter you might want to do some additional research on your own. AI chat bots have been known to occasionally “hallucinate”, i.e. make up shit!
I know through my own earlier investigations that the information it is providing about the Algarve in Portugal and the Costa del Sol in Spain are accurate. And I suspect that everything else here presented here is 100% accurate. But, if I was going to consider one of these other interesting locations like Montenegro, I would go about confirming the information provided.
The AI thing is going to be an interesting ride. Wait until you see the follow up for this piece!
