I let AI plan my summer vacation to Barbados, here’s how it went

I let AI plan my summer vacation to Barbados, here’s how it went

If you've been on the internet for any amount of time during the last year, you’ve most likely heard of Artificial intelligence and all the magical things it can do. While I know there are many concerns around using it (and the lingering fear that it could one day take my job), I have to admit - watching the millionth content creator plan their entire vacation in just 5 minutes was intriguing. 

I also happened to be in the middle of planning my summer getaway to Barbados, and after looking at the seventh or eighth listicle titled ‘The best beaches in Barbados’, I was more than intrigued - I was convinced that it would be so much easier to put my plans in the (non-existent) hands of the AI.

Would Artificial Intelligence be able to understand the nuances of planning a trip? Or would it be a disaster from start to finish? Only one way to find out. 

I would let AI choose what I did and where I went in my holiday itinerary…and here are the (very mixed) results. 

Choosing the right AI

The first step in getting an AI to plan my itinerary was deciding on which AI to use. While we’re all familiar with the popular kid on the block, ChatGPT, there are also a number of other platforms that have come up specifically for travelers.

First, I gave ChatGPT a try, by prompting it to provide a 7-day itinerary with my arrival and departure time and budget.  It initially gave some not-so-great results. CHAPTGPT Itinerary prompt

ChatGPT first try

But with a little tweaking and some prompt engineering magic (adding as many details as possible and asking it to pose as a travel planner), I had a budget-friendly itinerary that was just right for me.

CHAPTGPT Itinerary prompt

ChatGPT second try

Next, I explored GuideGeek, a specialized WhatsApp AI designed for travelers, and here's the result:

GuideGeek AI Prompt

GuideGeek WhatsApp AI

Not bad... Not bad… but one thing I noticed, neither itinerary took into account my energy levels. I didn't want to end up needing a vacation to recover from my vacation, which leads me to my first tip for anyone using AI to plan their travels:

Tip #1: Remember that AI doesn't know how you feel, so be sure to adjust your itinerary to fit your energy levels.

Once I fused both drafts from ChatGPT and GuideGeek, I realized that I would still have to do some searching myself. So, I made sure to cross-check with as many "things to do in Barbados" articles as possible - so I don't miss out on anything major. Good thing I did, I nearly missed out on the highlight of my trip - the Ostins Fish Fry!

In a world where AI was perfect, I wouldn't have had to double-check my itinerary at all. Just set and forget. But let's be real, we're not quite there yet. 

After tweaking the plan a few times, I was finally ready to pack my bags (or over-pack, in my case) and hit the road. 

Should you let AI choose where to stay?

Before diving into our plans, let's address the age-old question of where to stay. I tried using AI to find a good spot, but the results were less than stellar.

I personally think it's better not to rely on AI when searching for a place to stay. I found that many AI programs, like ChatGPT, only rely on past data to make recommendations, so they may not have the most accurate pricing information. 

Also, they tend to suggest only well-known hotels/accommodations, which may not always be the best fit for your needs. For example, my travel buddy and I were looking for a two-bedroom, two-bathroom configuration, which is a bit harder to come by in the big hotels and resorts. 

We ended up taking our friends' advice and stayed at BLR Beach Resort in St. Lawrence Gap. It was the perfect spot, with easy access to the airport, beaches, restaurants, nightlife, and more. 

Tip #2: To get more bang for your buck, don't rely on AI to find you a place, as chances are the lesser-known gem won't show up.

Day 1

AI itinerary:

  • Bridgetown walking tour 
  • Dinner by the boardwalk

What we actually ended up doing:

We arrived on a pink-eye flight on Tuesday night, and with not a lot of people around, we breezed through customs. Our friend picked us up, and we self-checked into our apartment and went straight to bed. 

The next morning, we strolled through St. Lawrence Gap to get our bearings. The cobblestone streets were lined with either hotels, bars, beaches, or all three - but it was surprisingly quiet and peaceful. 

St. Lawrence Gap

St. Lawrence Gap

We talked to a few taxi drivers to get an idea of how much it would cost to visit the places we had planned. As expected, it was a bit pricey (St. Lawrence Gap is a tourist area after all), but lucky for us - we had a friend willing to drive us around when he could. And he just happened to be free today to show us around Bridgetown!

Tip #3 - Don’t rely on AI prices, always ask someone on the ground (or the JFC community). Neither ChatGPT nor GuideGeek mentioned the cost of transportation to our activities, and as the ChatGPT disclaimer stated ‘the prices of tours can also vary depending on season and availability’.

Exploring Bridgetown with the help of a local was a lifesaver, as our plan to self-guide using the GPSmyCity app would have left us spinning in circles. But having the app gave us context and history of the island, making the experience even better. 

 Bridgetown Barbados


We originally planned to spend the entire day exploring the city, but the heat got the best of us, and we had to cut our visit short. 

But that just left us with more time to enjoy dinner at Happy Days bar in St. Lawrence Gap. And let's just say our first taste of Barbados' famous rum punch got us dancing the night away to a band of two as they sang through ABBA’s back catalog!  

Tip #4 - AI doesn't take into account the weather or the timing of activities, so plan accordingly! It wasn’t ideal to plan our walking tour around Bridgetown during the heat of the day - no thanks, AI. 

Rum punch

Day 2

AI itinerary:

  • Swim with the horses in the morning
  • Head to the wildlife reserve in the afternoon
  • Fine dining on Lawrence Gap

What we actually ended up doing: 

Unfortunately, we overslept and missed our chance to swim with the horses. On top of that, I realized that traveling to the wildlife reserve would have been a hassle as it was located on the opposite end of the island. So, I filled the gap by moving our visit to the George Washington Museum from tomorrow’s itinerary. 

Tip #5: Transportation is key! AI may suggest places far away from each other, so make sure to group locations together for easier travel.

It was also the perfect opportunity to try out the public transportation - "z" taxis, as they're called, to get me there. 

On the way, I had a bit of a mix-up with the bus conductor about change. He had a strong accent and it was hard for us to understand each other, but thankfully with the help of Google Maps and a kind stranger, I made it to my destination. 

The George Washington house is a fantastic visit if you love history, or like to think about what it was like living in the past. Although it was restored many years ago, it still looked immaculate and authentic, complete with little trinkets like these fancy shoes! 

George Washington soes

George Washington's shoes

The tour was self-guided — I was given a guide remote and a map and sent out on my adventure. 

Initially, it was a bit eerie being the only guest there (possibly due to visiting on a weekday during the slow season), but soon enough I was fully immersed in the 18th-century world. 

After viewing the short film, I made my way through the kitchen, bathhouse, and a museum on the top floor. There was also an underground tunnel which I noped out of, and instead opted for a drink at the quaint little café on the grounds and picked up a souvenir t-shirt. 

George Washington house

George Washington houseGeorge Washington

As I was leaving, I noticed that the National Museum was also close by, and I decided to check it out too. This is a site that AI didn’t include in my itinerary, even though it was so close. This museum was also self-guided, but without the guide remote.

The museum showcased all aspects of Barbadian life, from the flora and fauna to the history of Barbadian culture and, of course, priceless art. There was even an interactive science room for kids (and kids at heart). 



I got so wrapped up in the museum that I lost track of time, and before I knew it, it was closed - and I was locked in. Not wanting to have my own night in the museum experience (and also being hungry), I tried calling out multiple times, but there was no one around to let me out. After a few attempts to open the medieval gates, I finally noticed a smaller gate within the larger one, and it opened up to FREEDOM!

Afterward, tired and hungry I wandered through Garris Square, hopped into a z-taxi and headed to Chefettes (Barbados' more flavourful KFC)–the fine dining would have to wait another day. 

Day 3

AI itinerary:

  • George Washington's house tour
  • Beach day

What we actually ended up doing:

Another morning of sleeping in too late meant missing the horses at Pebbles Beach - again. But hey, we made up for it by having a chilled-out beach day at Dover Beach, which was perfect with its crystal-clear water, white sand, and blissful seclusion. It wasn't until we left that we found out about the nearby pink sand beach, but you can't do it all in one day, can you? For those counting, this was another site that AI didn’t pick up. 

Dover Beach

And that wasn’t the only place AI skipped out on: later in the day, we stumbled upon an archery spot while taking a walk along The Gap. Luckily, we got to secure same-day booking, and had lunch at Mimosas Trattoria Restaurant directly opposite while we waited. The food was decent, and the archery session was an absolute blast thanks to our incredibly patient tutor. 

Tip #6: Don't solely rely on AI to pick your destinations. We almost missed out on hidden gems like the archery place. And later found out about a vintage car museum and observatory.

We could definitely have spent the rest of the day perfecting our bow techniques, but we had to save our energy for the main event: the fly fish at Ostin's Market.

I had never seen anything like it before. There was a massive stage to the right and food trucks to the left. We ordered the famous fly fish, which was a treat. I paired mine with some fries and a local beer called Banks (which is pretty great if you like your beer less bitter). 

Fly fish

As we ate, we watched one performance after another, from choreography to dance-offs to DJ sets. The crowd was huge, which was surprising since this happens every weekend! 

Once we’d finished eating, we joined in on the party, walking through the market and checking out the souvenirs and trinkets. On the other side of the stage was a bar that played loud country music for the older folks (somehow, the music coming from the stage couldn't be heard from the bar at all). Truly something for everyone. 

We bought a few rounds of rum punch (yep, that’s a theme of this holiday!), headed back to the stage, and danced the night away with different DJs. We even made some new friends along the way.

Day 4

AI itinerary:

  • Submarine Tour
  • Harrison Cave

What we actually ended up doing:

I had a complete blast exploring Harrison's Cave and the submarine tour, but it didn't exactly start off on the right foot. I was out way too late the night before and ended up missing my bus for the prepaid tours (this makes it the 4th day in a row of waking up late - clearly we’re officially on holiday hours). 

Panic set in as I frantically searched for a taxi to get me there in a hurry (which meant spending an extra $100 BBD – about $50 USD). The kind old man driving the taxi did his best, but we weren't exactly breaking any speed limits. 

I finally arrived at the venue, ready to accept my fate of missing out on the tours, but luckily the tour manager had arranged for me to join the later crew, and I could breathe a sigh of relief. 

I started off exploring Harrison's Cave, which was absolutely breathtaking. The size and beauty of it all left me in awe. Plus, the venue had other activities like ziplining, obstacle courses, and even a *gasp* rum tour. But I had only planned on going through the caves, and that alone was definitely worth it.

Harrison Caves

After the tour, I was picked up by my guide and taken to the submarine tour. This was my first time ever being in a submarine: 10/10 would highly recommend it, but 0/10 recommend going when you're hungover. 

It's especially great if you're not a strong swimmer since it's probably the only way you'll see corals and shipwrecks. 


Fun fact: I went on the tour a day before the news about Ocean Gate broke...

Tip #7: AI may not take into consideration the time it takes to do things. So, you might find yourself going on back-to-back day trips or, like in my case, going to a late night event before an early morning tour. So, plan accordingly!

Day 5

AI itinerary:

  • Island tour

What we actually ended up doing:

Cue the break. At this point in our vacation, I was feeling pretty drained. We decided to skip the island tour and just enjoy another relaxing day on the beach, indulging in some delicious Cheffettes.

Day 6

AI itinerary:

  • St Nicholas Abbey
  • Speightstown museum.

What we actually ended up doing:

After a day of full resting, we finally got up early enough to swim with the horses - a last day miracle! The racing horses come down every morning to bathe, and their handlers were very friendly and let us help wash them.

Then, it was off to catch up with all the things we didn’t get to do in the other parishes.

We drove through Speightstown and stopped at the Speightstown Jetty for a quick photo op. After a bit of driving, we finally got to visit the wildlife reserve from day 2 - again, a self-guided tour. Although given the animals were mostly free to move about, I’d have appreciated a guide.

And after a lot of avoiding turtle… *cough cough* coitus, it was time to watch the chaos of feeding time in all its glory. 

Wild life reserve

Once feeding time was over, it was on to the Grenade Hall Forest. It was a little more of a tranquil experience - except if you’re directionally challenged like I am, as again the tour was self-guided (I’m beginning to think there just aren’t enough people on the island to lead tours)

I walked through the forest, which was great. But the fear of getting lost was greater, so I turned back and left.

Grenade Hall Forest

Grenade Hall Forest

The next stop was the St. Nicholas Abbey train tour, but we got there just too late. Instead, we spent the rest of the day taking in the countryside. And it definitely wasn’t a bad compromise :-)

Countryside view

My last dinner was at Champers - totally worth it for the views of the sunset alone, but the food was also amazing.

Champers restaurant

Champers Restaurant

And then it was time to pack up. I’ll say it again: don't be like me. Don’t over-pack.

The verdict:

Did I have a good time on my vacation planned by AI? Yes.
Did all go as planned? No, but it’s vacation, they never go as planned. 
Would I do it again? Yes, but I’ll only use it as a starting point. When prompting, I’d consciously ask it to consider things a human would unconsciously keep in mind like the weather, distance, and closing times for each activity.

If you haven't read any of the above and just want the tips, here’s the TLDR based on my experience.

7 Tips to planning your vacation using AI

  1. Remember that AI doesn't know how you feel, so be sure to adjust your itinerary to fit your energy levels.
  2. To get more bang for your buck, don't rely on AI to find your accomodation, as chances are the lesser-known gem of a place won't show up.
  3. Transportation is key! AI may suggest places far away from each other, so make sure to group locations together for easier travel.
  4. Don't solely rely on AI to pick your destinations just yet. We almost missed out on hidden gems like the archery place. And later found out about a vintage car museum and observatory.
  5. AI may not take into consideration the time it takes to do things. So, you might find yourself going on back-to-back day trips or, like in my case, going on a late night event before an early morning tour. So, plan accordingly!
  6. AI's prices may be a bit off. They may not always reflect the true cost of getting to your activities, and the prices of tours can also vary.
  7.  AI doesn't take into account the weather or the timing of activities, so plan accordingly!