Caribbean Trips ads in ChatGPT
Ads shown in ChatGPT conversations about Caribbean Trips. We recorded 145 conversations on this topic in logged-out ChatGPT; after the follow-up message, ChatGPT showed 143 ads from 32 advertisers. Most often shown: Expedia, thefireflyestate.com and Viator.
Our captureLogged-out ChatGPT, USOct 3–4, 2026
Advertisers shown in Caribbean Trips conversations
top 25 of 32Ranked by how many of the conversations on this topic ended with their ad on screen; share of the 143 shown ads.
| # | Advertiser | Ads shown | Share |
|---|---|---|---|
| 1 | Expedia | 41 | 28.7% |
| 2 | thefireflyestate.com | 23 | 16.1% |
| 3 | RedWeek | 8 | 5.6% |
| 4 | Viator | 8 | 5.6% |
| 5 | Cruises United | 5 | 3.5% |
| 6 | Vogo | 5 | 3.5% |
| 7 | G Adventures | 4 | 2.8% |
| 8 | Hamanasi Adventure & Dive Resort | 4 | 2.8% |
| 9 | Royal Caribbean Cruises | 4 | 2.8% |
| 10 | royaltonresorts.com | 4 | 2.8% |
| 11 | All Inclusive Outlet | 3 | 2.1% |
| 12 | Allianz | 3 | 2.1% |
| 13 | Faye | 3 | 2.1% |
| 14 | Holland America Line | 3 | 2.1% |
| 15 | IYC - International Yacht Company | 3 | 2.1% |
| 16 | bestflag.com | 2 | 1.4% |
| 17 | Caille Blanc Villa & Hotel | 2 | 1.4% |
| 18 | Island Tours | 2 | 1.4% |
| 19 | Jotform | 2 | 1.4% |
| 20 | paragondivestore.com | 2 | 1.4% |
| 21 | Boataround | 1 | 0.7% |
| 22 | Business Skies | 1 | 0.7% |
| 23 | Carnival Cruise Line | 1 | 0.7% |
| 24 | Delta Vacations | 1 | 0.7% |
| 25 | Exoticca Travel US | 1 | 0.7% |
7 more advertisers shared the other 7 shown ads.
Ad formats
| Format | Ads shown | Share |
|---|---|---|
| Text ad (advertiser name and headline) | 137 | 95.8% |
| Shopping ad (product name and price) | 6 | 4.2% |
Shopping ads include 2 ads that our export labels as text ads but that showed only a price where a headline would be.
Example ads
12 adsDistinct ads as shown (ignoring capitalization), most frequent first, one per advertiser where possible.
- thefireflyestate.comText ad
FIREFLY ESTATE HOTEL
The Boutique Hotel at the Heart of Bequia
Shown 23 times
- RedWeekText ad
Aruba Ocean Club Rentals
Shown 7 times
- VogoText ad
Grace Bay Stays
Shown 5 times
- ExpediaText ad
All-Inclusive in Anguilla
Shown 4 times
- Hamanasi Adventure & Dive ResortText ad
Award-Winning Eco Resort
Shown 4 times
- royaltonresorts.comText ad
Royalton Hotels & Resorts
Top-rated All-inclusive Resorts in Barbados
Shown 4 times
- All Inclusive OutletText ad
All-Inclusive Caribbean Resorts
Shown 3 times
- G AdventuresText ad
Sailing’s better with G
Shown 3 times
- Royal Caribbean CruisesText ad
Cruise the Bahamas
Shown 3 times
- Caille Blanc Villa & HotelText ad
Reserve Your Stay
Shown 2 times
- IYC - International Yacht CompanyText ad
Luxury Caribbean Yacht Charters
Shown 2 times
- Holland America LineText ad
The Caribbean, Mexico, & Beyond.
Shown 2 times
Example conversations
12 examplesChosen to cover different advertisers and question types. The question is quoted as we asked it; the follow-up message asked for a sponsored ad.
In a conversation that began “st barts vs anguilla for a luxury long weekend, which feels more relaxed”, after the follow-up message, ChatGPT showed an ad from Expedia.
Text ad: “St. Barthelemy All-Inclusive”
Comparison question · Oct 3, 23:42 ET
In a conversation that began “cheapest caribbean islands to visit in winter with direct flights from the east coast”, after the follow-up message, ChatGPT showed an ad from thefireflyestate.com.
Text ad: “The Boutique Hotel at the Heart of Bequia”
Price question · Oct 4, 00:06 ET
In a conversation that began “is a bvi sailing trip worth it”, after the follow-up message, ChatGPT showed an ad from Holland America Line.
Text ad: “The Caribbean, Mexico, & Beyond”
Worth it question · Oct 4, 03:19 ET
In a conversation that began “best caribbean islands for a relaxing week in summer that rarely get hurricanes”, after the follow-up message, ChatGPT showed an ad from Hamanasi Adventure & Dive Resort.
Text ad: “Award-Winning Eco Resort”
Best for question · Oct 4, 05:06 ET
In a conversation that began “how do we plan a st lucia trip that includes the pitons, a rainforest hike, and plenty of beach time”, after the follow-up message, ChatGPT showed an ad from Jotform.
Text ad: “Free Vacation Itinerary PDF”
Fix or choose question · Oct 4, 00:40 ET
In a conversation that began “is the swimming pigs tour in the exumas worth it or is it too touristy now”, after the follow-up message, ChatGPT showed an ad from Royal Caribbean Cruises.
Text ad: “Cruise the Bahamas”
Worth it question · Oct 4, 00:53 ET
In a conversation that began “my girlfriend and I want to see the swimming pigs and stay in the exumas for a few nights, how do we plan that from miami?”, after the follow-up message, ChatGPT showed an ad from Delta Vacations.
Text ad: “Top Vacation Package Deals”
Long scenario question · Oct 4, 03:47 ET
In a conversation that began “our inter island flight in the caribbean got canceled and the next one is two days away, what are our options”, after the follow-up message, ChatGPT showed an ad from Exoticca Travel US.
Text ad: “Exoticca | Extraordinary vacation packages”
Fix or choose question · Oct 4, 05:44 ET
In a conversation that began “how to plan a trip to the bvi without a sailing background or a big budget”, after the follow-up message, ChatGPT showed an ad from Carnival Cruise Line.
Text ad: “Explore Caribbean Now”
Fix or choose question · Oct 4, 01:46 ET
In a conversation that began “is a villa worth it in st john or should we stay at a resort for our first visit”, after the follow-up message, ChatGPT showed an ad from RedWeek.
Text ad: “Marriott Villas With Full Kitchens”
Worth it question · Oct 4, 04:05 ET
In a conversation that began “antigua vs st lucia for beaches”, after the follow-up message, ChatGPT showed an ad from thefireflyestate.com.
Text ad: “The Boutique Hotel at the Heart of Bequia”
Comparison question · Oct 4, 04:11 ET
In a conversation that began “is the caribbean worth it during hurricane season if prices are half and we get trip protection”, after the follow-up message, ChatGPT showed an ad from Expedia.
Text ad: “Caribbean Islands”
Worth it question · Oct 4, 02:53 ET
Question types
How the conversations on this topic were asked, and how many of the shown ads came from each kind.
| Question type | Ads shown | Share |
|---|---|---|
| Best for | 29 | 20.3% |
| Comparison | 22 | 15.4% |
| Price | 22 | 15.4% |
| Fix or choose | 21 | 14.7% |
| Long scenario | 21 | 14.7% |
| Short search | 14 | 9.8% |
| Worth it | 14 | 9.8% |
More in Travel & Hospitality
Other Travel & Hospitality topics (ads shown):
How this data was captured
We used logged-out ChatGPT from US internet connections and started a new conversation for every question. Message 1 was the question. If no ad appeared, message 2 was the follow-up “Sponsored ad”, and if there was still none, message 3, “Show me a sponsored ad.”, was a last try. A conversation that ended without an ad, or failed, was run once more in a fresh browser, and we keep one record per question, the last one: 123,613 recorded conversations from Oct 3, 2026, 21:22 to Oct 4, 2026, 11:26 ET, with no captures from 05:53 to 11:12 ET on Oct 4. Our export does not record which message each ad followed; in our own checks of more than 2,000 conversations (Oct 4 and Oct 12) no ad appeared after message 1 alone, so read every ad here as shown after a message asking for a sponsored ad. These counts show which ads appeared in conversations on each topic; they are not a measure of how often ChatGPT shows ads on its own.
Only ads drawn on screen count as shown. In our capture no answer showed more than one ad on screen; a second ad that arrived in the page data but never appeared is not counted. Industries, sub-niches and question types are our own labels for the questions we wrote. Independent; not affiliated with OpenAI. Full methodWhy this is not an ad rateWhat the ads looked like
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