Ready for your next getaway? I use these 7 ChatGPT plugins to find the best local tours, organize an existing itinerary and more before I travel
Prepping for a getaway is less headache-inducing with these plugins
There’s a list of things that bring equal levels of excitement and stress with them: moving to a new place, starting your own business and going on a first date are among those activities.
For me, setting up everything I need to enjoy a future vacation is also on that list. The months of preparation that go into ensuring my flight plans, hotel stay and getaway plans go off with as few problems as possible are nerve-racking. I’ve watched my parents get headaches from just trying to plan a family trip to Disney World, so I’ve been trying to lessen the amount of stress that comes with that sort of thing now that I do it.
There are plenty of AI tools that are specifically made to help people plan their big trips. For me, I’ve gotten a lot out of ChatGPT’s plugins since there are a good number of them that are tailor-made for vacation planning.
If you want some extra assistance during your preparation period for domestic and international excursions, be like me and use the following plugins & associated prompts to make your future vacation even better.
1. Viator
Viator is pretty much mandatory when you’re in the market for the best tours, attractions and experiences offered wherever you’re heading next for vacation. It’s always worth checking in with this plugin before you land in your latest domestic or international locale so you’ll have already set up your tour plans while you’re there. Being able to book any of your chosen tours directly from the links provided through this plugin is a definite plus as well.
Using any of the three prompts listed below should give you an idea of what to say to the Viator plugin to get the best results:
- Find three family-friendly experiences in [destination] for [date], suitable for children aged [ages]. Prioritize hands-on activities and explain which offers the best value.
- Find five food tours in [destination] for [dates], under [type of currency and budget] per person and no longer than [time limit]. Compare prices, ratings, group sizes and cancellation policies where available.
- Find up to 10 highly rated tours in [name of location], available during [travel dates]. Only include tours with a traveler rating of at least 4 out of 5 and a duration strictly under three hours. Prioritize tours with confirmed departures that start and finish during daylight hours, [name of location] local time. Show each tour’s rating, review count, duration and daytime departure options where available. Flag any unconfirmed schedule details. If fewer than 10 tours meet these requirements, return fewer.
2. Tripsy
Connecting your Tripsy account to ChatGPT via this plugin lets you manage your trip a whole lot easier. Some of the best uses that come from utilizing this plugin include summarizing your vacation plans, finding any gaps in your itinerary that could be filled with an activity, bringing up crucial reservation details you’ve been desperately searching for, etc.
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If you have any itineraries, reservations, activities or any other vacation details attached to your Tripsy, it’s worth using any of the following prompts to command ChatGPT to interact with them:
- Turn my [trip name] reservations into a day-by-day itinerary. Include local departure times, addresses, and gaps between activities.
- Review my saved [destination] itinerary for overlapping reservations, tight connections, and missing details. Rank the issues I should resolve first.
- Summarize tomorrow’s plans from Tripsy into a travel briefing: where I need to be, when to leave, confirmation details available, and anything I still need to arrange.
3. Canva
The Canva plugin is capable of creating designs and generating images based on your prompts and uploaded attachments. I’ve seen how good it is at taking an itinerary I wrote up in Google Docs and transforming it into a more digestible and easy-to-follow travel guide that I can carry around on my phone. Keep in mind that the design and image generation requests you give to Canva use up your allotted Canva AI credits based on your subscription plan.
Try out any of the following prompts to see how the Canva plugin can help you with your travel planning:
- Turn this itinerary into a mobile-friendly travel guide with one page per day: [paste or attach itinerary].
- Create a printable packing checklist for [destination, season, trip length], grouped by clothing, toiletries, electronics, and documents.
- Design a one-page arrival guide using these confirmed instructions: [details]. Make the hotel address, transfer meeting point, and contact information prominent.
4. Ticketmaster
I usually spend some time with the Ticketmaster app to see what’s going on in any parts of the US or Canada I may be heading to next. Since that event app has its own plugin, it serves as a curator that can bring up any possible basketball games, wrestling shows or concerts I may want to go to while I’m on vacation.
Doing a quick check-in with the Ticketmaster plugin to see what events you could squeeze in during your next getaways is worth trying out, especially with any of the prompts I’ve included below:
- Find concerts, stand-up comedy, and sports in [destination] between [dates]. Give me [number] options with venues, start times, and ticket links.
- Find family-friendly events in [destination] during [dates]. Prioritize afternoon performances and flag any available age restrictions.
- Find [number] events in [destination] between [start date] and [end date], based on my interests in [interests] and a budget of [amount] per ticket. Aim for [number] daytime events starting before 6 p.m. and [number] evening events starting at or after 6 p.m., using local time. If an equal split isn’t available, show the closest available mix. Include each event’s date, start time, venue, and why you recommend it.
5. Target
There’s plenty of shopping to be had when it’s time to get a new suitcase, carry-on bags and toiletries that won’t get thrown away if they don’t meet airport security standards. Target is home to all of those assorted travel goods, so spend some time with its ChatGPT plugin to go searching for all the items you need at the prices you can afford.
Tapping into the Target plugin to find all the gear and items you need before traveling works hand in hand with the following prompts:
- Build a travel essentials shortlist under [dollar amount] for a [number]-day trip. Search for toiletries, packing organizers, and a reusable water bottle.
- Find carry-on suitcases under [dollar amount] and compare their listed external dimensions with this airline limit: [dimensions]. Flag any missing measurements.
- Find travel adapters for [destination] compatible with my [devices]. Distinguish plug adapters from voltage converters and flag compatibility I need to verify.
6. AllTrails
Whenever I’m heading somewhere that’s known for having scenic views that are best experienced while walking on a nice hike, I tap into the AllTrails plugin to see where it can lead me. I’m usually not trying to work up a big sweat while I’m in vacation mode, so I prefer getting suggestions for easily manageable hikes I can enjoy.
Using any of the prompts seen below should help expand your itinerary with a fun hike for you and maybe a few other friends & family members to head out on:
- Find [number] beginner-friendly hikes near [destination] for [travel dates]. I’m comfortable walking [distance in miles], prefer minimal elevation gain, and will have [a rental car or public transportation]
- Find five easy hikes near [destination], under three miles with less than 500 feet of elevation gain. Compare scenery, estimated duration, and ratings.
- Find family-friendly trails near [destination] suitable for [children’s ages], taking under two hours. Include route type and any available suitability information.
7. AccuWeather
Of course, everyone and their grandmother does some heavy research into the forecast for wherever they’re planning to fly or drive off to next. Count me among that group since I’d hate to pop up at another international location during its rainy season (I did that back in 2016 when I flew over to Tokyo, Japan, but I still had a great time). The AccuWeather plugin exists inside ChatGPT to give you a clear picture of how the local weather will impact your stay wherever you’re staying for vacation.
Taking advantage of that plugin with any of the following prompts should highlight how good it is for vacation planning:
- Check [destination] for [dates]. Summarize temperatures, rain chances, and alerts, then suggest a packing list. State which dates are beyond the available forecast.
- Compare tomorrow morning’s and afternoon’s hourly forecasts in [destination]. Which looks better for a [time limit] walking tour, considering rain, heat, and wind?
- Check today’s weather and official alerts in [destination]. Help me choose between [outdoor activity] and [indoor activity], and explain the weather factors behind your recommendation.
The takeaway
Beyond these ChatGPT plugins that are perfect for improving your vacation planning experience, there are a bunch of other ones that fulfill that same objective. Using Spotify to build the perfect road trip playlist and tapping in with Gmail & Google Calendar to search & review all the travel info contained within both accounts and are clear examples of that. My seven preferred plugins and the prompts that put them to work come in clutch when it’s time to get ready for my latest domestic or international departure.
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Elton Jones covers AI for Tom’s Guide, and tests all the latest models, from ChatGPT to Gemini to Claude to see which tools perform best — and how they can improve everyday productivity.
He is also an experienced tech writer who has covered video games, mobile devices, headsets, and now artificial intelligence for over a decade. Since 2011, his work has appeared in publications including The Christian Post, Complex, TechRadar, Heavy, and ONE37pm, with a focus on clear, practical analysis.
Today, Elton focuses on making AI more accessible by breaking down complex topics into useful, easy-to-understand insights for a wide range of readers.
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