Travel planning is undergoing a transformation. Big players in the industry have released generative AI technology that promises to simplify the complexities of organizing your trips—for free.

In April 2023, Expedia and Kayak began offering plugins that integrate with ChatGPT 4, giving you the power to look at airline and hotel prices. Guide book company, GetYourGuide, followed shortly thereafter. April also saw publishers, the Matador Network, launch GuideGeek. This travel planning AI uses WhatsApp or Instagram to communicate.

Over the summer, Tripadvisor added an AI feature to its Trips section. To fill up your itinerary, just enlist the help of AI.

But how well does the technology work? It better than asking Google? To find out, I tested out some of the most talked-about AI platforms available for vacation planning.

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GuideGeek: The Social Connector

GuideGeek Homepage

GuideGeek is a travel assistant platform developed by Matador Network, the largest independent travel publisher in the world. It, too, makes use of OpenAI’s ChatGPT technology, but meets travelers where they are—on Instagram and WhatsApp.

It aims to offer personalized travel recommendations tailored to users’ needs and interests. And it has, unsurprisingly, gained traction among travel influencers who use it for both planning and on-the-go advice.

The Experience

All I had to do was message GuideGeek on Instagram, and it started offering to help. I told it I was planning a low budget, dog friendly road trip from Philadelphia PA (where I live) to Maine.

The app was conversational and well written, making me feel good about my choices and offering sound advice. Like stopping at Sleeping Giant State Park in Connecticut, which I never would have thought of otherwise.

But, it also suggested I “stop off” in New York City to explore Central Park. Which is doable, if you like a lot of traffic on your road trips.

I decided to google the same query and less than a minute later found a great itinerary on with practical information.

Final Thoughts on GuideGeek

GuideGeek can be useful for last-minute suggestions. Its social media integration is convenient. But, I wouldn’t stop there if don’t find what you’re looking for.

Vacay: The Specialist

Vacay stands out among other travel planning AI with its specialized chatbots catering to various travel niches, from luxury to pet-friendly trips. As someone who has a lot of questions, I appreciated that it offered a lot of information up front. Like an FAQ on how to get the most out of their chatbot experience.

The Experience

I tried the pet-friendly chatbot and was impressed with the detailed itinerary it provided for a road trip from New York to Palm Springs. It recommended boutique hotels like the Monaco in Pittsburgh, where dogs stay for no cost. But also the Alexander in Indianapolis, which had a $50 non-refundable deposit I only found out about from Googling.

Upon asking for budget options, it listed pet-friendly chains like Super 8 in Moab, UT, and La Quinta in Denver.

Hopping on to my desktop, I found a few of their non-AI resources helpful, like guides on hotels and dining.

Final Thoughts on Vacay

Vacay excels in specialized travel planning. It offers both luxury and budget options, making it a versatile tool for different types of travelers. But double check everything. Details can be light.

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Expedia – Chat GPT-4: The First

Accessible via the Expedia mobile app’s homepage or as a plugin on ChatGPT 4, the OpenAI-based chatbot offers recommendations about destinations, hotels, transportation, and activities. It automatically favorites hotels that it recommends during the conversation. Currently in its beta testing phase, Expedia’s AI tool is the first of its kind among major online travel agencies.

The Experience

Expedia’s Chat GPT-4 plugin seemed the most promising of all the apps I tested. It provided specific and relevant answers to my queries.

However, it’s important to dig deeper into the recommendations. For instance, the top dog-friendly hotel it suggested? It had a $150 per night surcharge and a $100 non-refundable deposit that wasn’t initially disclosed.

Final Thoughts on Expedia

Expedia’s plugin offers a lot of promise but requires the user to conduct extra research to verify the recommendations.

Roam Around: Living Up to the Hype?

Launched in February 2023, Roam Around was one of the first AI-powered travel planning apps to generate personalized itineraries. In its first month, the platform allegedly produced over 4 million itineraries. But, there hasn’t been much chatter since.

The Experience

Roam Around keeps it simple. A Google-like search bar is where you can input your destination. I typed in “Barcelona” and left the date field blank, because I didn’t notice it. So, the app defaulted to three weeks from the day.

The app did a decent job of grouping attractions by neighborhood, offering two viewing options: an itinerary view or a map view. But the itinerary seemed like a hodgepodge of AI-generated suggestions. It could serve as a starting point for further research, but it didn’t feel easier than Google. Actually, the pins on the map view were too small to identify easily, making it hard to correlate them with specific sites.

Then, I noticed Roamy, the AI assistant that I could talk to. So I told it I wanted to go with 7 of my friends and gave it some background about what we wanted to focus our trip on.

However, Roamy started to think, but never got back to me, failing repeatedly to respond to my queries about planning a fun night out in Barcelona.

Final Thoughts on Roam Around

While Roam Around offers a straightforward approach to travel planning, it fell short in execution for me. I tried it both on MacBook and an Android Phone, and it didn’t work well on either.

Tripadvisor: A Well-Reviewed Itinerary

Tripadvisor added OpenAI’s Chat into its Trips section, offering you the option of planning your next vacation alone or with an AI assistant. It asks you important travel information such as where you’re going and when, but also your budget and interests. The platform then creates a customized itinerary based on these preferences. Or you can keep talking to the chatbot for added personalization.

One of the unique advantages of the tripadvisor bot is its ability to leverage a vast collection of reviews, and then conveniently book hotels, flights, and activities directly through its site.

The Experience

I still wanted advice on my Barcelona trip with 7 friends next week, so I asked. Or, rather I filled out its prompts, which felt more reassuring. Although, nightlife isn’t a big option on Tripadvisor, but I knew that.

But the itinerary was impressive, offering a balance of sightseeing and eating, but it also made sense geographically. That said, I only know that because I used Google maps to double-check each suggestion.

Final Thoughts on Tripadvisor

I felt very confident that the recommendations would be good. This travel planning AI was fun to use, and engaging. It made it more enjoyable to put together ideas. I’d still want to look at options before settling on something just because it has the best reviews. But TripAdvisor’s AI did a good job of making suggestions on a realistic scale.

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More Travelbinger stories:

The pros and cons of traveling with your pet

5 best pet-friendly destinations in North America

6 expert tips for flying with your pet

5 reasons you should book a vacation rental over a hotel

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