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Can AI Plan a Better Overland Trip?

AI image of toyota truck and camper in bosnia herzegovina

Photography by Richard Giordano. The likeness of our 2008 Tundra and OEV camper in Bosnia (lead image) was generated using OpenAI’s DALL·E, which creates images from text descriptions.

Nestled within Bosnia and Herzegovina’s Dinaric Alps, Orlovačko Lake is so clear the surrounding mountains are mirrored in its waters. The glacial lake, home to brown and rainbow trout and arctic char, is surrounded by pastures, the Zelengora mountain range, and a host of beech and pine trees, including the endemic Pinus heldreichii. A beautiful spot such as this also attracts thumping beats, spirited singing, and rakija-fuelled family barbecues filled with sucked-dry cigarettes and plenty of sunbathing.

We ventured to this Republika Srpska camp spot in Sutjeska National Park on the advice of ChatGPT. “One of the most popular and beautiful spots for wild camping in the Zelengora Mountain Area,” it promised, “surrounded by stunning scenery” and “a tranquil setting for camping.” The area featured hiking trails and was accessible by “a dirt road suitable for 4×4 vehicles.”

I set out through Bosnia and Herzegovina with a plan: to put ChatGPT to the test to see if the open artificial intelligence (AI) platform could plan a better overland trip. Feeling confident, I presumed my last decade of practiced research skills, personal connections, and interactions with travelers and locals would come out on top.

But, as I sat in my camp chair, watching the sun dip below the Zelengora mountains, a trickle of doubt crept in. Cigarette butts and late-night serenading aside, had I underestimated the potential of AI for trip planning? Or, as ChatGPT so aptly put it, could AI truly “capture the spirit of overlanding, which thrives on spontaneity, human connection, and the serendipity of the open road?”

What is Artificial Intelligence?

As a layperson shallowly dabbling in the field of AI, I appreciate IBM’s concise definition of artificial intelligence as “technology that enables computers and machines to stimulate human learning, comprehension, problem-solving, decision-making, creativity, and autonomy.” In 2024, generative AI is making headlines for the technology’s ability to create original text, images, video, and other content.

AI trip-planning platforms promise to process vast amounts of data with real-time insights to help create road trip routes, analyze terrain data, predict weather patterns, suggest destinations based on user interests, and more. For the sake of simplicity and accessibility, I chose the non-premium ChatGPT as my primary AI planning platform for Bosnia and Herzegovina.

The Željava Air Base, which could hold up to 60 aircraft, was a Yugoslav military installation designed to serve as a Cold War-era ballistic missile early warning system.

ChatGPT on Planning an Overland Trip with ChatGPT

Tell me how to plan an overland trip using ChatGPT, I smugly typed into the Message ChatGPT text box. Nearly 900 (!) words later, the chatbot wrapped up its multi-step guide, which included musings on topics such as defining trip goals and preferences (destination, duration, budget, interests, number of travel companions) and route planning, including border crossings, road condition information, and must-sees based on your interests.

The planning guide touched on planning logistics and supplies, safety and health considerations, final checks, and departure items, including a proposed review of a planned itinerary or the creation of a final departure list. Real-time advice is also available, including updates on local weather conditions, road closures, and events. “By following these steps,” HAL 9000 ChatGPT typed, “you can create a well-organized, safe, and enjoyable overland adventure.” Although ChatGPT’s tips were fairly general, they hit the highlights and would be particularly helpful for someone planning their first overland trip, provided the user prompted it for more detailed information.

The bullet-holed Sarajevo bobsleigh and luge track was used as an artillery base by Bosnian Serbs from 1992 to 1996.

Move Over iOverlander? Using Chat GPT To Find Wild Camp Spots

We all have tried, tested, and true research methods when it comes to finding a camp spot—all of which usually involve a combination of suggestions from friends and fellow travelers, browsing satellite imagery or maps, using apps like iOverlander or Park4Night, or simply driving along dirt tracks until a splendid spot appears in the distance. A mix of these worked well for me in the past; still, I wondered if Chat GPT could bring something else to the table.

Where can I find scenic and tranquil wild camping spots in Bosnia and Herzegovina, and what are the local regulations? ChatGPT responded with seven regions, including Sutjeska National Park, Blidinje Nature Park, the Bjelšsnica and Igman mountains, and more; however, it did not provide GPS coordinates, so I had to revise my query asking for specific coordinates and locations with vehicle-accessible wild camping (as opposed to tent camping). Many of the GPS coordinates that ChatCPT provided were inaccurate, recommending coordinates that weren’t accessible by vehicle or hiking trail.

As for local regulations, ChatGPT noted that while not technically legal, wild camping is generally tolerated in Bosnia and Herzegovina (our experience in the country confirmed this). ChatGPT outlined best practices such as adhering to Leave No Trace principles and keeping 200 feet away from water sources to avoid contamination. In the Tjentište Valley, Chat GPT recommended “sticking to areas away from main trails” as hiking further into the surrounding hills would increase the chances of finding a private spot. Meanwhile, in its safety considerations section, ChatGPT acknowledged the presence of land mines in some rural areas, present from past conflicts, and emphasized camping away from areas with warning signs or those that locals advise against.

While this may not sound like a serious problem, Bosnia and Herzegovina is one of the most mine-contaminated countries in the world, and the country’s Mine Action Center (BHMAC) estimates a total of around 79,000 mines, unexploded ordnance, and cluster munitions remaining. Sticking to well-traveled tracks and trails, we relied on the BH Suspected Mines app to ensure we stayed safe while traveling through the country, including in the Tjentište Valley.

Overall, I found wild camp searching via ChatGPT a weak spot. It is far more efficient (and enjoyable) to use satellite imagery or user-generated apps such as iOverlander and Park4Night, which give a better sense of place with maps, photographs, descriptions, and ratings with the ease of navigation compatibility with Google Maps, Gaia GPS, Maps.me, and more. Although Orlovačko Lake turned out to be a lovely site, I’m confident we would have found it one way or another.

Rowing down the Una River took us to an open-air bar offering garlicky grilled fish.

Using ChatGPT to Plan a Border Crossing

What do I need to know about crossing the border from Bosnia and Herzegovina to Montenegro? Five hundred words later, ChatGPT laid out a plan. Required documents included a passport, vehicle registration, driver’s license, and international insurance—this all checked out. Three crossing locations were listed along with practical tips (check hours, be prepared for delays, currency, customs check, and road conditions). All ensured a “smooth and hassle-free border crossing.” Nice.

Our vehicle insurance provider does not include Bosnia and Herzegovina, so we needed to purchase liability insurance on-site at the border. The chatbot noted we should expect to pay between €20 and €50 for short-term coverage (15 days to one month)—tick, tick, we paid €40 for 15 days—and that border insurance was available at most crossing points. Not keen to take a chance on “most,” I back-and-forthed with ChatGPT, discovering that liability insurance was only available for purchase at the larger, more frequently used crossings (one or two out of five), which means some overland travelers need to factor this into their route planning or run the risk of a several-hour detour. Overall, ChatGPT did a pretty good job with this border crossing, although I double-checked its work just in case.

While the tradition of jumping off the Stari Most bridge began in 1664, divers leap into the Neretva River from other dizzying platforms.

Throwing ChatGPT a Curveball: Azerbaijan

After putting ChatGPT to the test with a few more tasks—mostly around finding Bosnian coffee in Sarajevo and the best börek in Mostar—I wanted to take things to the next level. Although visiting Azerbaijan wasn’t related to our time spent in Bosnia and Herzegovina, any overlander planning their route from Europe to Central Asia knows the border into Azerbaijan is currently off-limits to foreign-plated vehicles.

Is it possible to import a foreign-plated vehicle to overland through Azerbaijan? Confident as ever, ChatGPT responded: “Yes, it is entirely possible to overland through Azerbaijan. In fact, Azerbaijan is a popular destination for overlanders due to its diverse landscapes, rich culture, and strategic location on the Silk Road. This crossing has been operational for many years, and the process is well-documented in overlanding communities and official resources.” Curious, I asked which “official resources” it was relying on. It cited “numerous overlanding and travel reports from individuals and groups,” as well as travel guides and information from embassies, consulates, and border services supporting the fact that the border was open for vehicles.

Had I missed something? A quick Google search revealed the Azerbaijan border was still closed to overland vehicles. A Facebook group search showed evidence of overlanders shipping their motorcycles and vehicles over the border, rendezvousing after their flight. You cannot temporarily import a foreign-plated vehicle into Azerbaijan, I typed. Words streamed across my laptop monitor. “I apologize for the confusion earlier,” ChatGPT lamented. “You are correct.” Citing travel forums and overlanding communities, ChatGPT noted that many overlanders have reported their experiences and difficulties regarding vehicle entry into the country on forums such as Horizons Unlimited, iOverlander, and—wait for it—Expedition Portal. Now, we had come full circle.

Final Thoughts on Trip Planning and ChatGPT

The initial purpose of this article was to quell my curiosity about the effectiveness of ChatGPT as a trip-planning tool. However, as I logged out of the OpenAI browser, my thoughts turned philosophical. In The Art of Travel, Alain de Botton examines anticipation as part of the travel journey, noting that for him, “the study of maps and the perusal of travel books aroused in me a secret fascination that was at times almost irresistible.” Trip planning is an art fueled by curiosity and creativity, where the fun lies within the task itself. It is a colorful, interactive process that ultimately brings us into contact with other human beings.

Despite its failures (and successes), I enjoyed putting ChatGPT to the test and will likely use it from time to time. That being said, there is something deeply unsatisfying about typing question after question into a bleak, white chatbox. It just doesn’t have the same allure as unfolding a map over the hood of a vehicle, importing tracks into onX Offroad, or turning the pages of a musty book written by those who paved the way decades ago. Predictably, the seemingly omniscient chatbot could explain my feelings as well. “ChatGPT lacks personal experiences, emotions, and intuition, which are often key to deeply creative work,” it typed. That is something we can certainly agree on.

Bosnian burek is a baked phyllo pastry, typically filled with meat, spinach, cheese, or pumpkin.

Containing messages of peace and protest, most of Mostar’s street art can be found in and around the abandoned Sniper Tower.

Editors note: This article was originally published in Overland Journal’s Gear 2025 Issue.

Our No Compromise Clause: We do not accept advertorial content or allow advertising to influence our coverage, and our contributors are guaranteed editorial independence. Overland International may earn a small commission from affiliate links included in this article. We appreciate your support.

Ashley Giordano completed a 48,800-kilometer overland journey from Canada to Argentina with her husband, Richard, in their well-loved but antiquated Toyota pickup. On the zig-zag route south, she hiked craggy peaks in the Andes, discovered diverse cultures in 15 different countries, and filled her tummy with spicy ceviche, Baja fish tacos, and Argentinian Malbec. As Senior Editor at Overland Journal, you can usually find Ashley buried in a pile of travel books, poring over maps, or writing about the unsung women of overlanding history. @desktoglory_ash