Day 74 - July 24th: Derailed
Dubrovnik to Herceg Novi: 29.65 miles / 2,095 total
We just arrived back in Cavtat, Croatia, at 10:15pm—exhausted, hungry, and not where we were supposed to be. The plan was to finish the day in Herceg Novi, Montenegro, but while I completed the run, Christina never made it across the border. The Hertz rental from Portugal didn’t include the original ownership documentation required to enter a non-EU country, and Montenegro wasn’t letting her through without it.
While I ran, Christina detoured to the Dubrovnik airport—on our route—to explore solutions. She tried to secure the paperwork which would need to have come from Portugal since that was its origination, swapping cars but Hertz is franchised in Europe and they didn’t want our car from Portugal, and even renting a new one but it is high season with limited supply and wouldn’t allow us to take outside of EU. Nothing worked. Meanwhile, I reached our hotel in Herceg Novi—still in my running clothes—only to realize I was stranded.
Hours later and with no clear options, I found someone to call me a taxi and returned across the border to the Dubrovnik airport so we could regroup. We booked a last-minute room in Cavtat, grabbed what food we could find, and just made it to our room at 10:30pm. Tomorrow we figure out the next move—because from here on out, nearly every country we’ll pass through is non-EU.
More to come on the actual run, but for now: sleep and a new plan.
To be continued…
In the Morning…
We said goodbye to Dubrovnik, a magical city that offered a brief but much-needed respite from the road. At 6:30 a.m., I stood in the main plaza, nearly alone—save for a couple getting married, who clearly knew that to capture a photo in front of the church without crowds, they had to be there at first light. I sat on the steps with my cappuccino and pastries, the rising sun casting soft pastel hues across the white stone buildings. The quiet moment etched a lasting image of Dubrovnik that stood in stark contrast to the previous days and nights packed with tourists.
I climbed up from the old city to the coastal road via a punishing set of zigzagging steps—breathless but confident. For the first time on this trip, I felt complete physical and mental alignment. Today also marked the start of a new logistical challenge: non-EU countries and their pet entry requirements. While Jax has an EU pet passport, Montenegro (and other non-EU countries ahead) require a rabies titration test. We had it done before we left, but Portugal required the passport to validate the results—so we mailed it to Monica. It still hasn’t arrived, leaving us without documentation. Options? Wait at a border hotel or leave Jax in boarding back in Dubrovnik. Neither ideal. Hopefully Christina can work her magic.
After a long 6 km climb, the road unfolded above the coastline, revealing yet another beautiful series of coves and villages tucked into the cliffs. As I descended along the right-hand side of the road (with traffic), a scare jolted me: the screech of locked brakes behind me. I turned to see a man gripping his phone, oblivious to the road—or to me. Near miss.
Despite feeling sharp the night before, I began to experience a deep internal pain in my lower back or kidney area—a dull ache made worse by the bounce of running. I eased into a walk to see if it would pass. Days off are tricky…
The route then turned inland through a deep valley surrounded by jagged mountains. Villages clung to the slopes like stair-stepped terraces. After 30 km, the valley narrowed into a gorge. High up along the right side I spotted a stone-buttressed road hugging the mountain. It paralleled my route and looked like it could have been part of the original mountain pass—perhaps centuries old, maybe once used by caravans, pilgrims, or Ottoman-era merchants traveling between the Adriatic coast and inland trade centers. This area historically marked the meeting point of Venetian and Ottoman zones of influence, and such routes often evolved from even older Roman tracks.
After a 6 km ascent, I reached the Croatian border post. A quick passport stamp, no cigarette or drug inquiries, and I was through.
The descent into Montenegro was dramatic. I passed a 2-km line of cars waiting to enter. As I trotted by, a hand extended from a vehicle holding a water bottle. I paused. “Is that for me?” I asked. “Yes,” they replied, smiling. Two Middle Eastern couples living in London, touring the region. When I told them I had run from Dubrovnik, they handed over bananas and more water. Kindness is everywhere.
I arrived in Herceg Novi—an enormous horseshoe-shaped bay with one of the longest promenades I’ve seen: nearly 4 km of pizzerias, beach clubs, gelato stands, souvenir shops, and swimmers under the massive Dinaric Alps. The medieval old town above is laced with fortresses that once guarded this critical entrance to the Bay of Kotor, which has been a maritime stronghold since Illyrian times and later ruled by Byzantines, Venetians, and Ottomans.
But there was one problem: no Christina. She had been blocked at the Montenegro border because the Hertz rental from Portugal lacked the special vehicle ownership documentation required for non-EU countries. We also learned that no rental car companies allow travel to Turkey, and some restrict Albania and North Macedonia too—making the road ahead increasingly complicated.
So now I sat, still in my running gear, in a foreign country, with no change of clothes and no support vehicle.
Houston, we have a problem.
Appreciate the support!
David.
