5 Tips for A Better Travel Experience Without a Plan

Guest Author: Michael Bonocore

5 Tips for A Better Travel Experience Without a Plan

There are two types of travelers in this world. Those who meticulously plan every little detail about their forthcoming journey and those who prefer to ride the wave as it comes. I have never been an overly organized person, and it shows as my travel planning is almost non-existent. I don’t pack until hours before I depart, and I rarely have sleeping accommodations arranged before I arrive. This relaxed approach to travel has led to incredible experiences that I would have never had if I had been so regimented with a timetable that forced me to be in a certain place at a certain time. While my style of travel isn’t for everyone, I always try to urge others to not be completely locked into a long, detailed itinerary, as they often miss the candid experiences that make travel unique and special.

No matter which type you are, or if you are somewhere in the middle of both, hopefully the following tips will help you have better travel experiences, whether it’s on a road trip through Idaho in a campervan or driving cross country through Cuba.

Make Friends Everywhere

Making friends everywhere is easier said than done. I am an extrovert and I don’t mind random conversations with pretty much anyone I come in contact with. In fact, I feed off of them, especially when I am in my ‘travel zone.’ Introverts, on the other hand, should attempt to make an effort, as uncomfortable as it may be, to meet people along the way. After the initial awkwardness, I can promise you that the comfort of conversation will take over and you will be drawn into the stories that people hold. And who knows, this new friend might have a tip on a locals’ only spot for you to check out. Or you may even get into an adventure together. 

I once found myself sipping rum in Havana, Cuba after winding down from a photography workshop I had just led. Knowing I had three weeks left in the country, I wanted to explore outside of the tourist triangle of Havana, Trinidad and Vinales. As the buzz began to kick in, I went to the square to find a cab to take me back to my guest house. I quickly discovered the young cab driver, Jayro, spoke great English and we quickly sparked up a conversation. I came to find out he was on the Cuban Olympic Team for Bicycling and he had saved his entire life savings to purchase a 1995 VW Jetta, which was his pride and joy. The next night, I returned to the square and asked Jayro if he would drive me across the entire island of Cuba. To my surprise, he quickly agreed. What followed was an incredible three week journey that I will never forget that would have never been possible if I hadn’t made friends with Jayro and his VW Jetta.  

Spend more time enjoying the moments as they come and not to trying to keep up with your itinerary

I often think of Clark Griswald in the movie European Vacation. His family had won a vacation on the game show ‘Pig in a Poke’ and they eagerly took flight for Europe with the gameshow’s rigid itinerary in hand. Fortunately for us in the audience, everything goes horribly wrong and they don’t stick to that itinerary. But that visual of Clark holding the manilla envelope holding their step by step directions always made my skin crawl. 

“I learned a long time ago that trying to micromanage the perfect vacation is always a disaster. That leads to terrible times.” - Anthony Bourdain

From what I have found in my years of travel is that people with such perfectly laid out itineraries and time frames are often so fixated on keeping their plan intact that they simply don’t see or appreciate what is right in front of them. Their vision is always focused on the future, which makes their minds become absent from the present. Having a rough game plan is great. But don’t let the plan consume you so much that you miss the moments that make travel special. 


While on a road trip for Visit Idaho, I woke up in Wallace, Idaho, otherwise known as the Center of the Universe. For this trip I did have an itinerary, and I was due to arrive at Schweitzer Mountain Ski Resort in the early afternoon. Without a campervan to make my morning coffee, I stopped by the local coffee shop to get my fix. While waiting in line, an intimidating looking man approached me and said ‘Were you too good to talk to me at the brewery last night?” I immediately recognized him from the other side of the bar, but he was holding court and had a crew surrounding him, hanging on every word. Caught off guard, I stuttered, not knowing what to say. He laughed and lightly punched me in the arm. Based on his sweatshirt that read ‘Spokane Boxing,’ I realized I probably got off lucky with such a light love tap. 

I wound up sitting and talking to this man, Rick Welliver, for hours. I sat and listened to his stories in awe. What an incredible life he had lived. Instead of continuing my trip on the predetermined schedule, Rick and I drove to the old silver mine outside of town, the base for the folklore that the gritty town of Wallace is built on. 

To this day, Rick is one of my favorite people that I have ever been lucky enough to meet on my travels. He quickly became a really good friend, and I visit him often in Spokane and in Wallace, where he hosts a popular ‘Fight Night’ event that brings the entire town together in the old, beat up gymnasium. 

In the moment after Rick punched me jokingly in the arm, he asked me to sit and join him for a coffee. Being that I was on a ‘schedule’ I often think about how I would never have had this incredible friendship in my life if I turned the offer down, all in the name of ‘keeping to my schedule.’

Hotels? We don’t need no stinking hotels! 

Hotels serve a great purpose. Their rooms provide a warm bed and hot water. But most people book hotels far in advance of their trips, locking them into the dreaded itinerary. While this might not be such a bad thing if your vacation only consists of visiting one city like Boise, this practice can hinder most road trip adventures. Either booking a campervan or bringing camping supplies can free you from the expensive commitment that comes with booking a hotel in advance. 

Never did this approach work better for me than a photography trip to Iceland over the summer solstice. Being so far north, the sun in Iceland doesn’t fully dip below the horizon in the month of June. This leads to incredible sunset skies of pink and orange that last for hours, usually between 10pm and 2am. Since the weather is such a factor in Iceland, we would scout the weather patterns and drive for hours across the island to get to the place where we thought we would have the best chance for amazing sunset photos. We didn’t have a campervan, so after the light would disappear, we would drive to the nearest campsite and set up our tents for our chilly morning naps. Looking back I wish we had booked a campervan instead, but at the end of the trip, we were very happy with the approach that we took. If we had booked hotels in advance, our itinerary commitments would have prevented us from making changes on the fly. And those changes on the fly not only led to some incredible photographs, but also created a bonding experience between myself and the two friends that I had traveled with. That human connection was well worth the chilly nights we spent trying to keep our tents grounded in the hurricane force winds. 

Roads? Where we're going, we don’t need roads!

Pavement is for suckers. There, I said it! By far, my most memorable adventures have been made far from the comfort of smooth pavement. Luckily, campervans make driving down these rugged dirt roads a breeze. True to the theme of this article, you never know what you might find at the end of these dirt roads, or how long you might want to stay in your own little slice of paradise. 

But my road analogy doesn’t just mean actual roads. As the cliche saying goes, it’s best to get off the beaten path. While there is usually always a comfortable route to follow on your travels, that doesn’t necessarily lead to the most rewarding experiences. You can gleam all of the information you want off of travel sites, but that just means you are following in the footsteps of those who went before you. If you want to live the experiences that others haven’t, look for the road less traveled, or at the very least take the long way. 

While on my cross country road trip through Cuba we arrived at Baracoa, on the far eastern coast. My Cuban friend Alain, who had accompanied Jairo and I on our adventure, decided to walk the last two miles to the town square. We walked off of the main road to find a lush and quiet neighborhood. Along the narrow, dusty dirt roads surrounded by dense trees, quaint homes stood in the middle of the modest plots of land. And in front of each of these homes, families sat listening to music and laughing. As we passed, the locals raised an eye and immediately knew we weren’t from around there. So they did what any good Cuban would do. They called on us to come and join them in their home. Rum, coffee and fruit were quickly dispatched, appearing seemingly out of nowhere. Family albums were dusted off and opened to illicit the beaming smiles of the generations of family members who lived in these homes. House after house after house. Our quick 2 mile walk wound up taking over 10 hours, as we were enthralled by the people we met and the stories they told. To this day, this is one of my most memorable experiences of any trip I have taken. And it would not have been possible if we simply stayed in the comfort of Jayro’s 1995 VW Jetta for the road’s final 2 miles.  

Give Back to the Communities You Visit

In probably the easiest way to roll with a loose itinerary, working with local non-profit organizations is a certain way to have a unique travel experience. Whether it is nature and wildlife conservation or volunteering your time with local children’s groups, nonprofits can give you a foot in the door with locals that you would have never met otherwise. Of course, based on who you meet and connect with, this can drastically change any preconceived plans that you had before your arrival. 

While traveling out of the United States, I often work with local nonprofit organizations to teach children the art of photography with the donated cameras I bring with me. 

These relationships often have me walking through the children’s neighborhoods with them. These are places that most travelers would never think to visit, and in fact, if they did they would most likely be lost and feel out of place. For me, walking through the streets with the children of the neighborhood opens doors and fosters new conversations and relationships that would have otherwise been impossible. These experiences are much more unique and unforgettable. And the best part? You leave a lasting impression and a bit of yourself with the work that you did. It binds you closer to the place and its people. It inspires you to return and continue the work that you started. And it reminds you that you don’t need to have a minute by minute agenda, and that the most impactful experiences that come from traveling happen when you toss the playbook in the trash. 

Michael Bonocore