The planner vs. the free spirit – Traveling with your opposite

I’m a planner. I thrive on itineraries, pre-booked accommodations, and knowing what’s next. 

Not to mention, I’m a suitcase girly who prefers luxury trips, 3-5 star living quarters, and the efficiency of hiring private drivers or cars to sightsee. 

One of my best friends, Amanda, is the complete opposite. She embraces spontaneity, avoids booking too early, and believes the best experiences happen when you either don’t plan at all or plan on the go. 

She’s a seasoned backpacker and hostel stayer who loves to take the long scenic routes by public transit. 

Traveling together? It seemed like a recipe for disaster. Yet, despite our differences, we decided to plan a trip to Italy together. 

Fast forward to a few days before our trip – we had nothing booked. 

I finally forced us to at least book the first night. But it quickly became clear we had very different ideas about how this trip would go. I knew this trip would test our friendship, but I didn’t expect to seriously consider leaving her stranded in Italy.

Looking back, here’s what the trip taught me about traveling styles.

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I thought doing things her way would give me a chance to relax and enjoy being more spontaneous. I was wrong.

Before our departure, we shared a running Google doc of possible activities and accommodations (most of which were already booked up by the time we were ready to go). We also brainstormed possible itineraries and tried to figure out how many days to stay in each city. 

My beautiful, free-spirited friend was busy with work and life and kept delaying her research. Luckily, I did a lot of research beforehand, so I had a pretty good idea of all the sites we should hit.

I also reached out to Sky, one of Travel Lemming’s writers, and asked her about her Italy highlights. She recommended the Path of the Gods and I am so happy I had her inside scoop on this life-changing hike for my friend and I to experience together.

Overall, it was a very loose itinerary because my friend insisted we just “figure it out as we go.” To me, this sounded like a mix of both exhilaration (I was so excited to give up control)… but also stupidity. However, I decided to lean fully into her way at the start. 

That was until we were wandering the streets of Florence at 1 AM. 

We were exhausted and walking in circles with our bags, searching for a non-existent taxi to take us to the only available Airbnb couch to crash on. We would only be there for the night as we’d poorly planned to take a (non-refundable) morning train to our next destination. 

We had to catch it just a few hours later. 

Things went from bad to worse, and the challenges began to affect our friendship.

At first, the unplanned plan was thrilling. But it took its toll on me. 

Waking up early to catch trains and staying up late to research and book a new place to stay the next night was physically and emotionally exhausting. It felt inefficient.

I could feel my patience running out while she seemed completely unfazed, laughing at how “adventurous” our day had become (when we missed 3 of our bus routes).

There were two points when I wanted to leave her in Italy. 

The first was when we met for lunch on the patio of COMO Castello de Nero, a 5-star castle overlooking the Tuscan hillside. This was right after the most relaxing massage and spa experience of my life (and probably my lifetime). This place also had one of the most epic views of the trip. 

My peaceful euphoria was interrupted when we had a heated argument over spending too much money. 

The argument ruined the moment when all I wanted was to take in the breathtaking scenery, relax, and enjoy a delicious lunch. I thought, pick your battles, timing is everything!

The tension between us ironically reached its peak on the top of Positano Island. We went out the night before and I wanted to let off some steam. I am pretty sure this was her breaking point with me because she didn’t talk to me the entire ferry ride to the Island. 

We temporarily hashed it out so we could get to our next accommodation. The place we had booked looked like a 10-minute walk to the heart of town, but we had to hike hundreds of stairs to get to our bed and breakfast. Yet another annoyance.

She also had to take work calls on this vacation, which she didn’t tell me beforehand. She often needed to find WiFi to take her calls. This bothered me as it often messed up our dinner plans. Talk about a lack of work-life balance.

However, I soon realized not being on the same page about budget, transportation, and activities was getting in the way of our friendship. I had to cool off and eat dinner alone.

It was nice to have space, but it would have been beautiful to share the meal with her since I had discovered one of the most gorgeous restaurants in town. 

I couldn’t deny that I envied her ability to stay so relaxed and adapt to any travel obstacle while she envied my ability to plan bucket-list-worthy experiences.

At that moment, I realized something: maybe we both had something to learn from each other.

We found a middle ground by compromising on our itinerary and responsibilities and determining our non-negotiables.

As much as her carefree approach drove me insane, I had to admit that it also led to some of our best moments. 

Like when she had me try hostels again in my thirties. We stumbled to the hostel’s rooftop pool area and were rewarded with gorgeous views overlooking the heart of Florence and the Duomo Cathedral. 

The hostel also hosted a farmers market meetup where we discovered a hidden food hall gem that wouldn’t have happened if I planned too much. 

If I had controlled every detail, we definitely would have missed it.

At the same time, my planning helped us cover enough ground and destinations in Italy. Even she had to admit, “Okay, maybe having some reservations isn’t the worst idea.” After all, most highly desirable Italian activities book up much faster than you think. 

By the halfway point of our trip, we figured out a compromise that worked for both of us:

• A loose itinerary with flexibility. We agreed to book a mix of hotels, hostels, and BNBs for at least the first few days in each city along with our connecting train tickets. We also booked 1 activity at least every other day, but we left room for unexpected discoveries.
  
• Dividing further responsibilities. I took charge of restaurants and finding the next day’s activities while she booked trains and logistics to make it all happen.
  
• Establishing non-negotiables. I needed mornings to myself while she needed unscheduled afternoons for her work calls. 

The takeaway? This trip made us better travelers and friends!

By the end of the trip, something had shifted in both of us. 

Sometimes what seems like a bad circumstance (like accommodation in a location you don’t love) can be a gift in disguise (like finding a hidden gem because of the inconvenience). 

I learned to let go a little and to leave space for the unexpected. I learned to embrace budgeting more and gave public transit and even hostels a second chance. 

As much as I love my comforts, I realized how these choices not only save money, but they make European travel easier. It also connects you to the rhythm of the city in a way that feels more authentic and alive. 

And, when I came home, I immediately bought a great travel backpack to invest in my next Euro trip.

She, on the other hand, started to see the value in pre-planning novelty for your trip. 

She learned that some one-of-a-kind experiences are worth spending a little extra for like hiring a driver or renting a car to reach harder-to-access destinations. Or designing your souvenirs. After all, time is money, too.

***

Traveling with your opposite isn’t easy, but it stretches you in ways you don’t expect. It forces you to see the world from a different perspective, challenges your habits, and can help you grow as both a traveler and a friend. 

Would we do it again? Absolutely. 

But next time, we’ll book at least the first few nights’ stay in advance, making peace with a blend of hostels and luxury splurges. We’ll also buffer in some mid-trip alone time for a more balanced and sustainable approach, especially as we near 2 weeks together.

Thinking of booking a trip with friends who have different approaches to travel? Up next, check out Lea Rose’s article on group travel tips to help you survive (and thrive) on your trip!