You know that feeling when you come back from a trip and think, Wow, I need a vacation to recover from my vacation? Yeah, I’ve been there.
For years, I thought traveling meant squeezing in as much as possible – seeing every famous landmark, following a packed itinerary, and trying to “make the most” of my time. But the truth is that approach left me exhausted rather than happy. Now, I plan my trips differently – not by being totally spontaneous (because, honestly, unexpected situations stress me out a lot) but by finding a balance between structure and flexibility.
I usually have a list of places I’d like to visit, but I decide each day on the spot what to do. Restaurants? I almost never plan those in advance. Most of the time, I check Google Maps at the last moment or rely on a short list I’ve saved from Tripadvisor – always making sure the places are either local favorites or a mix of locals and tourists (but never just a tourist trap). This way, I enjoy the experience without feeling rushed or overwhelmed.
So, let’s cut to the chase – here’s how I plan my trips to maximize joy, stay organized, and actually enjoy the journey.
Table of contents:
- Choosing a destination with purpose
- Planning with flexibility, not a strict itinerary
- Prioritizing local experiences over tourist attractions
- Food as a core part of travel joy
- Creating moments, not just photos
- Traveling with others: making it enjoyable for everyone
- How to plan a trip for maximum enjoyment (without the stress)
- The joy of traveling your way
Choosing a destination with purpose
Some people have a bucket list of dream destinations, but I keep things a bit more flexible. When I start planning a trip, I don’t just pick a random spot – I consider a few key factors:
- budget,
- how I want to get there (plane or train, never by car because I prefer not to drive on trips),
- and the time of year.
Since I usually plan about a month in advance, I also look at what kind of weather and crowds I might be dealing with.
But for me, the real question isn’t where do I want to go? – it’s what kind of experience do I want to have? I love places that feel authentic, where I can be surrounded by locals instead of getting trapped in a tourist bubble.
A perfect example? Ischia. This small island in southern Italy isn’t as famous as nearby Capri, but that’s exactly why I love it. I had visited a few times for day trips, but one summer, I decided to skip Naples entirely and spend a whole week there instead. It was the best decision.
Unlike other tourist-heavy destinations, Ischia felt real. I stayed near the castle, where the streets were filled with locals, the food was ridiculously good (I still dream about the pizza from a tiny kiosk surrounded by Italians), and the beaches? Completely packed, but not with tourists. Italian families – grandparents, parents, and kids – sat squeezed together, talking loud, laughing, and just enjoying life. Normally, I hate packed places, but this was different. It felt alive, and I loved every second of it.
That’s the kind of travel I aim for – not just seeing a place but actually experiencing it.
Planning with flexibility, not a strict itinerary
I love structure. I like knowing what to expect. Unexpected situations? Not really my thing. But when it comes to travel, I’ve learned that some flexibility actually makes the experience way more enjoyable.
That doesn’t mean I go completely unplanned – far from it. I always have a general idea of places I want to visit, but I don’t lock myself into a rigid schedule. Instead of planning every hour of every day, I decide on the day what I feel like doing. Some days, I’m up early and ready to explore. Other days? I slow things down.
I’ve realized that after a couple of days of sightseeing, I need a reset. That means waking up late, getting in a workout (yes, even on vacation – my workouts go where I go), and heading to a local café for coffee and cake. Then, I just wander – taking photos of less-known spots, browsing souvenir shops for gifts, and checking out pastry shops for something sweet to bring home. If I’m at the beach, I switch into full relaxation mode: lying in the sun with a book while other people swim and enjoy the water nearby.
One time in Ischia, a local was walking between beach beds, selling warm pastries dusted with powdered sugar and filled with custard, chocolate, or marmalade. I still think about how ridiculously good they were. I believe they’re called Graffe Napoletane. Traditionally, they’re made with potatoes, but if you’d like a potato-free version, you can try this recipe for graffe senza patate. If I had followed a strict itinerary that day instead of deciding to have a spontaneous beach day, I would have completely missed out on that delicious experience.
Because I don’t over-plan, I also get to enjoy spontaneous experiences – like last year, when I went to Seville for my birthday and decided on the spot to take a train to Córdoba for the day. I explored the Alcázar, visited a mosque-turned-cathedral called Catedral de Nuestra Señora de la Asunción, and ended up at a seafood tapas restaurant that was so good people were constantly waiting in line to get in. Easily one of my best days in Spain.
This balance between structure and flexibility takes the pressure off. I get to enjoy what I planned but also leave room for the unexpected, good kind of surprises – without the stress of a packed itinerary.
Prioritizing local experiences over tourist attractions
I love LOVE visiting new places, but I don’t want to feel like I’m just ticking off a list of “must-see” attractions. The truth is, famous landmarks are great, but they rarely give you a true feel of a place. What I enjoy most is experiencing a destination as it really is, not just how it’s presented to tourists.
That’s why I always try to stay where locals live, eat where locals eat, and do things that locals actually do. It’s not about avoiding tourist spots entirely. I still visit some, especially if they’re historically or culturally significant, but I never want to be in a place that feels designed just for tourists.
One of the easiest ways to experience a place like a local? Skip the overpriced hotspots and go where everyday people go. In Venice, instead of paying a fortune for a mediocre aperitivo in Piazza San Marco, I went to the university area, where cafés and bars cater to students. There, I had a proper Spritz and a plate of cicchetti (small bites served on bread) without feeling ripped off. The food was better, the price was fair, and the atmosphere felt real.
Another time, when I first visited Ischia for a day trip, I decided to have a beach day like some of the locals. That meant skipping the bagni (local beach establishments) and instead laying my towel on the rocky formations at the foot of the castle.
Was it comfortable? Not at all – because, well, rocks aren’t exactly known for their softness. It wasn’t the most relaxing sunbathing experience for me, but it definitely made for a unique and very local beach day.
The same goes for activities. When I visited Capri, I could have followed the typical tourist route – just like my mom did when she traveled to Italy with my stepdad (can you believe that?). They completely missed the true beauty of the island! Most visitors take a bus to the shopping district, join a packed cave tour, or rent an overpriced boat to see the famous Faraglioni rock formations. Instead, I took the hiking trails. And let me tell you, it was the best decision ever. I saw a completely different side of Capri – quiet, scenic, and with zero tourists around. The views? Stunning. I even found a perfect spot to take photos of the Faraglioni without having to battle through a crowd.
Finding these experiences takes some research, and luckily, I actually enjoy that part now. I use local blogs, Italian sources, Google Maps, and tips from Airbnb hosts to find spots that aren’t just written for tourists. Hosts often give the best suggestions: where to eat, hidden corners to visit, and small details about local sights that only locals would know.
Of course, some tourist attractions are worth seeing, and I don’t skip them just to be different. But for me, the real joy of travel isn’t just about seeing famous places – it’s about experiencing authentic places.
Food as a core part of travel joy
For me, food isn’t just something you eat when you travel – it’s an experience. It tells you more about a place than any guidebook ever could. The flavors, the way it’s served, where people gather to eat. It all adds to the feeling of being there.
How food connects me to a place’s culture
One of my favorite ways to experience a new destination is through its food. Not fancy, Michelin-starred meals, but the everyday, local dishes that people actually eat. There’s something special about stepping into a tiny, family-run restaurant where no one speaks English and just pointing at something on the menu, hoping for the best. Or sitting in a crowded café, sipping an espresso while watching locals chat animatedly over their morning cornetto.
Food isn’t just about taste. It’s about atmosphere, tradition, and the way people gather around a table. And that’s what makes it one of the best parts of travel.
My approach: trying local dishes, markets, and hidden spots
I rarely plan my meals in advance. I prefer to find places on the go or rely on a small list of restaurants I’ve saved from my research (often using Tripadvisor, but focusing on spots that locals frequent). The rule? If it looks like a tourist trap, I skip it. If it’s full of locals, it’s a yes.
I also love exploring food markets. They’re perfect for tasting different specialties without committing to a full meal. In Denmark, I grabbed hotdogs that I still think are some of the best in the world. In Bulgaria, nothing beats getting a döner kebab or a portion of kebapcheta. For example, in Varna, where I’m from, there’s a kiosk that makes the best döner ever – huge, packed with meat and veggies, and topped with a white sauce that no one really knows how it’s made. Rumor has it that potatoes are somehow involved, but whatever the secret is, it’s absolutely delicious. And sometimes, the best food finds happen completely by accident.
A food memory I’ll never forget
One of the most memorable food experiences I’ve had was in Saint Petersburg, Russia. It was winter, and I spent a week between Moscow and Saint Petersburg, flying back to Italy just before Christmas. While Moscow wasn’t exactly the friendliest place for non-Russian speakers (people were openly rude when they realized I didn’t speak Russian), Saint Petersburg felt completely different, especially when I stumbled upon a tiny bakery tucked away in the city.
Surprisingly, some of the staff spoke a little English, and they were incredibly polite. But what made this place unforgettable was the food. The cakes were amazing – especially their carrot cake, which happens to be my all-time favorite. And then there was the coffee. They served something called Raf coffee, a creamy, frothy drink made with espresso, cream, and vanilla sugar. I took one sip and was immediately obsessed.
I was in the city for only three days, but every single morning before sightseeing, I made my way to that bakery for coffee and cake. I stuck to the carrot cake (because once you find perfection, why switch?), and I tried different local cakes on the side whenever I could. It became my little ritual: warm drinks, sweet treats, and a quiet moment before diving into the icy streets of Saint Petersburg. And when I say icy, I mean it – it was -17°C. At the time, I was living in Sweden and was used to freezing temperatures since winters often hovered around -15°C for months. Long walks in the snow, even for an hour or two, were part of my routine. But the humidity in Russia was on another level. It seeped into my bones, and no amount of layers or thick socks could keep me warm.
Anyway, it wasn’t a famous restaurant. It wasn’t a tourist attraction. But that cozy little bakery became one of the highlights of my trip.
Why food is such a big part of my travel experience
As I said, for me, food isn’t just about eating. It’s about discovering a place through its flavors, traditions, and everyday rituals. It’s about the tiny cafés that serve the best espresso, the hole-in-the-wall bakery that makes a pastry you’ll dream about for years, and the local restaurants where families gather for hours over shared plates.
That’s why, no matter where I go, food will always be one of the first things I explore. Because some of the best travel memories aren’t just about what you see; they’re about what you taste.
Creating moments, not just photos
I love taking photos when I travel, but I don’t want my trips to feel like a never-ending photoshoot. Sure, it’s nice to have beautiful pictures to look back on, but what I care about most is actually experiencing the moment – not just capturing it for Instagram.
I’ve seen it happen so many times. People rush to a landmark, snap a quick photo, and leave without even looking at what’s around them. They’re so focused on getting the perfect shot that they don’t take a second to soak it all in. I never want to travel like that.
That’s why my approach is different. I take photos, of course, but I make sure they don’t take over my experience. Some of my favorite memories don’t even have a photo to go with them – like the time I took an impromptu bus trip to Ljubljana, Slovenia, to explore the Christmas market, or when I headed to Cesenatico, Italy, for Il Pesce fa Festa.
It’s also why I love slow mornings when I travel. Waking up late, having a coffee in a quiet café, people-watching as locals go about their day. Those little moments are just as important as sightseeing, if not more. They’re the ones that make a trip feel personal, like it’s yours, not just something copied from a travel guide.
So yes, I’ll take photos, but only after I’ve actually enjoyed the moment. Because at the end of the day, the best memories don’t need a filter or a perfectly framed shot. They just need you to be there.
Traveling with others: making it enjoyable for everyone
Traveling with someone else – whether it’s a partner, friend, or family member – can be amazing, but it can also be challenging. Different habits, different energy levels, and different interests all come with you on the trip.
One of the biggest lessons I’ve learned is that you need a balance between structure and spontaneity that works for everyone. Maybe you love having a rough plan so you know what to expect, while the person you’re with prefers to decide on the day. A good middle ground is to agree on the main things you’d like to see, then leave room around them for how you feel in the moment.
It also helps to know what excites each person. You might be drawn to historical sights or museums, while someone else cares more about food, nightlife, or nature. When you plan a trip together, it’s worth making space for both: a stop at a pastry shop or archaeological site for you, and something that’s high on their list as well. That way, the trip doesn’t feel one-sided.
And of course, there will always be moments when your travel styles clash. Maybe one of you wants to hike to a viewpoint at sunrise, while the other would gladly take the cable car at noon. In those cases, compromise (or sometimes splitting up for a few hours) can save the mood of the whole day. Traveling together doesn’t mean doing every single thing together – it means respecting each other’s limits and still enjoying the shared parts.
In the end, what makes traveling with others enjoyable isn’t a perfectly aligned travel style. It’s communication, flexibility, and the willingness to adjust so everyone gets something they love out of the trip.
How to plan a trip for maximum enjoyment (without the stress)
Travel should be exciting, not exhausting. Over time, I’ve refined a system that helps me plan trips that are organized, flexible, and actually enjoyable. Here’s my go-to checklist for making the most of every trip:
1. Choose a destination that matches your travel style
Not every destination is for everyone. Before booking, ask yourself:
- Do I want a cultural, food-focused, or relaxing trip?
- Do I prefer authentic local experiences over heavily touristic areas?
- How easy is it to get around without a car?
2. Have a general plan – but stay flexible
- Create a list of places you’d like to visit, but don’t schedule every hour.
- Allow room for last-minute discoveries and spontaneous activities.
- Plan only one or two major activities per day to avoid burnout.
3. Pick transportation that works for you
- Decide whether flying, taking a train, or using public transport fits your trip best.
- If you don’t plan to drive, make sure your destination is well-connected.
- Consider ease of movement – some places require walking, while others may need pre-booked transport.
4. Find the right balance between sightseeing and relaxation
- Don’t try to see everything – prioritize quality over quantity.
- Factor in downtime, whether it’s a slow morning at a café or an afternoon walk with no set agenda.
- Mix sightseeing with casual activities like strolling through markets or checking out local bookstores.
5. Choose local food over tourist hotspots
- Research restaurants that locals actually go to (avoid places with only tourists).
- Check reviews from locals instead of just generic travel guides.
- Explore food markets for a taste of regional specialties without committing to a full meal.
6. Plan for unexpected situations
- Always have a backup plan in case of bad weather or closures.
- If you’re staying at an Airbnb, ask the host for recommendations on hidden gems.
- Don’t panic if things don’t go as planned – some of the best travel experiences happen by accident.
7. Pack smart for the trip you’re taking
- Consider the local climate and the type of activities planned.
- Pack comfortable shoes if you plan to walk a lot.
- Leave extra space in your luggage for souvenirs or food finds.
8. Don’t overplan meals
- Be open to last-minute food choices rather than scheduling every meal.
- Use Google Maps or Tripadvisor to find well-rated spots on the go.
- Try at least one local dessert (because food memories last forever!).
9. Accept that you can’t see it all
- Every destination has more to offer than you can experience in one trip.
- Focus on what excites you most, and leave the rest for a future visit.
- Traveling should feel like an experience, not a race.
10. Learn basic local phrases (if visiting a non-English speaking country)
- Even simple words like “hello,” “thank you,” or “check, please” can make a difference.
- Download a translation app for quick communication.
- Understanding basic phrases can help in restaurants, transport, and local markets.
11. Be aware of local customs and etiquette
- Research tipping culture – some countries expect it, while others don’t.
- Dress appropriately for religious or cultural sites.
- Learn if there are any gestures or habits that might be considered rude.
12. Prioritize experiences over perfect photos
- Take photos, but don’t let them take over the experience.
- Allow time for unexpected discoveries.
- Make sure you’re actually enjoying your trip, not just ticking things off a list.
The joy of traveling your way
For me, that means finding a balance – having enough structure to feel organized but enough flexibility to enjoy the unexpected. It means choosing destinations that feel authentic, prioritizing experiences over checklists, and making space for both adventure and slow moments. Over time, I’ve realized that the most memorable trips aren’t the ones where I’ve seen everything – they’re the ones where I’ve truly enjoyed the experience.
So, if there’s one thing I’ve learned, it’s this: travel should never feel like an obligation. Skip the things that don’t excite you. Make room for the experiences that do. After all, the best trips aren’t measured by how many sights you visit – they’re measured by how much you actually love the journey.
How do you plan your trips to make them more enjoyable? I’d love to hear what works for you!