How to Enjoy Your Holiday When Nothing Goes to Plan
Three years ago, I booked a four-day holiday to Anafi with somewhere to stay for only two nights. Then, when I landed in Santorini, I discovered that the boat that was supposed to take us there had stopped running because its captain had been arrested. A few years earlier, this would have been enough to ruin my holiday before it had even begun. This time, I decided to treat the whole thing as an adventure.
It began with an impulse.
A friend and I were discussing what we might do in August when one of us said, “Why don’t we go to Anafi?” Anafi is a small Greek island near Santorini. Neither of us had been there before, and I had very little idea what travelling there involved. You can either take a ferry from Athens for around twelve hours or fly to Santorini and then take another boat for an hour and a half.
We decided to go.
I immediately booked flights to Santorini and boat tickets to Anafi. We would stay for four days. Simple. Then I tried to find somewhere for us to sleep. Booking.com showed no availability. In fact, it kept suggesting hotels in Santorini instead. Airbnb gave me the same result. I eventually discovered that Anafi has very few hotels and rooms to let, and August is hardly the ideal month to book a spontaneous holiday on a tiny Greek island. The only available room I found cost €400 a night. We weren’t feeling quite adventurous enough to pay €1,600 for four nights, so we decided to keep looking. If we found nothing, we could stay in Santorini instead. It is a large island. Surely we would find something there.
I also discovered a local website listing rooms to let, and we began calling them one by one. Still nothing. Every three or four days, I went back onto Booking.com to look for cancellations. Finally, around ten days before our trip, a room became available at the same hotel, this time at €200 a night. There was just one small complication: it was available for only two nights. We booked it.
Our new plan was to arrive in Anafi, stay at the hotel for two nights and look for another room once we were there. Perhaps finding something in person would be easier. And if it wasn’t, we could return to Santorini. Or sleep on the beach for a night or two.
What made this entire situation even stranger was that I had never travelled like this before. I used to plan my holidays from beginning to end. I researched the restaurants I wanted to visit and the beaches I wanted to see. I probably knew which beach I would go to on which day. Leaving accommodation, transport and large parts of the holiday to fate was completely out of character for me. But this time, I was fine with it. I will treat it as an adventure, I thought, and smiled to myself. After all, Adventure is my word of the year.
We flew to Santorini. We had just collected our suitcases when my phone rang. It was a woman from the hotel asking how we planned to get to Anafi. “By boat,” I replied. “We have tickets.” “Well,” she said, “that boat hasn’t been running for the past couple of weeks. The captain was arrested, and there is no other captain to operate it.”
I was speechless.
“What can we do?” I asked. She explained that another couple staying at the hotel had the same problem. A small boat had been arranged to take them across, and she would find out whether they had already left. If we could reach the other side of Santorini in time, perhaps we could join them. We jumped into a taxi, made it in time and crossed to Anafi with the other couple.
We had arrived. We had a room for two nights. Now we needed a car. There was only one car rental company on the island, so I called.
“I don’t think I have anything available,” the man told me. “Call me again in an hour.”
I called him an hour later. “Who are you?” he asked. “I called you an hour ago about renting a car.”
“Oh, yes. Let me check.”
We spoke again later. He still didn’t remember me. Eventually, my friend and I decided that our best chance was to go to the village and meet him in person.
“Hi,” I said when we found him. “I’m the woman who has called you several times about a car.”
He looked at me blankly. I wrote down my name and telephone number. When I called again, he finally told me that he had no car for that day, but he could give us one the following day for twenty-four hours. “We’ll take it.”
The hotel then found a room for us for one more night. One problem solved.
The next day, when we returned the car, I asked whether there was any chance we could keep it for another day. “No, it is already booked,” he said. “But let me check. I’ll call you if I find something.”
We left. Fifteen minutes later, he called. “You can come back and get it. You can have it for one more day.” Another problem solved.
Finally, we found a cabin on the ferry travelling directly from Anafi to Athens. It left at five in the morning, one day earlier than we had originally planned, but it gave us an easy way home.
Somehow, everything worked out.
We found a way to reach the island when our boat ceased to exist. We found somewhere to stay when the entire island appeared to be full. We found a car, lost it and found it again. And we found a ferry cabin to take us home.
The most surprising part was that I never felt stressed. In the past, the uncertainty alone would probably have ruined my holiday before it had even begun. I would have wanted every problem solved in advance and every detail safely organised. This time, I dealt with each situation when it appeared. I accepted what was happening, looked for the next available option and continued enjoying myself. I went with the flow. And the holiday became exactly what I had decided it would be: an adventure.
That holiday taught me that how much we enjoy ourselves has less to do with everything going according to plan and more to do with how we respond when it doesn’t.
Here are my dos and don’ts for making the most of your holiday:
Be adventurous
Don’t aim for the perfect holiday.
Make your plans, book the places you want to visit and look forward to the experiences you want to have. But leave some space for the unexpected.
A beach may look very different from the photographs. The restaurant you wanted to visit may be fully booked. Your ferry might even lose its captain.
Stay open. Go with the flow. Be curious about where an unexpected change might lead you. Sometimes the story you will remember for years begins with something going completely wrong.
Be present
Give yourself permission to stop solving your problems for a few days. Most of them will still be waiting when you return, and thinking about them throughout your holiday will rarely solve them.
This is your time to rest, recharge and have fun. And you can only experience any of that when you are actually there.
Put your phone down. Stop scrolling aimlessly and have a real conversation. Let your gaze wander. Notice the people around you, the sounds, the colours and what is happening beyond your screen.
Take photographs, of course. But after you capture the moment, return to it. Experience where you are instead of spending your holiday documenting it.
Be accepting
Something will probably go wrong. A flight will be delayed. The weather will change. Children will be screaming at the table next to yours in the restaurant. Someone in your group will become tired or irritable. The hotel room may bear very little resemblance to the carefully edited photographs online.
When something you don’t like is already happening, getting stressed, angry or complaining about it will not change it. It will only take away more of your peace.
See the situation as it is. Ask yourself whether there is something you can do. If there is, look for a solution. If there isn’t, accept it and decide how you want to experience the next moment.
Acceptance allows you to be at peace with what is. And when you are at peace, you have the clarity to make better choices.
Be grateful
Look for what there is to appreciate.
The warmth of the sun. The sea. A beautiful sunset. A delicious meal. An intimate conversation. Laughing with friends. Reading a book with nowhere else you need to be.
These moments can appear small while they are happening, yet they often become the memories we value most.
Gratitude brings your attention back to what is already here. And when you are present enough to notice it, you may discover that your holiday doesn’t have to be perfect to be wonderful.
Be yourself
Don’t turn your holiday into another list of things you should do.
Listen to what you need. If you are tired, rest. If you want to spend the afternoon reading by the sea, do that. You don’t have to visit every attraction, accept every invitation or spend every moment with the people you travelled with.
A holiday spent trying to please everyone can leave you needing another holiday when you return. I know, because that is exactly how I used to spend mine.
A holiday gives us the space to experience a different way of living: to be more adventurous, present, grateful, accepting and true to ourselves. But what is more important is that we can continue living this way when we return home. These are some of the ideas I explore in my book, As I Am, where I share what helped me move from self-doubt and overthinking towards presence, peace and joy.
Have you ever had a holiday where nothing went according to plan? I would love to hear what happened and how you responded.
