How to Plan the Perfect Holiday

Just recently on Instagram I asked our followers what they would like to see on the blog. I left suggestions like photo editing and interior styling but one answer I didn't anticipate was the 'planning' stage of travel. And I'm so glad it came up! Surprising to those who know how spontaneous my holidays can be (I've actually jumped in a taxi to the airport without having received my boarding pass yet 😬), when it comes to the details of what I want to do on a trip I have those plans building in my head for years. 

Even when travel seems waaaay off, like the current lockdown situation, I find a lot of enjoyment in dreaming up trips and itineraries which only simplifies the booking process once I'm ready to go. So today I'm sharing the main steps I take towards planning the *perfect holiday.

*And by perfect I mean, what is most important to you, on your dream trip. And step one is all about discovering just that...

Step 1. Find your perfect. 

Ask someone for recommendations on what to do/see in any given destination and you'll be bombarded with "you have to see (insert landmark here)". And while I'm absolutely guilty of doing this (always with the best intentions) your own travel goals can get lost in the noise. 

Firstly, think about exactly why you want to visit a particular destination. Is it because you need to disconnect from work life or is it because you're fascinated by a particular landscape or culture? Write down these goals so that you can refer to them and stay on track during the planning process. 

I'm going to use an example during this blog post of our trip to Spain and Portugal. This is the most recent trip to Europe my husband and I have taken and we put a lot of things into practice that we had learned from past planning mistakes. Goals for our trip were:

  • eating tapas
  • drinking sangria
  • photographing Spanish villages
  • just generally living the good life 😉

Not really much in the way of resort-style relaxation but more of an 'explore alleyways in search of food and wine' kind of trip. The photography aspect of our goals also dictated which locations we prioritised. I was seeking out small sleepy villages rather than big city landmarks. 
 Spanish Tapas

Eat all the goat cheese: ✔️

Step 2. Choose when to go and for how long. 

The time of year you visit a destination will greatly impact what you can experience there. The weather can change quite drastically, not to mention the crowds and the cost! I recommend choosing a time that fits your work or study schedule best to lessen the impact on your income when you return. This is different for everyone of course, but as my husband and I are both freelancers we don't have any annual leave and try to choose the quietest time between projects to travel. 

If you have the freedom of unlimited time, be sure to revisit the duration as you work through your itinerary. One affects the other and you may want to add more time for certain activities.

We opted for 4 weeks in September which is when our work is seasonally quiet every year. 4 weeks is also a duration that we've found works when you want to explore 2 countries in depth. I know what you're thinking, only two!? But in the past we have done this in Italy and France and then again for Greece and Turkey. We've found it's a good balance between seeing the majority of the country and moving at a relaxed paced. There are still places in those countries that we didn't explore but it allowed us to immerse ourselves in the towns that appealed to us most. 

Spain Moped

Step 3. Make a wish list. 

This part is the most fun, making a wish list of everything you dream to see and do. I honestly find it best to include everything regardless of your timeframe. That way you're not going to risk overlooking anything and you can let the list dictate your schedule a little. It also makes you think about your priorities later in the planning phase if you've got every option to choose from. 

Pinterest travel planning

Some of my travel inspirations from Pinterest.

Step 4. Research. 

This step is an obvious progression from list-making. As you research recommendations for what to see and do, add new discoveries to your list. Make a note of events that might be on in each region. This is a step that I've been guilty of neglecting, only to find that I've missed a local festival by a day or two. Being a visual person I prefer to research from blogs that are photographic in nature. I often search fashion blogs for my given destination because I find they're more image heavy which I absorb better than text. I do use notable travel guides like Lonely Planet to form a basic list and then branch out by searching the key terms in Pinterest. 

For example, I pinned an image on Pinterest of a white village in the south of Spain well before I ever had plans to travel there. I had no idea where the photo was taken but once I started planing our trip I dug a little deeper. I found it was taken in Frigiliana, a quint whitewashed village not far from the south coast. We ended up planning our road trip through this town for a 3-night stay and it became the highlight of the whole trip. 


The street that inspired our detour through Frigiliana, revealing itself on an afternoon walk.

Step 5. Map it out. 

To take the next step towards nailing your itinerary it really helps to group everything on your wish list into regions. By doing this you can instantly see which cities need more time or which are just too far out of the way.  I usually put everything under sub-headings grouped by town. Or in the case of somewhere like Japan, I arranged them in order from north to south to figure out the best route by rail. You can always screenshot your destination on Google maps and mark out each site so that you don't have to keep track of them in your head.  

Once I did this for our Spain trip I found that Madrid was going to take up too much of our time. We couldn't get any direct flights from where we were planing to drive along the south coast and knew we'd have to double back to continue our drive in to Portugal. This leads me to more about timing...

Step 6. Set some boundaries.

These are a few rules we've come to live by that maximise your time spent travelling:

No doubling back: Okay so there's a place you want to see with only one way in and out. Say a remote peninsular or a place that doesn't have many connecting flights. If the journey in and out is long (with not many options to sightsee on the way) I usually drop it off the list. This depends on your timeframe and how important that location is to you, but canceling a round trip to one site can seriously add breathing room to the rest of your itinerary. 

No stays less than 3 nights (unless you're in transit to your next destination): Now this might seem extreme but it's a must for your sanity. On our first few holidays we didn't have this rule and spent 1 or 2 nights in places that we thought didn't need a lot of time. Let me tell you, the relentless unpacking and packing of your suitcase (or not unpacking for fear you'll get too comfortable) can really burn you out. With a minimum 3-night stay you get to actually unwind and forget about the logistics of getting to your next destination. It also means there's less risk of you missing something amazing in that town because you just didn't have the time to explore it all. 

Don't rule out domestic flights: There's something appealing about public transport when you're travelling that you just wouldn't buy into at home. 6 hour ferry to the Greek Islands, sure! Why not throw in a 5 hour bus ride in Turkey too. I've learned to pick and choose public transport carefully in Europe because often it's actually more expensive than jumping on a quick flight. Of course there are moments where you want the romanticism of taking a train through the countryside but there are also times when a domestic flight will streamline your itinerary.

Postcards from Frigiliana

Postcards from Frigiliana. 

     Step 7. Bring it all together. 

    1. Grab your wish-list of things you want to see, grouped by city or region.
    2. Cross off anything that doesn't fit within your realm of transport. Are you driving? Do you have to stay near major train stations? Or are you limited by ferry timetables and flight connections?
    3. Cross off anything that doesn't fit in the season you are travelling. For example, beachside towns in the midst of winter. 
    4. With the places that are left, pop 3-nights next to each major town, adding nights spent at the airport or stopovers during a road trip.
    5. Look at the total number of nights. Are you waaaaay over your timeframe? If so, look back at your priorities. Remember, removing one city will give you back at least 3-nights worth of time. 
    6. Look for any areas where you can cancel a long day in transit with a quick flight. 
    7. Now you have the crux of your trip, start entering places on calendar dates. You will soon find if flights aren't available on certain dates or if hotels in small towns are booked out on the weekends. This is where you can start to manoeuvre solid bookings into place. 

      Of course things will change fluidly between all of these steps. The main goal here is to enjoy the process of creating you dream holiday knowing that you're planning for quality rather than quantity. By following these steps you'll be on your way to experiences that are unique to your own priorities, making for some memorable moments. 

      If by chance you're planning a trip to Spain and Portugal too, feel free to leave any questions you may have below. 

      Happy travels,


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