Top tips for planning the perfect trip away

One of my favourite things in the world is organising trips away. Some people hate it, but I can't think of anything more perfect than a whole afternoon curled up on the sofa with a notebook & pen, a laptop and the wonderful anticipation of an upcoming holiday.

A large part of my job involves organising amazing trips away for our whole team and it’s honestly one of the most satisfying parts of what I do. I love creating bespoke itineraries that are the perfect balance of relaxation, education and good, clean healthy FUN. Whether it’s a day trip over to Leeds, or a four day stint in Lisbon, I love ensuring that every moment is memorable. This is also the case when it comes to planning my own trips away - there are so many [SO MANY] amazing places in the UK to visit, let alone the world, so I always intend to only visit somewhere once to try and get as many places visited as possible in my lifetime. I therefore try and cram as much of what’s on offer at each destination into my time there, so I can come away feeling like I really experienced the place.

A trip to Ronda, Spain, earlier this year.

Now, I still love a good old R&R holiday, spending days lounging at the pool or beach with a good book and a Piña Colada to hand, don’t get me wrong. But for me, they have to be few and far between in order for me to fully relax and not feel guilty about not exploring.

A few people have commented on my ability to organise trips, so I thought I would put together my top tips when it comes to creating amazing itineraries, to help you make the most of trips away. One bonus tip before we even get started is to ensure you have as much time as possible to plan for a trip - spread it over a few different days to avoid information overload and allow yourself time to think things over, as it can get a little overwhelming.

Now, without further ado, here we go…

1. Arm yourself with these two staple research tools.

Google and Trip Advisor are my best friends when it comes to planning a trip away. I’ll use Google to research everything from must-see sights through to the best areas to stay, and then I’ll back up any suggestions I find with Trip Advisor to see what the most recent reviews are saying about a place. I also sometimes use Pinterest to find niche little blogs about places, as these can be great sources of “off the beaten track” ideas.

2. Clue yourself up on the place you are visiting.

The first thing I will do when I’ve chosen a destination is Google everything about the place. There are some great websites like The Culture Trip and Lonely Planet that have general overviews about pretty much anywhere in the world, to give you an idea of what a place is famous for, its traditions and culture, and top sights/attractions. I will make a note of anything I find particularly appealing/interesting.

3. Pick the best accommodation.

I use both AirBnB and Expedia to book accommodation, but I’ll always search on both to see what prices are like. Expedia has a great rewards scheme: you earn points with each booking and these equate to money off future bookings. I will often search for articles online that recommend certain areas of a place as opposed to just opting for a central location, as these often have golden nuggets of information regarding cool/upcoming neighbourhoods that will be cheaper, but still accessible to all of the main places of interest.

4. Create a custom Google Map for when you’re there.

One of the best tips I can give you is to use Google’s My Maps tool, to create custom maps on which you can highlight key points of interest, labelling them with specific icons so you know what’s what. The best part about this is that you can load these maps up on your phone while you’re on holiday, allowing you to navigate to where each activity/restaurant/sight is. Watch this tutorial on how to create your own map. I always add my accommodation as soon as I’ve booked it, and then add potential places as I’m researching so I can see how viable they are in terms of travelling to and from. Other staples I add to the map are good coffee spots, gelato shops, restaurants [split into breakfast, lunch and dinner options] and where the airport is.

The map I created for our Orillo Away Trip to Rome this summer.

5. Plan your days cleverly.

Once you’ve added everything you’re interested in to your map, you can start planning out the days you’re there in a really effective way, grouping together activities based on location to ensure you’re not wasting too much time travelling from one place to another. You can also plan where you want to eat or grab coffee based on any that you’ve highlighted that are within easy distance from the activity(ies) you’re doing that day.

6. Book in advance.

I would always advise to book at least some activities/restaurants in advance, to avoid any disappointments. This is more if you’re in a large group, but even if there’s only two of you, if there’s something you really want to do/see, just pre-book it to be on the safe side. It may also mean that you get to skip queues at larger attractions, thus saving more time to fit in even more to your holiday 🥳

The Orillo Team at an evening opening of the Vatican Museum.

7. Think about luggage.

If you have awkward check in/out times at your accommodation or they don’t align with your flight times too well, make sure you factor in what you’re going to do with your luggage, as there really is nothing worse than traipsing around with a heavy bag. If you’re staying in a hotel, you can almost guarantee they will have luggage storage free of charge for guests. If you’ve opted for an AirBnB, most cities now have bag drop facilities, so just have a quick look online to find one near your accommodation. You also need to bear in mind the time it will take you to pick your bags up before catching a flight, on top of actual travel time to the airport. The only thing worse than dragging luggage around with you is dragging it along when running through the airport about to miss your flight!

8. Find useful places near your accommodation.

I always find coffee and food options that are as close to the accommodation I’ve booked as possible. This can be a life saver if you’re running late and need to quickly grab food before heading off to do something. Nearby supermarkets and pharmacies are always handy to have marked up too.

9. Always have a Plan B.

You never know what might happen when you go away. Bad weather, attraction closures, random acts of God - you should always have a list of additional things to do on top of your chosen itinerary just in case something falls through.

10. Allocate more time than you need, as well as crucial down-time.

Things will always take longer than you think, so give yourself plenty of leeway when it comes to the timing of things. I would only try and fit one or two main things into one day, unless you are only visiting for a few days, in which case I would suggest some careful planning with a 30 minute buffer for each thing you want to do. I would recommend allocating a few hours of down time into at least one of the days you are away, to allow time to relax - sightseeing can be super exhausting, and a little bit of time to just mooch around or enjoy a lie down in the sun will be much needed in order to avoid feeling burnt out!

We used our "down-time" wisely and hired some electric bikes. Best afternoon ever.

The most important thing with any trip is to embrace the place you’re going, soak up the culture and enjoy every moment, even if things don’t go to plan. You might want to opt for a more laid-back approach to holiday-planning, but for me this way guarantees you see the most of a place and use the time you have there as effectively as possible.

I’ll be posting regularly about trips I’ve been on with specific itineraries to give you ideas, and of course I am always happy to help if you have any specific questions - just drop me a message and I’ll get back to you!

Let Me Know What You Think

Proudly created with