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Living, Travel

Lessons in Holiday Planning


Thanks to social media, it can sometimes feel like we’re the only ones not on holiday (yes, I’m aware I can often be fuelling that fire!) and we are constantly bombarded by holiday porn. I for one get completely bogged down, putting just about everywhere that looks pretty down on my mental bucket list which can make trip-planning tricky when you want to go just about EVERYWHERE.

However I’ve got much better at deciphering where and when to go places and like to think I have a pretty good back-up plan as a tour operator under my belt after lots of intense but successful flight-juggling-destination-hopping. So here are my tips for choosing, planning and enjoying trips to the max.

Make a Bucket List for the Year

This may sound super OTT but it really helps narrow down exactly where you want to go and budget for it. Ok, if you write down, Bora Bora, Iceland, Australia, Brazil and the Maldives, you might be in for a pretty unrealistic year. But a couple of weekend trips and a couple of longer stays could be doable. We can all get side-tracked sometimes and end up doing trips because they’re there rather than because we really want to go somewhere. I often find making a list of places I really want to do rather than naming every country in the world, helps me focus, plan and save to make them happen.


Try and Leave Perfectionism at the Door

I’m a recovering perfectionist and while it sounds like a great thing in job interviews, it can be really damaging in life and holidays are the worst for it. We sit around daydreaming for weeks, sometimes months, about that amazing trip we’ve got in the diary, picturing every detail, every meal, every outfit (guilty), and surprise, surprise, the reality of the holiday often falls slightly short of what you picture. I’m a big planner when it comes to trips; I want to go to every beach, every foodie recommendation, see every view and wander every pretty street all while being perfectly relaxed, easy-going and spontaneous of course. Needless to say these two sides of me never quite marry up and I’m learning to realise that there’ll always be one not-so-great meal, one underwhelming ‘must-do’ and one day where you just might not feel your best self. Learning to accept that not every trip will be 100% perfect is even harder in the age of instagram when everyone else is professing they’ve just had ‘’. But take what you see online with a good healthy pinch of cynicism and relish your holiday for what it is. I’m still battling with this and still want to cram everything in and sometimes confuse what I want to do with what I think I should do. However, I can say I’m now a total pro at not freaking out when it rains on holiday and am realising you will rarely, if ever, do everything you want to in a week let alone the two days I’m often in one place for. But most of all, I’m learning to love the control-freak side of me that wants to plan the perfect trip because when it comes down to it, wanting things to be amazing for both you and your travel companions isn’t exactly a terrible quality.


Sometimes it’s O.K to Fly and Flop

We can all feel the pressure to explore on holiday which is a credit to our generation I think. Rather than going to the same European spot summer after summer, we can often feel both the desire and the pressure to make the most of our time of earth and cram as much as humanly possible into trips. Sometimes this it totally worth it (I did a great 10-day whirlwind tour of Rajasthan a few years ago) but other times, it’s o.k to just go and lie on a beach for a week. Modern day life can really take it out of you and there’s no shame in booking a nice villa or a hotel for a week in one place. Maybe this is just my predicament, but I often feel guilty for going back to somewhere I’ve been before or only staying on one place. But this year, I really enjoyed going on holidays with friends to familiar places and have already decided I want to spend a week in Ibiza next summer, casually going between old favourite places and new places I’ve never been to before. Basically, listen to what you really need from a trip and know that sometimes it’s ok to relish the familiar and make a holiday a holiday rather than an adventure.


All-Inclusive Isn’t Always a Dirty Word

All-Inclusive doesn’t exactly fill you with thought of boutique luxury does it. But when it comes to certain hotels, it can be worth it. If you’re going to the Maldives or any kind of long-haul resort where there’s not lots of different restaurant options within walking distance, it can be worth going for the all-in option. The Maldives are famous for excessively expensive food (everything’s imported so it kind of makes sense) so it’s much nicer to go knowing everything is already included is kind of liberating. No one wants to sit around on a special trip deciding whether or not they can afford lunch. It’s always worth remembering to check out the prices of food, drink and extras before you go and keep money back for that. You might have afforded the cost per night but remember that’s just the first piece of the puzzle.

Dig Deep with Accommodation

When it comes to booking hotels or apartments, get all the info to save being stung. Ever ended up in a hotel that’s miles away from where you want to be or an Air BnB that’s on a really busy road that keeps you up all night? Yeah, it’s annoying. I really go the extra mile when I book somewhere to stay. I research, research, research. Read the reviews, have a look at the pictures on Tripadvisor (if it looks nice on tripadvisor you’ve found a winner seeing as everything looks kind of rubbish on there I find), ask your Airbnb host key questions and check out things like parking, check out time and location carefully. Google street view can be super helpful for checking out Airbnb’s location or hotels. Also, compare everything; sometimes it’s better to stay in the nicest room in the cheaper hotel than than the smallest room in the super expensive hotel. Worth comparing the two to see what works out as better value. My favourite sites for finding hotels are Smith Hotels, i-escape (they also have a really good ‘where to go in which month’ secion which I find amazing for inspo) and Tablet Hotels to name a few and I rely heavily on Conde Nast Traveller for telling me about new, off the beaten tracks B&Bs, hotels and destinations. I’ve also liked Goop’s travel guides when planning on where to eat, sleep and and what to see too. Instagram is obviously a great tool in itself and I use the save tool a lot for hotels to find places that might not be so easy to find or remember. Just keep in mind everyone is different. One woman’s trash is another’s treasure after all, so just because someone swears you must stay somewhere or posts the shit out of somewhere lavish on instagram, it might not be for you so always triple check it.

Think Outside High Season

I think school holidays are ingrained in us all and we all automatically think of June, July and August when it comes to escaping to Europe, but don’t overlook April, May, September and October for some of the busier destinations. I’m about to go to Positano for a weekend (it’s mid-October if you’re reading this at a later date) and touch wood, it’s looking like it’s going to be a sweet and sunny 21 degrees. Sure the weather is a little more uncertain but one thing I can be sure of is it will be significantly emptier and cheaper than even a month before. Southern Europe gets amazing weather all the way through to October so think outside the box to stretch your wallet and minimise photo bombs.

Shop Around for Flights

If you can be flexible for dates, I use the ‘whole month’ tool on Skyscanner to find the best price for flights. Sometimes flying Tuesday to Tuesday is much more economical than Friday to Friday but obviously you don’t get the bonus of the second weekend. Skyscanner is my go-to for all flights. It draws in easyjet and Ryanair etc as well as the bigger airlines and I find the breakdowns for stopovers really easy to understand etc. Double check prices to different airports too; for example, there are three international airports in Jamaica so it’s worth checking which is closest to your hotel and which has the best flight prices and times for you so you can weigh everything up.

Don’t be Fooled into a False Economy

Flying from or to that airport might be £100 cheaper but are you going to have to spend the same in cabs to get where you want to go? Shop around for cheap deals but take into account any extra costs to balance it out. Make sure you google map the driving distance from your accommodation to the airport and map any transfers between hotels if you’re moving around too and take this into account when booking your accommodation.


One Size Doesn’t Fit All

I’m lucky enough to have worked in travel long enough that I get to visit and stay in hotels I might not otherwise be able to in exchange for reviews and photography. Plus, being self-employed with a focus on travel writing and photo-journaling my trips, I try and see travel as an investment in my career as well as a much-loved passion, so I try and see as much as the world as I can while holding down a homelife in London. Combine the two, and I’m away for more than your average 25 days a year normally, and often in need of mixing up who I take with me. There are some trips I would only want to do with my boyfriend, not necessarily because they’re super romantic, but because they’re longer, meatier and to be frank, we can argue over directions in the car before laughing it off and swiftly moving on. Something that’s not always as easy with a friend for me. However, there are other holidays or trips I want to do with a group or just one friend and just lounge around in a villa for a week, laughing till we cry and talking about everything from feminism to face wash. There are some friends you’d want to hole up with in a cosy spa for a weekend, others who you want to dance until 5 A.M with, and some who you can do both with, so make sure you base who to travel with on the trip itself. It’s not a reflection on the quality of friendships but it’s definitely easier if you both want similar things out of a trip. If one of you wants to do yoga and be in bed by 11 every night while the other wants to bar hop and sleep late, you might struggle to make it work for both of you. Compromise and being upfront about what you need from a holiday is key.

Lastly, Pack Smart

I’m a serial overpacker so I’m most definitely not the person to dole out advice for how to pack for a week in a carry-on. However, I am the person who has everything you could possible need so you know, swings and roundabouts. A few things I’ve learnt are always worth having to be said smug person who is never caught short are below.

– A proper medicine kit incl. immodium and dioralyte (not cool or glamorous but if the worst happens, who wants to leave their sick bed and explain to reception what they need), pain killers, plasters, antiseptic, melatonin (if you use it for jet lag etc) and anything else you personally might need. Side note, if you’re going somewhere really exotic and are travelling around, take a course of probiotics a month before you go to support your gut. Second sidenote, never, ever travel to the U.S without travel insurance. After having to go to a doctor in New York once fashion after getting Olbas Oil in my eye and blistering it and $2000 later, I had my eye drops. Luckily I was insured but lesson truly learnt and that was just a simple, non-emergency doctor’s important.
– Two bank cards of some sort (one you can leave at home/in the hotel and one you can take out with you) – especially relevant if you’re going to to be partying hard/prone to losing things.
– The right batteries for the right cameras and the right chargers. I went to the Caribbean earlier this year and took the wrong charger for my camera battery so I had no digital camera for the whole trip. I almost cried and spent a whole morning calling around camera shops in Miami before our flight to no avail.
-A photocopy of your passport left in safe hands at home.
– Good quality sun cream. I for one do not want to have to rely on Hawaiian Tropic for a week.
-If you’re weird like me, take your own pillow case if you’re going to an Air BnB. I never used to do this and maybe I’m getting old and fussy but I’ve found it instantly makes me settle in somewhere easier and sleep better. Likewise wax ear plugs and an eye mask come everywhere with me.
-Comfy clothes for chill time. I’m not at all chic about it; marl PJs and a hoodie or long sleeve loose tee works for me, but I need something to lol around in, especially if I’m travelling for work and every minute of down time counts.
– Double check the weather at night. The first time I went to L.A I was ready to wear teeny tiny shorts and dresses every night but it was actually really cold and windy at night so I basically froze every night. Likewise, if it’s July in Greece, you don’t need that extra jacket or jumper (we Brits like to pack for every eventuality).



What are your top travel tips?