Ultimate Travel Planning : Where To Go When ?
It all starts with an idea.
A sun-drenched summer city break.
A bucket-list trip to the Caribbean.
A cosy winter escape to Europe’s magical Christmas markets.
There are so many places to go — but never quite enough time, annual leave, or money.
And while booking a holiday should be exciting, it can feel overwhelming…
Where should you go? When’s the best time? What’s actually worth it?
That’s exactly what this episode is here to solve.
Imagine a guide that walks you through every single month of the year, showing you:
The best destinations for good weather and stunning scenery
Where to travel on a budget
The top events and unique experiences worth flying out for
Sound like something you need?
Luckily, that’s exactly what I’ve created — and it’s all in this episode.
🎧 Click here to listen on Spotify — and start planning your best year of travel yet.
If you’re here because you’re not ready to listen yet, no worries. I’ve gotchu. I’m going to give a teaser of what we cover in the episode, so you’re in the know until you are ready to hit play :
January is actually a brilliant time to go away — even if it’s freezing in a lot of places. While most people are recovering from the holiday chaos (and their bank accounts are crying), that’s exactly why you’ll find some of the best travel deals of the year.
Airlines and hotels want to fill empty seats and rooms — so if you’re looking to save money, January is one of the best months to book a holiday. The savings can be wild.
Now, weather-wise, it’s a mixed bag — some destinations are better avoided, and others are surprisingly perfect this time of year. 🎧 Listen to the full episode to hear where I wouldn’t go in January, and where I definitely would.
The best places to travel to in January are typically anywhere that has super iconic New Year celebrations ; because lets be real - other than my birthday (whoop whoop) January is a pretty boring month. London, Sydney…to name a few.
February falls just outside the peak tourist season — so you’ll often find lower prices on flights and accommodation, although not quite as low as those post-Christmas January deals.
One destination I highlight in the podcast is Morocco — and honestly, it’s a hidden gem for this time of year.
With a growing reputation as a go-to spot, Morocco is still super affordable in February, especially if you’re smart about when and where you book.
It’s not just the price that makes it perfect — the weather hits a sweet spot too. Expect sunny days around 20°C, ideal for that perfect sun-tan-meets-city-exploring combo.
🎧 Want the full lowdown, including other February favourites? Listen to the episode here.
March is the sweet spot for the Canary Islands — especially if you’re after sun, warmth, and great value. It’s one of the cheapest months to visit, and the weather is seriously good.
If you’re after heat, put Lanzarote at the top of your list.
☀️ Fun fact: It’s the hottest of the Canary Islands — thanks to its proximity to the Sahara Desert. Expect sunshine, warmth, and golden landscapes that feel worlds away from grey March skies at home.
Not feeling a sun-soaked break? No worries.
Why not head to Dublin and dive into St. Patrick’s Day celebrations? From lively parades to a legendary pint of Guinness (or ten...), it’s a cultural event worth experiencing at least once.
That is the first quarter of the year touched on already !
🎧 In the rest of the Ultimate Travel Planning: Where To Go When? episode, I break down the best months to visit Thailand, Australia, Switzerland, Japan, and loads more — don’t miss it! Click here to listen.
Whether you’re chasing the sun in Lanzarote, soaking up the vibes in Dublin, or ticking off new destinations on your travel bucket list, the key to great travel is planning ahead. As we’ve seen, each month offers unique experiences — from bargain holidays to unforgettable events.
If you’re looking for more tips on where to go when, check out the full episode of the Ultimate Travel Planning podcast to get all the details.
And remember, the best way to start your travel adventure is by getting involved in our growing travel community. Join the conversation on Instagram at @winginitwisely and share your own travel ideas, tips, and experiences!
Happy travels, and don’t forget to Wing It, Wisely!