How to Plan a Multi-Stop Adventure

Want to make the most of your annual leave and see multiple places in one trip? You’ve come to the right place.

Over the years, I’ve developed a serious love for multi-centre holidays. I’m almost certain that it was my group tours in 2015 that planted the seed: my travel style changed from week-long all inclusive holidays to stopping off in a new destination every couple of days and I couldn’t get enough. After those organised tours gave me a taster, I went big, organising a backpacking adventure that took me across eight different countries and I’ve been pretty confident in constructing my own adventures ever since.

This takes us nicely to the point of the article: if you’re new to planning a multi-stop trip, how do you get started? While going through travel agencies can be incredibly valuable, their tours can also be expensive so if you’re considering booking a whole multi-centre trip for yourself, this blog post is for you. It can seem overwhelming, tiring and downright stressful at times but I promise, it’s worth it. By splitting it down into small steps, I hope this guide on how to plan a multi-stop trip will help the process to feel easy and manageable.

Step 1: Do your research

Okay, let’s begin with the obvious. If you have an idea of where you’d like to visit, getting started feels much less overwhelming. Write down the length of time – from a few days to an epic year long adventure – and approximate budget you have to work with alongside the different places you’d like to see.

How carefully you need to plan depends on the length of your trip. If you’re backpacking, you may want to have a more flexible plan so you could map out a rough route of which destinations you’d like to visit, making sure to include entry and exit points for each country. On the other hand, city breakers might need a firmer plan to maximise time.

With an idea of where you’d like to visit and when, it’s time for the fun bit. Grab a cuppa, snuggle up on the sofa and start reading. Before I went over to Australia, I watched tons of YouTube videos on Working Holiday Visas, planned the best time of year to head over (that fitted with the seasons and my saving plan) and read blog posts galore with different itinerary ideas. Hopefully, after you’ve got this far, you should be able to start forming the outline of your route.

Two key factors to consider

Geography: the key to logical planning

In school, Geography was never my forte. Actually, if I’m totally honest, I’m still pretty terrible at being able to name where different cities in my own country are located. But planning a logical travel route is really important when it comes to both saving time and money. If you get stuck, tour companies, travel blogs or agencies specialising in multi-stop itineraries can help you to get a handle on how to find your way around a particular region or country. You may feel like you’re following the crowd but actually, creating a rough multi-stop route based on this advice can be really bloody useful.

Time of year

Before I book any holiday, I search “best time of year to visit ***” to check out the weather. If you’re staying close to home, chances are that this won’t be so important but on longer trips, you could be in for a surprise. For example, different parts of Australia have different climates and if you fly into Melbourne in June, you’d be in for a shock if you were expecting hot and sunny weather. Rainy seasons can play havoc with transportation in less developed countries and accommodation prices can soar during peak seasons. If you want decent weather without the crowds, seek out mid (or ‘shoulder’) seasons where you can usually bag a lower price.

Step 2: Assess your budget

Once your route has started coming together, it’s best to check out the money side of things before you become too emotionally invested. I foolishly left my dream destination of the Philippines until the end of my backpacking adventure and when it came to crunch time, we didn’t have enough money to pay for the costly internal flights we needed. Luckily, we had an unexpectedly amazing time in Malaysia but it could have been a real downer to the end of our backpacking trip.

Your research from step 1 should have given you a rough idea but to get a better idea of costs, start by searching for those big spend items. Your flights (or whichever form of transport you plan to use!) and accommodation should come first, followed by any activities that you definitely can’t miss. If you have the luxury of time, taking slower modes of transport could save you cash but if you’re on a short break, you may need to spend more to see more.

If you have exact dates that you need to stick to, I’d check out Skyscanner to see whether your flights are affordable before doing anything else. This way, if the prices are at an unexpected peak on a specific date, you could rearrange your itinerary to fit before you’ve locked in places to stay. On the other hand, if you find a really good price, snap it up before it goes! Unless there’s a special sale fare, flights will only go up in price from when they’re released.

Step 3: Lock in the key elements

The shorter trips

It’s time to get booking!

If you’ve followed the first two steps, you’ll know why you want to visit each place, have an idea of the attractions you’d like to see in each and be confident that you can come in on budget. I rarely book packages as I find that I can usually get better deals by securing my flight and accommodation separately. I’ll virtually always book my flights first, then check out where I’d like to stay. Comparing hotels on Booking.com often comes out at the best price for me but you can sometimes get extra perks from booking direct so it’s always worth shopping around to grab the best deal.

The longer adventures

If you’re backpacking with a loose plan, this process will be slightly different. You don’t want to commit to an entire, jam-packed itinerary months ahead of time because let’s be honest, flexibility is one of the best things about being on the road for weeks or months on end. Howver, getting the balance right is important because leaving things too last minute can mean missing out on the best deals.

If your trip depends on a visa, get that in the bag before you commit to booking anything else. Considering a Working Holiday Visa in Australia or New Zealand? I felt nervous about planning a multi-stop trip alone so I booked onto a 7 night Work and Travel package through STA Travel which was a great comfort blanket during my first week. They’re definitely not an essential but if you want help with the logistical details (or just to make a few friends), I’d recommend checking them out.

Next up – flights! If the thought of travelling felt surreal before now, this will suddenly make it hit home! Whether you choose to book in all your connecting flights between destinations or just get a one-way ticket, you’re taking the first major step of that journey right now. I’d also recommend booking at least a weeks acommodation in your first stop to help you acclimatise without needing to worry about finding a place to stay.

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Step 4: Get excited

As if you needed telling!

Once the main elements of your multi-centre trip are sorted, the remaining time before you leave is all about making plans, tying up loose ends and making sure you have enough money to live your dream – whether it’s for a few days or a few years!

Regardless of how long or short your trip is, don’t forget to buy travel insurance! It’s usually better to do this as soon as the first component of your trip is booked as many policies will cover you in case of an unavoidable cancellation. To find the best deal for my annual insurance policy, I usually use a comparison site like Compare the Market – 2 for 1 movies is a great perk if you buy through them!

To round up…

Planning a multi-stop trip is amazing! All the research you do makes your trip feel way more personalised, not to mention the sense of achievement from arranging a complex holiday alone!

Whether it’s twinning up city breaks or heading off on a longer backpacking trip, multi-stop holidays can be a great way to travel. You get to explore two (or more!) places, instead of just one, and it feels like you’re really making the most of that precious annual leave.

Of course, this style of travel isn’t perfect. On very quick trips, you’ll only have time to scratch the surface of the places you visit and we could question how valuable it is to rush through places just to ‘tick them off’. But there can be some amazing benefits from using one trip to see multiple destinations, including reducing your environmental impact and saving money by taking less flights. In my eyes, seeing as much of the world as possible can only be a good thing.

I’d love to know if this guide on how to plan a multi-stop trip helped you to create your own itinerary! Let me know where you’d like to go in the comments.

Laura x

Still not sure? How about a group tour?

Check out my experiences of Contiki and Sail Croatia on my Group Travel page.

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