Travel like a pro: the best way to plan a multi-city trip

words Al Wood

A big part of the enjoyment of a multi-city trip is being spontaneous. Still, to get the most out of every moment of your journey, a certain amount of planning is essential.

Think ahead and you’ll be able to visit those bucket list cities, unearth those hidden gems and pack in a whole host of experiences you’d probably miss with spur-of-the-moment travel… and you’ll most likely save yourself a lot of money! 

In this article, we look at four essential tips to make your multi-city trip a memorable one.

multi city trip

Be flexible when choosing your destinations

The best approach is to start with a single destination. Maybe you’re attending a wedding, concert or another kind of event in a certain city. Or maybe it’s a bucket list city that you’ve always wanted to visit. In which case, build your journey around it.

Use a travel destination tool and research the surrounding areas, making a list of potential destinations. You could rank them in order and research the common routes that airlines or train operators take. That way, you can take a flexible approach and get the most out of the experience.

Put together a proposed itinerary, then expand on it

Sketching out a proposed itinerary can really help when arranging a multi-city trip. Having a framework makes it so much easier when it comes to searching for flights at the right times and dates, booking accommodation and finding cool tours and activities.

Accommodation is especially important and should be a focal point in your planning. You might have a personal preference – hotel, Airbnb, hostel or some other type of accommodation – so get a feel for the price and availability of each.

Some flexibility is definitely an advantage here. You might find that one destination has really cheap Airbnb rentals close to the places you want to visit, while another might be renowned for great hostels where you can meet new people. If you can, mix things up for a more rewarding, cost-effective experience.

If you’re backpacking or travelling for an extended period of time, making a spreadsheet and filling in sections as you book is a good idea. This way, you can make the most of every city you visit and keep in the loop with offers, events and activities, while generally staying on top of everything.

Keep in mind that there are now some great online templates and apps that you can use to help you plan your trip in detail.


“Planning a multi-city trip can be overwhelming, but having a structured itinerary and staying open to different forms of accommodation can make all the difference. Utilize online resources for assistance in navigating routes on Android devices, and you’ll be traveling like a pro in no time.” – Founder of Route4Me

multi-city trip

Use travel planning tools for flights and points of interest

Booking flights for multi-city travel used to be complicated and stressful. But nowadays, there are some incredibly advanced, easy-to-use flight booking tools at your disposal. For instance, Volario’s journey planner enables you to book flights with your choice of connections and preferred airline. If layovers are required, it even rates how difficult or easy each connection would be.

Being able to book your own self-connecting flights means more flexibility and choice around flight times and dates, as well as being able to save money and make the most of long layovers. If you want to save even more money, consider heading to a site like FlightList to book one-way tickets for less than the price of a takeaway!

Multi-city travellers can also use apps like Google My Maps to bookmark must-see landmarks, museums, top-rated restaurants and other places of interest. That way, you have a list of places to go and you can navigate to each one at a moment’s notice.

Don’t forget the practicalities

When planning your multi-city trip, the key is to balance budget with convenience. Planning in advance and locking down those money-saving travel options is great – think cheap train tickets for interrailing, multi-city bus passes, or even ferries to hop around islands – but shouldn’t come at the expense of practicalities.

So, try and figure the distances and timings between connections and consider whether you’ll be able to easily make them (Volario is a good tool for this). A cheap flight or train ticket might seem great for your budget, but does it mean waking up before sunrise and making a mad dash across town? Yes, keep costs to a minimum – but don’t forget how great it feels to travel stress-free.

Finally, don’t forget to check visas and other requirements for each of your destinations. You may have to think of supporting documents like boarding passes or ticket collection – again, a travel planning spreadsheet is a great way to keep track of all those little practical things that make for a smooth trip.


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