This post contains affiliate links. I may earn a small commission at no extra cost to you. Thank you for supporting Snowflakes & City Lights Travel.
It always starts with the fun stuff: pinning dream spots on Google Maps, watching vlogs, and imagining yourself wandering through new neighbourhoods and eating street food. It’s quite the rabbit hole.
Planning a multi-city trip is exciting, until it’s not. Suddenly you’re juggling a hundred tabs, itinerary ideas, transport logistics and second guessing your ‘nights per city’ all while feeling the pressure of getting it just right and wondering how to start.
This guide breaks down how to plan a multi-destination trip step by step, creating a framework to help you make the decisions on flights, pacing, transport and logistics without locking you into a rigid plan.
Over the last 20 years, I’ve planned multi-city and multi-country trips across America, New Zealand, several trips across Japan (with side trips to other countries) and most recently a Hong Kong – Macau – Hanoi holiday with our nine year old son. I’ve learned how to make even complex itineraries feel realistic, flexible and fun.
I might be crazy, but I enjoy the planning and research part almost as much as the trip itself. I say that as someone who is not organised and doesn’t like rigid plans. If you’re unsure where to start or worried about missing something important, this framework is designed to help you plan with confidence. Even if, like me, you aren’t a spreadsheet person.
Each of these sections builds on the last, and you can pause once you’ve made that decision. Most people plan a multi-city trip over several sessions and this framework is designed to support that.
Quick navigation:
- Where to start
- Choosing flights
- Building your itinerary
- Where to stay
- Getting between cities
- Pacing your days
- Tools we use
- Admin reminders
Where do I even start?
Start with the basics: Where do I want to go? When am I available to travel?
For us, that usually means working around school holidays and work schedules. Those dates will determine flight prices, availability, and how much flexibility you realistically have. Ideally, you have a few days of wiggle room and don’t need exact dates.
You also want to look at the climate here too, especially in destinations where heat, humidity or winter conditions affect how much you will be able to see and do. Our goal is always to see and do as much as we can, so we make sure we can allocate more time to a snow trip as we know that mountain days won’t be sight seeing days. Humidity often slows our pace down a little too.
Generally by the time you are ready to plan, you know where you are going. If not, go back to vlogs and daydreaming! Explore ideas of locations – but keep it general. You don’t want to start pinning down specific restaurants or beaches yet. Don’t worry, you’ll find them again when you get into the research phase. But you need to know the cities / country / countries you will be visiting.
How do I choose flights?
This is always my biggest hurdle and I can absolutely see why you might decide to run to the local travel agent and hand them all your money at this stage. Once we have decided on a destination, booking our flights comes quickly after, as far in advance as we can. Flight sales are rare and the prices will only increase. This may be specific to the Australian market, or because we are booking during peak times such as school holidays, but I highly recommend doing this early.
Phase 1 – Investigate the routes on Skyscanner
At this stage, the goal isn’t to find the perfect fare. It’s to understand routes, layovers, which airlines are available, how different combinations and orders change the price and shape of the trip.
- Start with the basic route: What’s your entry and exit city / country and other non-negotiable stops.
- Play with the order: On our last trip, we saved $200 by flying to Hong Kong first instead of Hanoi.
- Can you fly into alternate cities: For us, Osaka is usually cheaper to fly into than Tokyo.
- Compare across your travel window: A one day change can make a big price difference.
- Look for open-jaw opportunities: These are flights into one city and out of another. For our Taiwan–Japan trip, we booked Perth–Taipei and Osaka–Perth as one multi-city booking and added a one-way flight between Taiwan and Japan. It was cheaper and gave us better flight times.
- Decide on time spent in each location if booking multi-city in the same booking: When we booked Taiwan and Japan we had an open jaw ticket. so could later decide when to leave Taiwan; however, our Hong Kong, Hanoi trip was all in one booking so we did need to already know the break up of time per country, while the order was flexible.
This is also where you figure out your non-negotiables:
- Are red-eye flights okay?
- How long are you willing to stop over? How many stopovers are your limit?
- Do arrival times matter?
- Are you avoiding or preferring certain airlines?
- Budget carrier or full-service?
- Are you okay booking through third parties, or do you prefer going direct?
- Is your priority budget or better flights?
Note: Smaller regional airlines often release their flights later than major carriers. If you’re relying on one to complete your open-jaw route, check the same route on different dates to get a sense of the price. These prices usually stay consistent, so you can book later without big surprises.
Phase 2 – Book your flights
By this point, you likely have a fairly good grasp on which route is going to be the best suited to your plans and preferences.
Now it’s time to book. You’ll need to decide whether to go through a third-party platform (like Skyscanner or Expedia) or book direct with the airline. We always book direct. It may be slightly more expensive, but we’ve found it easier to manage changes or issues that way.
Double-check your dates, flight times, layovers, and cancellation policies before hitting confirm, and you’re done. It doesn’t hurt to sign up to any loyalty programs before booking too!
How to Build a Realistic Multi-City Itinerary
Time to build your itinerary. But first, you get to do the fun bit!
Build your dream list
Go all out and research your destinations. What’s possible, which cities catch your interest? Use blog posts, vlogs, Facebook groups, social media and tourism websites to build your dream list first. For each potential location:
- Create a list of anything that excites you (sights, activities, cities)
- Keep food spots (restaurants and cafes) in a separate list from attractions. These usually don’t drive how many nights you need.
- Mark:
- Must dos
- Nice to haves
- Pin everything to Google Maps.
- Helps with navigation when you arrive
- Shows whether attractions are clustered together or spread out, which impacts how long you need.
Leave a little unplanned space if time allows, even if that means dropping a location. You want to have time to just be in a place and leave unstructured space for spontaneity. It doesn’t have to be perfect because if you’re like me, you’ll still be googling ideas right up until you complete the trip. But you will have a good idea of what you want to do in each location and a bit local context for each city.
Reflect on your travel pace
Everyone travels differently and there is no right answer. But in order to map out your dream list, ask yourself:
- Do you prefer exploring fewer places more deeply, or covering more ground at a faster pace?
- How much, if any, unscheduled time do you want within each day / across the trip?
- Do you enjoy filling every moment, or having space to sit in a café and wander?
From here, you can start adjusting your itinerary.
- Which destinations are non-negotiable?
- Which stops feel like filler?
- Is your pace sustainable, especially with kids or during peak travel periods?
General night-per-city guidelines
- 3 nights minimum is a solid rule of thumb. This gives you two full days and buffers for travel, packing, check-in, and fatigue.
- 5 nights gives you breathing room. Enough time for must-sees, a day trip, and spontaneous exploring.
- 1–2 nights is best when:
- You’re stopping just to sleep
- You only have one thing to do there
- Transfers are very short and simple
Once you’ve assigned rough night counts to each city, you’ll have a “mud map” of your itinerary: where you’ll be and when, plus a clear sense of your must-see attractions. Your day to day plans don’t need to be locked in, but you will know what matters most to your experience.
How do I decide where to stay?
A quick Google search of ‘where to stay in … ‘ will bring up the main areas and usually a few descriptions of. what to expect there. Backpacker vibes, shopping, culture etc. Spend a few minutes reading about them but do not get bogged down in this. First instinct is usually the right one.
Then you need to look at your accommodation budget and what you need in a room. List out your priorities and use them to filter your accommodation searches. Consider:
- Type of accommodation: Hotel, Airbnb, homestay etc
- Budget: What are you willing to spend per night?
- Room & accommodation amenities: Bed configurations, pool, breakfast included etc
- Location: Do you want to be close to public transport, specific sites. or areas?
We use booking.com for all of our hotel bookings. The filters quickly narrow the field and makes the decision making process much easier. You can search by budget, location and amenities.
How to I plan to move between locations?
This is one of the most underestimated parts of multi-city travel and taking the time to plan travel between cities carefully, whilst it can. be a challenge, will make your trip run smoothly.
Take our travel day from Niseko to Tokyo. It looked simple: one hour drive to Sapporo, one short domestic flight. In reality, it took nearly the whole day. Packing up, driving to Sapporo, finding the luggage forwarding depot (where no one spoke English), dropping off the rental car, taking a bus to the airport, checking in, waiting, flying, arriving, getting out of the airport, then into a taxi and finally checking into our hotel. It started at 8am and we weren’t settled again until after 5pm.
You will need to work out what your personal priorities are for each transfer. We usually aim for shortest time and most convenience. But this doesn’t always lend itself to the budget. Sometimes a quick, direct route is best, other times you want flexibility to stop and sight see along the way.
The best way to get around depends on the country.
- In Japan, we rely heavily on trains in cities and the shinkansen between them, but we always hire a car in snow towns or when exploring outside metro areas.
- In New Zealand, a car is essential.
- In Southeast Asia, we mix internal flights, trains, ferries, Grab and taxi rides.
Each region has its own strengths and it’s worth adjusting your expectations accordingly.
Some key tools we use:
- Skyscanner to see available flights and compare routes
- Blogs to learn how locals or travellers typically move between places
- Google Maps to estimate travel times and modes
- 12go, Klook, and JR East for train and car hire options
- Grab in Southeast Asia (like Uber)
Once we know the route, we consider what mode makes the most sense for us. Flights are faster for long distances, but need more time built into the itinerary around it. Trains are great for direct city-to-city travel, but less ideal if you’ve got bulky luggage or want to detour, and of course they vary across countries. Car hire gives flexibility, but needs to be booked well in advance (and there are some countries where we wouldn’t want to drive!). If you do choose to drive, make sure you have an International Drivers License organised.
Some transport require advance booking and others can can be more flexible. For example, the ferry to Macau was fine to book when we were ready. Shinkansens are usually available, but as the tourist numbers have increased during peak periods seats can sell out, which was never an issue on our first trips.
We’ve seen families land in Queenstown hoping to rent a car on arrival, only to find them sold out. In Japan, car hire is surprisingly expensive and sometimes tricky to return in a different city. Wherever possible, we book these early.
What to consider when choosing your transport mode:
- Luggage: Can you manage bags on public transport or will you need to send them ahead?
- Travel time vs energy cost: Is the fastest option actually the most practical for your family?
- Budget: Will a flight save time or blow the budget? Is the train worth the upgrade to first class?
- Kids’ tolerance: How long can they handle in a car, on a train, or in transit without a meltdown?
- Scenic value: Will a slower option let you see more along the way?
- Pick-up and drop-off logistics: Are the stations or airports conveniently located?
- Car return options: Can you return it in another city without huge fees?
How do I handle travel days?
On travel days, keep your other plans light and flexible. We will rarely book a ‘must do’ on our arrival and departure days, and instead use them for exploring our new local area or taking a last look around and do any last things we want (purchase a quick souvenir etc). Of course, we are also guilty of getting ambitious on the day and push it to the wire. If you’re an adrenaline junkie I dare you to take one last look through Coventry Markets in London while you should be in the international departure terminal!
Before planning around the travel, consider these in your plans for the day:
- Packing up
- Checking out
- Getting to stations/airports
- Waiting (delays, queues)
- Luggage handling and drop-offs
- Transferring at the other end
- Checking in and getting settled into your next stay
If travelling as a family also factor in snack, bathroom and play breaks as well as recovery time from travel. It adds another layer of time to your movements.
But it absolutely doesn’t mean that it’s too hard and you shouldn’t do it – it is worth it.
How do I pace the days?
Once your cities and nights are set and transport is considered or booked, it’s time to think about how each day might look, without locking in every hour. Pacing makes a big difference when planning a multi-city trip.
Start by pre-booking any experiences or attractions that book out in advance. For us, that’s included Universal Studios Osaka (and the express pass), ski school for our son and concert tickets. We’ve also missed out on things like the House of Dancing Water show in Macau and TeamLabs Tokyo by not booking early enough.
Beyond this, we try to alternate between high-energy days (like theme parks or day trips) and nature or slower days. Grouping activities by location also helps avoid bouncing all over the city and spending half your day on logistics. It also helps to spread similar experiences out. No-one wants to see ten temples in one day, but seeing them spread over a few days between variety is a different story.
Our general plan is to have a flexible itinerary with a list of things we want to do, a general idea on which days they might fit into, or at least which things would go together on the same day, and then move it around as we feel on arrival.
Trip Planning Tools That Actually Work
There are so many tools available for organising trips. I’ve never found one that I have liked or been able to stick with (but I’m working on it!). For us, its a simple shared Google Doc, Google Maps and an email folder.
- Google Maps
Saved places for attractions, cafes, and anything we’ve come across in research or vlogs. - One shared Google Doc
Holds our rough itinerary, accommodation, notes, costs, to. do list and a running list of ideas we can move around. - One email folder
All booking confirmations go here: flights, hotels, passes, booking confirmations so that nothing gets lost. - Booking.com
We use this for most accommodation since it’s easy to manage multiple bookings in one place. - Flight search tools (like Skyscanner)
Just for exploring routes. We always book directly with the airlines.
Admin reminders
This is your quick reminder to double-check the boring-but-essential things that can derail a trip if missed. These will vary by destination.
Checklist:
- Entry requirements and visas
- Internet access (eSIMs, local SIMs, or roaming setup)
- Payment methods and cards
- Luggage logistics between destinations (carry-on only? forwarding services? Storage needed?)
- Travel Insurance
- International Drivers License
- Medication planning
- Adapters and charging set up
- Emergency contact and document back up (coming from someone who has lost their passport twice, this is so important)
- Download relevant apps (Google Translate, local taxi apps etc)
When to do this:
About 4–6 weeks before your trip, check through this list and note anything that needs early action, especially visas or SIMs that need shipping. Set reminders for anything that needs to happen closer to departure.
Multi-city travel doesn’t have to be overwhelming when you approach it step-by-step. If you found this guide helpful, stay tuned for more planning tools and real-world itinerary ideas coming soon.
Free planning resources coming soon!
*Want to see this in action – click here to see my “Plan with me” post on our latest trip to Hong Kong, Macau and Hanoi
