How I Plan a Multi-Destination Holiday

Topher & I’s honeymoon was a whirlwind of a two-week adventure that we spent in three American cities. There were four flights, six hotels and a two-day road trip in the middle. We travelled with hand luggage only and we were on a budget. That holiday was planned right down to the last detail.

I have a bit of anxiety with trips like this where I don’t like to be unsure. I don’t want to be wandering round for hours trying to find somewhere decent to eat, I don’t want to be getting lost and I certainly don’t want to miss out on really seeing a city.

Topher said this was the best trip he’d ever been on and I agree. We saw so much in so little time, we didn’t have a single bad meal, and we kept to our budget; even going home with money in our pockets and extra souvenirs.

We had a plan in place and adjusted it whenever we needed to.


This blog post is how I planned it and tips on how you can plan your own multi-destination holiday.

Put the kettle on because this is going to be a long one!

So a quick disclaimer when I say multi-destination; I mean multi city (usually in the same country) where there is so much to do and very little time. Not one of those relaxing beach holidays. Because with those, it’s super easy to go with the flow and relaxing is in the title for a reason.

Also, this is just what I do. This isn’t for everyone. It can seem quite restricting to some people but I think it can be quite useful. Particularly for fellow anxious people who want to go on a holiday like this but are put off by all the uncertainty of being in a completely different country and not knowing what to do.

Hell, I got freaked out by having to use the New York subway for the first time so I looked on Youtube beforehand to see how it was done. It definitely saved me from holding up all the locals when I went through the barriers for the first time. Research is my friend. It gives me confidence.

Anyway, enough rambling, let’s dive in.


Set the dates

bullet journal setup - calendar & japan savings

Back in the days where my husband didn’t work in a school – I’d just pick these randomly. Decide on a month and then go with what’s the cheapest. Tuesdays are usually good days to fly but not everyone has that option. We certainly don’t anymore! You do you. Fit your dates into your schedule.

Remember to consider things like time of year and weather depending on the country you’re going to. Because who wants to mess that up? I certainly did when I booked Disneyland Paris in February on a whim. And then forgot my hat and gloves. So fricken cold! Will definitely be picking a milder time of year next time.

Also remember that weather is not always the same between the different cities you’ll be visiting too. I picked September for our honeymoon as I discovered that San Francisco is actually pretty cold in the summer months.


Get a spreadsheet

Or a notebook or bullet journal but trust me spreadsheets are awesome for this kind of planning as they are so easy to edit and they will be edited a lot!

I usually start with a spreadsheet early on where I dump all the information I find during my research so that everything is in one place.


Do a lot of research 


San Francisco - segway

I start by looking up what kind of things we want to do in each location. What are the major sites and do not miss experiences? Use travel guides, books, blogs, Google, Pinterest and also ask people who have been.

Make a list and then you’ll be able to see approximately how much time you need in each location. Decide on what your priorities are. What do you want to see on your holiday?

Do you love shopping? Museums? Sight-seeing? Food? Do your research and find cannot miss locations. I personally can’t recommend blogs enough for this. I spent some time making a list of activities that kept popping up on people’s recommendations along with stuff that Topher and I would be interested in. This led me to amazing things like The Color Factory in San Francisco. Thanks Instagram!



This is the same technique I used for activities. Good food on a budget is very important to Topher and I did all the research for this too. I used Pinterest and blogs and took note of the same places that kept coming up.

It’s especially handy to get recommendations from locals (I bloody love the internet). Though Trip Advisor is great for reviews of hotels and activities, I’ve heard that using them for restaurants tend to lead you to places that are just full of fellow tourists. Not always bad, but it’s nice to get a mix of famous places and stuff the locals love.


Google Maps are a saviour

Google Maps allow you to save locations on your smart phone and it’s a great tool for holiday planning. So all the activities and food locations I’ve dumped into a spreadsheet, I save in Google Maps. It allows me to see where everything is and if we’ll be able to get there.

There was plenty of food places that I wouldn’t have minded visiting on our honeymoon but there were just too far out of the way. And I wouldn’t have realised if I hadn’t have used this tool.

Plus it saves so much time when you’re actually there. If you’re in a country where you have access to wifi or you’re on a “feel at home” type plan like I am then use it. It’s ideal for getting to places quickly and reducing your chances of getting lost.



Los Angeles - hotel room
I tend to save hotels until after I know vaguely where we’re going to be going. Using Google maps, take a look at everything you’ve saved and where would be the best place for you to stay. Because as nice as that hotel you’ve found is, who wants to be schlepping back and forth to something that’s no where near anything you want to do?

Don’t forget to look into what kind of areas are good for staying in too otherwise you could end up somewhere that’s good logistically, but not so much in terms of atmosphere!

And of course, check the reviews. I actually forgot to do this for the last hotel of our honeymoon and it wasn’t the nicest. It’s something that we laugh about now but I’ve certainly learned my lesson. Trip Advisor is your destination for this, though take some reviews with a pinch of salt as some people just can’t be pleased.


Allow for travel time

It’s highly unlikely that the cities you’ll be visiting will be right next door to each other so allow for travel time. And how will you be traveling? For our USA adventure, Topher and I mainly had to rely on planes (NYC to California) but we also hired a car and drove between San Francisco and LA. That drive can be done in a day but we decided to stretch it out over two in order to pace ourselves and get an extra morning in at San Francisco.

Figure out what the best transportation option is for you. Next year when we visit Japan, we’ll be using trains. But people on a tighter budget may consider buses and people who have a much bigger budget can just fly between cities. It all depends on you.

And then make sure to factor in how long your chosen transport will take. Will this eat into some of the activities you planned on doing? This is where the spreadsheet can really come in handy because you can lay it all out.

Madonna Inn - rental car


I leave this until last to plan as you might have dates set in stone or you might just see what kind of deal you get when you book. But it’s usually one of the first things I book. Since I plan big holidays more than a year in advance, it’s too early for flights. Plus you can’t know what flights you need until you know how long you’re staying in each place.

So once it’s less than a year, I tend to use Skyscanner to search for flights. Use an incognito window to search each time as not doing so can affect prices. Damn cookies. Anyway, I also set up an email alert, check back often and when the price is right – jump!

Another tip, if you’re ok flying indirect do it, as it’s usually cheaper.


Set the itinerary

Once you know everywhere you want to go, eat and where you’re staying. It’s time to slot everything into place.

Remember to be realistic. Set one activity for each portion of the day – figure out how long things will take including travel time. Don’t book yourselves a lunch reservation across town when you’re doing something that takes all day.

Also find out things like opening times. Sometimes tourist attractions are closed on random days of the week and it’s so disappointing to find out when you arrive. And some things you need to book in advance. For example, if you want to go up the Statue of Liberty you need to book at least a month in advance. Sometimes more depending on the season. Otherwise you can only go to the island and look at it from the outside.

But then I’ve also messed this up as we tried to visit a specific food market and I got the day wrong. Oops! It would have been funny if we hadn’t walked miles to get there. Don’t do this.

Once again, this is where your saved locations in Google maps is super useful. Link up things that are close to each other to do and eat on the same day so that you’re not zigzagging across the city. A waste of time, money on travel and on your energy.


Budget Baby

Budgets are sexy!….but they really aren’t. Still, I always set the budget after I’ve done my research. Definitely before I book anything though. As our household doesn’t have a lot of disposable income, I like to make sure we can book the holiday far enough in advance that we’re able to save up for it.

This is where the spreadsheet gets edited a lot. Hotels are switched out for cheaper alternatives and I keep a note of everything that will cost money including travel and activities.

To make a food budget I had a quick look at my chosen restaurant’s menus online for prices so I could gage how much we would spend. In every instance I would over budget so we would never be short on cash. And it definitely worked! This was the main reason why we ended up coming home with spare money. Also you find out things like portion sizes. But remember that you can’t know everything before you go. If I’d known how big these pancakes in LA were going to be then Topher and I would definitely saved money and shared a stack.Spoiler alert – I didn’t finish mine. Neither did Topher.

Los Angeles Food - diane vs pancakes

Know what you can afford and plan your holiday accordingly. Because who wants to be stuck with a load of credit card debt, right? And please don’t try the YOLO argument with me because my credit score is flawless baby.


Adjust the plan

Plans are there to be adjusted on the fly. I’m not saying that you must stick rigidly to your plan. It’s just there so you can have an understanding of what you’re doing and not waste your time on getting lost. Shit happens and that’s ok.

For example, when Topher and I were exhausted in San Francisco (and kinda sunburnt), we changed our plan. We’d hiked to this amazing pie shop to find that they didn’t have any air-conditioning and it was hotter than hell inside. We skipped it. I love pie, but not that much.

In fact, we were so tired that we skipped our stroll through the Mission District afterwards and headed back to our hotel. We bought snacks along the way and stayed in bed the rest of the afternoon watching Family Fortunes and Princess and the Frog. Perfect!

If you’re tired and want a break, you just have to ask yourself – will I be sorry I missed this? We’d already been on a bus through Mission District earlier that day so we kinda saw it anyway. It was definitely worth the break for us.

So if you need to adjust the plan, just adjust it. The world won’t end.


Extra crazy planning steps

For our honeymoon I looked up directions to everywhere ahead of time and wrote them in a little notebook. Right down to bus numbers and walking paths. Very weird but in my defense we never got lost and I didn’t have to think about anything because it was already sorted out. This may be a step too far for some people but it really helped me out and made me feel calm.

I actually see myself doing this for Japan too as we don’t speak the language and apparently not all the streets have names. Can someone confirm this for me?

I also kept track of what we spent each day while we were there. Some days we went over, some under. This helped a lot as we knew that we had extra money we could spend. Hello Yoda backpack for Topher.

disneyland californai - yoda bag


How do you plan a multi-destination holiday? Let me know your tips in the comments.

And please tell me if you’re as much of a planning freak as I am. Let me know I’m not alone! But it’s ok if I am – I’m happy in my weird planning bubble. 

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