I am an absolute fanatic when it comes to planning itineraries. maybe it’s the thrill of potentially seeing all the things or the organizer in me who wants everything planned out.
Today I am sharing with you the step-by-step guide I have used (and still do!) to plan my itineraries, every single time. These are my tried-and-true methods, and I hope you will find these helpful in planning your adventures as well.
To use this guide, it is assumed that you have finalized your general destination already.
Step 1. Research
Before we get into the nitty-gritty details of what you want your days to look like, the most important first step is to research your destination inside and out. Here are couple things you should have a good idea of before we move onto the next step:
1.1. Total travel time for a return trip
Getting to and from your destination takes time, sometimes these can eat up quite a bit into your entire vacation allotment. Taking into account layovers, time zones, and time of day on arrival, sometimes your actual vacation might not start until 2 days after you have already left.
Especially for those who are limited in vacation days, I suggest leaving the evening of your last day of work to maximize, especially if your destination is overseas or take 5+ hours to get to.
1.2. The expected climate for the duration of the trip
The climate of the destination can affect your itinerary as a whole in the following ways:
- Operating hours: Depending on the time of the year, certain attractions may operate on a different schedule or closed altogether.
- Packing: If temperature is mild, should you bring that extra jacket along or would a scarf suffice?
- Attractions: How many attractions are outdoors? What are the chances of rain? Depending on how far in advance you are planning, sometimes the closer you are to plan your itinerary the more accurate the weather. I usually start planning my itinerary 3 months in advance, and shift my outdoor versus indoor days closer to the trip in case certain weather conditions arise.
1.3. Travel advisories in effect
Always, always check if there are any travel advisories currently in place for your destinations. Usually, you can find this information on your government website or check with your embassy. This information is extremely helpful especially if you are planning to solo-travel or traveling without a tour guide.
1.4. Visa/visiting requirements (if applicable)
Some countries have additional requirements for visitors and tourists. Again, check with your country’s government website or the embassy of your destination for full details. Certain countries (ex. France) also require that your passport is valid for a certain amount of time up to and post-completion of your travels, double check on this information as well in case your passport need to be renewed ahead of time.
1.5. A list of potential attractions
As straightforward as this sounds, it’s a list of attractions at your destination. These could be popular tourist spots or special celebratory activities, also include your must-see attractions here. And for everything you come up with, don’t forget to include the following information as well, they will come in handy later:
- Phone numbers and website
- Hours of operation
- Admission costs
We will be coming back to this list as we plan out the days in your itinerary.
1.6. Potential day trips
These can be cities and towns nearby, amusement parks, or an attraction that usually requires a full- or half-day commitment. Day trips typically do not require you to travel far distances to get to and usually take up a full day including transportation to and from your accommodation.
1.7. Estimated trip expenses
Getting your major travel costs down the earlier the better means more flexibility to budget for money to spend during your trip. These costs include but are not limited to airfare, car rental, train tickets, food costs, and accommodations.
Step 2. Finalize your travel dates
You’ll need a calendar, pen, and paper because we are going to come up with a list of potential dates for your trip! This step is my favorite, there’s something about looking at a fresh calendar that lights up my love for planning.
The reason we want to nail down the travel dates ASAP is because usually, this is the bottleneck that many of us get stuck on. There are so many variables to consider such as price, season, and our personal availability. Which is why in this section, I have gone ahead and listed out a few things to consider as you decide on the best dates that work for you.
Once you have your dates down, go right ahead to book your tickets. By the end of this step, you should have your ticket confirmation all set and calendar booked in.
2.1. Travel budget
In the first step of this guide, you have determined a rough breakdown of your travel budget. Take that number into account as you look at potential travel dates, sometimes a difference of a few weeks can be a few hundred dollars in price. Of course, prices also depend on demand, which leads me to the next point…
2.2. High vs. low seasons
All destinations have high seasons and low seasons. Sometimes these seasons may not be determined by the climate of the destination but by the tourist demand. For example, Hawaii has pretty good climate all year round, however, during the North American winter months, flights to Hawaii are extremely expensive, probably because everyone wants to escape the cold winters. However, in March the prices are cut by almost 50%, likely due to the imminent Spring weather.
Look out for timeframes that are outside of the high seasons or school breaks. In addition, national holidays and special celebrations at your destination are also factors that might contribute to a higher price point. Not sure if you have time to keep checking flight prices? Kayak offer price alerts that automatically track prices when they go down.
2.3. Long weekends and holidays
Chances are, you have a full-time job and a limited number of vacation days a year, in which case the availability you have to travel might not be the most flexible.
Look at your national holidays and office closures and mark them in your calendar, see which ones fall right before or after a weekend. Holidays that fall on the weekends are great ways to get back a day or two in your vacation balance or bonus days that you could utilize to extend your trip by a little bit more.
2.4. Stopovers or open-jaw
Are there anywhere you want to stopover on the way to your destination? If time permits, stopovers are great ways to save some money and see more places, like going to destination A, then B, all part of a single booking.
For example, with Icelandair Stopover, they offer free stopovers up to 7 days when you fly from North America to Europe without any cost in additional airfare. So if you have been dreaming of going to Iceland and Europe, this is a great option to visit 2 places for the price of 1!
Open-jaw, on the other hand, works in similar ways except you would book to go to destination A, but return from destination B, in which case you will have to arrange the transit in between on a separate booking.
I consider this as an advanced consideration for those who want to maximize their trip without costing an extra few hundreds of dollars. Booking a red-eye train or flight means you are departing late at night to arrive early the next day. Although these travel arrangements are great to save time to do more at the destination, it is also important to be informed that these arrangements can be more tiring than you think, usually because they occur at odd times and sometimes require some sort of compromise on sleep (ex. midnight transfers, which means waking up in the middle of the night – not so great).
2.6. Award Flights
If you have been collecting travel rewards, now’s a great time to check up on that balance to see if there’s a free flight you can redeem. Award flights help immensely in offsetting some of the cost when it comes to travel. Not a believer in flight rewards? I have 10 reasons for you to reconsider.
Step 3. Deciding what to do
Based on the research you’ve done in step 1, come up with a list of what your must-see attractions are. This is also the step where you are going to start putting together all the pieces for your itinerary.
3.1. Utilize Google My Maps
I am a huge fan of Google Maps, and their My Maps tool is hands down my best friend when it comes to planning my travel routes. All you have to do is create a new map and then plot your places of interest on there.
The great thing with the tool is you can create different “Layers” of attractions, I usually like to use it as a way to layer out the different regions of my itinerary, for instance: each city is a layer, with the different attractions inside. Or I could divide my layers up as days in my itinerary, for instance: day 1 is a layer, then day 2 is another layer, and so on.
To see examples of actual maps I have created, check out my itineraries.
3.2. Research tour packages
Tour packages are great alternatives if you want someone else to plan your travels, whether it be a single day, multiples days, or just half a day
One of my favorite thing about tour packages is they usually come with the transportation and admission tickets pre-arranged, which means you can save some time with planning your own travel arrangements and lining up to get your own tickets. The caveat is tours usually do cost a bit more than buying everything on your own, but with the added convenience, sometimes it might be worth it to go with a tour.
I recommend Viator as the go to for tour packages. Of course, as with all service-based practices, reviews are king so definitely do your research before booking them on the fly.
3.3. Potential closures / disruptions
One of the things most people miss as they are planning their itinerary is researching into potential road closures or service disruptions that are occuring at or near their places of interest. As most attractions have their own website nowadays, usually that information is posted online.
A good rule of thumb is not only should you check their official website, check any recent reviews as well – I usually go for reviews posted within the last month from your travel date. TripAdvisor is a great resource for this type of information.
3.4. Nearby places of interest
As you map out your places of interest on Google (step 3.1), you will slowly began to notice clusters of attractions that fall in the same regions. These clusters are great indicators on how your itinerary should pan out. For instance, day 1 of your trip could be everything in cluster A, day 2 is cluster b, etc.
Step 4. Book all the things
Now that the bulk of your trip is pretty much finalized, it’s time for my favorite part – booking all the things! These includes hotels, car rentals, ferries, trains, city passes, advanced tickets… you name it. Anything that can be pre-booked or reserved should be done at this time.
Travelling to and from your destination
Whether you are travelling by air, train, or ferry, always book the travel between your homebase and destination first.
If there is a popular restaurant you have decided that you must visit, reserve a table there as well (provided there is no language barrier of course). Be sure to print a copy of each of your reservations with your trip.
Getting your tickets booked early have many benefits. From cheaper costs to better seat selections, to ensuring a stressfree trip. You could be traveling by air, train, road, or even sea, but figuring the times that work for your schedule is also really important. When you have your arrival and departure times down, everything in between is free for you to adjust however you like, having a set arrival and departure time is also the key to ensuring you do not over plan your itinerary.
Bonus tip: make sure you have signed up with the airline mileage program you are planning to book with and associate your membership number to your booking. You never know when they’d come in handy!
Step 5. Finalize the itinerary
By the end of the last step, you should have a pretty good visual of where you are going to go, where you are staying, and what you are going to do during your trip.
Before we jump in on this final step, here’s a gentle reminder of what your itinerary must include:
- Departure / arrival / return information
- Transit times
- Accommodation information
- Places of interests
- Restaurant information
This is also the order of information I like to follow as I am laying out my physical itinerary, starting with my departure / arrival / and return times, then any travelling I will do while I am at my destination, then my accommodation information (including check-in/check-out times), then my places of interests for each day, and finally, any restaurants I am planning to visit.
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