How to Design The Perfect Travel Itinerary

For over 25 years, I’ve been planning and booking independent trips, creating the perfect travel itinerary to suit our personal interests, available time and budget. For me, this process is an absolute joy, and something that really adds to the enjoyment of a trip — the more I research and pull together the itinerary, the more I start to anticipate all the wonderful experiences to come!

Over the years, friends and readers have asked me about how I create a travel itinerary, and the process I use, so in today’s post I am sharing all my tips and suggestions for how to design your own travel itinerary.

For each step, I’ve provided suggestions on things to think about and questions to ask yourself. Working through all of these step-by-step will help you decide on, shape and refine your trip plan. I usually cycle through sections 2-5 a few times before I settle on a definite destination and trip duration and can then finesse the itinerary.

Hand writing onto a note pad the text "how to design the perfect travel itinerary"

How to Design Your Own Travel Itinerary – Contents

1 Maintain A Wish List

Whether you call it a Bucket List – a bit of a morbid idea in my mind – or a Wish List, the key is to create and maintain a list of places you want to visit and things you want to do, that you can reference when it’s time to plan another trip.

This is, for me, the easy bit. I have a Travel Wish List document on my phone so that I can enter ideas for places to visit as and when I come across them… watching TV, chatting to a friend about their travels, reading an article in a magazine or online, or even just a particularly enticing image on Instagram!

I keep meaning to add labels to categorise places in the list by factors such as continent or region of the world, main holiday type or activities suited to that destination, and other factors such as whether or not it’s great for food, wildlife, culture, history, architecture and so on. Right now, that’s still on my To Do list, and all I have is the list of places, occasionally with a few notes added next to them.

Notepad listing places on a travel wish list, sittig on a map, coffee cup and pen
Now we’re into the nitty gritty, you will likely need cycle through How Long Have You Got?, What Kind of Trip Do You Want?, Where Should You Go? and What’s Your Budget? a few times before you finalise them all and can move on to drafting and finessing an itinerary.

2 How Long Have You Got For This Trip?

Most of the time, one of the key driving forces in my travel plans is how much time I have available to travel (the other being budget). Like many people, I have a fixed number of days Leave that I can take in a holiday year.

Back when I was freelancing as an IT contractor, I was able to take longer breaks at the end of a contract (before taking on a new client), but even when I didn’t have hard time constraints, I still found it helpful to start with an approximate trip length, and adjust it later.

Calendar with days marked and notepad with travel destination ideas

  • Have you already thought about how many breaks you want to take in the year and how to divide your available days? I like to take one longer trip of two to three weeks, a couple of long weekends (4 to 5 nights away) and some time off at home for birthdays, and around Christmas and New Year.
  • Make sure you’re familiar with your workplace rules on annual leave. Is there a maximum number of days or weeks you can take in one block, and can your manager allow an increase to that at their discretion.
  • If you have limited days of annual leave available, try and factor in weekends and national holidays to make your time stretch further. Does your workplace permit you to take unpaid leave over and above your paid leave allowance?
  • Once you’ve narrowed down destinations to a small shortlist of two choices, check the travel options to get to each one (and whether they work with the days of week you’d planned to travel there and back). Revise your duration to give you the number of days and nights on the ground, once you subtract travel time from the total time away from home.
  • An extra factor for some is to look at any essential medication that you take, and confirm that you are able to obtain enough to cover the entirety of your planned holiday duration. I usually add an extra few days of meds in case of unexpected delays getting back home.
  • For those with pets or family members for whom you provide regular support, is there a maximum duration that you can book (from a care-provider, kennel or pet sitting service) or that friends or family may be willing to cover?

3 What Kind of Trip Do You Want?

What kind of travel do you enjoy most?

Spending some time working out what kind of trips appeal to you the most makes it much easier to pull together your trip planning. For many of us, there are multiple kinds of trips we enjoy, and we may be in the mood for a particular type of experience for our next trip, or open to any.

Jotting travel ideas on notepad
To get you thinking, here are categories of trips that I love to take and some that are popular with friends and family:

  • Multi-centre city-breaks that offer food, culture, arts, architecture, history.
  • Natural habitats and landscape holidays where we can observe local animals and birds, or enjoy beautiful views.
  • Places which are great for adventure activities and sports.
  • Destinations known for their beautiful beaches.
  • Countries or regions well-suited to road trips or to train-hopping.

Or maybe you have specialist interests, that you can base a trip around?

  • Visiting the ruins of ancient civilisations or cities known for architecture.
  • Places that offer educational opportunities such as language lessons, cookery schools. painting classes, dancing tuition.
  • A region or country known for its cuisine, whether that’s fine dining, street food or everything in between.

4 Where Should You Go?

Two sets of arms pointing at places on a map

  • Now refer back to your travel wish list and start working out which of your categories of travel each of those places fulfills and which of your interests you want to be central to the trip you are planning. I love many different types of trips but often I’ll have a certain type of trip in mind for a given holiday, such as a city break that combines local cuisine with culture and history.
  • The length of time you have available for a given trip will often steer you towards and away from particular places on your wish list. My preference for safari wildlife holidays is to spend least two weeks in the chosen destination, whereas I’ll happily spend just a few days in a city for a city break trip. And the longer the flight, the longer I want to spend at my destination, to justify the extra travel time!
  • Lastly, if you have already pencilled in the time of year when you can take this trip, does that rule out some places because the weather isn’t great, and help focus on others which are at their best during that season?
  • Combining your available time (and when you can take it) with the kind of trip you want to take should help you narrow down to a handful of possible destinations, which you can narrow further based on budget and travel costs.

5 What’s Your Budget?

Knowing how much you have to spend is essential not only in deciding where to go, but also the style in which you’ll be able to travel, and how much you can spend on accommodation, food and drink, and activities.

Jar labelled Travel full of folded dollar notes on table in front of world map on wall

  • When you are working out your budget, it’s important to consider how much the cost of travel to and from the country takes out of your total. Indeed, for international travel, those travel costs can add up to a big chunk of your total budget. Often, I have a handful of destinations on my shortlist for a given trip and do a first pass rough estimates investigation into travel costs for all of them. Sometimes I’ll then favour one destination over another purely based on the travel options I’m able to find, especially if I can take advantage of a special offer or sale on flights.
  • One you’ve taken the main there-and-back travel costs out of your total budget, it’s easier to start approximating how much you can allocate per night accommodation, and how much that leaves for internal travel costs, sightseeing and activities, food and drink, and shopping? At first, these are guesstimates but as you do more research, you’ll be able to make a more accurate budget for each element.
  • Does this initial research on destination costs confirm that your total budget is realistic for that country, in terms of pricing for travel, accommodation, food and drink, and sightseeing? If so, we are all good, and can continue to the next step!
  • If not, is your budget waaaay out or just a little? If it’s just a little, you may have wiggle room to make some savings on travel (taking a train instead of internal flight), dropping the level of accommodation and food (a few nights self-catering rather than hotels and restaurants all the way) and sightseeing (are there interesting free activities to enjoy alongside spendy ones?). If your budget is still too low for the duration you want in the destination you are leaning towards, can you reduce the length of the trip without sacrificing too much of your plans, or would it be better to pick a different destination that is less pricey?

6 How To Draft, Revise and Finesse Your Itinerary

By this point, you have chosen a destination, have a good idea of your trip duration, and a fair idea of how much budget you have available for various aspects of the trip. During the research you did whilst narrowing down your destination, you probably also identified a few places and sights you’d like to visit during your trip.

  • The next step is to think about about many nights you want to dedicate to each place given your research and your key interests, as well as your personal travel style. I tend to favour slow travel which also fits with my strategy for coping with migraines when travelling.
  • Start slotting places and numbers of nights into a provisional itinerary. Use a map to work out a logical geographical order. Available transport options between the various places in your itinerary will play into this too.

Table surface with globe, post it notes with Vietnam destinatons, and a handheld digital device showing an online map of Hanoi

  • To finesse the itinerary, make sure you’ve considered time and costs of transport from one place to the next. Sometimes the time it takes to reach somewhere you only want to spend a day in takes it off the table but sometimes it’s a must do and you are willing to sacrifice another place or extend the duration of your trip so that you can include it anyway. Sometimes you can only reach a particular place via an internal flight or private road transfer that blows your budget out of the water, and you either reluctantly cross it off or go back to the drawing board on the entire trip!
  • I prefer to visit less places and give them sufficient time than to rush through more places with not enough time in any of them. Others prefer to get a full overview of a country or region, with the intention of coming back to their favourites on a future trip. There’s no right or wrong answer on this, it’s all down to preference.

Hand writing on a pad to create a travel itinerary

Now you have finalised your destination, travel budget and itinerary you can start planning and booking the various elements such as travel, accommodation, sightseeing tours, specialist activities, and even restaurant reservations if relevant.

Look out for my next post on how I organise all the booking details for a multi-stop itinerary.

Passports, tickets, currency, compass and sunglasses on a vintage map

Please leave a comment - I love hearing from you!
21 Comments to "How to Design The Perfect Travel Itinerary"

  1. Martin

    Travel planning is almost as fun as the travel! You get to have a brain holiday before the actual one. Great tips!

    Reply
    kaveyeats

    I have occasionally taken trips planned by others and I have to say, I really really really miss the enjoyment that the planning itself me gives me!

    Reply
  2. Rachelle

    Great post – a lot of it is really similar to how I plan trips myself. And since I work in education I always know when my vacation time will be, since it never changes. Luckily I have about 5 months a year to work with, although I can’t leave or afford to travel for all of that time.

    Reply
    kaveyeats

    Great to know you follow a similar process. I think there’s a lot to be said for having more time, even with a lower travel budget, because you can afford to spend the time to research and plan to bring the travel costs down. Often slow travel can be much cheaper (per day) than a short fast trip! Now I’m permie, I can’t take as much time off work but I still try to keep budget in check through research and planning! 😁

    Reply
  3. NickyB

    I do adore the planning element of the trip, the anticipation is a big part of the experience for me. I can’t face it at the moment but hopefully as the world starts opening up and I’ve been able to see family the urge will return! Great post that looks very like my own planning process 👍👍

    Reply
    kaveyeats

    Yes, I can’t quite allow myself to even provisionally pencil in dates for our next overseas leisure trip, but I am just about ready now to start doing the trip research and planning for one, even without knowing the dates. I know budget will be a little more of a guesstimate since I won’t be able to look up much on travel or accommodation costs!

    Reply
  4. kaveyeats

    So pleased it’s going to be useful for you. For the budget, I think it can be really hard if you set your heart on a single destination before having worked out if it’s feasible or a good choice on the budget you have, and once you have decided, it’s easier emotionally to throw the budget out of the window than to switch tracks. So I find looking at it early on, and cycling it into the decision about where to go, can help with that!

    Reply
  5. Michelle

    These are all such great ideas. I especially love the idea of maintaining a travel wish list. Marty and I have this and call it our “unbucket list”. LOL!

    Reply
    kaveyeats

    Love that! I’m not keen on the idea of a bucket list — I don’t need the mental image of dying to spur me into following the dreams! So I love your idea of flipping it into an unbucket list!

    Reply
  6. Anja

    Great advice! Also checking the bank statements… I have to book my annual leave a year in advance, so I have a list of “possibles” for every one but the past year has messed up tha tlist somewhat

    Reply
    kaveyeats

    Yeah the last year has made it harder to keep on track with travel dreams for sure!

    Reply
  7. Renata

    These are great tips – and I’m commenting as an expert: For me, planning and organizing a trip is almost as important and fun as the actual tour 😀 The only downside is that I really have to make sure to leave a teeny bit of flexibility for unexpected…pleasures 😀

    Reply
    kaveyeats

    We always leave a fair bit of flexibility in our itineraries, but plan the structure (how long in each place) / accommodation / transport etc and some key activities. For the rest I have a list of things we might want to do and we decide depending on what we feel!

    Reply
  8. Agnes

    Great travel tips for planning a trip. Very helpful and accurate. I also plan my trips step by step, and I love the planning part.

    Reply
  9. Carol Colborn

    I love planning our trips. With 4 months of timeshares, I pretty have know where to spend those 4 months. And then there’s the visit to kids and grandkids in 3 different countries plus 4 different states. As a retired couple, the time and budget is set. We just have to plan our explorations of those areas.

    Reply
    kaveyeats

    Yes quite a different prospect when you have 4 months already allocated to timeshares and more to visiting the kids and grandkids! 🙂

    Reply
  10. Sage Scott

    I love your process! Our family does something similar but adds a step to categorize all that we want to do and see at a destination to ensure that we all get to see as many of our A items as possible.

    Reply
    kaveyeats

    Aah great point. Yes as I’m only planning for the two of us and have a good handle on what Pete would prioritise, I kind of do that as I go. It’s also part of the next step when I get to drilling down that itinerary further. Another post on that coming soon!

    Reply

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