Last Updated on June 26, 2021 by Maggie McKneely
Want to travel more but are overwhelmed by the idea of planning a trip on your own? It’s not as scary as it sounds! Read on for my tips to create the perfect vacation itinerary.
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How to Create a Vacation Itinerary
I hear it all the time – “I want to travel but planning everything is just so overwhelming!” “I don’t have time to figure out all those details!” “It’s just too difficult – it’s less stressful to just stay home.”
I get it – at no other time in history have so many places in the world been so accessible. And along with that comes about 4 million different options that you have to decide on when planning a trip. Where are you going and when? Will you fly, drive, ride a train, or hitchhike?
What about accommodations – hotels? Hostels? Airbnb? CouchSurfing?! And once all those arrangements are made come the decisions about what to actually DO on your vacation. Will you choose to go on guided tours or just wing it? What sites do you want to see? Will you do a road trip or just stay in one city? If you do a road trip, then there are all the questions about the rental car and figuring out how to pump gas in a foreign country.
SO MANY CHOICES!!!
So yes, when I hear people are too daunted by trip planning to actually plan a trip, I get it.
But I’m also here to say that creating your own vacation itinerary is not as difficult as it seems. And the outcome is very rewarding: you get to travel the world and take a trip exactly tailored to what you want it to be. Making your own arrangements is usually cheaper than going through a travel agency, and once you do it once you know you can do it again. You just need a plan. Some direction, some key steps to guide you through the process.
If you’re interested in learning how to make travel plans without being overwhelmed by the task, read on for my how-to guide for creating a vacation itinerary.
Creating a Vacation Itinerary
Step 1: Decide when to travel
It may be counter-intuitive, but picking your destination is not the first step. Deciding when you’re going on vacation is. That’s because what time of year you travel has a huge influence on what destination you choose to go to.
Since I work with Congress, my vacations must always take place when Congress is on recess, which helps narrow down my options. You may have to plan your travels around your own jobs or your kids’ school schedules. Maybe you’re more flexible and prefer to travel during a particular season. Whatever your reasoning, once you have your timeframe picked out, you can move to step 2.
I’m going to use my vacation itinerary for Portugal as an example throughout this guide. For that trip, I picked the week after Easter as my timeframe because I knew Capitol Hill would be a ghost town that week and I’d be free to be away from work.
Washington, DC in springtime
Step 2: Pick a destination
Once you have your time frame figured out, you can move on to the more exciting parts of planning your vacation itinerary, beginning with picking your destination.
Do you have a particular place you want to go to? What are good places to visit during the dates you picked out? What kind of weather do you want to have on your vacation? Snow for skiing, or sunshine and warm breezes? What about crowds – do you want to go to a popular tourist destination during the busy season, or would you prefer somewhere off the beaten track?
Also, take into consideration the prices for traveling to certain places during particular times of the year. Cheap flights are easier to find during the offseason. For example, it’s significantly cheaper to fly to New Zealand during June-August than it is in December. That’s because in the Southern Hemisphere, June-August is winter, i.e. offseason. Christmas falls during the height of summer break, so flights to NZ during that time of year are astronomical. Most destinations have on and off seasons, and the cost of getting to those places will reflect that.
So once again, lots of things to consider! It just depends on what your priorities are.
For my trip: Easter break is one of the busiest weeks for a lot of destinations in the world, so I knew I didn’t want to pick a tourist hot spot. But, I did want to visit someplace I’d never been before and that would have pleasant weather in April. And because my mom would be going with me, it had to be a destination that would appeal to both of us.
Portugal is a popular country, but still not as packed and touristy as some of its other European neighbors. The country is also famous for its wine (and port!) and food, has beaches (for my mom) and history and beautiful countryside (for me). It checked off all the boxes for the type of destination I was looking for.
Venice is great, but it floods in March. Timing matters.
Step 3: Create a rough itinerary
Once you know where you’re going and when you’re going there, create a rough vacation itinerary. Figure out what you want to do on your vacation and roughly how many days you’ll need to accomplish everything on your list.
Are you taking a road trip? If so, how many days do you want to spend in each destination? Are you spending most of your time in one city? What’s a reasonable amount of time to get everything done that you want to?
It doesn’t have to be an itinerary with every single activity you want to do or every detail figured out. In fact, at this point in the process, it shouldn’t be. You haven’t purchased plane tickets or booked hotel stays yet! This is just a rough outline of your trip to help you plan.
My rough itinerary for Portugal looked something like this:
- Day 1: Land in Lisbon
- Day 2-3: Duoro Valley
- Day 4-5: Porto
- Day 6: Lagos
- Day 7: Lisbon
- Day 8: Sintra
- Day 9: Home
Step 4: Plane tickets
I always feel like this step is the most momentous of the vacation itinerary creation process. Once you have those plane tickets in hand, the trip is actually official! (Mostly because we all know getting a refund on those tickets is harder than driving out of DC at 5:30 PM on a weekday).
I never purchase plane tickets before I have the dates of the trip worked out (duh) but I do buy them pretty far in advance (4-6 months out). I know some people like to wait until the last minute in the hopes that some amazing flight deal will pop up, but I’m not one of those people. I’m a planner – I couldn’t deal with the stress of still not having my international flight figured out until a few weeks before my trip.
Certainly, deals DO appear a few weeks out (thanks Dollar Flight Club for all those emails…), but I’d rather not risk it. Instead, I set up price alerts for flight prices for the dates and destination of my trip (Google Flights is my favorite website to use, but Skyscanner is also great). Once I see a price that’s reasonable and I’m within that 4-6 month time frame, I buy my tickets.
For our April trip to Portugal, I bought our flight tickets in November. I haven’t seen lower prices for those tickets since then.
Flying over Santorini!
Step 5: Hotel accommodations
Step 5 for creating a vacation itinerary is for making sure you aren’t homeless during your vacation. By now, you know when your flights land and depart, and you have your rough itinerary to tell you what days you’re going to be where. Take those pieces of information and start doing research about accommodations.
My favorite websites to use for this are Airbnb and Booking.com. If you’ve never used Airbnb, I won’t use this space to go into details about it, but know this: I love it, and I personally have never had a bad experience with it. Just make sure to read the reviews and descriptions thoroughly; chances are, you’ll have an awesome and unique experience you wouldn’t in a hotel. As for Booking.com, they offer a wide variety of hotels, B&Bs, hostels, and rentals, and give you direct access to each property’s owner or manager.
For Portugal, we are staying in 4 different places – one hotel, one B&B, and a couple of apartments. We’re doing a road trip, so hence all the moving around! Obviously, you won’t need that many if you’re primarily staying in one city.
The famous Fairmont Lake Louise – expensive and in high demand. Book early if you dream of staying here!
Step 6: Itinerary details
Now the REALLY fun part – the rest of your vacation itinerary! You’ve got your flights booked, you’ve made sure you won’t be homeless by booking accommodations, now you just have to figure out what you want to do on your trip.
This is highly individualized. Some people like to just wing their entire trip – show up in their destination city or country and then figure out what to do from there. If that’s you, that’s fine! But for those who are planners like me, it’s helpful to do research beforehand so that you don’t waste any precious vacation time figuring out what to go do. Doing this type of research will also help you plan your trip financially, by knowing how much what attractions cost and what the most efficient or cost-effective types of transportation are.
Another reason I like to do this ahead of time is because sometimes I want to book a private tour or some type of excursion that sells out in advance. For example, when my mom and I went to Venice, we were only there for 10 hours. So instead of wandering around aimlessly, I found a private tour guide to show us around and help us make the most of our limited time. It was extremely helpful and informative, but I had to book that tour months in advance. So figuring out those sorts of itinerary details before you go can be very useful!
For my final itinerary, check out my Portugal itinerary post. You can also check out my Glacier National Park itinerary or my Tuscany itinerary for more ideas on what this looks like!
I believe everyone can and should travel, regardless of your job or the amount of time you have to plan a trip. Hopefully, this post was helpful and proved that creating a vacation itinerary is not as bad as it sounds.
And if you ever want help….I love creating itineraries. Please feel free to drop me a message with any inquiries and questions!
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These are great tips! I tend to follow roughly the same process, but with a whole lot of winging it! And sometimes I find a really cool accommodation first, and then plan the dates and locations around going there. š
Great tips! I like to use Google Maps during the rough itinerary part to see where all the sites I want to go to are, and then in the detailed part I’ll pare it down to what’s realistic and what are my priorities. It helps a lot!
Great tips! I am like you – I typically book my flights so far in advance. It makes the trip feel more real for me!
Sometimes the planning can be half the fun – – it builds up all the anticipation for the trip. This is a good way to go about it. I know that feeling once the flight is booked – – then it’s for real!
Great tips, I pretty much follow the same formula you do. I loe planning a trip. I think its a fun part of the process makes me more excited for the trip.
Awesome step-by-step tips! Very helpful when planning a trip.
I do lodging before flights because we use timeshares. Otherwise, yes, to all the steps!
Solid suggestions! I think you can tell a lot about a traveller by how they choose their itinerary. Kind of like when your wife asks you what you want and you ask her to give you a list. Word to the wise, always pick the first one on the list.
Anyway, your first and primary constraint appears to be time – when to go. A lot of people think of where to go first. For us, we think of what to do first and let everything else short itself out.
Great tips. I love planning my vacations almost as much as I love taking them. I follow a pretty similar process to what you’ve laid out, though I have a bit more flexibility on timing because I’m not limited to a certain time of year.
Good tips, Maggie! I practice similar steps.
As a solo female independent traveler, I enjoy tailoring my trips. In fact, I enjoy the whole process from researching destinations, planning itineraries, searching flights, accommodations … to taking trips and reflecting on them afterward.
But, yes, researching and planning are always much fun for us planners.
Great post! I’m currently at step 4 planning my London/Scotland vacation. I’m also using a trip advisor for additional comments, suggestions, however, why do people feel a need to add sarcastic comments regarding the plans of others? (rhetorical question) I’m going solo but meeting Irish friends in Edinburgh…fun!
I pretty much end up doing the same thing, only I check for cheap flights to choose the destination first. It’s easier to travel for cheap that way š
“4 million different options that you have to decide on”. When you put it like that it does seem a bit scary. š
Love how you picked your own trip as an example. The best way to explain it, that’s for sure. Good suggestions, really useful.
Great post on how to plan an itenerary! I’m going to pin this so I can look back at these tips later!
Planning travel itineraries is one of our core jobs. Hence, we learned a lot from this blog post. We will definitely use this knowledge in the future.
Thanks a lot.
This is so helpful! I struggle with this sometimes creating my own itinerary, so I’m definitely pinning for later. š
Useful tips as planning a trip, especially trying to book well-priced flights can be quite difficult. Mrs W hates flying so we have to know the airline, type of plane and exactly where we’ll be sitting. Saying that she did complete 27 flights last year. Although apart from the flights, we do love planning a trip, it’s all part of the fun
This is super helpful. My family could use a lot of help in this area.
Good steps. Personally, I tend to spend the most time picking the destination. After I decide that, everything seems to always fall into place.
I’m a plan-aholic when it comes to travel! I’ve tried to be a little more relaxed with what to do when I get there, but I love reading about my destinations and see what I can do when we get there. And I also book my ticket right away. I’ve never had a great deal pop-up at the last minute for the places I want to visit either š
Hey!! Great post. Planning a vacation is so much fun but creating an itinerary is something that needs efforts. I always face trouble while creating it. These steps mentioned by you to create a vacation itinerary is very helpful for me. Keep sharing more such posts. loved it.
Iām currently at step 4 planning my London/Scotland vacation. Iām also using a trip advisor for additional comments, suggestions, however, why do people feel a need to add sarcastic comments regarding the plans of others?
your first and primary constraint appears to be time ā when to go. A lot of people think of where to go first. For us, we think of what to do first and let everything else short itself out.
I do my planning that way because I work full time and have to plan my vacations around when I can take off, but I understand other people don’t have that same constraint and can plan differently!
Such great tips to begin your travel plans. And a great reminder that I need to book a hotel for August!