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 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

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 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, 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.

Fairmont Lake Louise

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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Would you like to travel more but are too daunted by actually planning the trip? Check out my how-to guide creating the perfect vacation itinerary! #travel #itinerary #tripplanningĀ  Ā  Would you like to travel more but are too daunted by actually planning the trip? Check out my how-to guide creating the perfect vacation itinerary! #travel #itinerary #tripplanning

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