While I’ve always wanted to travel and explore new places, my appreciation for it really grew when I met my husband. Brendan has an infectious energy and sense of curiosity, and he has helped me see how wonderful it can be to explore the world outside of your own city.

As Brendan is also a much less anxious person than I, he has been instrumental in getting me to see travel as an opportunity to unwind and relax. Of course, I can’t fully change my overly structured ways, so I know proper planning is an essential aspect for me to have a stress-free trip. This way I can prepare for what I need, stay focused, and get everything squared away so I don’t have to rush or feel overwhelmed while preparing to travel. I know this can be a daunting task for everyone, so I am sharing my travel planning checklist to help you organize your next trip!

Travel Planning Checklist

Step One: Select Dates

First things first: before you’ve even started planning your travel, it’s important to figure out when you can go. This allows you to take care of requesting time off and taking care of important things like pet sitters and childcare (if traveling without).

This is also an important step to do early because timing is important for selecting your destination. After all, there’s a big difference between visiting a place like Savannah, GA in late July versus late October (I’ve been there both times and I found October weather was much better for exploring!).

Step Two: Set a Budget

As lovely as it would be to travel without a budget, that is not realistic for most people. Therefore, one of the first things I do is factor out exactly how much we can spend on our travel. This allows us to be reasonable about planning the details. For instance, my husband and I both like staying in boutique hotels, so we’re more likely to pick an off season to go to a certain destination to save money and ensure it aligns more with our budget.

Step Three: Select a Destination

This is my favorite part: selecting where you are going!

Destination depends on several factors: budget, when you are traveling, how much time you have, and what you are hoping to get out of your travel experience.

How I like to handle choosing a destination is by keeping a running bucket list and then reviewing it to see which destination aligns with the timing and budget. For instance, do we have the time and the funds to leave the country or does regional travel make more sense for us? Road trips can always make for a fun option when that’s the case.

It’s also important to look at what is going on in the destination at that point in time. Is it a time of year when things will be closed, or will it be so busy you can’t do anything (this is key for theme parks – how many horror stories have you heard about lines at Disney?)? Will the weather make it uncomfortable to explore? Factoring all of this in will help make your travel experience more enjoyable.

Step Four: Those Pesky but Important Details

I worked in international travel for several years and, while this is (in my opinion) the most boring part of travel planning, going over the following details is also one of the most essential steps. Taking the time to consider these details can save you so many headaches during travel (the number of Visa related meltdowns I’ve witnessed…). Always consider:

Do you need a passport or a visa?

I swore by this website while working in travel, but when it comes to things like Visas I do also recommend following up. It’s better to be certain you have everything you need rather than end up stranded somewhere while without.

Is your passport current?

It is super important to note most countries require your passport to have at least six months validity remaining, so if your passport is expiring soon, this would be a good time to get it renewed. I’m paranoid enough I like to have at least a year’s validity.

Do you need vaccinations?

Even before COVID, checking out vaccinations needed for international travel was an important step. The easiest way to do this is to check in with your healthcare provider or your local health department to see about travel guidance. My experience with this has been painless…aside from the needle. When I needed vaccines for a trip to India, I was able to get it all squared away at Walgreens.

Have you alerted your bank you’ll be traveling?

Nothing is worse than being away and not being able to pay for anything with your credit cards – don’t forget to let your bank know you’ll be traveling so you don’t run into this issue! If you use an App, it should be easy to do so online and then you won’t have to worry.

Have you considered Travel insurance (even before COVID I was a strong proponent for this)?

I always opt for travel insurance on my airfare because I’ve been in positions before where I’ve needed to cancel, and I would have been crying had I not. I also highly recommend checking the cancellation policies for everything you book, as you don’t want to be caught off guard regarding cancellation fees.

Have you updated your cell phone plan?

Make sure you have your data plan up to date for where you are traveling. These days, it’s easy to do a temporary updated plan with your network carrier to ensure you can reach people in case of emergency. After all, depending on wifi isn’t always the best method.

Make sure you have cash on hand

I never carry cash anymore and that usually works out just fine…until I’m traveling. It’s always a good idea to make sure you have enough cash on hand for things like toll roads if driving, gratuities for hotel staff, or even just for purchasing souvenirs.

Check on your medications

I always bring my prescription medications in their pharmacy bottles to have on hand, even though I use a weekly pill case to sort everything. This helps cover your bases in case anyone has questions about what you are carrying with you. If you take any medications requiring refrigeration, it’s a good idea to check with your doctor on best practices, as well as see if you can arrange for extra accommodations on a flight or in your hotel.

If traveling to another country, it’s also a good idea to check and see if any medications are prohibited so you can go through the proper channels to make sure you’ll be okay during your time away.

Emergency info list

Finally, I always like to make sure someone has my travel details and contact info while traveling. This includes departure and return info, how I’m traveling, where I’m staying, and any other pertinent information. I find it’s always best to plan for the worst so if something does go wrong while you are away, family members being able to find you won’t be an added stressor.

Step Five: Book Your Accommodation/Tickets/Reservations

As I mentioned above, Brendan and I are suckers for a boutique hotel. We can admit it: it makes us feel bougie. We also like finding a location walking distance of what we want to spend most of our time doing, as we like to explore on foot. We’ll spend a lot of time researching hotels and getting this part squared away is always a huge relief for us. While your choice of an accommodation could be very different (Airbnbs, for example), applying the same logic of figuring out what you like in a place to stay and where you’d like it to be located can be helpful.

You’ll also want to see if you need a rental car and get that squared away ahead of time. This will save you a lot of time and frustration upon arrival – especially as it’s not a guarantee cars will always be available. To save even more time, I also recommend seeing if Kyte is available where you are going. Brendan and I used this service on our Denver trip and it was so convenient having the car delivered to us and then picked up for us – so easy!

What activities will you be doing and do any require reservations or tickets ahead of time? For instance, Brendan and I are very food focused individuals, so we are going to ensure we’ve made reservations at the restaurants we most want to try and booked food tours if they are available.

Once I have all our details taken care of, I’ll then go into the Out of Office App to build out my itinerary. I love being able to have easy access to all of my trip details on my phone and this app is really user friendly and great for this purpose. (Full disclosure: I am a brand ambassador for OOO and receive a commission when you use my link, but I wouldn’t recommend anything I don’t absolutely love.)

Step Six: Create Your Packing List

Once you know where you’re going and what you’ll be doing, creating a packing list becomes a much easier task. I like to tackle it in sections:

• Toiletries (toothbrush, toothpaste, contacts, glasses, medications, SPF, etc.)

• Clothing (underwear, pjs, dressy clothes, casual clothes, dressy shoes, comfy shoes for walking, jacket, pashmina, etc.)

• Tech (chargers, iPad, phone, Kindle, etc.)

• Misc. (Makeup, jewelry, etc.)

I also covered tips for how to pack for a weekend trip on the blog. Read the post here for some more helpful advice. You can find my packing checklist here.

Vacation Planning Checklist Template

I know this is a lot of detail to throw your way, and so I’ve created a travel planning checklist template for your use! This downloadable form will help make it easy for you to make sure you are taking care of all the details while planning a trip. Get it here!

Hopefully this will help make your travel planning nice and easy. Until next time, cheers and happy traveling!