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Writer's pictureKatie Oliver

How to Plan Your Next Adventure



A guide on how to create your own itinerary, find the best deals, and make the most of your time while traveling!


I have had a lot of recent questions about how we plan our vacations, how we find all of the best things to do, how to get the best deals. So I wanted to share with you some of our favorite resources that make our vacation planning process possible!


 

Where to Go (and When)



Bucket List Brainstorming

  • Start a list on your phone of all the places you want to travel and don't be afraid to dream big!

  • Search for inspiration: TV series, Pinterest (follow me @katievirantoliver), word of mouth, friends and/or celebrities on social media, computer screen savers, etc

  • When in doubt, throw a dart (or close your eyes and point) at a map and use that as your inspiration!


When to Go

  • Weather: avoid the extremes of summer/winter/monsoons, tailor towards your plans - ie snow/cold weather is ok if you intend to ski

  • Peak Tourist Times: do your research to find good shoulder seasons - where the weather is nice but not peak tourist times. This makes a huge impact on overall costs as well as your general experience. We have great success avoiding peak tourist times by doing much of our travels in February and October each year.

  • Your Availability: ultimately it comes down to when your schedule allows you to travel. Finding time off work for you and your travel partners can be challenging but I urge you to make time to experience the world! It works wonders on your mental health.


 

Transportation: getting there and getting around


Airfare

Once you know where and when you are going, you have to coordinate getting there! If driving is an option, weigh the pros & cons of driving vs flying - cost, time, your sanity...Most places Tom & I travel to are too far for driving. Here are some of our favorite resources for finding the best & most affordable flights:

  • Hopper: website & app that predicts prices and helps you book your flights and hotels at the right time

  • Cheap O Air: website & app for cheap discount flights from a variety of airlines

  • Expedia: website & app for cheap discount flights from a variety of airlines

*always compare various flights before you book!


Ground Transportation

One of the things that makes me feel like I'm on vacation is getting out fo my usual habits of transportation. When on vacation, Tom & I get creative in our transportation means and have fun exploring the different types of local means of transportation from the subway to tuk tuks and more.

  • Ride sharing apps: Uber, lift, local (ie: Grab in SE Asia)

  • Rental Car

  • Public Transportation: subway, sky train, bus system - buy pass in advance (ie Japan Rail Pass). Often times subways/rail systems can be intimidating. If you have the opportunity, I recommend challenging yourself to try a new system and learn by exploring!




 

Must Do, Must See


Brainstorming

  • Blog surfing: I use both Pinterest and google to find "top 25" lists. From there, I create a running list of top recommendations to later condense & review.

  • Trip Advisor

  • Word of Mouth

Google Maps

I like to take my list of top things to do and add all of them to my favorite list on Google Maps. This helps me on a few different levels: 1) The sites are saved for reference when we are there and trying to find things to do if we have extra time, 2) I can now see my list in a geographic manner which allows me to clump points of interest together to make the most of our time, and 3) I start to become familiar with the geographic layout of the city so it's easier to find our way around when we are actually there.



Timeline

  • Geographic: This is where Google Maps comes in handy! It helps to clump things together by geographic location when planning your trip. This should help eliminate you running all over town and wasting time with unnecessary, back-and-forth travel.

  • Day by Day: Once I have things clumped geographically, I like to see what I can fit into each day. I sometimes have to look up how long to spend at certain locations to best plan this. For example, I had no idea how much time to allow us for Pearl Harbor in Hawaii - 1 hour? 6 hours? I did some research and decided to allow us a full morning (8a-12p) to spend there. This better helped me plan our trip and fit something appropriate in that afternoon.

  • Be flexible: Clearly, I am a huge planner and totally recommend thorough research before traveling, but all that having been said, at the end of the day, you have to just go and enjoy yourself. Use your itinerary as a guideline and book certain things in advance, but use your research to roll with the punches and live in the moment and make the most out of each day you're there. Do not get too bogged down with sticking to an hourly itinerary.


 

Accommodations


Location, Location, Location

Use your rough itinerary as a guideline when looking for a hotel. We always try to find accommodations in central locations - close to markets, rail stations, etc.

**Pro Tip: If traveling for more than a week, consider finding coin laundry at your hotel!**



Resources

  • Use online blogs as a resource to find some recommended accommodations. You can also use this as a spring board to find good areas and average price ranges to better aid your own personal search.

  • We mostly use Hotels.com to book our rooms and are able to earn free rooms for every 10 nights we book!

  • We also look at AirBnB often but find variable success. The room rates themselves may be a better deal however pay attention to the specific fees applied afterwards!


 

Packing


Luggage

Choose your luggage based on what fits your needs for each specific vacation - rolling carry-on vs duffel bag vs camping backpack. Ask yourself these questions:

  • What is covered by your airline?

  • What type of travel are you doing? Staying at one all-inclusive resort or hopping from hostel to hostel each night?

  • How long are you going for?

At the end of the day, use the type of luggage you own!


Attire

Check the weather!

Consider the local culture: bring cardigans and pants to cover your knees & shoulders for temples.

Bring comfortable shoes for lots of walking

Pack your mini toiletries: I bought little bottles and refill them with my daily toiletries

Try rolling your clothes to make some extra space!


*Pro Tip: Make sure to leave room in your suitcase for souvenirs on the return trip!


 

My Pinterest Inspiration Board - Travel Inspiration


Hopefully these tips & tricks provide you with some guidance in planning your next big vacation! Get inspired, dig deep into your resources, and then let go and enjoy. Live in every moment!


Comment below if you have any questions or need help planning your next holiday!


XOXO,

Tom & Katie

"The Wandering Olivers"

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