How to Plan A Trip: Step-by-Step Guide to Travel Planning in 2021

Updated: Jan 4, 2021

Travel can seem daunting. I know - I have been there! When I started seriously traveling at the age of 21, I literally would just "wing" everything. As most millennials do, I lied about using excel on my resume and could not even formulate a plan if my life depended on it. Throughout the years, I have honed in on these skills and personally think I can now plan a mean travel excursion! If planning a trip is holding you back, never fear; Kath is here! (deletes blog). Here is a step by step guide to planning the most magical trip without the stress.

This article is written in consideration of COVID, but steps I would have taken prior to the pandemic. It is always important to consider the health and safety of others around you when traveling in the coming year. However, I am optimistic about the shift in tourism with the release of the vaccine. Do your part, wear a mask!

Pick a Destination - Best Season v. Shoulder Season

Often the destination I am choosing is dependent specifically on the time of year. At the beginning of each year, I create a note on my phone called "2021 Travel Goals." I continuously refer back to this note as motivation not to spend $5 on a coffee & keep my priorities in line. There is nothing more satisfying than crossing something off that list as well, for all you list junkies out there.

Based on this list and my availability with work, I then start researching based on my list what each place has to offer as far as "shoulder seasons" and weather for that time of year. "Shoulder season" is essentially off-peak season for a destination. A huge reason to travel during this time is the cost of flying goes WAY down and creates a more affordable trip. When I visited Japan, it was in the shoulder season, and I saved many dollars on flights. However, this is a double-edged sword.

Most individuals generally want to have nice weather to walk around freely, not pack as many layers & of course, photography. Peak seasons are peak for a reason, but also come with an abundance of tourism. I suggest googling what the weather is like a month before peak season begins, as generally, the weather changes are mild, and you will not see nearly as many tourists. For example, I traveled to Greece in early May, about a month before peak season began, and there was NO ONE. I mean NO ONE. Considering that Greece, specifically Santorini, runs 80% of their off tourism, it was incredible to have beautiful weather with minimal people.

Just a little food for thought on this subject, but no matter when you travel, you're doing it, so go you!

Book Hotels

Kathryn, why is this so early in your planning list? I have a story for you. I had a circumstance where I booked a trip to Nashville (flights, friends confirmed, the whole thing) and did not realize it was the weekend of the Country Music Awards. Big oops. The biggest issue was that every hotel was either sold out or the price was insanely high, so we ended up in a sketchy part of town in a not so lovely Airbnb. The moral of the story is that it is easier to alter plans when you start booking hotels instead of flights.

Determining where you will be on specific days makes the ease of planning more solidified. I am a giant Expedia & Airbnb user, so those are the places I typically go to first to find hotels and homes in my price range. This will also ease your flight booking process as you can book multi-city travel (I talk about this more in the next section!).

Booking Your Flight

Now that you have picked your destination and mapped out your hotels/cities you will be staying in, time to book your flight! I started utilizing a trick a few years ago to put your google chrome into incognito mode when booking flights (demonstrated in the video above). This process can save you money as airline websites use cookies to track your browsing habits and study the seeking flights. If these airlines see you coming back to seek the same flight, they may increase the pricing to ensure you make your purchase. There are hundreds of testimonials out there of people saving significant money when booking this way!

I also recommend using websites like Skyscanner and to compare different rates & layovers for flights to get the cheapest or the fastest flight to your destination, depending on your budget. Booking on sites like Skyscanner also lends itself to multi-city flight booking (booking a flight into one city and out of another city). Although it is arguably cheaper to do a roundtrip flight, I can visit more places with a multi-city flight booking as I do not have to double back to my arrival city.

Post About It

If you already have a travel companion, this may not be as potent of a tip. However, for the solo travelers out there - this is for you! I never wait for other people when planning and booking trips. Often it can delay or deter you from actually traveling. I suggest going ahead with the booking and taking the time to post about it on Instagram. I don't share all my personal information, but merely share where I am going and referring to solo travel.

Last year, I had a situation where I had booked a solo trip to Slovenia, Austria & Germany and posted about it on my Instagram story. Within an hour, a friend of mine from college messaged me asking about the trip. By the end of the day, she confirmed coming along with me, and we had the BEST girls trip (shoutout to Alexis, the real MVP). I shared the actual Instagram story that started our trip above! You never know what will come out of the woodworks when you share your travels with others!

"Planning" Your Itinerary

Full disclosure, I am very type B when traveling. I love not to have too much planned when adventuring to a new place and enjoy what I am looking to do at the moment. Incredibly odd as I identify as Type A in the real world, but I am sure there is a cool, psychological reason for that. Let's pick my therapist's brain about it later.

First, I go nuts on Google, Instagram geotagged locations, Trip Advisor & Pinterest to get an idea of what I will be doing on a trip. Instead of a plan, I like to refer to this as a "bucket list." My bucket list is typically kept in a note on my phone to refer back to when applicable. I included an example with my recent trip to New England, highlighting all the restaurants, retail stores, & other locations I researched and would like to visit.

After creating my bucket list itinerary, I then see if something specific needs to be planned before the trip. When I planned my trip to Japan, an itinerary item was driving "Maricarts" around Okinawa's streets in Pokemon costumes. After researching, I realized you need to attain a temporary driver's license to operate vehicles anywhere in Japan. So I was able to plan to visit AAA in the US before we booked the carts. The research process can be tedious but 100% necessary if you have something on your list you'd really like to accomplish!

Another element to travel planning that I like to do is google maps the destinations you want to hit from your hotel or Airbnb. Finding how far away specific places are from your hotel can sometimes alter your hotel plans for the better!

Check for Visas

A quick note to check on ensuring that the visiting countries do not require a visa to enter. A friend of mine did not realize you needed a visa to enter Australia from New Zealand, which landed a 45-minute delay in exiting the airport with her group. A practical step to ensure you enter and exit the country smoothly! Websites like iVisa are great for checking entry fees into any country in the world.

Travel Insurance (Optional)

Purchasing travel insurance really depends on the type of trip I am taking (usually trips outside of the United States), but purchasing travel insurance is another step I take when booking travel. Is it necessary? No. Does it offer tremendous peace of mind? Absolutely. In the past, I used World Nomads to purchase travel insurance when I made my trip to Yacht Week. Lending myself to drunken nights on a boat in the middle of Croatia was only made more sound with purchasing insurance for things like lost luggage, injuries (pictured), or canceled flights.

Specifically in COVID times, it is integral to consider taking precautionary measures as the vaccine is distributed. -



Pin it below!

After you've taken these steps, you are well on the path to having a successful trip! Are there any other steps you take when planning a trip? Let me know in the comments below!

Also, check out my YouTube Video below for a condensed version of the post :)



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