Let Me Explain: Planning a Trip Isn’t Stressful, You’re Just in Need of Some Structure

Growing up I thought that planning a trip must be so stressful because I watched the adults in my life run around the house like chickens with their heads cut off trying to get done all the items on some long, arbitrary list of things they just had to do before leaving for a trip. I’m here to tell you - and you may need to sit down for this one - planning a trip is not stressful or hard. You can do it! The best advice I can give you for planning a trip (besides of course buying my itineraries that includes lodging, restaurants, bars, clubs, and more!) is to have a template that you use every time you plan a trip to refer back to. Let me explain. 

Here, There, Everywhere

The first step when planning any travel is to book your transportation so you know where and when you’re going somewhere. If you can, go ahead and book both your transportation to and from any place you’re going, but at the very least book your transportation from Point A to Point B. I personally don’t worry about booking buses in advance and will usually wait to get them the day before to make sure plans don’t change, but flights and cross-country trains I recommend booking up to three months in advance. To book flights, I typically use Google Flights, SkyScanner, and my credit card travel website. There are so many flight booking websites out there. I recommend finding one or two you like and sticking with that. Local and commuter buses and trains can wait as tickets can typically be purchased on the spot. That being said, it’s a good idea to know in the back of your head how you’ll be getting around a city or from one city to another if traveling within the same country or region. For instance, I recently got back from a trip to Portugal where I traveled to four cities within the country. I booked my round trip flight from Washington DC to Porto three months in advance. Then I planned out which cities I wanted to see which were Lisbon, Estoril, Sintra, and Porto. I booked a round trip cheap flight from Porto to Lisbon a month in advance and then looked at how I could travel to all the other cities. Websites like Google Maps, Rome2Rio, Omio, and Rail Ninja are my go tos BUT the best way to find out how to easily get between cities has always been asking locals or friends and family that have been. Don’t be afraid to ask for a second opinion! I include transportation in all my itineraries as well so definitely check those out!

I Need a Place to Rest My Head

I use the same three sites to book my lodging no matter where I travel to and, depending on which website I use, I look for different things. I exclusively use Hostelworld, AirBnb, and Expedia to book my lodging for every place in the world I travel and that is always how I recommend others book accommodations in my itineraries as well. The three websites have a good reputation of being helpful with decent customer service and are widely used where you can always find reviews for every space you consider booking. I always put filters on when I search for my accommodation and I’m rarely if ever surprised or disappointed when I get there. I know what to expect based on the pictures, reviews, and general ratings and walk away satisfied. So step two is finding which websites you like to book through and have had the best experiences with and sticking with those. 

Who, What, Where

Before I travel anywhere I make myself a list of things I’d like to see, experience, or do and sort them accordingly. I find this step especially fun because it’s like building a Make Your Own Adventure for yourself. I look up and ask friends for recommendations of places to eat, shop, drink, dance, explore - you name it - and write them all down. Then, I go through and put them into one of three buckets: 1) Must Do 2) Would Like to Do 3) Would Be Nice to Do. Now maybe it’s the former teacher in me, but this process has never failed me. If you are someone who doesn’t enjoy looking these things up or doing the research, you know I got your back and have them already embedded into my itineraries. But on the off chance that you are planning to travel yourself, this trick is tried and tested by me a hundred times over! So make a list, sort them, and then you can go ahead and look into booking tickets or reservations in advance and have that done. I will say, I don’t always book everything in advance; sometimes it's the week before and sometimes it's the night before, but either way, I know exactly what I must see, do and taste before traveling to a new place and can move accordingly. I try to do all my Must Dos, a few of my Would Like to Dos and if I have spare time, I can tackle my Would Be Nice to Do. I try to always leave time for plans to change based on my mood, energy level, or something new I learn about while on the trip that I want to squeeze in. The nice thing about leaving some time and planning out my Must Dos in advance is that I always get to see the things that make the trip worth it and manage to strike a balance by leaving time to be spontaneous. If you do this ahead of your trip, even if it’s on the plane ride, train, or bus ride to a place, I promise it makes all the difference. 

Throw it in the Bag 

I used to always forget at least one (okay if I’m being honest with myself more like five) things every time I traveled and it would be annoying because it was either something I really needed or something that I couldn’t easily replace. I decided to make a general travel packing list with all the items I need and it has never failed me. In fact, my great packing was so exceptional that friends and family noticed and have been asking me to share my packing list with them for years because it’s that good. I have on my list things for year round, things for summer only, and things for winter only and, not to toot my own horn, it totally rocks. I highly suggest making this list for yourself, saving it somewhere, and always referring back to it every time you travel. This saves so much time in the future and can really make or break a trip. If you need a place to start, I offer packing lists with each of my itineraries and would be so happy to share with you. And before I forget, one pro tip is when you travel if there is something that you wind up needing that wasn’t on your packing list or something that you wish you had, write it down immediately so you can add it to your list for next time and be that much more prepared! 

Try These Out, I Got Your Back

There is an obscenely long list of things I recommend doing when traveling that I will get to in other blog posts. In the meantime, I hope this has been worth the read and takes away the stress of planning a trip, even if just a little. I cannot emphasize enough that there is no need to reinvent the wheel each time you travel. Use the same templates, websites, processes, and lists each time you travel and you will never be stressed while planning. 

Happy wandering, 

Raven