How I Plan A Trip in 8 Easy-ish Steps

I was sitting at my laptop with my cousin plotting out our road trip through Iceland, stressing and sweating like I was on my last life in a game of Frogger, when she said, "Planning a trip is hard work. I don't know how you do this multiple times a year." And I said, THANK YOU. Yes, it is hard work, in fact, it's a huge pain in the ass as I mentioned in this post, but I felt very validated in that moment when someone really recognized that this was no picnic. But, to do the things we want, almost inevitably we have to wade through a ton of shit we don't want to do, and that, ladies and gentlemen, is why nothing in life is free. NOTHING. Travel is amazing; planning travel, not that much. Anyway.

My commitment to DIY trip planning has less to do with my actual love for organization and research, and more to do with my unwavering knowledge that surely I can do this and surely it will all be worth it (it always is) and surely travel agents are extinct and even if they weren't that sounds like rich people stuff and anxiety. I am not a professional traveler, or planner, but my experience here as a regular person could come in handy for anyone who doesn't know where to begin, so, here we go, internet.


STEP 0 - Get Some Coffee

This step is optional, but I highly recommend it. You can go out and buy a coffee, or make it yourself! I'm not here to tell you how to live your life!


STEP 1 - Decide Where You Want To Go

Where do you want to go? How much time do you have? How long will it take to get there? How much are flights? How experienced are you with traveling? Do you speak any other languages? Is there an event you really want to attend? A bucket-list sight to see? These are all common sense questions that will help you choose a destination. I can't help you too much with this part, because I am not inside of your brain.


STEP 2 - Pinterest

You've decided where you want to go! Great! Now I can be somewhat useful.

Pinterest is a cruel beast, and my feelings about it are worthy of an entire separate post. I both love it (great for bookmarking and making note of things that I like and will want to revisit) and hate it (every single heinous image with horrible text over it that people pin ad nauseum). If you're new to Pinterest, it's essentially a visual bookmarking tool that will help you to gather and organize everything into one place where you can view it easily and access it anywhere you have an internet connection.

Anyway, start by making a board. I am currently in the midst of planning both a West Coast road trip for next month and a second trip to Iceland for 2016. You can pin content either by searching within Pinterest, or by finding things online and pinning them manually. Once you begin pinning things on a certain topic, Pinterest will help (or annoy) you by automatically feeding content on that topic onto your dashboard.

When looking for things outside of Pinterest, I'm pretty old-school in that I tend to just Google what I'm looking for. I also like to use Bloglovin' to find first-hand info from bloggers, Thrillist for great recommendations on bars, restaurants, and nightlife, New York Times for itineraries and culture info, and Instagram (see 1A) for tips from locals and travelers alike. Another great resource is guide books (very old-school) and local websites for the place you're visiting (think Time Out New York but for Iceland - great tips on events & local hangouts/happenings).

**Side note: it's important to Google things you find on Pinterest, especially if they only link through to a photo on Flickr, because there's no real vetting process and you will definitely come across misleading and inaccurate information. A lot of this will be revealed when you get to step 2, Google maps.


STEP 2A - Instagram

I'm still getting into my groove with Instagram, but when planning travel it's a great tool for finding out what's good from people who actually go to the places you're interested in. Start by following travel accounts like @withthelocals, @natgeotravel, @travelchannel, and @lonelyplanet, and also by using the search/explore tool to look for what you're interested in. There is no shortage of amazing travel photographers who feature awesome global destinations as well as local tastemakers (apologies, that word is terrible) who are in the know and will point you to the best places to eat and drink in a given area. Geotags also help you to see what a place will really be like when you get there. You can access Instagram in your browser and then also, guess what, pin the best Instas to ya damn Pinterest board! Easy.


STEP 3 - Google Maps

Alright so now you've got your pretty handy Pinterest board of ALL the things you wanna see and do. Next, open up your Google account and get a Google map going. Detailed instructions on how to do that are here. Whether or not you're doing a road trip, this is the part where you visualize geographically where all the things you want to see/do are, and how do-able that will be in terms of time and transportation. I know Pinterest has a built-in map feature, but I find it clunky and not ideal for our purposes here.

So you'll start by mapping everything on your Pinterest board. Then you'll probably realize, "Oh, I do not have time for all of this," or "Oh, I will not be able to hire a donkey in the dead of winter to visit the volcanic lake I wanted to see," you know, stuff like that. Now, use your brain and common sense and my highly helpful and detailed post to determine what you can do, how long you'll need to do it, and make a rough daily itinerary. This is also the step where you should be cross-referencing things online and making sure that not only are they do-able time wise, but you can afford them as well. That Game of Thrones Fire & Ice helicopter tour does sound rad as hell but it's also like $500 so maybe save that one for your honeymoon?

 Iceland 2016 road trip map is in progress.

Iceland 2016 road trip map is in progress.


STEP 4 - Book

Ok, so now you've got a rough daily itinerary. This is a great foundation and probably the hardest part. Next, the super important step of making all this real and booking things. Now that you have an idea of where exactly you will be and when, you can book transportation between places as needed, accommodations, and any attractions that require purchasing tickets in advance.

For accommodations, I like to use Hostel World (cheap accommodations and lots of user reviews), Booking.com (good prices and oftentimes flexible cancellation policies), and Airbnb (stay with locals for cheaper than hotels and get an inside look at another person's life.)

And an important note here: anything touristy bears doing some research on before you show up. For example, I had no idea that the Anne Frank Museum in Amsterdam required tickets purchased in advance. Needless to say, I did not visit the Anne Frank Museum. When in doubt, Google! Cover your ass! Be prepared!


STEP 5 - Track Costs

So most people would considering straight-up budgeting a step in their planning. I'm not the sort to do a traditional budget, rather I try to figure out what I want to do, then as I go, figure out the cheapest ways to do it. From there, you can kind of ballpark what you're going to spend, and then make and keep yourself to a budget limit if you choose. Even if you're not budgeting strictly per se, I think it's wise to keep track of how much you're spending and on what. As you book, keep notes in a Google spreadsheet of what you're booking and what the cost is, so things don't get totally out of hand. (And if you're like me, so you don't forget what you've spent). Another good way of tracking your spending is with website/app Mint - it syncs with your bank and allows you to categorize your transactions.

If you're traveling with someone, a partner or friends, this will be critical to keep track of costs and split them as needed. I use a great app called Splitwise for this which lets you enter in costs of things, make groups with those with whom you'll be splitting, and then does the math for you once everything has been tallied up. When it comes to making and receiving payments from friends, Venmo is my preferred method to do so.


STEP 6 - Make A Packing List

I feel like packing lists online have gotten a little out of control, what with the abundance of them on the aforementioned Pinterest (How To Pack For A 51 Day Tropical Vacation In A Carry-On Only!) but it is helpful to make a list of everything you'll need, and if you're me, are likely to forget. At this point it's also smart to make note of your airline's restrictions regarding carry-on/checked bags, if you'll be charged extra to check, weight limits, etc. Especially if you are flying a budget airline, because this is where they gouge you. If you DO need to check, be sure to pay for it online in advance, it's much cheaper usually and will save you some surprise and hassle when you get to the airport.

Now, I don't make packing lists for every possible situation that could occur, this part is up to you. Exercise common sense. Try to make your packing list a good bit in advance, so that if it requires anything unusual that you don't have on hand, for example a headlamp/travel towel/small dog papoose, you'll have time before your trip to get anything extra you'll need.


STEP 7 - Pack

You've got your list! You've got your stuff! Put your stuff in your bags! Don't forget anything on the list! Check weights and sizes of your bags! Remove that cat from your bag!


STEP 8 - Go

You did it! You planned the trip! Now you are going on the trip! Hooray okay bye bye now!!


And that is how I plan a trip in 8 easy-ish steps. That wasn't so hard was it?

But of course everyone is different - what do you know that I don't? What are your favorite resources for trip planning?