The Ultimate Guide to Travel and Adventure
Note: I started writing this post months ago, considered selling it as an eBook, then had to wait til Amazon's publishing rights ran out to publish it here--so don't mind that I talk about planning Iceland even though I've already taken the trip. Enjoy!
Full disclosure: this post is going to be a beast. It's absolutely packed with the basics of how to plan your next trip.
We’ll go over the basics today, talking about how to determine your travel style, choose your destination, decide whether to travel solo or with a group, know how much to plan, and decide what and how to pack.
If you’re interested in digging even deeper and getting into the real nitty gritty, step by step process of how I plan every trip I take, including access to the resources I swear by, you might be interested in Two Weeks to Travel, a free email course where I send you a lesson every day for two weeks with a video, an article version of the video, and actionable homework steps to get your trip planned in two weeks flat.
It takes about 20-60 minutes of effort a day, and at the end you’ll have a fully planned, completely tailored to your interests trip. You can sign up for that right here:
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Both the Two Weeks to Travel course and this post today will be the most useful if you know you want to travel, but haven’t gotten much further than that. We start at the very very beginning. If you already know where you want to go, or are somewhere in the planning journey, that’s great too! We just start from that amorphous sort of feeling we get from time to time that I like to call the ‘travel bug’, and turn that into an actual, booked, amazing trip.
Determine Your Travel Style
So before we get started thinking about where to go or when to travel, the first thing you should do is to decide what type of traveler you will be—or, maybe it’s more correct to say that you should discover what type of traveler you’ll be.
Just as there are many wonderful types of person, there are many wonderful types of traveler. I would hate for you to get the idea that some types are better than others, because that results in an unfortunate tendency to try to be a type of traveler that you may simply not be. When this happens, travel becomes uncomfortable, anxiety-inducing, or tedious rather than what it ought to be: mindblowing, exciting, and fun.
The key, then, is to determine what types of things are mindblowing, exciting, and fun for you. My guess is you have a pretty good sense of this already, but let’s explore the options a bit, shall we?
The first type of traveler we'll discuss is the typical tourist. The tourist prefers to book through a service that arranges everything from plane tickets and airport pickup to guided tours that hit the high points of every destination. They don’t tend to stray too far from the group, but often do stray from the bounds of their ordinary lives. The tourist will experience new things and create wonderful memories that they’ll cherish for years to come. They don’t worry too much about how many other people are taking the same photos and creating the same memories—after all, the particular activities are popular for a reason, no?
My guess is that if you’re reading this post, you suspect that you may not be that type of traveler, and I have to say, I quite agree. Those travelers do not need this post, they need the number of a great travel agent. Side note: if you do read this and then decide ‘nah, this still sounds overwhelming and terrible,’ I am happy to plan your trip for you. We’ll chat via Skype or phone call and I’ll do all the rest. Take a look at my services page for details.
Let’s move on to the types of traveler you might actually be. Now before I get started, it’s important for you to realize that most people are actually a combination of a couple of these. That’s perfectly fine, there’s room for all of your traveler selves on your journey. It’s just important to identify those traveler selves so you can incorporate the things that will make this trip the perfect trip for you.
The Adventurer seeks exciting experiences above all else. They want to summit the peak, if only for the sake of the beautiful view from the top—oh, and for the jolt of adrenaline, which is one hell of a drug.
Adventurers often push themselves to the very edge of endurance when traveling. You’ll find them in the wilderness more often than in cities, though they can certainly get wild with the best of them in hostel rooftop bars or dingy underground nightclubs.
The Instagram account of the Adventurer is filled with gorgeous natural vistas, artsy (and not at all staged, I’m sure) campfire photos, and A-frame cabins that make one want to sell one’s possessions and live off the grid.
The Bon Vivant
The Bon Vivant lives the good life, and demands nothing but the best. These travelers prefer to jetset in style—you’d never catch them in a hostel dorm. They look for luxe hotels that stock artisanal handmade bath products, dine at world-renowned restaurants, and see the sights in comfort and at their convenience.
The Bon Vivant looks for premium experiences, and is prepared to pay well to have them.
The Instagram account of the Bon Vivant is more well-curated than GOOP—sorry, Gwyneth!
The Historian is in search of anything that ever showed up in their history, philosophy, or anthropology textbooks. They get such a thrill from seeing a place they’ve only ever read about in real life—it’s really quite charming to behold (well, at least at first).
You’ll hear the Historian spout off fun facts they learned from the guidebook or their lecturer sophomore year or that book they read that one time.
The Historian’s Instagram account is rather caption-heavy, I’m afraid, if short on hashtags.
The Sage is on rather a spiritual journey. They are seeking knowledge of themselves, self-love, perspective, or healing. The Sage is looking for meaningful experiences—whether they be late night heart-to-hearts in the women-only hostel dorm or at the top of a mountain through meditation guided by a monk.
They tend to travel solo more frequently than the others, but not exclusively so.
The Instagram account of The Sage is filled with inspirational quotes set against beautiful photographic backgrounds (or has been deleted as part of the spiritual journey).
Now here’s where it gets complicated. It is quite possible for one person to be each and every type of traveler on the above list depending upon phase of life, destination, traveling companions, and the book they most recently read.
In order to find the most happiness from your journeys, it’s important to identify what type of traveler you’re likely to be on each particular trip.
Part of this is for planning purposes, of course—you wouldn’t want to sign on to a Sherpa-led trek in the Himalayas if you’ve been really looking forward to some rest and relaxation. Take a moment, then, and decide what part of yourself will be foremost on the trip you’re currently planning.
It’s also vital to keep your travel style in mind when choosing your traveling companions. It isn’t always possible to choose one’s traveling companions—for example, if you’re traveling for work or with your family (no, it isn’t usually acceptable to leave even the whiniest child at home if the rest are accompanying you).
If you’re traveling with friends, though, it is entirely reasonable to invite only those who will be ecstatic to travel with you in the same style as you prefer. If you plan to drive the Ring Road in Iceland in the middle of winter and climb the volcano Hekla, it would be unwise to invite your friend whose idea of adventure is a cruise to the Bahamas.
If she pouts about being left behind, make sure to tell her in minute detail exactly what you have planned. Chances are, she’ll realize she wouldn’t have any fun. With your travel style in mind, let’s move on to the fun part—choosing your destination.
Choosing Your Destination
There is a whole, wonderful world out there—which makes choosing where to travel just about impossible if you let yourself think about it too terribly much. The dreaded Analysis Paralysis kicks in if you are silly enough to try to narrow down your destinations from literally the entire planet.
You simply must have constraints of some sort, or it’s all too much and you’ll spend the entirety of your time off trying to decide where to go.
Don’t believe me? Go choose a movie to watch on Netflix. Right now—I’ll wait. I jest, I won’t actually wait, because I would be here for eternity.
How many times have my dear Matthew and I sat down to watch a movie together and taken over an hour to agree on something—just for me to fall asleep ten minutes after the movie starts?
But if I told you to go choose your favorite Disney movie—well, it still might take you some time to sort through such a glorious repertoire, but you’d settle on something within five minutes.
The same principle applies here. Begin with your travel style. Even if all of the styles we discussed in the last chapter were appealing, there was probably one that whispered into your heart that yes, that’s me.
Chances are good that you can find adventures just about anywhere, but when you think of yourself as an Adventurer, are you picturing mountains (I’m in a mountain phase myself at the moment), rapids, diving, caving? Then look for places notable for your particular fancy.
Are your options still overwhelming? Of course they are, you could probably find all of those on every continent in the world (fine, I realize you probably wouldn’t consider Antarctica to be a premier diving destination, but you take my point). The next step is to identify any other constraints you might have.
How much time off do you have? If you’ve only got a week, that limits your options tremendously already. You certainly don’t want to waste two days traveling somewhere very remote, then spend three days in adventurous bliss (leaving aside the likelihood of jet lag and gastrointestinal distress from new foods, but those are for other blog posts), only to spend another two days on your return home.
How much money do you have? If you’re on a small budget, you have a lovely constraint right there. That 'lovely' sounds sarcastic but I promise it is not.
I just booked a trip to Iceland for 5 days because the plane ticket was only $250. If I had been choosing a destination from the entire world, Iceland would maybe not have been my first choice—but seeing a cheap plane ticket to a beautiful country made the decision so easy.
Side note: Iceland is rather an expensive country once you’re there, but I am traveling with other budget (read: we’re all broke) travelers and we’ll spend most of our time outside of Reykjavik, so I’m hopeful that we’ll manage.
My brother is in the military and stationed in Germany. His wife often plans amazing trips last minute simply by taking a look at her favorite budget flight website and booking the deal that looks best. She knows that her next trip isn’t too far off (that lucky woman), so there’s no pressure to choose the perfect location—only an incredible one.
That last part just might be key. If you plan your trip as though it’s the only one you’ll ever take (even if it is—but it probably isn’t), then you must choose the very best destination. If you plan your trip as though it’s your next trip of many, it gives you permission to choose one of the many best destinations. Because honestly? There isn’t just one best option.
When you’ve identified as many constraints as possible, it’s entirely likely that a destination already suggests itself. If there are still several options that sound good, then do some initial research. I don’t mean that you should plan a full itinerary, but do a quick Google search, click over to the images, and see what’s prettiest. You’ll never regret going somewhere beautiful.
Solo or Group Travel?
Do you recall that I mentioned traveling companions earlier? I wanted to take a moment to point out that traveling companions are not at all a prerequisite for travel.
In many cases, traveling companions are terrible flakes or nobody wants to travel the way you do to the places you want to go. If you wait for the right person to come along, you may never actually go anywhere.
Rather than wait around, why don’t you simply go by yourself? I know, I know, solo travel sounds rather intimidating, especially if you’ve never really been anywhere much different than where you’re from.
Not only are you hundreds or thousands of miles away from home, but you don’t know another soul? Sounds like a recipe for disaster, I realize. If you're a woman, your family members in particular might be extra worried for you.
And yet…there are a few decided benefits to traveling on your own. The first is perhaps obvious: you can do whatever you want, whenever you want. There are relatively few times in a person’s life when that’s true, actually, and indeed it might take a bit for it to sink in that your time is your own.
Nobody will interrupt your lie-in, trying to convince you that no, 7:00 in the morning is not too early to go down to the beach. If you decide last minute that you’d rather take the glacier tour than the horseback meadow tour, there’s nobody to complain (except the poor forgotten horses, that is).
It is a remarkable sort of freedom to not have to consider someone else’s happiness (for the first time ever, for some of us).
That comes with the caveat that your trip experience is entirely your own responsibility. Sometimes working out logistics is a headache, but if you don’t do it, then who will? To mitigate this inertia, I recommend planning just about everything before you set foot in this new place (which we'll talk about in the next section).
Solo travelers do not tend to remain solo the entirety of their trip, unless they take steps to ensure it. Hostel dorm rooms, that favorite of solo travelers, often become late-night social clubs, and you’ll be able to tag along with someone or they with you if you hit it off.
Solo travel is great for introverts or ambiverts. With fewer (ahem, exactly zero) people along, you can choose solitude when it suits you and socialize at other times. I won’t say that solo travelers never get lonely—one can feel really quite forlorn getting off the plane and seeing fellow passengers greeted enthusiastically by their families while you’re heading off to find a taxi.
But don't confuse solitude with loneliness—they're not at all the same thing.
There are, of course, also benefits to traveling with companions. I, for one, am rather a braver creature when there’s someone along with me.
I would love to pretend that it’s because I’m bolstered by their friendship and love—but to be straightforward with you I must confess it’s because I would rather die than admit I can’t do something that they can.
If you choose the right travel companions, you'll be surprised at how deep your friendships get over the course of your trip. (Corollary: if you choose the wrong travel companions, you'll probably never speak again.)
On a more pragmatic note? If you travel with companions, you can split many of the expenses and save money.
There are points in favor of both solo and group travel, and I’ll leave it to you to decide which is better for you. Perhaps you can combine them—travel to your destination solo and make friends to accompany you on adventurous outings.
As long as you don’t let the lack of willing, enthusiastic traveling companions keep you from traveling, I’ll be delighted.
Let’s take a deep dive into how exactly you should go about planning your trip now that you’ve chosen your travel style, destination, and whom to invite (if anyone).
Each traveler has a different comfort level when it comes to planning. Some won’t feel comfortable stepping foot onto an airplane unless their itinerary has been planned down to the minute. Others feel quite confined by that level of detail, and would prefer instead to largely—for lack of a better term—wing it, even to the point of not booking lodging until they arrive.
I fall in between. I want to have a rough trip-wide itinerary that includes my personal must-sees or must-dos, with a general idea of which day of the trip would work best for each. The idea of flying somewhere and not having a place to stay is enormously anxiety-inducing for me, so I book lodging for every single night. Since I’m typically staying in hostels, it wouldn’t break the bank if I change plans and end up somewhere else occasionally.
My planning style requires a good bit of work—almost an overwhelming amount of work, except that it gives me great joy to plan trips. If you do not feel the same, but share my planning style, what are you to do?
As with any large task with innate potential for overwhelm, it helps to break it into ever-smaller and imminently doable tasks. I’ll tell you how I plan, and you take what helps you and leave the rest behind.
I keep a new tiny notebook for every trip I take. I write down confirmation numbers, addresses, and my itinerary. You won’t always have Wi-Fi or cell phone reception and it’s better to not rely on that for your important information. Have it on you in a physical form. Plus, I’d much rather tear out a piece of paper to hand to a cab driver than hand over my phone.
I begin by creating a master wishlist of every single thing I would do on a dream trip to whichever destination I happen to be planning.
To compile this list, I visit the bookshop or the libraryand get a Lonely Planet guidebook on the destination. I like to have a hard copy in my hand to thumb through. I take notes as I go, typically with paper and pen.
I write down the name of the attraction or town and a couple of words reminding me why it’s on my list, and I tend to group things into regions of the country (when it’s mentioned) so I know how to schedule later on. I don’t read every page, but I do look at every section that interests me.
When I’ve gone through the guidebook, I go through my list to make sure I have the general region noted for everything I’ve written. If I don’t, I pop it into Google Maps and categorize it appropriately.
Then, I Google Image search everything on my list. I’m a person who very much appreciates beautiful views and buildings and towns, and I would prefer to know ahead of time if something is going to be underwhelming aesthetically. It doesn’t automatically knock it off of my list if there are other redeeming qualities, but it does affect that item’s priority level.
Once that’s done, I have a lovely if not absolutely perfect list. If I’ve broken things down by region as I went through, then a rough itinerary begins to suggest itself.
It’s time at this point to decide whether you’ll want to rent a car or if you’ll be able to take public transportation to get to your important sights. Some destinations almost require guided tours for particular attractions, so if that’s the case, figure that out now.
As I’m planning this Iceland trip, for example, I decided to rent a car so that our group can self-drive. It gives us much more freedom with our schedule, and means that we don’t have to rely so much on expensive tour guides. We’ll be able to drive as much of the Ring Road as we wish, seeing the mostly free sights on our own.
However, we will be taking a guided glacier tour for the simple reason that we don't wish to fall into a snow-covered crevasse and perish. An experienced guide, in this case, has skill and expertise that we cannot hope to gain before our trip, and is well worth the cost.
At this point, you'll have a lovely huge list with every wonderful thing you could find about your destination. However, it isn’t typically feasible to see or do everything on that list. There are a couple of ways to decide what makes the cut.
First of all, identify the experiences that you would certainly regret skipping. Sometimes there’s one particular feature or attraction that decided you on that particular destination—so naturally, it should be on your must-see list. If there are places that took your breath away from just the Google Image search, then it should almost certainly be on your must-see list.
Otherwise, consider location and cost when compiling your rough itinerary. For my Iceland trip, the vast majority of my must-sees were clustered in the southern part of the country. There are a few other must-sees dotted around the rest of Iceland and I very much hope we’ll be able to make it to those as well.
However, we have only five days in Iceland, and it’s entirely possible that we can see either the many sites in southern Iceland or the few sites in the rest of Iceland, in which case I’d rather see as much as possible. Those scattered must-sees become ‘would be nice to sees’ instead.
It isn’t always easy to accurately gauge how much time you’ll want to spend at each item on your must-see list. You can get a general idea from other people’s accounts of their trips, but it’s best to just build in extra time so it’s there if you need. If you speed through your list much more quickly than anticipated, how wonderful! You’ll get to more of your ‘would be nice to see’ list.
That’s a much more desirable scenario than assuming you’ll scurry through everything and becoming stressed and agitated if members of your party want to linger or there are unanticipated lines or it takes longer than expected to get that beautiful photograph you wanted.
One thing that’s terribly helpful with this rough but flexible itinerary is flexible cancellation policies. I know, for example, that if I cancel my hostels and guesthouses a day ahead of time for my Iceland trip, I get a full refund of my deposit. I’m rather hoping that we make use of this, because it will mean that we’re traveling much further along the Ring Road than my realistic itinerary suggests.
Given how much wiggle room I build into this itinerary, why bother making one at all? Well, there are a couple of reasons. The first is that I would hate to miss something amazing simply because I didn’t know it was there.
Also, I suffer from analysis paralysis. If there are too many options for what to do, I can’t decide—and thus do nothing. If I have a list, though, it’s much easier to say, ‘Ah, this is next! Let’s go.’
One last note about planning for those of you traveling with companions: it is not required that you do everything together.
If some of you want to take the horseback tour and the rest have done it before and so would rather hang out at the bar in town—that’s okay! That’s great, in fact, because it means you’re all having exactly the trip you want. As long as you have a rendezvous point and time, you’re good to go.
Oh, and one final note: plan your souvenirs ahead of time. I used to just buy whatever caught my eye, only to get back home and realize how tacky it was. My rule now? I don’t buy anything as a souvenir that I wouldn’t purchase back home.
This has saved me from uncountable shot classes, gaudy picture frames, and other trash. Rather, I try to buy something I’ll actually use or wear or display in my home.
I must admit that I really treasure getting to accept a compliment on the beautiful silk scarf I brought home by saying, “Oh, thank you! I found it in this marvelous little shop in the Grand Bazaar in Istanbul.” Call me vain if you will--we all have our faults.
Moving on to packing—not the most exciting of topics, to be sure, but I have learned some lessons the hard way and wish to save you the heartache (and backache, and shoulder…well, you get the idea) of learning them yourself.
I fall firmly into the ‘I’d rather have it and not use it than need it and not have it,’ school of thought—except when it comes to packing. On my very first trip abroad, that five week journey to Turkey that we discussed earlier, I took the world’s hugest rolling suitcase, firmly convinced that this was the only proper way to do things. I was packing for over a month, after all, and would need many things.
Oh, the sweet summer child I was—silly, silly, silly. True, the rolling luggage was helpful in the airport. But as soon as I climbed out of my cab (which naturally stopped at the bottom of the hill leading to my hostel), I learned the struggle of heaving rolling luggage over cobbled streets.
It is a nightmare—especially since I was pulling it up the world’s steepest hill (don’t fact-check me on that claim, please, it’s hyperbole). Once I had it in the hostel, I then had the pleasure of navigating the world’s prettiest but most narrow spiral staircase up two flights to my hostel dorm, where my suitcase would not fit under my bunk bed.
At this point, I was quite prepared to pitch the whole thing out the window and into the Bosphorus—fortunately, I was too exhausted to heave it up to the sill.
That was but the first incident of a five week lesson in inappropriate luggage. Fortunately, I learned from that. I looked around at what my fellow archaeologists and hostel dormmates packed.
When I went back the following year, I had a much smaller (but still enormous) hiking backpack instead. Y’all, this was revolutionary.
I would never have believed that it would be preferable to carry (on my own back!) the things I would need for yet another five week expedition in Turkey. It was so much easier. Getting on and off public transportation was no longer an awkward, sweaty struggle. Getting up and down those cobbled hills? Well, that was still terrible, but much less so (I do have rather a loathing for cardiovascular activity, so I would despise those hills even without carrying a thing).
And yet…the tubelike shape of my pack meant that I had to take everything out to get to the things at the bottom. It was such a pain that it wasn’t long until I just started wearing the few things that were on top, keeping my toiletries in the outer pockets for easy access, and (I cringe to write this) leaving things behind or donating them at every stop to make my pack lighter since I wasn’t using them anyway.
It would seem, especially for a longer trip, that you need to bring a lot of stuff. Turns out? You don’t need to do that at all.
First of all, laundromats exist. I didn’t need to bring five weeks worth of clothes, just one. In my case, there were almost a hundred of us sharing just one or two laundry machines, but there was still ample opportunity to wash clothes onsite.
I know it seems like you’d get tired of wearing the same clothes all the time, and I did! But everyone else onsite was wearing the same three outfits as well, and outside of the site? Well, it isn’t as though I saw the same people over and over again. My outfits were new to everyone I met, if not to me.
So if my rolling luggage was not the right answer, and the hiking backpack was better but not exactly good, what’s a girl to do?
Lucky for me, other people were experiencing a similar struggle, but had the resources to solve it. I pack in the Tortuga Outbreaker backpack now (the largest size).
It is carryon size (don’t look so shocked! It’s entirely possible to pack for even the longest journey in the coldest destination in just a carryon--I'll write a post on that later). It’s a backpack but! It unzips like my rolling suitcase did rather than like typical backpacks.
That’s the feature that sold me originally, actually, but I was blown away by the design and execution of the pack. It’s big enough to fit everything I need (really, it is! I’ll do a blog post on packing in a carryon to show you), but small enough that it doesn’t make me want to die to carry it.
It’s well organized, with enoughcompartments to be useful (but not so many as to cause overwhelm). Y’all, this is not sponsored, I’m just genuinely delighted by this pack. I'll do an in-depth review later on. They’re pricey (about $300), but they have a great educator discount and since I travel often, it was a no-brainer.
Your destination will have a big impact on what you need to pack, of course, but I can guarantee you need to pack less than you think.
Choose your clothes in a ‘capsule wardrobe’ style—in other words, pack things that you can mix and match and make more outfits from. Nobody will know that you’re wearing the same pair of jeans twice in a row (and really, who doesn’t do that at home anyway?)
Bring accessories to make the same outfit feel different but minimize packing space. You’d be surprised what a scarf can do. Wear your bulkiest items on the plane—for cold destinations, that means your boots and coat. For tropical destinations, maybe that’s your floppy hat (because it will get crushed otherwise).
If you forget something or it turns out that you did need something you chose to leave behind, well okay—buy it when you get there. With few exceptions, you should be able to source anything you need, if at a higher price, when you arrive.
There’s a reason that experienced travelers suggest to lay out everything you need to pack, leave fully half of that at home, and take twice the money you thought you’d need.
Air travel is one of my very favorite things. I know, I know, people enjoy complaining about the inconveniences and irritations of traveling by plane, and there are certainly some parts of flying I could do without.
I just haven’t lost that sense of wonder about the fact that I am in the actual sky. I get to look out my window and see so many beautiful views—and the clouds? Don’t get me started on how gorgeous the clouds can be from the air.
There are some ways to make air travel more comfortable and less of a hassle if you aren’t as wonderstruck as I am. I've put them all into a free, easily printable PDF called The Flight Guide.
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So what do you think? Are you ready to plan your next big adventure? What's your travel style? Let me know in the comments!