18 Planning, Preparation, and Travel Tips For Making Your Dream Trip A Reality

Alsace France

Admit it. You have a dream trip in your mind that has yet to be taken.  That one place that has always seemed just out of reach, just around the next paycheck, and is usually used with the phrase “I’m saving it for when…”. You probably already have the details mapped out in your head, and one day, some day, that trip might become a reality.

Well guess what?

Life goes by quickly, and the sad reality is that your dream trip might not happen. I’m 29 and I just got diagnosed with skin cancer. That’s not cool. I’m too young for that. Sure, they say I caught it early, but it sets the thinking wheel in motion. Don’t save for later what could be done today, because eventually, all of us run out of tomorrows.

On that note, I’m not taking my dream trip right now, but actually my wife’s. For the past 10 years she’s wanted to go to Italy, and for her 30th birthday, we just said screw it: We’re going to Italy. We will drink wine by the bottle and pizza by the pound and try to not screw up while ordering coffee. We will wear superfluous sunglasses, make an effort at white pants, and gesticulate wildly with our hands. We will go on a dream trip to Italy, because quite frankly, life’s too short not to.

I’m currently 30,000 feet in the air on a route from Maui to San Francisco to Newark to Paris to Rome on a trans-Pacific, trans-Atlantic, double red-eye that will transport us from palm tree to Pope, and needless to say, we’re excited.

To be fair, however, dream trips don’t just pop up out of nowhere. They require planning, commitment, and a healthy amount of preparation. As an ardent backpacker and merchant of wanderlust I will always hold that “less is more” when it comes to crafting an itinerary (there is such a thing as “over planning”, after all), but for as hipster as it can be to let the Universe craft your next move, the reality is that most trips require a healthy dose of preparation whether you want to admit it or not.

With that being said, in an effort to help make your own dream trip a reality, here are some travel tips and steps to take to help make your adventure a reality.



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1. Stop making excuses and just go.

More often than not, the largest hurdle to taking your dream trip is pushing all of the excuses out of the way and just doing it. There will always be bills, and there will always be reasons not to. If you want to go, then just go.

2. Where do you really want to go?

Think of someplace you’ve always wanted to go. The place you get jealous when you hear other people are going there. Is it trekking in Nepal? Hanging with mountain gorillas in Rwanda? Or perhaps bareboating a catamaran and bouncing from port to port down the Caribbean chain. Think of a few places you’ve always wanted to go, and then set about figuring how to get there.

3. How much time do you have?

For all the idealistic “life is short” thinking, there is still a degree of reality that needs to be involved (a dream trip of 3 weeks in the fjords of Norway, for example, is much more attainable than 3 years biking across Latin America). How much time can your realistically take off? How much time will your dream trip require, and how much time can you realistically get away for? 2 weeks? 3 weeks? A month or longer? Find a realistic time frame, and work from there.  Just because you can only sneak away for 2 weeks, but you have a month’s worth of places you want to visit, doesn’t mean that you shouldn’t go at all. Be happy with the time you have, and make it the best possible time that you can.

4. When are you available to go?

When it comes to traveling, seasons are important. In the tropics, it’s usually rainy season versus dry season, and in other parts of the world it’s winter versus summer. If you only have a certain time of the year you can travel, think about if your dream destination matches the time that you have off. In 2007 I always wanted to go to Costa Rica. It was September, and the height of the rainy season, but I was determined to go to Costa Rica. We went anyway, and it rained torrentially for nearly every day of the entire trip. One entire town was evacuated by the Red Cross because it was essentially floating away. I mention this because it’s important to not force a trip. Your dream trip isn’t so dreamy any more if you go in the offseason when you have no business going. Either schedule your time off for the correct season of when you want to go, or, if constrained by a schedule, visit somewhere where you’ll actually have an enjoyable trip. Think to yourself, this is the time of year I can go, so what places are good for this time of year?

5. What experiences do you want to have?

Traveling can be overwhelming because there is simply so much to do, and one of the biggest mistakes many travelers make is trying to do it all. Think while preparing for a trip what experiences are the most important to you, and sculpt your trip around that. On this particular trip to Italy, we know that we only have three weeks in the country, and eating good food and drinking good wine are of greater importance than seeing “the sights”.  Given the focus of the trip, we scheduled a cooking class in Siena to switch things up from the usual itinerary of museums, cathedrals, and ancient sights (although the Colosseum is of course on “the list”).

6. What is Your Budget?

Again, this is a place where a dose of reality comes in to play.  Money is one of the largest barriers to travel (or rather, the lack thereof), although it doesn’t need to be an excuse for why to not travel at all. For a general idea of what things cost, you can travel comfortably in Southeast Asia for $50/day, South America for $65/day, New Zealand for $75/day, Australia for $100/day, and Europe for $100-$120/day. While you could of course travel for substantially cheaper as well as substantially higher, these prices reflect the ability to have a private room, take public transportation, and eat well for the duration of your trip. So what to do if your dream trip is in an expensive location (such as ours, in Italy)? Define a budget, save a little money, and then just do it. We’re budgeting $120/person/day for this trip in Italy. For 3 weeks that’s $2500/person (not counting flights which we got one-way on frequent flier miles), and while this is a substantial amount of money, there are definitely people who spend a lot more on vacations of considerably shorter length. Find your budget, be realistic, and then work towards prioritizing your expenditures to make it a reality.


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1. Book The Tickets

Now that you’ve decided to go, have figured out where you’re going, have determined how long you can realistically go for and how much you can realistically afford, it’s time to put the final stamp on it and book the plane tickets. I personally like Kayak and Sky Scanner when it comes to booking tickets, and I also rack up as many frequent flier miles as possible with United Mileage Plus credit cards. While travel hacking is an entire other post in itself, no trip can be considered official until you have the tickets in hand. As a final tip, be sure to watch the price for a while and do your research to see how the fares fluctuate. Find out from friends or online resources what a fair ticket price is, and then watch like a hawk until the price takes a momentary dip.  Once it does, that’s when you pull the trigger.

2. Learn a bit of the language

If you’re traveling internationally to somewhere with a different language, learning a bit of the language is not only helpful, it’s also respectful. Even making an attempt to use a couple of basics in the local language will drop numerous barriers, and strangers are more apt to help you once they see you’re making the effort. Even if it’s just learning “hello”, “thank you”, “how are you”, and “how much does it cost?” (and maybe learn a few numbers for when they respond), it’s an important skill that you can acquire while waiting for the day of your departure.

3. How do you plan to get around?

Now that you’ve booked the flight and can verbally navigate your way out of the airport, think about how you’re going to get around when you get there. Will you take public transportation? Will you rent a car? Or will you be part of a group tour where someone meets you at the airport and everything is taken care of? While public transport can of course be figured out once you get there, plans such as rental cars and group tours will of course need to be booked ahead. On this particular trip to Italy we decided to rent a car so that we can explore the Tuscan hill towns which aren’t very well-serviced by public transport. I used the car rental service carrentals.co.uk, an England-based company which automatically scans for the best price over a large network of rental providers. The booking process was simple and it found us a great price, and since this is a sponsored-arrangement I will be reporting more on this service when the trip is through. When it comes to your trip, if your destination requires a car or some sort of pre-booked transport be sure to book that part of the trip before setting out on the road.

4. Where do you want to stay?

Now that you have the flight, and you have the car (if you need it), the next step you need is the hotel. Personally, I only book a hotel for the first night of arriving in a new place, and then I leave the itinerary open after that as to where I want to stay. I’ve learned after the years that there is nothing worse than a full day of travel and then searching into the wee hours of the night for a hotel (here’s looking at you Mallorca and Lyon). I’ve also learned that sometimes the best accommodation options are found when you have no plan at all and you just wander around until something perfect pops up (such as the rooftop view from this bed and breakfast in Tossa de Mar, Spain). If you need to book a hotel when you get in, go ahead and make that your next step.

5. How do you plan to get money?

This is a matter of personal preference, although there are definitely ways more efficient than others. Most places around the world accept credit cards, although most cards will also charge a 3% foreign transaction fee (some don’t, and these are worth a look). Many places around the world also have ATM’s for withdrawing cash, although be aware that banks such as Bank of America charge as much as $5 each time you make a withdrawal, in addition to the $2-$3 fee assessed by the machine. In places such as Central America that will only dispense $200 at a time, an $8 fee on a $200 withdrawal is a pretty poor return on your money. Outside of ATM’s,  you can always use a money exchange to exchange your home currency for the local currency, although you will lose a healthy amount in the rates which are offered, and airports always offer the worst exchange. Personally I like to use a Charles Schwab checking account that has no transaction fees yet allows you withdraw money from any ATM on the planet at an accurate and current exchange rate. Not only that, but they will even refund the fee that is charged by the machine. Essentially you can go anywhere in the world and withdraw money at ATM completely free of charge. Granted, you need to also open up a brokerage account with them, but there aren’t any rules about funding it (so it can stay at $0 for a while if need be).

6. Do you have copies of all your documents?

If you’re going to be traveling internationally, it’s important to have extra copies of all of your documents in the event that something goes wrong (it only took us about 3 hours to get pickpocketed in Costa Rica). Make multiple photocopies of your passport, a copy of your driver’s license, and maybe make a separate photocopy of a credit card as well. Once you have the extra documents, leave one set of documents at home, and take a second set of photo copies with you. Of course, you wouldn’t want to keep them in the same place as your originals (such as keeping the copy of your driver’s license in your wallet), so split them up over multiple bags or in hidden, secret compartments (I always travel with a copy of my passport in the sole of my shoe).

7. Do you need immunizations?

If you’re dream trip is to go to Italy (or most other Westernized countries), this isn’t going to be a problem. If, however, you plan to travel to East Africa, India, or parts of Southeast Asia or South America, getting the recommended immunizations is a critical part of your planning phase. In some places such as Bolivia, it’s actually required that you display a yellow fever vaccination card at customs and immigration, though rarely do they actually check for it. For a full list of what immunizations are required for certain parts of the globe, check out this page on the CDC website that discusses the topic of global immunizations for travelers.

8. Do you want travel insurance?

When I was younger (read: dumber), travel insurance was a fear-induced waste of precious drinking money. Why would I spend money to avoid a disaster? After all, disasters are what make the best stories, right?

If there is one thing you take away from this article it’s that you should seriously consider getting travel insurance, particularly for your health. When it comes to medical insurance for traveling I recommend Travel Guard, simply because when my friend was bludgeoned over the head while solo trekking in the Himalayas (and nearly died), Travel Guard covered all of her medical expenses and took impeccable care of her. That spoke a lot to me, and I’ve recommended them ever since. Another great option for international medical insurance is DAN (Divers Alert Network), who will cover many major medical expenses for physical injuries sustained while traveling (but not for health-related issues). On a side note, if you’re dream trip is to go to New Zealand, the Kiwis have a phenomenal system of health care that even covers international travelers, so if you break your leg while trekking in New Zealand, you can visit a medical center for nearly free of charge.

In terms of protecting your valuables, the first place to check before you book a policy is to check with your credit card or your renter’s/homeowner’s insurance policy and see what the benefits for travel are. Oftentimes they will cover everything from lost luggage to stolen electronic devices, and in the past I’ve always used a renter’s insurance policy to cover my possessions while abroad.



Whew. Ok. So you’ve decided to go, you’ve bought the ticket, you’ve checked for immunizations, decided on insurance, booked accommodation, transportation, and activities (which is really only necessary when traveling in the peak season), and now it’s time to pack.

1. Rule #1: Don’t overpack

Nothing is worse than schlepping around a pair of pants you never end up wearing. Oftentimes, most travelers can cut the size of their bag in half by being ruthlessly realistic about what they’re going to need on the journey, and less is definitely more when it comes to packing. Baggage fees  are skyrocketing, and the inconvenience of being weighed down by luggage is sure to detract from the comfort of any trip. As a general rule, if it isn’t a specialty item such as a bathing suit, if you aren’t going to wear it at least three times, then you shouldn’t bring it. Or, if you have something you’re only going to need once on your trip, consider bringing a cheap version of it and just leaving it there. When I traveled through Southeast Asia for three months, I knew that I was going to need a pair of snowboarding pants for climbing Mt Kinabalu in Borneo. With 11 more weeks of beach time ahead of me, however, those pants would be a cumbersome and space-consuming pain. So what did I do?  I gave them to my porter and got on with my life.

2. Pack clothes for the weather.

This should seem obvious, but research what the weather is going to be like when you get there. Is it rainy season? Pack a rain jacket. Is it going to be over 75 degrees the whole time? Leave the parka at home.

3. Guess what? They sell that there, and it’s probably cheaper.

Most packers also have a fear of forgetting something. They pack the kitchen sink on the off chance that they might need something on their trip and can’t imagine being without it. “Well, the weather forecast says there is a 10% chance of rain during October in Cambodia, I better pack a jacket just in case”. Guess what? Cambodians like staying out of the rain as well, and on the 10% chance that it does rain during your trip, you can buy an $8 rain jacket for the one day that it rains and then give to a local person instead of carrying one around with you for the duration of the trip. Moral of the story: If you forget something basic, it’s going to be ok, because you can always buy it on the other side.

4. Leave room for souvenirs

Before you pull that zipper closed for the last time, be sure that you aren’t sitting on your bag to close it before you even leave for the airport. You’re sure to pick up a few souvenirs along the way, and I like to generally pack my bag about ¾ full when leaving for a trip.

If you’ve actually made it this far in this post, congratulations! It means that you must really want to go on that dream trip…

Of course, there are many other things to consider, and many other aspects of travel I would love to help out with, and if you have any further questions about planning your dream getaway I encourage you to be in touch by dropping me an email, ask me a question on Facebook, or send me a tweet.

There are few things I love more than helping fellow travelers, and I always love hearing from people who have made the decision to get out there and see the world. Safe journeys, good luck, and perhaps we’ll cross paths some day while out there on the road.

Parts of this trip have been sponsored by carrentals.co.uk as well as Viator Travel, for whom I am a freelance contributor. All thoughts and recommendations are my own, however, and I would never recommend a service I don’t personally trust.

{ 3 comments… read them below or add one }

Jon Brown May 21, 2013 at 3:16 am

Great post Kyle! I preach many of these same things too.

I’m a huge fan of planning for longer trips with les details. While I know that longer trips are really hard for a lot of people. One of the great advantages of going somewhere for several weeks or more is the ability to change local specifics.

For example a week and a half ago I was planing on heading to Burma from Thailand. When a cyclone was headed that direction it was easy enough just to stay in Thailand a few more weeks. That’s the same flexibility that lets one travel in the off-season to places when things are often much less expensive as well. The weather on Koh Phangan right now is just about perfect and the usual crowds are no where to be found.

I also find that nearly every type of activity I want to do is booked locally more easily and cheaply then if I tried to book it ahead. Obviously there are some exceptions with things that actually are sold out and unavailable but a little research ahead of time can identify those few things.

FWIW, I almost always book my very first night in new country ahead of time, too many times I’ve wandered out of an airport or train station half conscious and dizzy with jetlag and been thankful I had extra reasons to ignore all the touts and taxi drivers offering to whisk me away to their friends guest house.

Carolyn Ellison May 21, 2013 at 11:25 am

Great Advice!

Tim H May 24, 2013 at 1:28 pm

I’m sorry to hear about the skin cancer, but I’m glad you’re kick starting some positive change because of it. I hope others take your advice and stop planning and start taking action on their dreams.

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