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How I plan a trip : An extensive guide to getting you there.

How I plan a trip : An extensive guide to getting you there.

A big reason most people don’t travel is based in fear of the unknown, most people do not have the training of travel agents and see planning a trip as an overwhelming and stressfully daunting task. Trip planning is full of unknowns, Where to stay? When to go? How to get there? Do I have to learn a new language? What am I going to eat? What will I do there? All of these are important questions and to someone that doesn’t know where to find the answers, this is terrifying. Through trial and error over many trips, I have worked out a system that I now use with planning almost all of my travels. In a hopes to ease some of the anxieties that most new travelers feel, I have outlined my process.

The process can be applied to almost any trip whether its a month long journey to Southeast Asia or a weekend trip to the ocean. Try not to pay attention to the order of each step but to its importance as you will bounce back an forth from step to step while narrowing down and eventually finalizing your itinerary.

Step 1 : Deciding you want to go.

This seems obvious, but its a big hurdle for most people. There are usually ten times more reasons not to travel than there are to leave the comforts of your daily routine. The first step to going, is deciding that you want to. You have to be willing to sacrifice your time at home for the payout of a great escaping experience, even if that experience is just getting away for the weekend to a new town in your own state.

Step 2 : Deciding how much you want to invest.

Travel is an investment in multiple ways. You are investing your hard earned money, your time and often your comfort for the pay off of a great experience and lifelong memories. Travel investments come in multiple amounts, each with varying returns. A weekend out of town may only cost you minimal amounts of cash, but it also costs you a weekend that you could be doing work around the house, or running those errands you weren’t able to get to throughout the work week, even spending the whole weekend bingeing Netflix is sometimes worth more in a persons mind than spending hours in a car to see the ocean for a few days. On a larger scale, a three week trip abroad will obviously cost your bank account as well as your time bank considerably more than a weekend trip.

Deciding how much to invest starts with the length of travel you are willing to undertake. You have to take into account the distance from you and your destination and how long it will take you to get there. If you are looking at a place that is a few hours drive or a place that is a fourteen hour flight, you have to consider those factors. For the more far off destinations you will probably want to allow yourself more time in that place once you finally arrive. If your destination is a cabin town a couple hours down the highway, you can probably shorten the length of time you spend their.

A good rule of thumb when planning out a trip is distance needs to be equal to the time spent planning and the time spent exploring. At the same time distance is equal to the price scale of the journey. If you’re planning a trip halfway across the world, its obviously going to cost you more than a trip half way across your state.

Step 3: Pick a location.

At some point in everyones life they see a picture or watch a movie or even read a story and say to themselves “I want to go there.” Figuring out the location of your trip is relatively easy, you probably have a destination in the back of your head right now that you have been curious about and want to see more of. The reasons for a selected location vary person to person, for this upcoming trip to Europe it started with me wanting to go “somewhere” and then getting my girlfriend to agree to let me plan a secret trip for us. After narrowing down my bucket list of locations, I asked her “Southeast Asia or Europe?” This was the only influence she had over our trip and she chose Europe. I had been to a handful of countries in Europe but she had never experienced it. From this I narrowed it down to two countries that stood out in my mind when I traveled through Europe. I wanted places that were foreign enough to get lost in but not so foreign that it put my girlfriend so far out of her comfort zone that she had a miserable time.

I ended up choosing France and Italy and then from there I chose two to three cities in each of those countries. I had been to Paris before but only for a few days and always wanted to go back and explore the city. Nice, France had always been a location I wanted to visit, the fact that it had been raved about in luxury magazine features on the French Riviera had always made my mind file it away as untouchable, after some google searches I realized that it was in fact very reachable even on a budget. I had spent a good amount of time in Rome while I lived a short train ride away in Milan when I was modeling and it is probably my all time favorite city. Venice has held a storybook like essence in my mind for as long as I can think of, it was a given that it would be added to our itinerary.

When picking these locations I started in the same place I start all of my trips, I begin with search the internet for Top Ten lists, you would be amazed as to the inspiration you can gain from a simple “Top Ten things to do in Venice” search. I did this with probably 20 different locations before settling on our final itinerary and by a process of elimination, taking in factors of things like my girlfriend and I’s interests, the way we prefer to travel, our thirst for exploration and our level of tolerance to uncomfortable situations. For some an eleven hour train ride from Venice to Paris is just not worth it, but to me the eleven hours of scenic countryside passing through the windows of a passenger train is something I look forward to.

Pick your location and then dive in.

Step 4: Accommodations

A big factor I consider when picking a destination is the price my wallet feels when booking accommodations. This can completely change the place in which you are planning to go. For instance, when my girlfriend chose Europe over Southeast Asia, I immediately knew that this trip would cost considerably more than if she had chosen the latter. Purely for the reason that throughout Southeast Asia you can book a room for as little as five USD a night and stuff your face with gallons of noodles for next to nothing. Europe however is not so forgiving on the bank account, the price you pay for a more developed location. Although the Euro has come down a good amount from its weight over the dollar in previous years, it is still not the cheapest.

When searching out lodging for a trip you have to consider the type of stay you want to endure. Are you ok with staying in dorm like hostels with strangers sleeping feet from you? Are you looking for a more luxurious room with top of the line amenities and services? or are you somewhere in between? All of these are big questions you need to ask yourself and anyone joining you on this trip.

When I traveled solo through Thailand I booked cheap hostels through and also planned my trip to include some overnight train rides, thus saving on the price of a room while moving toward a destination I already intended to visit.

For our trip to Europe I chose some middle ground, booking stays through I like this option because you are staying in an actual home and get a better sense of how the locals live, at the same time you have a direct contact through your host for the non-googlable questions. I have also had AirBnB hosts offer to show me around and share their knowledge of the areas and where to eat, drink and what to see.

As on this trip and often many others, I mix it up with my lodgings, staying mostly in AirBnB’s but also booking a night or two in more fancy hotel to get a different kind of convenience.

After looking through some room listings in the area you’re planning to stay, you can start to get a better feel for the price your trip is going to cost. If the average rooms you’re viewing are around a hundred dollars a night you can begin to budget out your trip more easily and see if the location still suits your desires. If you only want to spend a thousand dollars but want to be away for weeks on end, those hundred dollar rooms will not get you far enough and you may need to reconsider either your budget or your destination.

Step 5: The Journey

After you have narrowed down your destination and a budget for your stay, now is the hard part, budgeting your journey. Wether it be a train, plane or automobile, its all going to cost you. When booking flights I use a plethora of different sites and apps to find out some key information before ever confirming any reservations. You need to think about the destination and the activities you want to be doing there, as well as the time of year you will be available to go. Again all of these factors could change your overall destination.

If you are trying to see Rome without the long lines of tourists at every stop, then traveling during peak summer dates probably isn’t your best option. If you don’t mind freezing your toes off while walking through a snow covered winter Paris, you may be able to save a few bucks on a flight. It all depends on what you are looking to get out of your destination and your overall trip.

For the most part, every location has an off season and if you choose to book your trip around those dates you can save hundreds if not thousands on flights and hotels while the supply is high and the demand is low. But if you are dead set on experiencing a hot summer day in Amsterdam, then you will have to pay for that luxury. For the most part the cost of rooms, flights and just about everything else rises by 25-45% during peak seasons. A simple google search will tell you the top months for peak season in any location, as well as the dates for off season travel.

Once you start to get a better idea of when you would like to go and the appropriate weather you desire, then you can start looking at flights, car rentals and train rides. Even in peak times of the year you can still save on all of these if you spend the time to look around and be creative.

I usually start with to check the general prices of flights during the months I want to be traveling. Once i’ve cut this down to a certain time frame I begin to look on other sites for deals and packages that may hold what I need. A great app/site that I use is Hopper. This app allows you to punch in your dates and destinations and through their algorithms it sends you notifications and predicts when the best time is to book your trip to save you the most.

A good tip for finding a cheaper flight, is to look at nearby cities to your destination. Often times flying into a nearby city that is not as heavily traveled and then hoping on a train or a bus is cheaper than a flight straight into the final location. On top of that, some times one way tickets may be cheaper as well, especially if you are flying into a country and then plan to explore throughout the country. In this situation I usually book a one way flight into one city and then a separate returning flight from a different city, making my way from one to the other throughout the duration of my trip.

I won’t go into the millions of ways I, and every seasoned traveler, have to book cheap travel, thats a whole other beast.

Step 6: Budgeting your life away.

Probably the most important thing to consider when planning a trip is your budget. This can help you narrow down your destination and the activities and lifestyle you will be enjoying there. Once you have looked at hotels and the costs of flights or train rides, you start to get a good sense of the cost of your overall trip. If your hotels are costing you an average of 50$ a night and you plan to stay for 14 nights, you can expect that your overall cost will come out to around 700$ for your homes away from home. I always round up to add some extra cushion to the cost, its better to have too many Yen in your wallet than to be stuck walking to the airport on your departure date.

Then you look at the cost of whatever form of transportation your trip needs. If the cost of flights is anywhere between 600$ and 800$ I would budget out 900$. This extra cash can help pay for any unexpected fees you might come across, such as checking a bag or pre-flight drinks at the airport lounge. Once you have these two major parts of your trip priced out, you can start to build a budget around that.

Already you know that you need around 1600$ just to get off the ground, now to some that might sound like a lot but having a numbered amount is the first step to making your dream trip a reality. Now you have a goal, and thats the first step to reaching it.

Without moving any further you can assess your activity levels while on your trip and begin to get a better numbered amount. If you are planning on sitting on the beach all day drinking happy hour Mai Tai’s then your activity level is probably going to be pretty minimal, but if you plan on taking tours of museums and trying every food item on the Italian menu, your activity level begins to rise. The higher the level of activity, the higher the cost of your travels and the more you will have to add into your budget.

If your the first traveler, staring at sandy beaches and consuming two for one drinks all day while you work on your tan, you can assume that your daily cost for food, drinks and activities are going to be relatively low, depending on your alcohol tolerance that is. And on the other hand if you are planning on packing every day with tours, food, theater tickets, cooking classes, museums and night clubs, your cost is going to be reflecting of those things. The general prices of these experiences can easily be found through a search engine and also knowing the general economy of the region in which you’re visiting. I’ll again use my Southeast Asia reference where I was paying about 8$ a day for all of my meals and an additional 12$ for tours and transit.

The first traveler may budget out as low as 40$ per day for these activities, while the second may bump that number to a 100$ or more. Either way, you now have a general number you can add into your overall budget for your trip.

Finally you come to a good idea of what your trip is going to cost you. For this example I will use the more active traveler and say that on top of the 1600$ for flights and hotels, you now have to add in another 1400$ for day to day expenses while away, bringing your grand total closer to 3000$.

This is where most people abandon traveling all together. They see the price and feel the weight of every dollar hit them and all of the other things they shoulda, coulda, woulda spent that money on. I am here to tell you that no matter the cost, it is possible and if done correctly, when its all done you won’t even think of the dent in your bank account.

First you have to look at your own finances, a scary thought for most. You have to look at what you make monthly on average, if you are an hourly worker I suggest you round down for this part. Next you need to add up all of your unavoidables, things like your insurance, rent, phone bill, internet and car payment. These are things that need to be paid for you to live a stable and happy life. Then you need to look at your waste and what you are willing to sacrifice, things such as eating out, going out for drinks, those new shoes, that cup of Starbucks, taking an Uber when you could just walk. All of these things are where your bank account really takes a hit and are easily sacrificed and worked around if you are truly dedicated.

Lets say on average you make 2000$ a month, your rent is 600$ , phone bill is 75$, car payment 125$, and Internet, electricity and water is 150$, that leaves you with 1050$ after all of your unavoidables are deducted. Then you factor in your weekly cost of food, lets say 100$ a week on groceries times four, you have 650$ left over. Then give yourself some of what I call sanity cash, this is the money you use to treat yourself maybe when you’ve had a rough week at work or its a friends birthday and you go out for a drink, 150$ for the entire month. After all of this you are left with 500$ to save every month, now if you are able to stay to a strict budget, depositing 250$ immediately each pay day and no unexpected bills come up, you will have enough for your trip in about 6 months. The hardest part is keeping yourself honest and holding on to your goal when that pizza delivery tempts its way into your weekend.

A pretty obvious, but often overlooked expense with a trip is your life back home when you are away. The lights need to stay on for your return and rent has to get paid. I suggest adding in these additional costs when tallying up your travel budget, no one wants to come back from paradise but especially if your coming back to an eviction notice.

Step 7: Planning your days away.

Now that you have your budgets, your flights, your destination and your lodging somewhat mapped out in your head, you can begin to find things to pack your day with. You have your fork, your knife and your napkin, now its time to fill your plate. This is by far my favorite and most inspiring part of planning any trip, its where you begin to imagine how your time spent away will play out and it always ignites my excitement for the upcoming journey.

Again, I google. I start by simple searches of “top 100 things to see in…” and then move on to topics such as “Most unique locations in ….” or “Top unknown attractions near…” and then start to take quick notes in my journal. I will usually write the name of the place with a vague description of what it is and why it interests me.

“Montparnasse Tower. (View of Eiffel Tower/Paris skyline)”

I spend days or even weeks going through every website and social media platform that I can get my hands on, slowly accumulating a list of possible attractions in any place I will be staying. Once I feel as though I have enough items to dig into, I begin doing a more thorough analyst of each item on my list. I start to eliminate things that don’t fit, maybe some are just not as interesting as others, maybe some are too similar to another attraction I plan on seeing, and some may just be unreasonable to reach on this trip.

I like to have all of this in my journal so that when the time comes and I am actually on the trip, I have back up information in case something falls through or I end up having extra time in a place.

After crossing off a good portion of the list and highlighting the “Must See” section, I begin to look at the possibilities for daily itineraries. I try to balance each day with a portion of planned events and a good amount of free roaming. I find that this enables me to check off the bucket list items and still have time to feel and explore a new place. You never want to have your trip so planned out that it feels as though you are not able to experience any of it, a rushed or over packed trip often leads to unnecessary stress and an overall disappointing trip. In order to get a real feel for your destination it is imperative that you spend time lost within its streets, if not you might as well just be looking at it through a travel magazine. You want experiences that are truly your own and not a cut and paste plot provided by an idea of a place rather than what it truly is.

Step 8: Food

Some of you may skip this part but for me this is essential but can be done pretty quickly. For me food is a huge component to a great trip and gives me another reason to travel. Every corner of the world has different cuisine that they specialize in and their locals always claim the best in the world title, I wish to taste it all. I use a similar method to the activity planning as I do for the food planning, I google! (are you catching on to this theme?)

I start with finding out the top regional dishes and then search through the plethora of food blogs out there to find restaurants in each location that specialize in the dishes I am looking to engulf. All of this being written in my journal. I usually don’t factor this into an actual daily itinerary but make a composite list of all of the dishes and note a restaurant for a few of them. With this I am able to choose a food and/or a restaurant on the fly. Whenever I am running around the city exploring and hunger hits, I just run through the list, make a choice on restaurant, jump on some free wifi and pop it into google maps and instantly I have a new destination to reach and an exciting pay out.

For the more adventurous travelers I suggest researching the most unique foods of that region, Im all about the idea of trying everything at least once, including BBQ’d crickets from street vendors in Bangkok.

Step 9: Booking specialized activities.

Some exploring is best done with someone that knows what the hell you are looking at. I used to be very against tours, comparing them to cruise ship vacations where everything in front of you is fabricated to please but lacks authenticity. Then while visiting Rome, I met an art collective made up of some historians, tour guides, fashion designers, photographers and models and my entire perception changed. These new friends took me on tours of the city, explained the history and showed me the little details I would have missed on my own, this experience was incredible and opened my eyes to a whole new level of exploration. Since then I have began to book tours in most places I go.

For this I turn back to AirBnB, this time for their “experiences” section. In this you can book unique, small group, personalize tours in a variety of fashions that are sure to meet exactly what you are looking for. Do you like to ride bicycles? why not take a bike tour at sunset through some of Londons prettiest parks? Do you enjoy the spookier side of history? Book a ghost tour in New Orleans. Want to learn how to cook a classic French meal? You can find it on AirBnB.

These tours are usually run by locals with extensive knowledge of the area and often offer a different perspective and more intimate history than some commercial driven tours at usually a cheaper price tag.

Step 10: All of the extras

By this point you should have a large portion of your trip planned out, you have your budget, you have your flights, your lodging and where to eat and what to see, now its time for the extras. The extras are all of the little things, such as what to pack? how many coats you need? whats the best way to get to and from the airport? Do you have proper shoes for the weather? Do you have to upgrade your phone plan for oversees communication? or is it better to opt into only using wifi when available? how available is wifi? Do you have proper luggage?

All of these questions and answers can usually be found online in one way or another, often you are not the first to ask these questions and there is a forum full of answers out there. Take all things into consideration but keep in mind that you can never fully prepare for any trip, and you really shouldn’t try to. The best way to have a real authentic experience is to throw out all conceptions and expectations you may have and spend time walking down streets that lead to places not marked on your map, keep your wits and a sense of humor and I promise you will come home with a trip packed full of unique personal memories.

My contact information is listed below for booking trip planning or for any questions you may have. I have outlined a general way that you can plan your trips, I also offer services where I do all of the above for you and take out the stress and time consumption of planning a trip.

Brandon Tobiassen

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