Principles for planning the most epic trip of your life

Planning plays an essential role in making things happen. This is true especially when it comes to travel. I just recently took what I would call the most epic trip of my life and can honestly say it was largely due to a well thought out plan that was executed almost seamlessly. Let’s explore some of the key principles that I believe can be adopted in order to replicate this for yourself.

Journey to the place of your dreams

Life is too short to not venture out of your comfort zone. When considering what sorts of experiences people want to have in life, traveling to foreign lands usually makes it into their top five (at least!). There’s almost an innate sense in us to want to see places that are radically different from where we’ve come. Dare to dream big about where you want to go and have the courage to make it come true. For me, I’ve always been drawn to the birth place of Western Civilization in the Mediterranean especially Greece. I had the opportunity to travel all around the mainland of this beautiful and historical country with my Fraternity while in University but have been drawn to go back ever since, specifically to tackle the islands. This past month my partner and I decided to make the investment to do just that in addition to a whirlwind tour around Turkey.


Determine the scope of your trip

It can be a daunting task to plan an epic trip. The most challenging part is usually moderating the list of all the places you want to go. Depending on how much time and money you have to work with, cut the possibilities down to a manageable amount so that you have time to relax and internalize the experience between stops. While I am an ambitious traveler, I recognize that  always feeling rushed to get to the next destination is never fun and could ruin the whole thing. In determining the scope of the trip, the most important factor is to consider the travel time between the towns/cities that you want to visit. Be realistic about the amount of days that you have and how much you are willing to spend on getting around. For doing initial iterations about your travel plans, I recommend using a program like Evernote to keep track of notes as well as share with your travel buddies as we did.

Evernote Greece & Turkey Trip

Taking the above into account, my partner and I determined we’d be able to visit the Greek Islands of Santorini and Mykonos (with a stop over in Crete and Samos given the travel routes) as well as Cappadocia and Istanbul (with a pass through Kusadasi to visit the ancient city of Euphesus) in Turkey. This was over the course of 12 days. It was an ambitious trip to fit into this amount of time but it never really felt rushed. We had a full spectrum of experiences from laying on black sand beaches to navigating busy cities that ended up being just the right amount to handle.

Set up a financial budget for your trip

Traveling is an expensive proposition. To cut down on surprises, take the time to lay out a financial budget in a spreadsheet like with Microsoft Excel prior to planning.
While sometimes its worth going above your means to put together an amazing trip, I would recommend never going into huge amounts of debt to do so. At the outset, make some simple estimates about how much you want to spend on the following:

  • Primary transport tickets
  • Supplemental transport tickets
  • Average night for accommodation
  • Average daily spend for food/drink
  • Fun/learning experiences
  • Souvenirs for family/friends

Microsoft Excel - Travel Expenses 2013-08-20

As you go through the planning process, you can get more granular with your estimates by basing  them on the actual costs you are incurring. Keep your budget with you on the trip so that you can update it along the way to know what’s happening compared to your expectations. Exchange rates can be a bit of a pain if you are traveling outside the country so be prepared to make some conversion calculations. There are some helpful apps out there than can keep your travel expenses organized (e.g. TripSplitter) but we ended up doing it the old fashioned way.

Make all of your key reservations

Once a general scope for the trip has been defined, I suggest using a calendar (e.g. Google) that you will be traveling with to schedule some major items before your trip gets underway. Having a flexible structure and guiding force in place is invaluable in my opinion to reduce tension/confusion during the trip. Start with modes of transportation (by air, water, or land) between the places you’ve selected. If you feel as though the time it takes to get around leaves little time to actually spend at your destinations, consider cutting your list down.

Google Calendar - Google Chrome_2013-09-27_19-11-54

Only after booking the modes of transport between locations should you consider booking accommodations due to the possibility of there not always being ways to get there on time. With your budget in mind, check for hotels, hostels or unique places (like castles, churches, monasteries or other cool finds on Airbnb) to stay that also have good reviews on travel sites like Trip Advisor or Hostelworld. If you are a budget traveler, prepare to suck up some gross occasions when sleeping or showering.

For our epic journey to Greece/Turkey, we had our plane tickets (four legs via air not including the primary flight to Europe), boat tickets (four legs via ferries across the Aegean), and shuttle tickets in place a few weeks before departure. We also had a clear sense for how to make it to/from other critical points via public transportation to cut down on costs. In addition, all hotels and hostels were  reserved to know that we had a place to lay our heads at night sometimes splurging on much nicer hotels with ammenities to better the peak experiences.

Tentatively plan your peak experiences

While I recommend securing your key reservation prior to the trip, I think leaving significant flexibility in your plans for various activities once at your destinations is the best way to go. It’s good to have a general sense for what you want to do but trying to plan every last detail down to the 15 minute interval takes some of the fun out of the uncertainty of travel. I recommend collecting information about all sorts of cool things to do in Evernote. Peak experiences are a key component of self-actualization and travel provides one of the best opportunities to go after these gems. Consider the following categories when determining what you want to do during your epic journey (with examples of what we did):

  • Pursue experiential learning: By going to experience museums, galleries and historically-signficant sites, the past of our ancient ancestors starts to awaken in such a way that is not possible simply by reading in a book. I love going to witness first-hand the places and artifacts that were taught to me in school growing up as it brings another level of appreciation for the cultural evolution that we have gone through as a human race. During our trip, we visited and experientially learned about the Palace of Knossos in Crete (epicenter of Minoan culture), an archaeological site in Santorini (uncovered from ancient volcanic ash), the Ancient City of Euphesus (once the third largest in the world), the Open Air Museum in Goreme (an UNESCO World Heritage site in Cappadocia), and many amazing places in Istanbul including Hagia Sophia, the Blue Mosque, Basilica Cistern and much more.



  • Participate in cultural activities: There’s nothing like understanding the people of a different part of the world than going through their traditional customs. It’s very difficult to assume another’s perspective on the world without witnessing or better yet participating in the activities than are staples of their society. During out trip, we made sure to pursue a few key things that would give us a real taste for the culture such as haggling with shop owners in the Grand Bazaar of Istanbul, bathing at a Turkish Hamami, attending a Whirling Dervish ceremony, amongst other things.



  • Splurge on bucket list items: Spend a little more money on marking off a an item or two (or more!) on your bucket list during your epic trip. For the purposes of a single trip, we can expand the notion of a bucket list to include those things that would be most memorable after all is said and done. These activities will essentially change your consciousness given the beauty, exhilaration, and other emotions that are experienced. For me, our trip included a few of these activities such as catching the sunset and eating dinner on the cliffs of Santorini, scootering around Mykonos exploring exotic beaches, exploring the white washed alley ways of Mykonos afterwards having a sunset dinner in its “Little Venice”, hot air ballooning up and down the valleys of Cappadocia, and the list goes on.



Seek the advice of locals and other travelers

The best way to plan for an epic trip is to seek out those people who have had similar experiences. Take the advice of other travelers in order to be better prepared for what awaits you.  There are many good travel blogs and forums that provide valuable tips that should be leveraged. Here are a few things that I would share based on my experience this time around:

  • Invest in a few travel guides: We ended up buying and lugging around two Lonely Planet travel guides that turned out to be very handy. Access to the internet can be very sparse during some long legs of the trip so its a good idea to have paper-based material to give you ideas during down time.
  • Ask lots of questions on the road: When in doubt, ask questions… to anyone! If you have hesitations in talking to strangers, I strong suggest getting over that very quickly. No matter what situation you are in (even for the smallest thing), don’t be afraid to ask the first person you see. If they don’t know, ask the next person.
  • Have your finances all situated: Dealing with finances during your trip can be a bit of a hassle. I made the mistake of bringing traveler’s cheques with me (apparently this is “old-school” now) which local banks were unwilling to convert. My advice would be to bring some cash (to be converted to local currency at major airports) and a debit card with enough cash in the bank to last your whole trip (check on withdrawal fees though from foreign ATMs). My primary suggestion though would be to purchase as much as you can on an international credit card (like United MileagePlus) to avoid conversion fees. In a pinch, you can use a credit card to make a cash advance which I had to do a few times but for a penalty fee. Finally, be conscious of exchange rates.
  • Document your epic journey: Be sure to document your trip as thoroughly as possible. This is something that you are going to want to remember in vivid detail. Take pictures at every step of the way and video if you have the capabilities. In the end, we came back from our trip with about 1,500 photos and numerous videos most of which weren’t the best but it gave us a good amount to select from when choosing the best of the best. Blogging or writing in a journal can also enrich your journey but at the same time it can take you away from the direct experience especially if you are traveling with people you want to share every moment with.

Hopefully this provided some valuable tips for your future travels. I’d be great to hear from you  in the comments below about any epic trips that are coming up for you. Here’s to greater self-actualization through travel!




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