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How to Plan Your Trip! Best & Easy Steps

“For my part, I travel not to go anywhere, but to go. I travel for travel’s sake. The great affair is to move.” – Robert Louis Stevenson

Mortimer J. Adler and Charles Van Doren wrote a brilliant book by the name of “How to Read a Book”. This book teaches you why conventional reading skills are insufficient for understanding difficult books, how to acquire more sophisticated reading skills and how to apply those skills to analyzing great books.

On the one hand, one may think planning a trip is quite an easy task just like reading a book. If you are thinking about planning a 1-2 week trip, then you can skip this article. However, trips above three weeks (especially if they are to multiple destinations and include transportation within the destinations) do require more planning. Similar to the book mentioned above, this article will provide you with a “copy paste” skill that will serve you well for planning any of your future trips.

There is a saying “the way you do one thing is the way you do everything.” I relate to this saying, especially when it comes to being organized and structured. I’m the kind of guy who likes to have a plan. So, when I recently tackled the task of planning our honeymoon, I started from a zoom out perspective in order to give my ideas some structure. This structure is what I would like to share with you here.

My idea is to give you a schematic outline specifying what comes first, what comes next, that you will be able to apply to any trip you do, regardless of how long or the destination.

Step 1: Decide where to go
No tips on this one because as you know, beauty is in the eye of the beholder. You know better than anyone where you desire to go and for what reasons.

Step 2: Decide when to travel
If your decision is driven by work obligations, then you do not have many options here. However, if you are flexible and can go when you please, there are certain things to take into consideration, mainly, weather and budget. For example, Costa Rica is a country that can be visited all year long, however, between May and November, on any given day in any given part of the country, it can be raining so hard that you will be looking to get aboard Noah’s Ark. In such a country, where nature is the primary attraction, optimal weather conditions are key to getting the most out of your vacation. On the other hand, one benefit of travelling off season is that prices (both flight and hotel) tend to be substantially lower.

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Step 3: Decide on the length of your trip
Budget, work and family obligations (how long can you take off work, how long can you leave the kids or alternatively take them with you, etc.), visa restrictions/limitations and more will influence this decision.

Step 4: Purchase your flight tickets
One thing that is important to mention is that there are contradictory rumors about the best time to purchase your ticket in order to find the cheapest price. I recently read an article that said that studies show that the best time to order your plane ticket is 57 days prior to travel. All I know is that I purchased two roundtrip tickets from San Jose, Costa Rica to Auckland, New Zealand and then returning from Bangkok, Thailand to Costa Rica for $1225 each, nine months prior to travel. When I checked back 57 days prior to our travel date on the same airline, same route, the tickets were priced at $4350 each – 3.5 times more expensive! Conclusion – AS SOON as you know your destination and timeframe, dedicate a maximum 7-14 days to monitor flights and then purchase them!

Step 5: Visas and vaccinations (if necessary)
If you purchased your plane ticket less than 90 days prior to travel, it is a good idea to begin the process of obtaining entrance and/or transit visas, if required by your destination country. Unfortunately, this is something that cannot be done many months in advance. The process can become a bit tricky if you are planning a multiple destination trip and there are no embassies or consulates of your destination country in your country of residence. For example, for our honeymoon, we had to apply for three visas for my wife – New Zealand, Australia and Thailand. We had to Fedex her passport to the USA for the New Zealand visa, and we could not advance with the other two visas until we received the approval and passport back from the USA.
Regarding vaccinations, some vaccinations or medications (such as anti-malarial) need to be started six to eight weeks before departure. Some countries require vaccination certificates (such as a yellow fever vaccination certificate) for entry into the country. You can often find this information on host country, consulates or ministry of health/tourism websites. If in doubt, you can also refer to a family doctor who can provide you with all of the appropriate medicines and vaccinations to keep you healthy and safe during your trip.

Step 6: Create your route
This step will likely be the most time consuming. There really is no right or a wrong way to do this, but there are many variables to take into consideration. The best method, like in many other areas of life, is word of mouth. Consult with friends and family who you know have previously been to your desired destination. After consulting within your circle of friends, family, colleagues, my next preferred information tool for planning a trip is Trip Advisor and especially its forums. Dated information on any destination is available by bulk on the web, however, what I love about the Trip Advisor forums is the interaction with destination experts who will respond to basically any question you ask and the feedback is fresh. Our initial plan for our 3-week trip to New Zealand was to rent a camper van, but I received great advice from a local I engaged with in a Trip Advisor forum who went into great detail on why I should change that plan and rent a regular car. For me, Trip Advisor is the site where I have received the most comprehensive information and evaluation on a certain company as well.

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Step 7: Book your accommodation
Now that you have created your trip route and know how many days you will spend in each place, it is time to secure your hotel or accommodation. If you are a traveler who likes to wing it and does not have a lot of requirements for the standard of accommodation, then you may suffice to just reach a town and look for a dorm bed in a hostel or a hotel room and not have anything planned. Or in the case where you would rent a camper or R.V, obviously, you have no need to make hotel arrangements. However, if you want to know where you will be staying prior to departure, this would be the moment to begin your search for the
hotels/accommodations that suit your travel plans. There are many websites available to help you book hotels.

Step 8: Purchase travel insurance
Purchasing travel insurance so long in advance may seem a bit odd to some of you, but it was a lesson I learned the hard way! I used to book travel insurance 3-5 days before departure, until I had an incident which had I been insured at the time would have saved me $1500. To understand the importance of insurance, bear in mind two universal laws: S**t happens Murphy’s law When doing your research for insurance, make sure that it covers two types of emergencies: (1) Medical incidents: accidents, sickness, doctor visits, hospitalization etc. and (2) Travel incidents: delays, flight cancelations, lost luggage etc. I use World Nomad’s insurance policy which is the most complete coverage, both on health issues and travel issues, that I have found to date. The signup process is simple and the one time I had to file a claim with them, it went smooth and I was reimbursed 6 weeks later. However, I recommend you do your own research (for UK and Australia citizens there are great local options as well).

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Step 9: Decide on your method of transportation
What type of trip are you planning? Would you like to hitchhike through the Patagonia? Would you like to take Greyhound or Mega bus across the United States or use the Stray Travel or Kiwi Experience in New Zealand? How about taking advantage of dirt cheap airfare within Asia with companies like AirAsia and Tiger Air? Or would you be better off being totally independent and renting a car? How about traveling by train? Check out this site for worldwide train routes: seat61.com
If you decide to rent a car, make sure you have an international driver’s license (or that your driver’s license is valid for use in other countries).

Step 10: Equip yourself with equipment
Some trips require equipment that most people may not have in their garage. The first option might be to borrow from family or friends. One VERY important item to purchase, regardless of where you go, is a universal travel adaptor for your electronic and mobile devices and do not forget your USB cables for your mobile phones, wireless headphones etc. if you decide to travel with them.

I believe in local SIM cards – this is the cheapest, most efficient way to stay connected with your mobile phone. You can either buy them upon arrival, but if you want to save the hassle and be connected as soon as you arrive at your destination, then pre-purchase online. This way, you will insure that you will get customer service in your native language (or for sure in English). Stay away from global SIM cards, as those work based on roaming, and will cost you a fortune. Always look for a local company that sells them online and that offers a package of GB and calls, not a “pay per MB of usage” plan, as those will become extremely expensive. Make sure your phone is unblocked for international SIMs. If you are from the US, Canada, UK or Australia, check with your local cellphone provider first, since many operators now allow their customers to consume from their data plan while abroad in certain countries.

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