How to Plan a Trip

There are two extremes of travel planners/travelers.

The first extreme is the “fly by the seat of his/her pants” traveler. This traveler, wanting to be free and spontaneous, often ends up going to museums when they are closed, pays walk-in rack rates for hotels in a late-night bid for someplace to sleep, and waits two hours for the ferry when he or she could have slept longer.

The second extreme is the “plan every last detail” traveler. This traveler, wanting to have certainty in all aspects of life, researches and documents everything related to a trip in a master spreadsheet (including money spent each day on gelato), checks off each site visited and rates it on a scale of 1 to 10, and drives his or her traveling companion crazy.

Most of us fall somewhere in between the two extremes. I’ll admit to being toward the second extreme, but I’m learning to lighten up.

The first tip to planning a trip is to decide where to go and how much time you have available. That’s not always so easy to determine.

There are so many places in the world to discover and most people underestimate the time needed to get somewhere and enjoy it as a vacation. This might be as simple as “I have two weeks vacation and I want to see the highlights of Italy.” Get agreement from your travel companion on this up front (usually one of you is the instigator and planner, the other just packs the morning of the trip).

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Second, decide what places to visit and how long to stay in each place. This can be a difficult call when actively touring. Staying too short of a time might make your vacation seem like a scavenger hunt on steroids, and staying too long of a time might make you feel like you have retired to Boca Raton to play shuffleboard.

I build a text document that I call the “travel plan” where I list each day of the trip. I start with the travel days on either end, and then add in the places I intend to be for each day. I usually end up editing this document many times before the day of departure. At first it is a rough guide, but it gets refined as I make more definite plans and reservations.

The travel plan is the repository of all of the information I need for the trip. I print out a copy and take it with me. It typically is only two to four pages long, depending on the length and complexity of the trip. I will also bring printouts of any confirmation emails and necessary maps. As I go through the trip, I throw away anything no longer needed. If you are bringing a computer, keep an electronic copy (perhaps also on a portable memory drive).

You might think that you will use your smart phone and just look things up as you go. Maybe that will work for you, maybe not, depending on the type of phone you have, what country you are in, your phone plan and cost structure, available local coverage, etc.

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If you’re like me and can’t sleep on a plane, remember to allocate one full day at the start of the trip to get over jet lag and adjust to the new time zone. Don’t think you are going to walk all over Paris on the first day of the trip or your travel companion will push you under the Metro train.

I next plan out the routing between the places (i.e., the order in which to visit). Should I go in a circular route or an “open-jaw” route? For this step, I check Google Maps and Viamichelin to make sure the route is efficient and logical.

When it comes to places to stay, it depends on where I am going, for what purpose, and for how long. I always print out my correspondence (including addresses, phone numbers, and confirmation numbers) and relevant maps. Consider apartments instead of hotels. There are pros and cons to both of course. Some benefits of apartments are kitchens to have breakfast and make a lunch, more living space, cheaper accommodations for families instead of multiple hotel rooms, and separate sleeping rooms for parents and children.

If you are adequately prepared with your travel plan, you can relax and enjoy the trip. You can have the right information at your fingertips, even when the battery in your smart phone is dead. You don’t have to use every detail, but having the information there allows you to be flexible and avoid many common travel pitfalls. Information is power!

(All photos in the post courtesy of Steve Skabrat)


Steve Skabrat caught the travel bug when he first went to Europe as a small child to visit his grandparents.  As he got older, his desire to see the world increased.  He’s usually stuck in a little grey cubicle at a high-tech company, but from time to time he ventures to distant shores.  Entertaining narratives of his adventures may be found at Escape from Cube Land.


Published: January 16, 2012