Building an Itinerary

Itinerary development is an evolving process that is sometimes still underway even as a trip unfolds.  Itineraries have goals but also limits, unique to each trip.  The balance you are looking to achieve will shift for different destinations and life circumstances. Below, we describe a guide to building a great travel itinerary within your constraints.

Before you begin the itinerary development, there is a brainstorming phase that will inform your choice of destination. After you have your itinerary, there are opportunities for improvement and contingencies for your trip. Our Travel Planning Overview guide will give a good summary. Travel planning should enhance your trip, not only by making you prepared, but also by building the anticipation.

The Flow

Without intending to, we developed a basic flow for building itineraries that works across the scope of trip types and constraints that you are likely to consider.  In fact, I had not acknowledged or defined this process until I started to write this post.  But as I outlined the approach, I realized there is indeed a general order to trip planning decisions.  We will often refer to groups of planning activities as “steps” or stages. However, the flow is seldom executed in distinct sets of activities.  The general process flow, summarized in the diagram below, is iterative and the steps often overlap. Along the way, there are a few milestones that mark progress, such as buying airline tickets or reserving activities.

One way to think about building an itinerary is to draw an analogy to building a house.  The scoping and layout steps are like finding the lot and laying the foundation.  Booking the key activities and updating and routing are analogous to putting the structure and roof in place.  Solidifying/improving and contingency planning are akin to finishing the trim, plumbing, and electrical, then forecasting for the inevitable change orders during the construction.

A Key Note

An important point about trip planning, itinerary construction in particular, is that it should be enjoyable.  Find ways to make sure that investigation and planning are not onerous, but exciting instead.  The process described here is a guide, designed to get you started or help you improve your planning, and is not intended to be a strict step-by-step.

Initial Scope of a Trip

Once you know the destination(s), it is time to begin to construct an itinerary.  An itinerary is usually defined as a schedule and route, but before you get to those details, it is helpful to articulate both the “why” and the constraints.

(Click images for a larger view.)

Goals and constraints

The goals of the trip are usually understood as you prioritize and decide on the destination.  However, if you are traveling with family or friends, it is sometimes helpful to get everyone on the same page by spelling them out.  The priorities of individual travelers may need to be melded, even reviewed, as the trip plans come together.  Some travelers may have a visit to the Louvre as their top priority, while the “foodies” have certain restaurants in their sites. Whether the priorities require much discussion or not, there will be choices as the constraints are considered.

The scoping step for the trip should answer:

• How much total time and what time of year?
• What is your total budget?
• What pace will you be required to keep and does that fit with your wishes for the trip? (don’t overbook!)
• What percentages of time and budget should be devoted toward different categories of experiences? These categories would include physical activity (e.g., hiking, walking tours), down-time, culinary, social engagement, intellectual pursuits (e.g., museums, tours), other (e.g., aid organizations, concerts).  

Weather / Climate / Daylight Hours

Checking weather and climate sites and daylight hours (see sunrise-sunset.org) are helpful when considering the time of year for a trip.

Check for Other Constraints

Travel books for your destination also have helpful information on conflicts and crowds. Check local calendars for events, festivals, or parades, which can either be a positive or a negative depending on your interests.

Your goals and constraints will not always be hard limits on time/budget or be formally documented.  As you consider the options and route, you may loop back to this scoping step and reconsider time or budget.

Key Activities / Limited-Access Activities

During the scoping phase, it is important to identify any particular events or activities, upon which the trip goals rests.  For example, let’s say your desire to visit New Orleans is largely predicated on going to the Jazz Festival. In that case, the dates, daily schedules, and ticket availability are primary drivers.  The details of sights and restaurants in the French Quarter are secondary and can wait until the festival plans are firm.  Similarly, you may need to obtain dates for limited-access activities (e.g., Phantom Ranch in the Grand Canyon stay) before you continue planning.

Rough Layout of Itinerary

Schedule

Lay out an initial schedule for the target number of days.  Consider the following: What specific logistics and time are required for each activity of event and associated location (city or area)?  What is the price range for various accommodations?  Are there any dates that might pose a problem (e.g., holiday crowds, scheduled closures)? 

You can change your start-date to “slide” your initial itinerary around on the calendar. This allows for a fit that aligns with your personal schedule, weekends, holidays, etc.  You can also add or subtract days from the length as needed.  We use a simple spreadsheet for managing the itinerary options throughout this process. This sheet also serves an important reference as the trip unfolds.  See our El Salvador or Banff National Park posts for recent examples and templates to help jump start your planning.

Transportation Options

Once you have some potential trip schedules, you can look at transportation options for getting to your destination.  If flights are a cost driver, look at options for flight times and airports.  Does it make sense to fly with an “open jaw” (i.e., into and out of different airports)?  (Costs for open-jaw itineraries typically include not only flight costs but also extra rental car costs.)  Typically, booking early and watching cost fluctuations over a few weeks can save money.

As you develop this initial itinerary, you can investigate transportation for during the trip (e.g., car, RV, train) and accommodations.  Also, look for major issues that may cause a shift in plans, such as road closures or closure of sites. (See our tips pages on renting RVs)

Given a rough itinerary, you can generate a cost estimate as a feasibility check and adjust as needed.

Book Your Key Reservations

At some point in this process, it comes time to nail down the key drivers of cost or schedule.  As alluded to in the previous steps, these drivers are often the primary transportation and/or a hard-to-get accommodation or event.  The best time to pull the trigger on booking is largely determined by balancing availability and cost with maintaining your flexibility. The longer you wait, the more key reservations may cost, or an attraction might sell out. But keeping your options open is often helpful.

Committing to these critical activities provides a concrete sense of progress in planning.

As you watch for a price break or wait for reservations to open, continue to explore options, keeping good notes.  Sometimes you make important new discoveries before you make the key commitments. At the very least, your continued research will allow you to better complete the itinerary later.

Update the Itinerary and Add Details

Routes

With the foundation laid, you are ready to update your itinerary with activities and related details.  Your chosen route is the supporting frame that builds on the foundation of your trip. Routes may be within a city, country, or around the globe.  We explore routes by reading through source material (websites, books, etc.) and simultaneously looking at maps with points of interest.  (Remember that you likely already generated a rough outline of a route in Step 2.) 

As we look at routes and associated sights, we might, for example, discover that it makes more sense to go counter-clockwise.  Looking at maps (e.g., GoogleMaps), we often discover possible stops along the way (historic sites, viewpoints, picnic spots, etc.). These discoveries can be surprisingly important additions to the adventure.  Sometimes we decide that we have too much and must cut out an area/leg.  Alternatively, we might incorporate new elements not anticipated previously.  In addition to spreadsheets, in this phase we typically use a mapping tool to capture our route.  It’s not a perfect product but we have settled on mymaps.googlemaps.com to document our routes and points of interests and save.

(Hint: As you drop sites and activities from your itinerary, keep the details you have researched handy.  They may well be useful in later steps, or on your trip, as you consider alternatives.)

Add Accommodations and Activities

As a workable route materializes, we can begin to make reservations for accommodations.  Looking at the geo-spatial sources (e.g., GoogleMaps) is, again, a good place to start.  For places with no penalty for cancelling or modifying, you may have started this part in earlier phases.  On the other hand, for some seasons, there may be no scarcity of accommodations; you might decide during the trip.

We find it especially helpful (and enjoyable) to work on this step together.  One of us reads aloud about sites and activities while the other looks at the map(s) and directions.  This allows us to integrate the information we have learned with the geography and logistics.  Additional insights often materialize and our individual learning styles (i.e., verbal versus visual) are put to best use.

Another useful hint is to organize the elements of the trip into day and half-day segments.  It is convenient to group sites and accommodations together that are near to each other.   You can move these segments and swap them within your developing schedule. In this way you can optimize the route, logistics, and pace.

Solidify and Improve

Returning to our house construction analogy, this step is like the finishing work of trim, painting, flooring, and appliances.  In the previous step, you put in electrical, plumbing and drywall.  But now the finished product starts to come in to focus.  However, this is where our analogy might be a little flawed.  The finishing part of a house is where you get to pick out the cool stuff and see what it all really looks like.  Solidifying an itinerary means chasing details and recording them, which is not necessarily glamorous.

It can be tempting to forget about the “cat herding” of details, and the organization and documentation of them, once you have the basic structure in place.  (I am not a detail person so this can be a problem for me.)  But there are two important reasons to persist with this step.

Increase confidence, reduce stress

First, having the details in hand as you are on the trip pays off in many situations and circumstances.  Some of the circumstances are predictable; some are not.  An obvious one is arrival in a new city and airport after an overnight flight.  Having your transportation, accommodation, and schedule details easily accessible (maybe on your phone? a printout?) is a no-brainer.  With jet lag, handy details (e.g., metro ticket and route info) will also be important for the next few days of travel.  (See more of our travel tips page for dealing with new places, jet lag, and fatigue.)

Catch problems or conflicts

Second, in pulling together the details, we often find more opportunities for improvements. We catch things we may have missed (e.g., closure and opening times).  For a recent trip, we discovered that we could not take our rented RV on a scenic road, due to its size/length (see our tips page on renting RVs).  Had we discovered this in an earlier step, it would have been easier to adjust our itinerary.  Despite angst late in the planning process, we were fortunate to discover the issue before we departed.  We were able to devise a feasible solution that was acceptable and, in many ways, better than the original plan.  (See our Glacier post for more details.)  There are also many examples of gems and nuggets that we have discovered during this phase.

Of course, some trips will require substantially fewer details and attention.  Trips that are a guided tour, planned and executed by professionals, are a prime example.  We don’t usually opt for this type of travel, as we have discussed elsewhere.  But sometimes, letting someone else manage and plan a trip, or even a day, is what works best for you.

Review and Contingencies

Review and sanity check

The final phase of itinerary development begins with reviewing the plan.  This review naturally flows from the previous step (solidify and improve) but focuses on the overall flow of the trip.  At this point in the project, it is time for a sanity check on the pace and density.  Sometimes, over the months required to scope and plan, your mood and desires can shift a bit.  You may need to adjust your outlook or your expectations. 

A big part of this process is to ensure that there are no costly design flaws in the itinerary.  But there is still time to adapt at this step if flaws are identified.  Usually, for us, review is about refreshing our memories, identifying/planning for contingencies, and creating anticipation of the awesome trip.

Contingency planning

Depending on the type of trip, thinking through possible on-the-fly changes is important, even crucial.  Having pre-planned alternatives can save money, time, and stress.  These contingencies may be identified based on things going wrong or right. Similarly, alternatives might be considered to suit a possible change in your mood, as the trip unfolds.  Already knowing what a change will entail, even in the middle of the trip, reduces anxiety and preserves your opportunity to enjoy.

In our guide on travel contingency planning, we discuss this important extension to your base itinerary.

In previous steps you will have eliminated certain activities due to scheduling problems, etc.  These actives often form the basis for contingency plans and might get re-incorporated, as things change.

When it comes to contingencies, you can’t anticipate every eventuality.  But a good, well-considered itinerary, with accompanying details, will set you up to find alternatives and replan when you need to.  Knowing the route and general distances, the towns with possible accommodations, the alternative sights, etc. gives you a head start and reduces stress and risk of mishaps.

Concluding Remarks

It is our experience that developing itineraries reduces the cost and improves the efficiency of our trips.  And if that were all, the approach might still be worth the effort.  But the most significant value is the joy and heightened experiences that result from the research, preparation, and anticipation (not to mention the fun of the process itself).

We have laid out this process to make trip planning easier and more approachable, not to make it seem difficult and complicated. It does take time and concentration to plan a good trip, but it is fun for most serious travelers. If you are a process-oriented person, it may be tempting to follow a process step-by-step. But this is a general approach to building a great travel itinerary within constraints, not a strict step-by-step.

Please leave comments with your thoughts on the information that is helpful to you. What are we missing? What do you like? The suggested itineraries? The routes? The photos? The descriptions and hints?