Why you should create a multi-year travel plan

By David Barclay | February 7, 2024

Travel for 2024 is starting out strong and this is the time of the year when many travelers start planning their vacations for the new year. Many of my clients take this planning process a step further, and together we develop multi-year travel roadmaps, which pay big dividends for the planning process and my clients’ eventual travel experiences. 

Who should consider creating a multi-year travel plan

While multi-year travel plans (or roadmaps) aren’t needed by every traveler, they can be beneficial to most travelers who travel on a regular basis.  The first group of travelers that can benefit from a long-term travel plan are those travelers who are still working.  While my clients who have retired or partially retired generally have some flexibility around when they can travel (if their ideal travel dates are challenged for availability of accommodations and activities), many of my clients who are still working generally have specific windows when they can travel, with maybe only a few days of flexibility for when they depart for and return from their vacation.  This time limitation can challenge getting the perfect experience unless we start the planning process well in advance.  These clients also tend to have a limited number of days they can devote to their travels each year and will want to ensure they maximize those precious vacation days.

The second group that may benefit from a multi-year travel plan are those travelers that still have children at home.  Especially for those travelers with children in or nearing high school, the remaining years where they can all travel as a family may be dwindling (as trying to overlap high school/grade school breaks with college breaks can be challenging).  These families can benefit from mapping out their remaining opportunities to travel as a family and ensuring those opportunities are used to complete the family travel bucket lists.

A third group of travelers that can benefit from multi-year planning are those travelers who want to start planning their bucket list trips.  Trips to Antarctica, the Galapagos, Africa, etc. can be life changing experiences, but they are also very popular and only a limited number of travelers can participate each year do to limited capacity (especially at the luxury end of travel).  A multi-year plan allows us to shift trips that have more availability for travel to the early years and move trips that require long-term planning to future years, giving us a leg up on getting the best options for those future trips.

The last group that can benefit from multi-year planning are those travelers who are in good shape now but may worry about their ability to handle more active experiences in their later years.  Experiences like sailing to Antarctica require travelers to get into zodiacs when disembarking on excursions and travelers go ashore through wet landings (the zodiac won’t touch shore and travelers need to hop into shallow water to reach the shore).  Guests may also take a kayaking excursion to get close to the wildlife.  While it is possible for an older traveler with mobility issues to sail on an expedition ship and view the wildlife and geography from the ship, it diminishes the experience if they can’t get onto the water and explore the shore.  A multi-year travel plan lets us prioritize some of these more active trips early on and reserve some of the trips more conducive to handling mobility issues for later in their travel lives. 

How to create a multi-year travel plan

Creating a multi-year travel plan is relatively straight forward and you can start to assemble a rough cut on your own, or you can gather all the required components and build the first draft together with your travel advisor.  In either case, you will want to engage your advisor relatively early in the process, as their expertise will help shape how the components of the plan come together.

Start by getting your calendar and map out when you can travel.  If your annual travel calendar is relatively consistent, you can feel free to map out many years into the future.  At a minimum, I recommend trying to map out at least 3-4 years.  Even if you only plan to travel a few times each year, it’s useful to map out every travel timing opportunity that you have, as this helps you pick the best time to visit your desired travel destinations.

Next, create a list of trips you would like to take.  If you end up developing an extensive list of desired travel locations, you may want to go back and prioritize the list (or at a minimum, sort the destinations into a few groups such as high/medium/low priority).  If you plan to travel with someone else (e.g. your spouse or partner), you may want to create the list together, or you may want to create separate lists and then compare which locations you each prioritized high and low on your lists.   Similarly, families may want to have each family member create their own prioritize list and then as a family you can review.  Some families might want to focus on those destinations that appealed to the greatest number of family members, while others might want to rotate the prioritization of trip ideas, so each family member has an opportunity to visit their highest priority destination.

Next, start matching the destinations on your list with the travel windows you laid out in your first step.  Starting with your highest priority location, assign it to a travel window that’s the ideal time of year to visit and length of time to travel.  For example, if you want to travel to Australia, you probably want to look for a time you can travel where it’s spring/summer/fall in the southern hemisphere and you have enough time to travel all the way there and explore.  In this example, you may have a lot of available time to travel in the months of June-August (summer break in the U.S.) but you may not want to travel to Australia in its winter.  Likewise, if you only have a week for travel in the spring (spring break) that may not be long enough for some trips even if the weather at the destination is ideal.  This is an ideal time to engage the assistance of your travel advisor, as they will be highly skilled in matching your travel destinations with your travel windows.

Creating your long-term travel plan may take several iterations to finalize, as you evaluate options for the trips you might take each year.  It’s also not a static plan, the closer in trips are likely to be firmer (and you may start planning one or more of those once you finish your multi-year travel plan) but you can think of the future years as placeholders with the option to revise if other destinations rise on your priority list over time.  You should revisit the plan at least once per year, again best done with your advisor so everyone is on the same page for your travel desires.

Benefits from having a multi-year travel plan

There are multiple benefits travelers get from their multi-year travel plans.  These include:

• Getting priority trips on your calendar so your busy life doesn’t make time slip away and you miss the opportunity to travel.  This is especially important for trips that require planning far in advance.

• It allows you (and your advisor) to start planning trips with the appropriate amount of lead time, ensuring you get what you want.  This is especially important for trips that require a year or more of advanced planning.  Recently, I looked at Galapagos cruises for a client who wanted to travel during the December holiday season.  His preferred cruise line was fully booked for the two itineraries that would have worked for the travel window his family had, and we were looking almost a year in advance of his target travel dates.  With a multi-year travel plan (and knowing the December travel period is busy everywhere) we could have looked at (and booked) those itineraries when the cruise line first released the dates and there was good availability on the ship.

• It ensures you will travel at the best time to each destination.  When creating the travel plan, we can assign trips to Europe for summer travel windows (or summer shoulder months), trips to the southern hemisphere for fall/winter/spring trips, and fill in with shorter trips, such as Mexico or Caribbean beach vacations, for cold weather months but where you have long weekend or other opportunities to travel.

• Gain alignment from fellow travelers, especially groups of friends or multi-generational family trips.  If you’ve ever tried planning a trip with multiple friends or with extended family members, you know it can take a long time to get everyone’s schedules aligned and agreement on the destination.  A multi-year travel plan allows you to discuss these ideas early with potential travel companions but with rough dates/timing, not just somewhat vague ideas of traveling together at some point to some undecided destination.

• Last, it can give you time to save up for your trips.  Many times, the trips that make it into the multi-year travel plans are some of my clients’ big bucket list trips.  Some of my clients may want to have additional time to save for these bigger trips, so they don’t feel like they must scrimp and can really splurge on those big trips.  Others may want to even out their annual investment in their vacations, not stacking multiple bucket list trips in a single year but complimenting those bigger trips with shorter trips or trips to regions of the world that are generally less expensive to visit.  A cruise to Antarctica can cost $20-25K/person, a luxury safari can easily cost $15-20K/person, and a cruise in the Galapagos can cost $12-20K/person.  For families with multiple children, or grandparents planning a multi-generational trip, the costs can quickly add up and they may appreciate the time to save up for the trip or having a general idea of their planned annual travel budgets over a multi-year horizon.