Planning a trip starts with a wish. The desire for a change in your routine, or to go to a cool location in August, or a warm spot in the winter months. The desire could be sparked by a destination wedding, or a conference you wish to attend. Like many things in life, travel doesn’t just happen; it takes intentional planning and preparation. Whether you are planning a 3-day weekend getaway or a more ambitious destination, the following questions will assist you in your planning process:  

When Do You Want to Go?

If you have flexibility in your travel schedule throughout the year this question can wait and may depend on the “where” as mentioned in the following question below. However, if you are working or have kids in school, your window of travel may fall into pre-determined time frames. In some cases, you can adjust your travel dates a bit if you have flexibility. Otherwise, I recommend starting on the front end of your travel window, and go from there.

Where Do You Want to Go?

Once you have identified the WHEN, you can work on the WHERE. You can also start paring down the universe of possibilities. I recommend having a specific region or city in mind. For example, going to Florence, Italy is easier to pin down than going to Europe. If you already have a city in mind, you can narrow down which part of town, or the attractions you wish to be closest to. 

How Will You Get There?

Flying or driving is the next typical question, but there may also be trains, buses, ships, or even ferries that need to be considered (such as if you are going to Martha’s Vineyard or Mackinac Island.)

If the travel logistics seem like more work than you can handle, you may want to consider traveling with a group tour. There are excellent options available, and they can do most of the heavy lifting when it comes to your travel arrangements.

How Will You Get Around Once You Are There?

If you have your own car, you will want to consider if parking is an issue. If you do not have a vehicle, you will want to explore local transportation options. I believe group tours were invented for people who recognize this aspect of travel could be challenging. While you may consider renting a car or relying on Uber, be aware that these options may not be available or as accessible as you may think. Some cities have excellent metro systems, and they can be the fastest way to travel in a large city. However, they may be difficult for individuals who struggle with walking long distances. 

Where Will You Stay?

I recommend researching this issue well in advance. It could be a disaster to assume that you would travel to an exciting destination and jump onto a discount website and get the deal of the day for a hotel room. Unless you have friends or family that you will be staying with, you will want to plot this angle out carefully.

Are there any conflicts?

The goal here is to never have to say, “What was I thinking?”

You may have personal obligations that may cause issues, or the place you want to visit is having ongoing transportation strikes or political upheavals. You may have missed the announcement of a major event at the city you wish to visit (think of the Olympics in Paris, France), or the one museum that you want to visit is being renovated over the next year. You may not realize that the middle of March is perhaps the worst time to go to Florida (unless you are a college student on Spring Break), but these are the types of conflicts you will want to consider. 

How Will You Pay for It?

The best way is to have the funds set aside in advance. Many AFG clients have specific vacation savings accounts. The term “credit card vacation” should make you wince. If you don’t have the funds in your Savings-to-Spend account, I recommend you reconsider your plans, or at least wait until you have saved enough money.

Does Professional Help Make Sense?

Don’t hesitate to get expert help if the caliber of your trip seems overwhelming. There are still travel agents who can help with large groups, multi-family trips, Disney trips, or other complex situations. 

At What Point Do You Commit?

You may have tossed many vacation ideas around in your head, but at some point, you do need to commit to your plans. The reason to do this is so that you and the other important people in your life can start planning around your future travel schedule.

I highly recommend putting the plan together, either in your head or on paper, and then sleeping on it. I’ve noticed bouncing the idea off a spouse or perhaps other veteran travelers can reinforce a good plan, or bring up issues you may not have thought about. If you have medical issues, get a green light on your travel plans from your doctor. 

If everything still feels right after your due diligence, I recommend putting your plan into motion. However, it is important to build in contingency plans where possible. That means verifying the cancellation date on hotel rooms, buying travel insurance for cruises or group/tour trips, and being aware of dates where final payment is due. 

What Else Should Be Considered?

Eventually you will want to bear in mind weather issues, packing limitations, and other details of your trip. These can all be addressed once you have committed to your travel plans and put them into motion. 

If you do it right, you will have a delightful experience and return home refreshed with a whole new perspective. Then you can look forward to your next adventure and start the planning process all over again!

Kristina Bolhouse, CPA/PFS, CFP®

Vice President/Shareholder

© 2024 Kristina Bolhouse and The Arkansas Financial Group, Inc., All rights reserved.

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