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Vacation in Retirement: Planning a Trip

Senior couple on vacation

Retirement is often hailed as a time of newfound freedom and exploration. Roy M. Goodman once said, “Remember that happiness is a way of travel – not a destination.”

There are many things to look forward to during your retirement years. More time to explore your interests and passions, spend time with family and friends, relax, and so on. However, one activity stands out among the rest as one of the top things that soon-to-be retirees look forward to.


According to a study by RBC Wealth Management, travel and vacation made the top 10 list of activities people aged 50 and older look forward to the most for their retirement.

With more free time, you don’t have to wait for an annual vacation, checking off the days until you get to experience the joys and wonders that traveling brings. You’re retired! You have the freedom to take more trips, see more of the world, and make more memories.

If you’re among the retirees ready to get away and explore the world, you have many options to choose from.

Fly to international destinations. Hit the road for a breathtaking road trip across America. Rest and recover at an all-inclusive resort.

However you choose to travel, there are a few things to remember while planning your adventures.

Start Planning In Advance

With retirement comes more planning. And that includes planning for travel and trips. And we don’t mean planning a few months in advance.

During retirement, you typically have a set amount of funds each year. Unless you still have a form of income while retired, you have limited funds to put towards traveling, so it’s crucial to include your travel plans in the early stages of your retirement planning.

Just like any other part of your financial picture, your retirement trips should be included in your overall financial planning. By planning many years in advance, you will likely have more opportunities to save and find discounts.

It’s important to note that we don’t mean you have to buy your plane tickets and book your hotels years in advance. But it will pay off to financially plan for your traveling 5-10 years in advance, so you have time to start saving, budgeting, and investing.

So while your initial financial planning should be happening years in advance, there are some other travel details that you should prioritize earlier than others.

Here is a quick reference to the best-recommended timing for booking trips:

Long-haul flights — about 115 days out from your travel date (CheapAir)
Short flights — around 64 days before your departure date (CheapAir)
Cruise — as soon as possible – multiple years in advance is best (RoyalCaribbeanBlog)
Accommodation — approximately one month in advance minimum (Afar)

Have an Annual Travel Budget

Once you’ve passed the pre-retirement planning stage, you’ll also need to work out annual travel budgets. These budgets will vary year by year, so these are budgets that you can work out closer to your travel dates.

Consider how much you can afford to spend on travel costs because they add up quickly. There may be things you’ll need to cut, some things you’ll be able to add, and time required to research deals and discounts to get the most bang for your buck.

Take Advantage of Deals, Discounts, and Freebies

On the same note, retirees have access to more discounts and deals compared to their younger counterparts. Researching and finding discounts and deals will save you money on your travels, giving you more financial cushion and even the ability to travel more than you initially anticipated.

Here are a few ways to save $$$ on your retirement travel plans:

  • Use points or other credit card travel rewards
  • Utilize senior or military discounts (inquire about discounts even if they are not mentioned upfront.)
  • Buy a Lifetime Senior Pass to visit national parks for a considerable discount
  • Look on Groupon for special deals
  • Take advantage of an AARP or AAA membership that comes with travel and attraction discounts

Those are just a few of the many deals, discounts, and freebies offered to retirees. For more ideas and options, check out this list of over 200 locations that offer senior discounts.

Assess Your Health and Fitness Ability Levels

We believe that age is just a number – many retirees who are members of our community are fit, sharp, and very active.

Still, unexpected health issues or limitations could arise, making your travel plans challenging or even impossible. That’s why it’s good to consider your overall health, fitness, and ability levels when planning your travels. It’s recommended that you plan the most strenuous and adventurous trips in the early retirement years and save the more relaxing and easy-going trips for later.

How you decide which trips are more physically demanding than others will slightly vary from person to person, but consider factors like layovers, elevation, timezone changes, walking distances, and accessibility when deciding which trips to take and when.

Buy Travel Insurance

One thing you should never skip out on to save a few bucks is travel insurance.

Some traditional health insurance companies provide certain levels of international coverage, and some don’t provide any coverage at all.

As you’re planning out your international travels, it’s important to check with your insurance provider to see what – if any – coverage they provide. Even if your insurance provider offers some coverage, look into the details of that coverage. They may cover medications, but they may not cover canceled flights, delays, or certain types of hospital visits.

NerdWallet has a great tool for helping you find the travel insurance coverage that is best for you.

While it’s an additional cost – travel insurance is typically budget-friendly and well worth the investment.

Focus on Experiences Rather Than Places

It can be tempting to put most of your focus on WHERE you travel vs. WHAT you do while traveling.

Noteworthy getaways like London, Athens, Paris, or Rome are appealing destinations to travel to, but with that appeal comes a higher price tag. If you only prioritize going to places because they are well-known, be expected to pay a higher price during your time there. However, it may surprise you that going off the beaten path can often lead to some incredible experiences at a lower price point. And even better, these options may offer you a more unique, individualized experience due to fewer crowds and tourists.

Remember – traveling isn’t about the destination. It’s about the memories you make with the people that matter most.

Don’t Wait – Start Planning Your Next Trip Today

Embracing retirement means embracing adventure. Yet, don’t fall into the trap of endlessly waiting for the perfect time or destination to start your journey. Regardless of where your travel dreams take you, the most crucial step is to begin. And it doesn’t have to be a grand leap; it can be a small step. Whether you start by exploring local gems or aim for far-flung destinations, the key is to just start. It’s in those first steps that you’ll find the spark of adventure, the magic of exploration, and the delight of experiencing new places and people. So, don’t wait. Your retirement is a new chapter, and every chapter begins with that first word. Whether it’s written in the nearby parks, remote mountains, bustling streets, or serene beaches – that’s your story to create.