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Planning an Unforgettable Retirement Trip

Nothing caps off a career quite like heading off on a retirement trip. Here are some tips for anyone planning an adventure.


Published on January 30th, 2024 in Travel Tips

You’ve finally done it.

After decades of gainful employment, it’s time to hang up one’s proverbial hat and enjoy the next phase of life: Retirement.

The end of one’s years in the working world can provide time to relax, do meaningful volunteer work or be of service to aging family members. Retirement can also be an excellent time to plan to go on trips. Without the confines of a job and with money and good health, there are any number of different adventures a person can embark on.

Today, we’re going to look at what it takes to plan an unforgettable retirement excursion. We’ll look at basics like timing, logistics and where to go. And we’ll also explore what’s needed to keep things running smoothly should the unexpected arise.

Why plan a retirement trip?

Chances are, a person doesn’t need an excuse to start planning where they’ll adventure to in retirement.

Perhaps we’ve all sat at our desks dreaming of bucket list trips like sitting on a beach in Fiji, exploring European castles or taking our loved ones on a Caribbean cruise, if only we didn’t have that 2PM conference call or run of holiday orders.

For anyone who might still be on the fence about whether or not they should have an adventure after concluding their career, here are five reasons to plan one:

1. A way to send off your career in style

People don’t have to start thinking about retirement after they’re out of their workplace for the last time. In the months or even years leading up to when a person concludes work, they can develop plans for a fitting end to their career.

For some people, a nice party or farewell dinner might be enough to cap off their working days. There’s nothing wrong, though, with desiring a little more. Embarking on an adventure can be a way to always remember one’s retirement.

And hopefully, a retirement celebration trip will be just the first of many adventures in one’s golden years.

2. Growing ease of travel for seniors

It’s not to say that earlier generations of older adults never traveled. Still, they sometimes had to go through more to do it, whether it was riding a boat to get to Europe or plunking down a small fortune for airfare or private guides.

Now, airfare is fast, safe and, factoring for inflation, considerably cheaper than it was decades ago. An abundance of senior-oriented travel clubs or companies like Overseas Adventure Travel, Road Scholar and ElderTreks also exist these days, helping older adults safely travel to a variety of destinations.

3. You finally have the time

People, particularly Americans, work a lot. Research by a Gettysburg College graduate found that the average person works 90,000 hours in their lifetime. That’s about 45 years of working full-time and it doesn’t even factor in all of the time a person spends getting ready, commuting to and from the job and going to extracurricular work functions.

This doesn’t go on forever, though, with the average person retiring at 61, based on a 2022 Gallup poll reported on by NerdWallet. There’s also still a lot of life hopefully left at this point, which means something else: A person finally has the time for the kind of trip that would have been infeasible during their working years.

4. It might be easier to travel at off peak times to score deals

Another facet of being in the working world is that a person is often somewhat confined on their days of travel. With many workers not able to take more than a week off at any given time, they might be forced to fly on Friday, Saturday or Sunday when airfare can be more expensive. (Same goes for hotel rates these days.)

Suffice to say, retired people have something that working people often don’t: The ability to fly on cheaper airfare days midweek without having to curtail the length of their trip or stretch a vacation into the middle of another working week.

It might also be easier for retired people to have control over what times of year they travel, allowing them to hit choice locales at the most affordable points.

5. This can be the only trip or the first of many in retirement

Some people reach retirement having traveled frequently throughout their lifetime. Others, however, might have been so focused on work that they haven’t traveled much, if at all. For either crowd, though, it can be good to plan an excursion.

Frequent travelers can keep doing what they love, at a time of life that can be dedicated to this for as long as a person has funds and physical ability to keep traveling. Whether they want to go to the Valley of the Kings in Egypt or Machu Picchu in Peru, there doesn’t have to be too many limits.

Things to do on a retirement trip

Just as a person might not need excuses to plan an adventure, some people might not need any help coming up with things to do on said trip. For anyone early in their brainstorming, though, here are a few things we recommend:

Take a longer trip than work would allow

American workers get, on average, 11 days of paid vacation each year, which equals two weeks and one day. People want to be able to take occasional personal days, too and not just have to go on vacation once a year. So what it all means is that the average working person is lucky if they get a week of paid vacation at any given time.

Retired people can work on entirely different timetables than someone who has to clock into an office. If they want to spend several weeks or a month in the Andes and they have the means to do this, a person can after they retire. No matter what they choose, there’s room to get creative with how a retired person travels.

Go somewhere you’ve always wanted to go

The same principle as above applies. Retirement, particularly the early years of it, is the time to leave nothing on the table when it comes to travel.

Anywhere a person’s never been before that they might have on their bucket list of destinations to visit, now’s the time to think about getting there. This can be true whether it’s Scottsdale, Arizona. for baseball spring training or the Earth’s most remote island with inhabitants, Tristan de Cunha.

People can easily fall into routines in retirement, like watching excessive amounts of television. Venturing to an unusual vacation destination is a great way to counter this.

Revisit somewhere special from the past

A person can be bold in retirement, make a bucket list and head to new lands. There’s nothing wrong, however, with taking a trip down memory lane.

Using a retirement vacation to go back to a treasured place from one’s past might mean taking a second honeymoon in the same place a couple went to years or decades before. It might mean recreating a post-collegiate backpacking trip to Europe – while hostels generally cater to younger visitors, there’s seemingly nothing that says senior citizens or families can’t stay in many of them.

Going back to somewhere comforting can even be something as simple as returning to a favorite camping spot. At the end of the day, it’s just about recognizing that an adventure in retirement can be whatever a person wants or needs it to be.

Spend time with loved ones

Trip planning can often focus on destinations or itineraries, but there’s another component of travel that’s arguably equally important: Who we get to enjoy the journeys with.

Senior travel can be a great way to get to better know one’s spouse or romantic partner. Senior couples who travel together get to put aside all the years of stressing over a job that might have clouded their off time and instead get to see each other in different, more relaxed lights.

Aside from romance, vacations might also include children, grandchildren or even just close friends. Whoever it is, there’s sure to be chances for quality time throughout the course of trips.

Retirement trip destinations to consider

The following is offered with the caveat that trips for older people can be whatever they want or need them to be.

If the ideal trip for one’s wish list sounds like going for a night or two to a hotel an hour from home, that’s fine. If it’s driving a few hours to spend a long weekend with one’s children or grandchildren, that’s alright as well. A retirement trip can be an extravagant tour or something simple that soothes the soul, whatever the mood calls for.

That being said, here are some destinations to consider for your next trip in retirement:

Southwest road trip

When some people retire, they might wholeheartedly fly thousands of miles to some distant land. Others might need to warm up to this, if at all. For the latter crowd, a road trip can be a great way to dip one’s toes into the world of retirement travel.

We recommend the American Southwest, in part because of how many great locations can be linked together in one trip. Aside from obvious stops like the Grand Canyon or Las Vegas, there are other good things to see such as: Mesa Verde in Colorado; decommissioned Route 66, which is still driveable through much of the southwest; and underrated and affordable cities such as Albuquerque, New Mexico.

For those that want it, it’s not that far on to West Coast cities like San Francisco, where the Embarcadero or 1.7-mile span of the Golden Gate Bridge is just waiting to be walked along.

Visiting Washington, D.C.

America’s capital city makes a superb place for seniors to visit in part because of its rich history and the vast number of low-cost things to do there.

Whether it’s going to the Smithsonian museums, getting a card from the Library of Congress or walking to sites like the Washington Monument, Lincoln Memorial or Vietnam Memorial, there’s always another important thing for history buffs and even just everyday people who visit D.C. to do for little or no money.

Taking a cruise

Around one-third of people who took a cruise in a recent year were over the age of 60, according to data reviewed by CNBC in 2022. Cruising is a popular activity for older travelers, with no shortage of potential destinations.

A retirement trip might consist of boarding a boat in Miami and cruising to the Bahamas or Barbados. It might go from Vancouver to Alaska, Long Beach to Ensenada, Houston to Cancun. These days, there are even good river cruise options, such as the Mississippi River.

Cruises are also great for the day trips that can be had during shore excursions. The entire adventure doesn’t just have to be had on-deck.

Going international

Retirement trips don’t have to involve globetrotting, though it’s also not wrong to plan these kinds of adventures, especially early in retirement. It will be easier to do a grand international trek at 65 rather than 80 (though it’s not to say that people can’t keep traveling well into their senior years so long as health and finances allow).

As of this writing, there are 195 countries in the world. While some might not be easily accessible or safe to travel for a retirement trip, that still leaves plenty of options. These can include:

  • The Canadian Rockies, where picturesque towns like Banff are worth a visit;
  • Cape Town, South Africa, which has a variety of fun things to do, such as Kirstenbosch National Botanical Garden;
  • Athens, Greece, a bucket list locale for all of its historical sites and ancient ruins. The city’s fresh seafood and traditional music can be drawing points, too.

Prepare for your retirement trip

Now that we’ve been over the ins-and-outs of retirement travel and looked at destinations, there’s one more thing we should cover: Preparing for the trip itself.

Retirement trip preparations aren’t just about setting a realistic travel budget, deciding on a destination or finding a senior travel company. It’s also about creating a plan to ensure that should something go wrong, you’re not in it alone.

This is where Emergency Assistance Plus® (EA+®) comes in.

We are a company that provides assistance to travelers and their loved ones, making it so that peoples’ worries about receiving quality care, getting transportation home, and protecting their wallet, can be eased in the event of an emergency. The things we do include but are not limited to:

  • Helping arrange medical care in distant lands;
  • Flying you home, or, if you’re along, sending a loved one to you and a trip gets derailed due to a medical emergency;
  • Even helping to provide medical assistance remotely.

More information can be found by reviewing our membership details or by calling us at (866) 863-4460.

Bon voyage!

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