8 travel experiences every retiree should treat themselves to at least once

Stepping into retirement is like opening a brand-new chapter—except this time, you’re the author, the editor, and the one holding the plane tickets.

After decades of routines, deadlines, and showing up for everyone else, you finally get to ask the question: What do I want to do with my time?

And for a lot of people, the answer is travel.

Not just the kind where you check off major cities and pose next to landmarks. I’m talking about soul-expanding, deeply satisfying experiences that you carry with you long after the suitcase is unpacked.

Whether you’re already globe-trotting or just starting to dream, here are eight travel experiences I think every retiree should treat themselves to at least once.

1. A slow train journey through a new country

Let’s start with something simple, elegant, and wildly underrated: the long-distance train ride.

In an age of instant gratification, there’s something almost rebellious about choosing slowness. No airports, no security lines, no layovers. Just a moving window into the heart of a place.

I once did the Bernina Express through Switzerland and northern Italy—four hours of pure cinematic scenery. Snow-covered peaks. Stone bridges suspended in the air. Pastures that looked like they were painted on.

You can get this kind of magic in lots of places. The Canadian Rockies. The Scottish Highlands. Even closer to home, Amtrak’s California Zephyr is a jaw-dropping ride from Chicago to San Francisco.

The best part? You can kick back, sip something warm, and watch the world unfold with no effort required.

2. A wellness retreat focused on rest and reflection

Here’s a wild idea: what if you didn’t wait until you were burnt out to prioritize your well-being?

Most people treat rest like a reward. But rest is actually fuel—and retirement gives you the perfect window to fill your tank.

I once stayed at a retreat center outside Sedona where the itinerary was simple: yoga, nature walks, clean food, and honest conversations. No phones. No agendas. Just room to breathe.

That kind of environment can do more for your nervous system than any spa day ever could.

Whether it’s a meditation retreat in the Blue Ridge Mountains or a wellness resort in Bali, these experiences offer more than relaxation. They offer clarity.

And let’s be real—clarity is one of the most valuable currencies post-retirement.

As noted by the Global Wellness Institute, wellness travel is booming, especially among retirees who want to extend their healthspan, not just their lifespan. If that’s your goal, this kind of trip is a smart place to start.

3. A cultural immersion that goes beyond sightseeing

If you've ever said, "I want to really experience a place, not just visit it," this one’s for you.

Cultural immersion isn’t about checking off monuments. It’s about living like a local—even for just a few days.

I still think about the time I stayed with a host family in Vietnam and joined them for their morning market ritual. I couldn’t pronounce half the ingredients, but I learned more in that one hour about local life than I did in all the museums combined.

More platforms are making this kind of experience easy. Road Scholar and Eldertreks are designed for older travelers seeking deeper, guided cultural exchanges.

Even Airbnb Experiences has options to join local artists, cooks, farmers, and musicians for authentic, hands-on encounters.

It’s not about having the perfect itinerary. It’s about making real connections—and that tends to stick with you longer than any souvenir.

4. A solo adventure (yes, really)

Let’s bust a myth: you’re never too old to travel solo.

In fact, retirement might be the best time to do it.

You’re not navigating school calendars, time-off requests, or other people’s preferences. You get to call every shot—from when to wake up to how long to stay.

Years ago, I took a solo photography trip along Iceland’s Ring Road. I stopped whenever the light shifted. I napped when I felt like it. I didn’t speak to anyone for hours—and I loved it.

Solo travel forces you to get comfortable with your own company. But it also invites spontaneity and self-trust in a way group travel rarely does.

Of course, safety matters. But companies like Overseas Adventure Travel and Explore! offer small-group tours with solo-friendly options, letting you dip a toe in without going fully off-grid.

The point is: if you’ve been waiting for someone to join you, stop. You might be the best travel partner you’ve ever had.

5. A multi-generational trip with the family

While solo trips offer introspection, multi-gen trips bring connection.

These aren’t just vacations—they’re memory-making machines.

Think about it: your grandkids will forget what you got them for their birthday last year, but they’ll remember roasting marshmallows with you in Yosemite or exploring tide pools in Maui.

And these trips don’t have to be expensive. Rent a cabin in the woods. Take an RV to a national park. Do a staycation with fun local outings.

But if you do want to splurge? All-inclusive resorts, cruises, and villa rentals are often built with multi-age families in mind. Everyone gets what they need without putting the planning burden on one person (read: you).

As relationship researcher Dr. Sue Johnson notes, “Connection is the key to emotional health at any age.” Traveling together creates space for that connection to deepen.

6. A bucket-list destination that once felt out of reach

You know that place that used to feel too far, too risky, or too extravagant?

It’s time.

Whether it’s Petra, Patagonia, or Paris, the dream trip doesn’t belong in the “someday” pile anymore. You’ve earned it. And guess what? Most of these places are more accessible than ever.

Flights are cheaper. Tours are safer. And travel insurance is better. If physical mobility is a concern, there are now entire companies that specialize in accessible travel for retirees.

The bigger hurdle is often psychological. We talk ourselves out of things because they feel "too much." But often, it’s nottoo much. It’s just unfamiliar.

Push past that. Take the plunge. Your future self will be glad you did.

7. A volunteer trip that gives something back

Not all travel has to be about taking in. Sometimes the most fulfilling trips are about giving out.

Voluntourism is a growing trend, especially among retirees who still want purpose, not just pleasure.

You could help with sea turtle conservation in Costa Rica, teach English in Thailand, or assist in post-hurricane rebuilding efforts in the U.S.

One couple I met in Mexico was building houses through Habitat for Humanity’s Global Village program. They told me it gave their retirement a new rhythm—travel with meaning.

Programs like Earthwatch, Global Volunteers, and even local faith-based missions offer structured options for short-term volunteering with long-term impact.

You bring wisdom, time, and heart. That’s a powerful combo.

8. A road trip with no fixed agenda

Let’s end with one of my favorite kinds of travel—the kind where you just… wander.

You pack a bag, fill up the tank, and let curiosity take the wheel.

No spreadsheets. No reservations. Just a rough direction and a willingness to see what shows up.

One fall, I drove from Oregon down to Big Sur with no real plan. I stumbled upon small-town farmers markets, impromptu music festivals, and some of the best pie I’ve ever had in my life.

Retirement gives you this rare luxury: unstructured time. Use it.

Even a few days on the open road can remind you how much adventure lives just beyond the next bend.

The bottom line

Retirement isn’t the end of the story—it’s a blank page begging for ink.

Travel, done right, isn’t just about escape. It’s about discovery—of places, people, and sometimes, parts of yourself you forgot existed.

Whether you lean toward comfort or curiosity, solitude or connection, rest or renewal—there’s a trip out there waiting for you.

And you don’t need permission. Just a backpack, a spark of interest, and a little willingness to go.

Because if not now… when?