Travel in Retirement: Goals for This Season of Life

Travel goals change as we grow older — at least they have for me. Those once fun-filled days of running into the ocean and playing in the waves have slowly turned into something a little more relaxed. These days, I’m happiest soaking up the sun with my toes in the sand, comfortably settled under an umbrella. Have you tried standing in the ocean lately and keeping your footing? It takes a lot more grace than it used to!

That said, even at this baby boomer stage of life, we still love our beach trips. One of our goals for this new year is to travel more, so I thought I’d share a few thoughts on what travel looks like — and feels like — in this season of life.

Short Getaways (2–3 Day Trips)

Short getaways are perfect for places you can reach with just a few hours of daytime driving. Personally, we enjoy staying off the expressways when possible — it’s less stress and scenic routes let you see more of the landscape and discover the charm of small towns along the way. That’s part of the appeal.

When the drive is only three to four hours, you can arrive with time to settle in, find a nice place for dinner, and still explore a bit that first evening. There’s no rushing, no exhaustion — just a gentle start to the trip.

If a guided town tour is offered, it’s worth considering. These tours give you a good overview of what’s available and help you decide how you’d like to spend the next day or two. Sometimes a little local insight makes all the difference.

We recently took a short trip to Hot Springs, and it was exactly the kind of getaway we enjoy most right now. We loved touring the town, visiting the historic bathhouse museums, and learning more about the area’s rich history. We even splurged a little — treating ourselves to an afternoon of massages and a truly pampering spa experience. It was relaxing, unhurried, and just the right mix of exploring and rest.

Longer Road Trips

Longer road trips can be incredibly rewarding in this season of life, but who you travel with matters just as much as where you’re going. A cross-country drive isn’t the time to discover that your travel styles don’t line up. You want a person—or maybe two—who are comfortable with long stretches on the road, who don’t mind taking turns driving, and who enjoy the journey as much as the destination.

Just as important, it helps to travel with people who share similar expectations. Some folks want to see everything and stick to a tight schedule, while others prefer a slower pace with time to wander, stop, or change plans altogether. Neither is wrong—but being on the same page makes the trip far more enjoyable. At this stage of life, the goal isn’t to check boxes; it’s to enjoy the drive, the conversations, the scenery, and the freedom that road travel allows.

A Few Road Trip Tips That Make All the Difference

• Talk about expenses before you leave. Decide how you’ll split gas, lodging, and meals ahead of time. It avoids awkward moments and keeps things relaxed.
• Be realistic about lodging costs. Hotel rates can be higher than expected, especially in popular or tourist-heavy areas. Build some flexibility into your budget.
• Discuss meal expectations early. Some travelers want three sit-down meals a day, while others prefer a light breakfast, snacks for lunch, and a nice dinner out. Knowing this upfront prevents frustration.
• Leave room for spontaneity. Avoid a steadfast agenda so you can stop at a roadside attraction, linger in a charming town, or reroute when something interesting catches your eye.
• Have a general plan—but not a rigid one. Decide on a rough route and a few must-see destinations before you leave, but stay open to detours along the way.
• Look up lodging before you arrive. Knowing what’s available at your day’s destination helps avoid end-of-day stress and gives you better options.
• Choose daytime driving whenever possible. It’s more relaxing, safer, and lets you actually enjoy the scenery you came to see.
• Build in rest days. A slower morning or a full day in one spot can make a long trip feel restorative instead of exhausting.
• Be flexible—and patient. Traffic, weather, and last-minute changes are part of road travel. A good attitude goes a long way.

Organized Bus Trips

We took our first organized bus trip this year, and it was fantastic. Honestly, I wasn’t sure what to expect—but it exceeded every expectation. There was no planning, no worrying about directions or parking, and being dropped off right at the door of hotels, restaurants, and attractions was such a treat.

One of the biggest surprises was how smoothly everything moved along. There was very little waiting at hotels, restaurants, or events because the logistics were already handled. That alone removed so much travel stress. Even better, the schedule allowed ample free time to explore on your own, rest when you wanted, or linger a little longer in places you enjoyed.

Organized trips offer the perfect balance of structure and freedom. Someone else handles the details, while you get to simply enjoy the experience. In this season of life, that kind of travel feels less like work—and more like the vacation it’s meant to be.

Group Travel & Cruises (7–10 Days)

We took our first cruise last year, traveling to Alaska and Canada, and it quickly became one of our favorite travel experiences. We went with friends and family, which made the trip even more special. Sharing those breathtaking views and relaxed evenings together added a layer of joy you just don’t get when traveling solo.

One of the things we loved most was that it was an all-inclusive package. Meals, entertainment, lodging—everything was handled ahead of time. There was no constant decision-making or daily planning, which made it feel truly restful. We enjoyed it so much that we’re already looking forward to finding another cruise in the near future.

Helpful Tips for Cruises & Group Travel

• Choose the best all-inclusive package you can comfortably afford. Not having to deal with tipping throughout the trip makes the experience much more relaxing.
• Use a knowledgeable travel agent. A good agent can advise you on the best months to travel, cabin choices, and itineraries that fit your pace and interests.
• Pack light—and pack smart. Magnetic hooks are a great tip for cruise cabins; they’re perfect for hanging jackets, caps, or lightweight bags on the walls.
• Read the fine print. Pay close attention to travel insurance details, cancellation policies, and what’s truly included.
• Do a little homework before booking. Watching YouTube videos about specific cruise lines gives you a realistic feel for the experience. Some cruise lines tend to be a better fit for a more relaxed, older crowd, while others—like Carnival—may skew younger and more high-energy.

Group travel and cruises offer a wonderful mix of adventure, comfort, and connection. In this season of life, that combination is hard to beat.

Final Thoughts

Just writing this post has me wanting to start planning for the year ahead. And the biggest reminder—for me more than anyone—is not to put it off. It’s so easy to say “we’ll do that later,” but later has a way of sneaking up on us.

I’m deeply thankful for the good health we have. It isn’t without its challenges, but the ability to travel—to get up and go, to enjoy the experience—is something that can be here today and gone tomorrow. That’s a reality worth paying attention to.

So maybe this is your gentle nudge, too. Start looking at those travel brochures. Watch a few YouTube videos. Talk with friends. Make a few loose plans. Travel in this season of life doesn’t have to be big or exhausting—it just needs to be intentional.

And sometimes, the planning itself is half the joy. 😊