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That trip you keep saying you’ll take “someday”? Here’s how we turned a Bucket List dream into something we actually put on the calendar and did.

Having a Bucket List is easy. Actually doing the things on it is a lot harder.

Money, time, health, logistics, fear of the unknown—or even a travel partner who isn’t quite convinced—can keep Bucket List travel firmly planted in the “someday” category.

Bill and I have faced all of those things during our travels around the world. But I’ve learned that I need to figure out what’s really stopping us, do the research, and take the next step.

Antarctica is one of my favorite examples because we almost didn’t go—and it became one of the greatest travel experiences of our lives.

Of course, this process can apply to any destination that is on your Bucket List.

Snow-covered Antarctic mountains reflect perfectly in calm blue water beneath a bright sky. Landscapes like this convinced us our Antarctica cruise was worth every dollar.

Step 1 – Pick One Bucket List Dream

A long Bucket List can be inspiring, but it can also be overwhelming. Where do you even start?

Pick one thing.

Maybe it’s the place you’ve dreamed about for years. Maybe it’s an opportunity that suddenly presents itself. Or maybe one destination just keeps rising to the top every time you think about where you want to go next.

You’re not committing to the trip yet. You’re simply saying, “This is the one I’m going to investigate.”

A group of king penguins gathers at Bluff Cove in the Falkland Islands, giving us our first close-up look at the second-largest penguin species in the world.

Step 2 – Figure Out What’s Really Stopping You

Before you can make a Bucket List dream happen, you need to know why it hasn’t happened already.

Is it:

Money?
Time?
Health or physical limitations?
Fear of traveling somewhere unfamiliar?
A trip that seems too complicated to plan?
A travel partner who isn’t nearly as excited about it as you are?

Sometimes the barrier isn’t even real. It’s something we’ve assumed.

For me, the Antarctica barrier was money. I thought an Antarctica trip would cost at least $15,000 per person, and that wasn’t something we were willing to spend.

Bill had a different objection.

“We’ve already been to Alaska. Isn’t Antarctica basically the same – a whole lot of ice?”

Sometimes it takes a little digging to figure out what’s really keeping you from pursuing a dream. In 9 Bucket List Barriers & How to Overcome Them, I explore some of the most common obstacles and practical ways to work through them.

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Step 3 – Investigate Your Bucket List Travel Dream Before You Decide It’s Impossible

Right before we left for our four-month trip through South America, a travel brochure arrived in the mail advertising a 17 day cruise to Antarctica for $2,900.

Wait. What?

Could you really go to Antarctica for $2,900? It had been at the very top of my Bucket List for decades.

That was all it took to send me down the research rabbit hole. I figured out which cruise the brochure was advertising and when it sailed. Then I pulled out our South America itinerary to see where we were supposed to be during those dates.

We had planned to spend a month exploring the highlands of Ecuador. Suddenly, that didn’t sound nearly as interesting as it had before Antarctica came into focus. (Sorry Ecuador—we’ll get to the highlands next time!)

If we changed our plans, we could also spend a week in Quito before the cruise and a week in Buenos Aires afterward—two cities we hadn’t originally planned to spend much time exploring.

The $2,900 fare turned out to be for an inside cabin. That wasn’t what I wanted for Antarctica. If there was ever a place where I wanted to look out the window, this was it.

But the brochure had already accomplished something important: it showed me that my assumption was wrong. There were ways to see Antarctica that didn’t cost $15,000 per person. So I kept researching.

That’s the lesson I’ve carried into other Bucket List travel planning: before deciding a dream is too expensive, too complicated, or otherwise impossible, find out whether what you believe about it is actually true.

If you want to read about what our Antarctica cruise cost in the end, I wrote a complete guide to that as well as some other planning tips.

Kari and Bill smile on the deck of their cruise ship with towering Antarctic peaks, glaciers, and floating ice behind them. We almost skipped this Bucket List trip because of the price until we discovered a more affordable option.

Step 4 – Find the Version of the Dream That Works for You

Once I knew scenic cruising was an option, the question changed.

It was no longer, “Can we afford to go to Antarctica?” It became, “What kind of Antarctica experience makes sense for us?”

We ultimately chose a 17-night scenic cruise from Buenos Aires. It wasn’t an expedition cruise where we would step onto the continent, but we would cruise through waters of the Antarctic Peninsula and see the landscape and wildlife I had dreamed about seeing.

It also meant making a choice.

The month we had planned in Ecuador would have cost us only about $1,000. Our Antarctica cruise would cost us more than $12,000, plus what we spent during our extra time in Quito and Buenos Aires.

That’s a pretty significant difference.

But once we understood our options, Bill and I could decide together whether this particular Bucket List experience was worth spending the extra money on.

Your version of a dream may look completely different from mine. That’s okay. The goal isn’t to take someone else’s perfect trip. It’s to figure out what version works for you.

People always ask how we can afford to travel so much. It all comes down to choices. Read more at How to Travel on a Budget: Where We Save & Where We Splurge

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Step 5 – Break the Trip Into Smaller Decisions You Can Actually Make

“I want to go to Antarctica” feels huge.

Individual questions are much easier:

When can we go?
What will it realistically cost?
How will we get there?
Where will we stay?
What do we need to book first?

You don’t have to answer everything today.

I’m the researcher in our household, so I start digging into the options and figuring out what’s realistic. Then Bill and I talk through the choices and make the travel decisions together.

One decision leads to the next, and eventually that overwhelming Bucket List dream starts looking like an actual trip.

Step 6 – Put Something on the Calendar

“Someday” is very accommodating. It will happily let you postpone something forever.

A date changes things.

It doesn’t necessarily have to be a plane ticket. Maybe you decide that by November 1 you’ll research three options. Maybe you request the vacation time. Maybe you choose the month you want to travel.

For Antarctica, we already had something incredibly useful: cruise dates.

Suddenly we weren’t talking about going to Antarctica someday. We were figuring out whether we could be in Buenos Aires in time to board that particular ship. Since we were already going to be in Ecuador, it suddenly seemed feasible.

And that made the dream concrete.

Sapphire Princess sits anchored off the coast of Antarctica during our 17-night cruise. Seeing the ship from the water gives you a true sense of its size before stepping on board.

Step 7 – Take the Next Step—Not All the Steps

This may be the most important thing I’ve learned.

You don’t need to know how the entire trip is going to work before you start.

Take one step:

Set a flight alert.
Research three hotels.
Check the price of the experience you think you can’t afford.
Request the time off.
Start a travel fund.
Make one refundable reservation.

Then take the next step. Eventually, all those little decisions become a trip.

And once you’ve decided to go, my How to Plan a Trip: 7 Simple Steps for Busy People guide will help you organize the research, transportation, accommodations, and reservations without getting overwhelmed.

Kari and Bill stand together in front of a wooden fence with the massive Perito Moreno glacier behind them. Reaching Patagonia was one of the major experiences they checked off their travel bucket list.

Sometimes Your Travel Partner Needs More Time

I was clearly much more excited about Antarctica than Bill was.

Remember, he thought we’d already seen Alaska. Why spend all that extra money to see more snow and ice?

It took some convincing.

But Bill is a great travel partner that way. He knew how much I wanted to experience Antarctica, so he agreed to go even though it wasn’t nearly as high on his Bucket List as it was on mine.

Antarctica turned out to be far better than he expected. And part of what made him glad we went was simply seeing how happy I was to finally experience a place I had dreamed about visiting for decades.

Not every Bucket List dream has to matter equally to both of you. Sometimes taking turns making each other’s dreams happen is part of the adventure.

Bill wore his down puffer jacket for this cruise.

Your Bucket List Won’t Happen All at Once

You don’t need to figure out how you’re going to complete your entire Bucket List.

Just choose one dream.
Figure out what’s really standing in your way.
Research the things you’ve been assuming.
Find the version of the experience that works for you.
Put something on the calendar.

Our Antarctica trip started because I opened a brochure and thought, “Wait—what?” Sometimes that’s all it takes to turn “someday” into “we’re going.”

More Bucket List Resources

Here are some more posts to help you create your Bucket List, overcome the barriers holding you back, and finally start achieving your dreams!

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