Last updated: November 6, 2026 by Anthony Watson, CFA, CFP®, RICP® and Michael Nemick, CFP®

KEY TAKEAWAYS

• Bucket lists usually stall over timing, not money. Without a date or a place in your spending plan, the items keep getting pushed back by more “sensible” expenses.
• Sort the list by energy, not by wish. Retirement spending tends to be highest in the active go-go years, so do the most physical items and anything tied to health or loved ones’ timing first.
• Price it, date it, and let it flex. Giving each item a full cost and a target year, then building it into a spending plan with risk-based guardrails, lets strong years fund the big items and tougher years shift to smaller ones.

Most of us have a retirement bucket list, whether it’s written down or just lives in our heads. Maybe it’s the trek you’ve talked about for a decade. The trip to Japan you keep saying you’ll take “when things settle down.” A summer with the grandkids before they’re too old to want one. Learning to sail. Seeing the friends who moved across the world.

Yet every year, something else pops up that seems to be a more “sensible” way to spend that money. The roof needs replacing, or one of your kids needs help with a down payment, and so the list just keeps sliding to the bottom of the pile.

As retirement planning specialists, our job is to help you get the most life out of what you’ve built, not just protect the balance. We understand that you didn’t build what you have by spending on impulse. But after decades of saving, the risk isn’t usually that the trip costs too much, but that the window closes while the list sits in a notes app.

So this guide is about making sure those retirement bucket list items actually happen: how to sort them, price them, and plan for them. First, it helps to understand why so many lists stall.

4 Reasons Retirement Bucket List Items Go Unchecked

Retirement bucket lists usually go unchecked for four reasons: the items have no dates, spending saved money feels wrong, spouses have different lists, and health and energy change over time. For households who’ve saved diligently, the reason is rarely the money itself.

1. No dates attached

When an item doesn’t have a year, there’s no moment when it has to be decided, so it’s not unusual that it just keeps getting pushed back.

2. Spending saved money feels wrong

You spent decades building the habit of putting money away, and retirement asks you to reverse that habit. Even when the numbers say you’re fine, pulling a big chunk out for a trip can feel irresponsible. That reluctance is also a form of anxiety over spending in retirement, which is more common than you might think.

3. Spouses with different lists

Two people can share a house for 35 years and still picture different retirements. One list has airports on it, while the other has a garden and a weekly tee time. When neither list is written down, the default compromise is often to do neither. It’s one of the things couples get wrong about retirement, and it’s easier to fix before the first trip than after.

4. Health changes the options over time

Most of us won’t wake up one day unable to travel. It’s more gradual than that. The long flights get a little harder, the mountain trails a little steeper, or the recovery a little longer. That’s not a reason to worry, just a reason to do the most physical items first, while they’re easiest to enjoy.

Anthony Watson, CFA, CFP®, RICP®

Most of the bucket lists people share with me don’t stall because of money. It’s because nobody ever gave them a year and a place in the plan. Once a trip is in the plan, booking it stops feeling like a splurge and starts feeling like following through.

What Makes a Retirement Bucket List a Plan?

A retirement bucket list becomes a plan once each item has three things: a cost, a target year, and a place in your spending plan. Without those, it stays a wish list. It’s real enough to talk about, but never real enough to make it into the budget.

A cost: You estimate that a trip might cost something, but that’s different from actually doing the research to see the full price. Most items or experiences end up costing more than the headline number. Knowing the full price upfront lets you say yes without second-guessing things later.

A target year: This is the piece most lists are missing. An item with no year never competes with anything, so it never wins. Giving it a specific year, even a rough one you change later, puts it on the same calendar as everything else in your life.

A place in your spending plan: A bucket list item should be part of your retirement spending plan, the document that turns your vision for retirement into dollars, year by year. It’s also part of a bigger strategy: knowing how much you can sustainably withdraw each year, and how to draw it in a way that keeps your taxes and your long-term plan in check. When the list lives inside that plan, a big trip year becomes something you planned for instead of something you have to justify.

Most people have the first one in their heads, rarely the second, and almost never the third. So here’s how you can start putting a price and a year on your bucket list items…

How to Put a Price and a Year on Each Bucket List Item

When you price an item on your bucket list, think about the full cost. When it comes to a travel experience for example, that could include:

• The experience itself: airfare, lodging, guides, and perhaps build in any extra days you may want once you’re there.
• Travel medical coverage: Medicare generally doesn’t cover care outside the U.S., so a travel medical policy may belong in the price of any trip abroad.
• Taxes: depending on where it comes from, the money you take out for a trip might be taxed if taken from a retirement account. So ensure you plan ahead to know which type of account you’ll be taking the money from in case you need to set aside extra for taxes.
• Ongoing costs: a vacation home, a boat, or club memberships keep billing after the first year, so they belong in your plan as yearly costs, not one-time items.

Then give each item a target year, although it doesn’t have to be exact. A rough year you adjust later is far better than no year at all, because it gives the item a real spot on your calendar. But which year? That’s where the shape of retirement spending comes in.

How the Retirement Spending Smile Affects Your Retirement Bucket List

Retirement spending isn’t flat. Research on retirees shows it’s usually highest in the early, active years, when people travel and do the most. It eases off through the middle years, then can tick back up late in life as health costs rise. Researchers call this the “retirement spending smile.”

Financial planner Michael Stein gave those three stretches of retirement names in his book, The Prosperous Retirement: Guide to the New Reality. Here's how they compare:

Plans that ignore this curve and assume flat spending are one reason retirement plans may be too conservative for careful savers. Your bucket list follows the same curve, so it makes sense to plan the two together.

How to Sort a Retirement Bucket List by Energy, Not by Wish

Sort your bucket list by the energy each item needs, not simply by how badly you want it. Assign every item to the go-go, slow-go, or no-go phase. The most physical items go first, and the gentler ones can wait.

Three questions do most of the sorting:

• Does it need stamina, altitude, or long flights? Put it in the go-go column.
• Does it depend on someone else’s timing? Grandkids who are 9 and 12 won’t be 9 and 12 again. Aging parents and old friends have their own clocks too, so consider putting those higher on the list.
• Could you still enjoy it with less mobility? A river cruise, a long train trip, or a season of concert tickets works just as well at 80 as at 66, so those could be items that can wait.

Here’s an example of sorting your retirement bucket list items accordingly:

The more an item depends on your body or someone else’s calendar, the earlier it goes.

How to Flex Your Bucket List With the Market

While there could be a down year in the market at any given time, you don’t need a perfect market to check items off your bucket list.

With risk-based guardrails, you can make adjustments based on how your plan is actually going. You start at a spending level that leaves the plan with a comfortable margin of safety, and you set the rules for adjusting in advance. Strong years can fund the bigger items, and tougher years can shift you to lighter, less expensive ones without shelving the list entirely.

Here’s an example of how the rules can be set:

• Withdrawal rule: Begin by spending an amount that leaves your plan with an 80% probability of success.
• Prosperity rule (upper guardrail): If your plan’s probability of success rises to about 99%, increase spending back to the level associated with an 80% probability of success.
• Preservation rule (lower guardrail): If your plan’s probability of success falls to 60%, decrease spending back to the level associated with an 80% probability of success.

Because the rules are agreed before the market moves, you’re not making decisions in the moment based on a headline or a gut feeling.

This approach is especially well suited to a bucket list. A list that’s front-loaded into your go-go years makes for lumpy spending: a $15,000 trip one year, a lighter year after. Rules based only on a withdrawal rate can read that big year as a warning sign. A risk-based approach sees it for what it is, a planned expense that’s already accounted for in the plan.

A tough year simply changes which item you do, not whether you do one.

Two things can help make this work:

• Keep a “bench” of smaller items. A weekend trip, concert tickets, a special cooking class. These are ready to step in during a down year, so the list keeps moving.
• Don’t let the market override your energy. A go-go item can slide a year, but not five. If a trip depends on your health or on a grandchild’s age, setting aside cash for next year’s items in advance can protect it from a bad market right before you go.

This flexibility is also what lets you spend more overall. Because you’ve agreed in advance to trim spending in a pessimistic scenario, you can often start with more income than a rigid rule like the 4% rule would allow. As retirement planning specialists, we see it again and again: the bigger risk for careful savers isn’t running out of money. It’s reaching the later years with the money still there and the list still unchecked.

A Sample Retirement Bucket List Plan

Here’s what a priced, dated, and sorted bucket list might look like for a hypothetical couple retiring in 2027, including a column to show a scenario of potential options in a tough market year. The prices are rough estimates for illustration only.

Notice how the plan bends: big items early, gentler ones later, and room to adjust when the market doesn’t cooperate.

Turn Your Bucket List Into a Plan You’ll Actually Use

A retirement bucket list isn’t really just about the trips. It’s about the life you saved all those years to have. The goal isn’t to spend recklessly, or to spend everything. It’s to make sure the things that matter most to you actually happen, in the years when you can enjoy them most.

Pricing the list, putting a year on each item, and building it into a spending strategy that flexes with the market turns “we should do that sometime” into a date on the calendar. It also takes the guilt out of it, because the decision has already been made with the full picture in view.

If you’d like to see how much of your own list your plan can fund, and when, that’s exactly what our complimentary Thrive Assessment can help you do. As flat-fee retirement planning specialists, we never take a percentage of your savings, and our job is to show you what you can actually spend to help make your goals a reality.

Frequently Asked Questions About Retirement Bucket Lists