Retire, Rejoice, and Roam: 18 Ways to Save on Travel

Admin • September 8, 2023

Retirement marks the beginning of a new chapter in life, a time to explore the world without the constraints of work schedules and deadlines. It’s an opportunity to indulge in the joys of travel. Still, concerns about finances can often put a damper on these dreams. 

The good news is that you can embark on incredible journeys without breaking the bank. Consider these 18 friendly and practical tips on how to save on retirement travel while still savoring every moment.

18 Ways to Save on Travel

These tips will help you save money without sacrificing your experiences. You’ve worked long and hard to get to this point, you deserve some well-deserved time off and enjoyment. 

1. Plan Ahead for Affordable Adventures

While spontaneous trips are fun, planning ahead can help you snag the best deals. Start by setting a travel budget to give you a clear picture of what you can afford. Research and choose your destinations well in advance. Good planning allows you to take advantage of early booking discounts and time to research local senior travel discounts and activities. Websites like TripAdvisor, Expedia, and Kayak can be your best friends when hunting for affordable flights, accommodations, and travel packages.

According to Frommer’s , you should consider these time frames when booking your airfare:

  • International: at least 6 weeks ahead
  • Domestic in summer: at least 47 days ahead
  • Domestic in autumn and winter: at least 62-69 days ahead
  • Domestic in spring: at least 90 days ahead

2. Embrace Off-Peak Travel

Retirement comes with the luxury of flexible schedules. Take advantage of this by traveling during off-peak seasons. Not only will you avoid the crowds, but you’ll also find significantly lower prices on flights, accommodations, and attractions. 

Imagine strolling through the charming streets of Europe or lounging on a serene beach without the hustle and bustle of peak-season tourists. Plus, you’ll have a more authentic experience, mingling with locals and enjoying a quieter atmosphere.

3. Hunt for Senior Travel Discounts

One of the perks of reaching your golden years is the abundance of senior discounts available. From transportation to accommodations to attractions, many businesses are eager to cater to the 55+ crowd. Don’t be shy—ask about senior discounts whenever you book anything. 

Some well-known organizations like AARP offer membership benefits that include exclusive travel discounts. Keep an eye out for special deals and promotions tailored to your age group, and carry your ID to take full advantage of these savings.

Did you know the National Park Service offers a lifetime pass for seniors aged 62 and older? The pass can be purchased for $80 and allows you and any companions traveling with you  (regardless of age) to gain entrance to over 2,000 recreation sites.

4. Explore Alternative Accommodations

While luxury hotels are lovely, there’s a world of alternative accommodations that can provide a unique and budget-friendly experience. Consider renting a cozy cottage, booking a stay in a local bed and breakfast, or even trying out a vacation rental through platforms like Airbnb or Vrbo

These options often come with kitchen facilities, allowing you to save on dining costs by preparing your meals with fresh local ingredients. If you are visiting an area where family or friends reside, consider staying with them for a few days.

5. Opt for Slow Travel

Rushing from one destination to another can quickly inflate your travel expenses. Embrace the concept of slow travel, where you spend more time in fewer places. Not only does this allow you to immerse yourself in the local culture entirely, but it also saves money on transportation costs. You’ll have the chance to explore hidden gems, connect with locals, and create memories beyond typical tourist experiences.

6. Consider Alternative Transportation

Renting a car can be expensive. Depending on where you visit, you can go sightseeing without a car. Consider alternative forms of transportation such as renting a bike, walking, ride-share companies, or public transportation.

Public transportation isn’t just cost-effective; it also offers a genuine way to experience a destination like a local. Many cities offer senior discounts on buses, trains, and trams. Instead of shelling out money for a car, hop on a bus and enjoy the scenery. 

7. Embrace Free and Low-Cost Activities

Entertainment and experiences don’t have to come with hefty price tags. Many destinations offer free or low-cost activities that allow you to explore the area without draining your retirement savings. 

Take leisurely walks through parks, attend local markets, visit museums on discounted days, or enjoy a beach day. These activities can provide just as much joy as more expensive options while keeping your budget intact. So before heading out on your trip, research the area you will be visiting to see what it offers.

8. Consider Group Travel

Traveling with a group can lead to significant savings on accommodations, transportation, and tours. Whether you’re exploring with friends, family, or fellow retirees, group travel often comes with bulk discounts that can add up to substantial savings. Additionally, group trips provide opportunities for shared experiences and memories, making your journeys even more special.

9. Be Mindful of Currency Exchange

If you’re traveling internationally, keep an eye on currency exchange rates. Fluctuations can impact the cost of your trip significantly. Consider exchanging money ahead of time or using credit cards that offer favorable exchange rates. It’s also wise to notify your bank of your travel plans to avoid any unexpected issues while using your cards abroad.

11. Use Travel Rewards and Miles

If you’ve been using credit cards that accumulate travel rewards or miles, now is the time to cash in on those benefits. These rewards can significantly reduce your travel expenses, from flights to accommodations. Check with your credit card provider to determine how to redeem your rewards for maximum value. You might even be surprised at how much of your trip can be covered through these rewards.

12. Consider Volunteer, Work Exchange, or Learn Abroad Programs

Retirement doesn’t necessarily mean you have to stop working altogether. Many destinations offer volunteer opportunities or work exchange programs that allow you to contribute your skills in exchange for free or discounted accommodations and meals. Not only can this save you money, but it also gives you a chance to connect with the local community on a deeper level.

Road Scholar offers educational travel programs that allow you to explore while learning. Whether you’re interested in music, art, golf, or birding, Road Scholars offers learning adventures for almost anything you might be interested in.

13. Pack Light and Smart

Packing efficiently can save you from costly baggage fees and the hassle of carrying around excess weight. Most airlines charge for checked bags, so try to fit everything into a carry-on suitcase. Additionally, packing versatile clothing items that can be mixed and matched can help you avoid over-packing. With less luggage, you’ll also find it easier to navigate public transportation and move around comfortably.

14. Use Travel Apps and Websites

Technology has made travel planning and budgeting easier than ever. There are countless travel apps and websites designed to help you find the best deals on flights, accommodations, and activities. 

Skyscanner , Google Flights , and Hopper are great for finding affordable flights, while Booking.com and Hotels.com offer competitive rates on accommodations. For activities and attractions, apps like Viator and GetYourGuide provide a variety of options at different price points.

15. Consider House Sitting

House sitting is another creative way to score free accommodation while traveling. Websites like TrustedHousesitters and HouseCarers connect travelers with homeowners who need someone to look after their property and pets while they’re away. In exchange for your services, you get to stay in a comfortable home without paying for lodging.

16. Research Local Dining Deals

Eating out can be a significant expense while traveling. Research local dining deals and happy hours to save money without sacrificing the culinary experience. Look for restaurants that offer fixed-price menus or lunch specials. Additionally, try street food and local markets, which often provide delicious and budget-friendly options.

17. Reconsider Souvenirs

While bringing back souvenirs can be a cherished part of travel, they can also add up quickly. Instead of spending money on trinkets that might gather dust, consider investing in experiences. Use your money to participate in activities you’ll remember fondly, like taking a local cooking class, going on a guided hike, or attending a cultural performance.

18. Stay Flexible and Open-Minded

Sometimes the best travel experiences come from being flexible and open to new opportunities. If you’re willing to adjust your plans based on last-minute deals, you might find yourself embarking on unexpected adventures that are both affordable and incredibly rewarding. Stay open-minded about destinations, travel dates, and even the type of accommodations you’re willing to try.

Let the Traveling Begin

Traveling in retirement doesn’t have to be a drain on your finances. With careful planning and a willingness to explore alternative options, you can embark on incredible journeys without sacrificing the quality of your experience. 

Schedule a meeting with Five Pine Wealth Management , and let us help you with your financial goals so you can pursue the retirement you deserve to enjoy. So, gear up, pack your sense of adventure, and get ready to create memories that will last a lifetime—without compromising your financial stability. Email us at info@fivepinewealth.com or give us a call at 877.333.1015. 

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April 1, 2026
Key Takeaways Taking early withdrawals from your 457 while letting your IRA grow can help you build a more balanced retirement plan. First responders with LEOFF or PERSI pensions can use their 457 plan as a bridge between retirement and traditional retirement account access. Rolling your 457 into an IRA at retirement removes penalty-free access to funds before age 59½. Many first responders in Washington and Idaho can realistically retire early. Thanks to pensions like WA LEOFF Plan 2 or ID PERSI, disciplined savings, and a long career of service, retiring at 55 is common. If you've been putting money into a 457 deferred compensation plan, you may be sitting on a sizable balance by the time you retire. As retirement approaches, you may be wondering: “What do I do with my 457 deferred compensation plan?” Many people unintentionally make a costly mistake. They roll their entire 457 balance into an IRA the moment they retire, thinking it's the right move. It might seem logical to combine accounts and keep things simple by moving everything into one IRA. However, this move eliminates a key advantage of a 457 plan: you lose penalty-free access to your money before age 59½. Let’s look at how this works and how you can set up your retirement accounts to stay flexible in your early retirement years. Early Retirement at 55: The Income Gap Problem Whether you're covered by LEOFF Plan 2 or PERSI, retiring around age 55 is entirely realistic. LEOFF Plan 2 members can retire with a full benefit at age 53 (or as early as 50 with 20 years of service and a reduced benefit). Idaho PERSI first responders can retire as early as 50 under the Rule of 80. The years between ages 55 and 59½ are a unique financial period. Your pension might cover a portion of your income needs, but often not everything. Social Security usually starts much later, and if most of your retirement savings are in IRAs, taking out money early can trigger penalties. This is where your 457 plan can be especially helpful. Unlike most retirement accounts, 457 plans let you take out money without the 10% early withdrawal penalty once you separate from service. This rule gives you a helpful bridge between retiring and the time when traditional retirement accounts become easier to access. You lose this benefit if you move your money into an IRA too soon. If your pension doesn't cover all your needs and you rolled everything into an IRA, you might face penalties or be unable to access your money. This early-retirement gap is exactly what good 457 planning can help you avoid. 457 Plan Withdrawal Rules Once you separate from service, whether you quit, get laid off, or retire, you can start taking 457 withdrawals from your 457 plan without a 10% penalty, no matter your age. Whether you're 55, 45, or even 35, the penalty doesn't apply. If you move money from your 401(k) or another account into your 457 and then withdraw it, that money loses the 457's penalty-free status. It’s now treated like IRA money and is subject to the 10% early withdrawal penalty. Only the original 457 money stays penalty-free. You will still owe ordinary income taxes on every withdrawal from a traditional 457, just like an IRA. The key difference is that you don’t have to pay the extra 10% penalty, which can save you thousands of dollars. Should I Roll My 457 Into an IRA? Now that you know the withdrawal rules, you might be asking yourself, “Should I roll my 457 into an IRA?” This is an important question, and the answer is: it depends. Usually, moving everything at once isn’t the best idea. Many people roll their entire 457 into an IRA at retirement because it’s often suggested as a way to “consolidate” and “simplify.” While there are legitimate reasons to roll some money into an IRA, doing it all at once at age 55 means you lose your penalty-free income bridge. A few of the advantages of rolling some money into an IRA are: More investment options Estate planning flexibility Roth conversion strategies A better strategy for most first responders retiring around 55 is to split your 457 balance into two parts, or “buckets,” each with its own role in your retirement plan: Bucket 1: Use your 457 account for early-retirement cash flow. This is the money you'll live on from age 55 to 59½ (or whenever your pension plus other income is sufficient). The 457 allows penalty-free withdrawals at any time, so you control both the amount and timing of distributions. This bucket bridges the gap until your other income starts coming in. Bucket 2: Roll into an IRA for long-term growth. Once you've determined how much you need for the early years, the rest can be rolled into a traditional IRA. The IRA bucket offers more investment choices and greater flexibility for estate planning or Roth conversion. Here’s an example: Jason is a firefighter retiring at 55 from Washington with $300,000 in his 457. His LEOFF Plan 2 pension covers most of his expenses but leaves a $1,500 per month gap. Instead of rolling everything to an IRA, he keeps $90,000 in the 457, which covers about five years of that gap at $1,500/month, and rolls the remaining $210,000 into a traditional IRA. The $90,000 stays accessible, penalty-free, and the $210,000 continues to grow. By the time he turns 59½, the IRA restrictions are gone, and he hasn't paid any unnecessary penalties. Deferred Compensation Rollover: What You Need to Know If you decide to roll part of your 457 into an IRA, the process is simple. You can move your 457 into another retirement account, like a traditional IRA, Roth IRA, 401(k), 403(b), or another 457 plan. There are a few things to keep in mind: Direct rollover is the best option. Have your 457 plan send the money straight to your IRA provider. If you get the check yourself, you have 60 days to put it into your IRA, and your employer will withhold 20% for taxes. If you miss the 60-day deadline, it will be treated as a taxable withdrawal. Roth conversions are possible, but watch the tax hit. You can convert your 457 to a Roth IRA, but be careful about taxes. If you do this soon after retiring, your income might be lower, which could make it a good time for a Roth conversion. Just make sure not to convert everything at once without checking the tax impact. Putting IRA money back into your 457 is usually not a good idea. Once IRA or other retirement plan money goes into your 457, it loses the penalty-free withdrawal benefit. Only do this if you have a very specific reason. Washington's DCP and Idaho's PERSI Choice 401(k) have their own rules. Washington state's Deferred Compensation Program (DCP) is administered by the Department of Retirement Systems (DRS). Idaho first responders may have the PERSI Choice 401(k) as well as other 457 plans. Be sure you know which accounts you're dealing with before starting any rollovers. Here are two helpful resources: Washington DRS (DCP information) Idaho PERSI A Note on Taxes and Required Minimum Distributions Even if you don’t pay a penalty, you still need to think about taxes. Every dollar you take from a traditional 457 counts as regular income for that year. If you're not careful with how much you withdraw, you could end up in a higher tax bracket, especially if your pension income is already high. This is one reason the bucket approach is helpful: you can control how much you withdraw from your 457 each year and keep your taxable income in a comfortable range. It’s also important to know that required minimum distributions from traditional 457 accounts begin at age 73 or 75, depending on when you were born. Beginning in 2024, Roth 457(b) accounts in governmental plans became exempt from RMDs under the SECURE 2.0 Act. This is another reason to think about whether Roth contributions or conversions are right for you. Talk With Us Before Rolling Your 457 The 457 plan is a powerful tool, and rolling it into an IRA without careful thought means losing the feature that makes it so valuable for retirees. At Five Pine Wealth Management, we help many first responders and public employees in Washington and Idaho. We know the ins and outs of WA LEOFF Plan 2, Idaho PERSI, deferred compensation plans, and the unique challenges of retiring earlier than most people. If you're within 10 years of retirement, or if you're already retired and want to make sure your money is set up the right way, we'd be happy to help. Call us at 877.333.1015 or email info@fivepinewealth.com. Before making a decision about your 457 rollover, let’s make sure your retirement accounts are working together as they should be. Frequently Asked Questions (FAQs) Q: Does a 457 rollover to an IRA count as a taxable event? A: A direct rollover from a traditional 457 to a traditional IRA is not taxable. Q: Can I take money out of my 457 while I'm still working? A: Generally, no. 457 plans don't allow withdrawals while you're still employed, except for very limited exceptions (such as an unforeseeable emergency). The penalty-free access kicks in once you separate from service. Q: What happens to my 457 if I roll it into an IRA and then need money before age 59½?  A: You lose the 457's penalty-free protection. If you roll 457 funds into a traditional IRA, you lose the flexibility of penalty-free early withdrawals and become subject to a 10% early withdrawal penalty
March 26, 2026
Key Takeaways Your retirement withdrawal order affects your taxes, Medicare premiums, and how long your money lasts. The traditional sequence (taxable → tax-deferred → Roth) is a useful starting point, but it isn't right for everyone. Drawing from multiple account types at the same time can help you manage your tax bracket year to year. Roth conversions in the early years of retirement can reduce your future RMD burden. If you're approaching retirement, there's a good chance you've spent decades doing everything right. You saved consistently, maxed out your accounts, and built a solid nest egg across multiple account types. But once retirement arrives, the question shifts. It's no longer "How do I save more?" It's "Which account do I pull from first?" It's a question most people haven't thought much about — and understandably so. You've spent years focused on building. But how you draw down your accounts matters just as much as how you built them up. Why Your Retirement Withdrawal Order Matters It's tempting to assume you can just pull from whichever account is most convenient. And honestly, in the short term, that works fine. Over a 20- or 30-year retirement, though, the sequence of your withdrawals shapes your tax bracket every single year, your Medicare premiums, the growth potential of your remaining accounts, and what you eventually leave behind for your family. Your retirement accounts aren’t taxed the same way: Traditional 401(k) or IRA : Tax-deferred, owing ordinary income tax on withdrawals Roth IRA : Tax-free, no taxes on qualified withdrawals Taxable brokerage account : More favorable long-term capital gains rate when holding investments for a year or more A thoughtful withdrawal strategy draws from each bucket in a way that keeps your taxable income as smooth and low as possible throughout retirement. The Traditional Withdrawal Order (and When It Makes Sense) For many retirees, the conventional wisdom goes like this: 1. Start with taxable accounts. Brokerage accounts and savings are often tapped first because the growth in these accounts is taxed annually anyway, and using them first lets your tax-advantaged accounts continue to grow undisturbed. 2. Move to tax-deferred accounts next. Your traditional IRA, 401(k), or 403(b) accounts are next in line. Withdrawals here are taxed as ordinary income, so drawing on them in a thoughtful, measured way helps you avoid unnecessary jumps into higher tax brackets. 3. Preserve Roth accounts for last. Roth IRAs aren't subject to Required Minimum Distributions (RMDs) during your lifetime, and withdrawals are tax-free. Letting your Roth sit and grow as long as possible tends to pay off, both for you and for any heirs who may inherit it. This framework is a reasonable starting point, and for some retirees, it works well. But it's not a universal rule. Where the Traditional Order Falls Short Here's a scenario we see fairly often. A client retires at 63 with most of their savings in a traditional IRA. They draw from their taxable accounts first — totally reasonable. But by the time they hit 73, their IRA has grown large enough that the required distributions push them into a higher tax bracket than they were in at the start of retirement. Throw in Medicare surcharges (called IRMAA), and what felt like a smart, conservative strategy in their 60s has quietly created a real tax burden a decade later. That's why we often recommend a more nuanced approach — one that considers what your tax picture looks like across your entire retirement, not just in the first year or two. Tax Diversification and the Case for Blending A blended decumulation strategy, rather than a strict withdrawal sequence, often serves retirees better than following one account type at a time. The goal is to keep your taxable income in a range that helps you stay below the thresholds that trigger higher tax brackets, IRMAA surcharges, and heavier taxation on Social Security benefits. Here's a practical example: if your expenses can be covered by a mix of Social Security and modest IRA withdrawals that keep you in the 12% tax bracket, you might also consider doing some Roth conversions that same year. You'd move money from your traditional IRA to your Roth while your tax rate is still low. Yes, you pay the tax now. But from that point on, your Roth grows tax-free — and your future RMDs shrink. It takes careful planning and realistic income projections, but for many retirees, it's one of the most effective tools available. The Behavioral Side of Withdrawal Strategy We've covered the math. But there's a human side to this that doesn't get talked about enough. A lot of retirees feel hesitant to touch certain accounts, especially ones they spent decades carefully building. We've worked with clients who had more than enough saved but were pulling too little — simply because spending down their IRA felt uncomfortable. That emotional hesitation sometimes led them to draw from the wrong accounts for the wrong reasons. Having a clear, written withdrawal plan takes a lot of that pressure off. When you know which account you're pulling from and why, you're far less likely to second-guess yourself when markets get bumpy or make reactive moves that throw off an otherwise solid plan. Think of it as guardrails: a defined spending amount, a clear account order, and a scheduled check-in to revisit when things change. There’s No One-Size-Fits-All Answer The right withdrawal sequence depends on things specific to you: how much you have and where it's held, your expected income in retirement, when you plan to take Social Security, whether you have a pension, how your state treats retirement income, and what you'd like to leave behind. A strategy that's a perfect fit for one person can create real headaches for another. That's why this is one of the first things we talk through with clients who are getting close to retirement — and one we revisit as things change. If you're within five to ten years of retirement and haven't mapped out a withdrawal plan yet, now is a good time to start. Before RMDs kick in is often when you have the most flexibility to plan. We'd love to walk through what this looks like for your specific situation. Reach out anytime at info@fivepinewealth.com or call 877.333.1015. Frequently Asked Questions (FAQs) Q: Does my withdrawal order change if I have a pension? A: Yes, it can. A pension provides guaranteed income, so you may already be covering a good chunk of your expenses before touching your investment accounts. That changes how aggressively you need to draw from tax-deferred accounts — and may create more room for Roth conversions early in retirement. Q: How does Social Security timing affect my withdrawal strategy? A: If you delay Social Security to boost your monthly benefit, you'll need to cover living expenses from your portfolio in the meantime. That gap period is often a smart time to draw down traditional IRA balances at a lower tax rate, before Social Security income pushes your taxable income higher. Q: Can my withdrawal order affect my Medicare premiums?  A: It can. Medicare uses your income from two years prior to set your Part B and Part D premiums. A large IRA withdrawal that bumps your income above certain thresholds could mean higher premiums (IRMAA surcharges) two years down the road. Keeping those thresholds in mind when planning withdrawals can help you avoid some unwelcome surprises. Five Pine Wealth Management is a fee-only, fiduciary financial planning firm based in Coeur d'Alene, Idaho. We work with individuals and families across the country who want thoughtful, personalized guidance — without the conflicts of interest that come with commission-based advice.