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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You've Maxed Your 401(k). Now What? A Strategic Guide for High Earners

January 26, 2026
Key Takeaways High earners maxing out 401(k)s at $24,500 are only saving about 8% of a $300,000 income in their primary retirement account. The mega backdoor Roth strategy can increase total 401(k) contributions to $72,000 annually with tax-free growth. A comprehensive approach can create nearly $3 million in additional retirement wealth over 20 years. It's 2026. You're checking all the boxes. You're earning upwards of $300,000 annually, and you're maxing out your 401(k) every year. You've reached the $24,500 contribution limit and feel confident about securing your financial future. Then you realize $24,500 represents less than 8% of your income. Over 20 years, this gap adds up to millions in lost opportunity. Thankfully, you're not stuck with the basic 401(k) playbook. There are sophisticated strategies beyond your contribution limit. 5 Strategic Moves for High Earners with Maxed-Out 401(k)s Here are five sophisticated strategies that can help you build wealth beyond your basic 401(k) contributions. All projections assume a 7% average annual return and are estimates for illustrative purposes. 1. Mega Backdoor Roth Contributions If your employer's 401(k) plan allows after-tax contributions, this could be your biggest opportunity. With employee contributions, employer match, and after-tax contributions, the combined 401(k) limit for 2026 is $72,000 ($80,000 if you're 50 or older). The mega backdoor Roth works because you immediately convert those after-tax contributions into a Roth account, where they grow tax-free forever. The catch: Not all employers offer this option. You need a plan that permits after-tax contributions and in-service Roth conversions. The impact: The available space for after-tax contributions depends on your employer match. With a typical employer match of 3-6% (roughly $10,000-$21,000 on a $350,000 salary), you could contribute approximately $26,500-$37,000 annually. At 7% average returns over 20 years, this creates approximately $1.1-$1.5 million in additional tax-free retirement savings. 2. Donor-Advised Funds for Charitable Giving If you're charitably inclined, donor-advised funds (DAFs) offer a way to bunch several years of charitable contributions into one tax year, maximizing your itemized deductions while still spreading your giving over time. You get an immediate tax deduction for the full contribution, but you can recommend grants to charities over many years. The funds grow tax-free in the meantime. The catch: Once you contribute to a DAF, the money is irrevocably committed to charity. You can't get it back for personal use. The impact: Contributing $50,000 to a DAF in a high-income year (versus giving $10,000 annually) can create immediate federal tax savings of $15,000-$18,500 while still allowing you to support the same charities over five years. 3. Taxable Brokerage Accounts with Tax-Loss Harvesting Once you've maximized tax-advantaged accounts, strategic taxable investing becomes your next move. The key is working with a financial advisor who implements systematic tax-loss harvesting throughout the year. Tax-loss harvesting involves selling investments at a loss to offset capital gains elsewhere. Done strategically, this can save thousands in taxes annually. The catch: Long-term capital gain rates (0%, 15%, or 20%) are lower than ordinary income tax rates, but you're still paying taxes on gains. It's less tax-efficient than retirement accounts, but far better than ignoring tax optimization. The impact: For high earners in the 35-37% ordinary income brackets, the difference between long-term capital gains (20%) and ordinary rates is significant. Effective tax-loss harvesting on $50,000 in annual gains over 20 years could save $150,000+ in taxes. 4. Health Savings Account (HSA) Triple Tax Advantage HSAs offer a unique triple tax benefit: tax-deductible contributions, tax-free growth, and tax-free withdrawals for qualified medical expenses. With 2026 contribution limits of $4,400 for individuals and $8,750 for families, this adds another powerful layer to your strategy. You can invest HSA funds just like an IRA and let them grow for decades. After age 65, you can withdraw the funds for any purpose, medical or otherwise. The catch: You must have a high-deductible health plan to qualify for an HSA. After age 65, non-medical withdrawals are taxed as ordinary income (like traditional IRA distributions), but you still benefit from the upfront deduction and decades of tax-free growth. The impact: Contributing the family maximum ($8,750) annually for 20 years at a 7% average annual return creates approximately $355,000-$360,000 in tax-advantaged savings. 5. Backdoor Roth IRA Contributions Not to be confused with mega backdoor Roth contributions! Even if your income exceeds the Roth IRA contribution limits, you can still fund a Roth through the backdoor method: make a non-deductible contribution to a traditional IRA, then immediately convert it to a Roth IRA. The catch: If you have existing traditional IRA balances, the pro-rata rule complicates things. You may want to consider rolling those funds into your 401(k) first if your plan allows. The impact: Contributing $7,000 annually through the backdoor Roth for 20 years at 7% average annual return creates approximately $285,000-$290,000 in tax-free retirement savings. What Compounding These Strategies Looks Like Over 20 Years Let’s look at approximate outcomes based on a 7% average annual return. 401(k) Only: Annual contribution: $24,500 Total after 20 years: ~$1M 401(k) + Mega Backdoor Roth: Annual contribution: $72,000 Total after 20 years: ~$3M Note: Mega backdoor Roth space varies based on your employer's match. These calculations assume you're maximizing the total annual limit. Comprehensive Approach (under age 50): Mega Backdoor Roth: ~$3.0M HSA: ~$350K-$360K Backdoor Roth IRA: ~$285K-$290K Strategic taxable investing with tax-loss harvesting Total retirement savings: ~$3.6M+, plus taxable investments Comprehensive Approach (ages 50-59): With higher contribution limits and catch-up contributions, total retirement savings can reach ~$4M+ over 20 years. Comprehensive Approach (ages 60–63 with enhanced catch-up contributions) Higher contribution limits during peak earning years allow for meaningful acceleration of retirement savings. The exact impact depends on timing, contribution duration, and existing balances. The Bottom Line The difference between stopping at your basic 401(k) and implementing a comprehensive strategy can approach $3 million or more in additional retirement wealth over time. Why Strategic Coordination Matters These aren't either/or decisions. The most effective approach coordinates multiple strategies while ensuring everything works together. At Five Pine Wealth Management , we help high-earning clients build comprehensive plans that go beyond the 401(k). We coordinate your employer benefits, tax strategies, and investment accounts to create a cohesive approach that maximizes your wealth-building potential. This requires working across several areas: Analyzing your employer's 401(k) plan for mega backdoor Roth opportunities Implementing systematic tax-loss harvesting in taxable accounts Coordinating Roth conversions and backdoor contributions Optimizing your HSA as a long-term retirement vehicle Ensuring charitable giving strategies align with your tax situation Maximizing catch-up contributions when you reach milestone ages As fiduciary advisors, we're legally obligated to act in your best interest. That means we're focused on strategies that serve your goals, not products that generate commissions. Ready to see what's possible beyond your 401(k)? Email us at info@fivepinewealth.com or call 877.333.1015 to schedule a conversation about your specific situation. Frequently Asked Questions (FAQs) Q: Does my employer's 401(k) plan automatically allow mega backdoor Roth contributions? A: No. You need a plan that permits after-tax contributions and in-service conversions to Roth. Check with your HR department. Q: How do I prioritize which investment strategies to use? A: Generally, maximize employer match first (it's free money), then fully fund your 401(k), explore Mega Backdoor Roth if available, max out your HSA, consider backdoor Roth IRA contributions, and then move to taxable accounts with tax-loss harvesting. We can help determine the right sequence for your circumstances.

What's the Best Asset Allocation for Someone 10 Years Away from Retirement?

December 22, 2025
Key Takeaways Your guaranteed income sources (pensions, Social Security) matter more than your age when deciding allocation. Retiring at 65 doesn't mean your timeline ends. You likely have 20-30 years of investing ahead. Think in time buckets: near-term stability, mid-term balance, long-term growth. You're 55 years old with over a million dollars saved for retirement. Your 401(k) statements arrive each month, and you find yourself questioning whether your current allocation still makes sense. Should you be moving everything to bonds? Keeping it all in stocks? Something in between? There's no single "correct" asset allocation for everyone in this position. What works for you depends on factors unique to your situation: your retirement income sources, spending needs, and risk tolerance. Let's look at what matters most as you approach this major life transition. Why Asset Allocation Changes as Retirement Approaches When you’re 30 or 40, your investment timeline stretches decades into the future. When you’re 55 and looking to retire at 65, that equation changes because you’re no longer just building wealth: you’re preparing to start spending it. You need enough growth to keep pace with inflation and fund decades of retirement, but you also need stability to avoid the need to sell investments during market downturns. At this point, asset allocation 10 years before retirement is more nuanced than a simple “more conservative” approach. Understanding Your Actual Time Horizon Hitting retirement age doesn't make your investment timeline shrink to zero. If you retire at 65 and live to 90, that's a 25-year investment horizon. Think about your money in buckets based on when you'll need it: Time Horizon Investment Approach Example Needs Short-Term (Years 1-5 of Retirement) Stable & accessible funds Monthly living expenses, healthcare costs, and early travel plans Medium-Term (Years 6-15) Moderate risk; balanced growth Home repairs, care and income replacement, and helping grandchildren with college Long-Term (Years 16+) Growth-oriented with a Long-term care expenses, decades-long timeline legacy planning, and extended longevity needs This bucket approach helps you think beyond simple stock-versus-bond percentages. Asset Allocation 10 Years Before Retirement: Starting Points While there's no one-size-fits-all answer, here are some reasonable starting frameworks: Conservative Approach (60% stocks / 40% bonds) : Makes sense if you have minimal guaranteed income or plan to begin drawing heavily from your portfolio upon retirement. Moderate Approach (70% stocks / 30% bonds) : Works well for those with some guaranteed income sources, moderate risk tolerance, and a flexible withdrawal strategy. Growth-Oriented Approach (80% stocks / 20% bonds) : Can be appropriate if you have substantial guaranteed income covering basic expenses and the flexibility to reduce spending temporarily as needed. Remember, these are starting points for discussion, not recommendations. 3 Steps to Evaluate Your Current Allocation Ready to see if your current allocation still makes sense? Here's how to start: Step 1: Calculate your current stock/bond split. Pull your recent statements and add up everything in stocks (including mutual funds and ETFs) versus bonds. Divide each by your total portfolio to get percentages. Step 2: List your guaranteed retirement income. Write down income sources that aren't portfolio-dependent: Social Security (estimate at ssa.gov), pensions, annuities, rental income, or planned part-time work. Total the monthly amount. Step 3: Calculate your coverage gap. Estimate monthly retirement expenses, then subtract your guaranteed income. If guaranteed income covers 70-80%+ of expenses, you can be more growth-oriented. Under 50% coverage means you'll need a more balanced approach. When to Adjust Your Allocation Here are specific triggers that signal it's time to review and potentially adjust: Your allocation has drifted more than 5% from target. If you started at 70/30 stocks to bonds and market movements have pushed you to 77/23, it's time to rebalance back to your target. Your retirement timeline changes significantly. Planning to retire at 60 instead of 65? That's a trigger. Every two years of timeline shift warrants a fresh look at your allocation. Major health changes occur. A serious diagnosis that changes your life expectancy or healthcare costs should prompt an allocation review. You gain or lose a guaranteed income source. Inheriting a pension through remarriage, losing expected Social Security benefits through divorce, or discovering your pension is underfunded. Market volatility affects your sleep. If you're checking your portfolio daily and feeling genuine anxiety about normal market movements, your allocation might be too aggressive for your comfort, and that's a valid reason to adjust. Beyond Stocks and Bonds Modern retirement planning involves more than just deciding your stock-to-bond ratio. Consider international diversification (20-30% of your stock allocation), real estate exposure through REITs, cash reserves covering 1-2 years of spending, and income-producing investments such as dividend-paying stocks. The Biggest Mistake: Becoming Too Conservative Too Soon Moving everything to bonds at 55 might feel safer, but it creates two significant problems. First, you're almost guaranteeing that inflation will outpace your returns over a 30-year retirement. Second, you're missing a decade of potential growth during your peak earning and saving years. The difference between 60% and 80% stock allocation over 10 years can mean hundreds of thousands of dollars in portfolio value. Being too conservative can be just as risky as being too aggressive, just in different ways. Questions to Ask Yourself As you think about your asset allocation for the next 10 years: What percentage of my retirement spending will be covered by Social Security, pensions, or other guaranteed income? How flexible is my retirement budget? Could I reduce spending by 10-20% during a market downturn? What's my emotional reaction to seeing my portfolio drop 20% or more? Do I plan to leave money to heirs, or is my goal to spend most of it during retirement? Your honest answers to these questions matter more than your age or any generic allocation rule. Work With Professionals Who Understand Your Complete Picture At Five Pine Wealth Management, we help clients work through these decisions by looking at their complete financial picture. We stress-test different allocation strategies against various market scenarios, coordinate withdrawal strategies with tax planning, and help clients understand the trade-offs between different approaches. If you're within 10 years of retirement and wondering whether your current allocation still makes sense, let's talk. Email us at info@fivepinewealth.com or call 877.333.1015 to schedule a conversation. Frequently Asked Questions (FAQs) Q: What is the rule of thumb for asset allocation by age? A: Traditional rules like "subtract your age from 100" are oversimplified. Your allocation should be based on your guaranteed income sources, spending flexibility, and risk tolerance; not just your age. Q: Should I move my 401(k) to bonds before retirement? A: Not entirely. You still need growth to outpace inflation. Gradually shift toward a balanced allocation (60-80% stocks, depending on your situation) and keep 1-2 years of expenses in stable investments. Q: What's the difference between stocks and bonds in a retirement portfolio?  A: Stocks provide growth potential to keep pace with inflation but come with volatility. Bonds offer stability and income but typically don't grow as much.