Bucket List Planning
You worked hard to get here. Now it's time to plan the retirement you actually dreamed about.
Your Retirement. Your Rules.
When you're young, you have time and health... but no money. When you're middle-aged, you have money and health... but no time.
When you're ready to retire, you want all three. This 8-page guide helps you plan the experiences that matter most, without jeopardizing your financial security.
- 10 interest categories to spark ideas
- Brainstorming questions you haven't thought of
- A prioritization framework that actually works
- A complete Route 66 sample trip, step by step
Four Steps to Your Best Retirement
Explore Your Interests
Travel, relationships, career goals, giving, entertainment, adventure, creativity, education, hobbies, volunteering. Ten categories to help you think bigger.
Brainstorm What Matters
Guided questions to uncover what you really want. Childhood dreams, foods to try, places to visit, people to reconnect with. Your list will be different from everyone else's.
Prioritize and Organize
Seasonal lists, "this year's" bucket list, combining categories for efficiency. Learn how to turn a wish list into a real plan with timelines and milestones.
Try One (With an Example)
A complete walkthrough of planning a Route 66 road trip. Dates, costs, lodging, vehicle, and the little details most people forget. Use it as a template for any goal.
Ready to Start Your Bucket List?
This 8-page guide is yours. No email required. No strings attached. Just practical ideas to help you plan the retirement you worked so hard for.
8 pages. Takes about 15 minutes to read.
Quick Answers
How do I make a retirement bucket list?
Start by brainstorming across interests like travel, family, giving, learning and adventure, then rank what matters most and give each goal a season or a date. Try one item first, like a road trip. Before a big trip, check that your health coverage travels with you and that your income and budget can carry the plan.
Key facts
- Medicare usually doesn't cover health care while you're traveling outside the U.S., with a few exceptions. Source: Medicare.gov
- Part B may cover medically necessary care on a cruise ship that is in a U.S. port or no more than 6 hours away from one. Source: Medicare.gov
- Medigap Plans C, D, F, G, M and N cover 80% of foreign travel emergency care, up to plan limits. Plans C and F are open only to people eligible for Medicare before 2020. Source: Medicare.gov
- Medicare drug plans don't cover prescription drugs filled outside the U.S. Source: Medicare.gov
- Route 66 was established on November 11, 1926, and runs about 2,448 miles through eight states, so 2026 is its 100th year. Source: U.S. Route 66 Centennial Commission
Bucket List Questions, Answered
What should I put on my retirement bucket list?
Start with ten areas: travel, relationships, career, giving, entertainment, adventure, creativity, education, hobbies and volunteering. Ideas range from all 50 states or all 30 Major League ballparks to writing the book, a scholarship gift, or time at a pet rescue. Ask what you still want to accomplish, what you dreamed of as a kid, and who you want to share it with. Your list may look different from your spouse's, and your ideas together can lead to new ones.
How do I prioritize and schedule my bucket list?
Ask what each goal will cost in time and money, who will do it with you, how much it matters, what's in the way, and whether it has a deadline or a season. Then give it a time and a place: a seasonal list, a few goals for the next twelve months, or one bucket-list weekend a month for smaller items. Goals with steps and dates get done.
Does Medicare cover me when I travel outside the U.S.?
Usually not. Medicare generally doesn't cover health care outside the U.S., with a few exceptions, such as some care on a cruise ship in a U.S. port or within 6 hours of one. Medigap Plans D, G, M and N (and C and F, for people eligible for Medicare before 2020) cover 80% of foreign travel emergency care, up to plan limits. Medicare drug plans don't cover prescriptions filled abroad. If you have a Medicare Advantage plan, ask it about travel coverage before you go.
When is Route 66's 100th anniversary?
Route 66 was established on November 11, 1926, so it turns 100 in 2026. The historic route runs about 2,448 miles from Chicago to Santa Monica through eight states, and Arizona's stretch includes Holbrook, Winslow, Seligman and Kingman. Many travelers allow about two weeks, and late spring or early fall avoids the worst desert heat. Price the trip before you book: hotels, meals, gas and any one-way rental.
What should I check before a big bucket-list trip?
At home, arrange pet care, plant watering and someone to keep an eye on the house, set bills to pay while you're away, and reschedule any medical appointments. Then protect the list: check that your health coverage travels, that the trip fits next to your regular expenses, that your income is steady enough to plan around, and what your plan is if your health changes.
Sources
- Medicare.gov: Travel outside the U.S.
- Medicare.gov: Compare Medigap plan benefits
- Medicare.gov: Choosing a Medigap Policy
- U.S. Route 66 Centennial Commission: Media resources
General education. Medicare information here does not recommend any specific plan or insurance company; check your own plan's travel rules before you go.
The full guide goes deeper. Get the guide above.
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