At Strategic Financial Services, we talk often about getting your decade — that special time when your career winds down and your life opens up. After years of working hard, raising families, and saving diligently, this next chapter is about something different: freedom.
Freedom to travel.
Freedom to explore.
Freedom to live your days by your own design.
For many of our clients, this new stage of life means saying yes to experiences — not just things. It’s the decade of long-postponed trips, reconnecting with friends who live far away, and discovering the world while you have both the time and health to truly enjoy it. With more freedom to explore, you can finally travel because you want to, not just when you can. Imagine savoring a sunset in Santorini, trekking through Patagonia, cruising the Caribbean, or simply strolling through charming villages in Tuscany — all at your own pace, with the luxury of time.
But while this is an exciting phase, it’s also a time to be thoughtful. The same smart financial planning that helped you reach retirement can also help make your travels worry-free. That’s why we encourage every traveler — especially retirees — to consider travel insurance as part of their trip planning. A travel insurance policy can help protect your trip investment if plans change unexpectedly, cover emergency medical care while abroad, and provide peace of mind that lets you fully enjoy the adventures ahead. Whether your decade takes you across the country or across the world, we’re here to help you approach it confidently — balancing joy and security every step of the way.
From Our Offices in Massachusetts and Rhode Island
We love helping our clients make the most of their financial freedom. Whether you’re planning a major trip or mapping out your broader retirement goals, our team can help you put a strategy in place so you can truly get your decade — the way you’ve always imagined it.
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If travel is on your horizon, consider incorporating insurance into your retirement travel budget. A little preparation today can help ensure your adventures tomorrow are smooth and stress-free.
Why Travel Insurance is a Good Idea
Let’s walk through some of the “why” behind travel insurance — particularly for retirees or those with more flexibility and more at stake.
Your trip investment matters. When you’ve booked flights, hotels, tours, maybe even paid in advance for something non-refundable, you’ve got a financial commitment. If something unexpected happens (illness, weather, cancellation, delayed connection) you’ll want a safety net.
Medical costs abroad can surprise you. Even if you’re healthy, something sudden can occur, and your domestic health insurance may not cover you fully (or at all) when you’re overseas. Travel insurance often covers emergency medical, evacuation, and treatment.
Disruptions are real. Delays, lost baggage, missed connections, cancelled flights/trips — even with the best planning, things happen. Travel insurance can help reduce stress and financial burden when travel goes off-script.
Peace of mind = better travel experience. Knowing you’re covered lets you relax more fully, enjoy more, and worry less about “what ifs.” That’s especially important when you’ve earned the freedom to travel on your terms.
Tailored for your phase of life. As a retiree (or soon-to-be), you may have more assets to protect, and more time sensitivity. Insurance helps you protect not just money, but perhaps your health, mobility, plans, and peace of mind.
In short: travel insurance isn’t just an optional extra — it might be one of the more important “extras” you pick up when planning your trip, especially if you want to travel confidently, independently, and joyfully.
Top 3 Travel Insurance Providers — A Quick Comparison
Here are three well-known companies, how they stack up, and what you might want to check when comparing them.
Provider | What stands out | Things to check |
Travel Guard (by Zurich Insurance Group/formerly AIG) | Solid reputation, multiple plan tiers (Standard, Preferred, Deluxe) with trip cancellation, medical expense, baggage, emergency evacuation. Wikipedia+3NerdWallet+3Travel Guard+3 | As with many providers, details matter: what is the medical coverage limit? Are pre-existing conditions excluded or covered? When must you purchase after booking to qualify for waiver of exclusions? Travel Guard+1 |
Allianz Global Assistance | Recognized in “best travel insurance” lists for strong medical/emergency coverage. NerdWallet+1 | Make sure you pick plan levels that match your age/trip type; check what happens with medical evacuation, and what exclusions apply. |
IMG (Global) | Good option especially for international travel and medical-emergency focus; flexible plans for travel medical coverage. WorldTrips+1 | Less focused perhaps on trip cancellation/interruption — so if you’ve booked a costly trip you may want a plan that emphasizes that too. |
Sample Comparison: What to Ask
When comparing plans, here are some of the specific questions you’ll want to ask (and make sure are answered in the policy documents):
What trip cancellation or interruption coverage is included? In other words: if you must cancel or come home early for a covered reason, how much is reimbursed?
What’s the medical expense coverage limit abroad? What about medical evacuation (getting you home or to the right hospital)?
Does the plan include baggage loss or delay coverage? Or trip delay reimbursement?
Are pre-existing medical conditions excluded, or is there a waiver if you buy soon after booking? (For older travellers this is especially important.) For example, Travel Guard’s Deluxe plan includes a “pre-existing condition exclusion waiver” if purchased early. Travel Guard+1
What is the “Cancel for Any Reason” (CFAR) upgrade option (if any)? That gives you more flexibility if you decide not to travel — albeit at higher cost.
Are you buying the policy right after booking? Purchasing early usually gives you more benefits (including some pre-existing condition coverage). NerdWallet
What about age limits, exclusions for certain activities (adventure sports, etc), and the fine print on claims (documentation, deadlines)?
What is the cost relative to your trip’s investment? Sites say that for many travelers, comprehensive travel insurance costs around 4–10% of the total trip cost. Squaremouth Travel Insurance
How to Move Forward With Your Trip Plans
Since you’re stepping into a phase of life when travel is less about “finding time” and more about “making memories,” here’s a smart workflow:
Pick your now- or next trip – Destination, dates, budget, what you’ll pre-pay (flights, hotels, tours).
Estimate the non-refundable/prepaid portion of that trip (this helps you understand your risk).
Shop travel insurance quotes – Use comparison tools or go direct to the providers listed above. For example, platforms like Squaremouth allow you to compare plans from 20+ companies. Squaremouth Travel Insurance
Check key policy details – as listed above (medical, cancellation, age/exclusion fine print).
Purchase early – The sooner you buy after your trip booking, the better your benefits often will be.
Keep your documentation – policy number, coverage summary, what you’re covered for, claim instructions, how to contact assistance while travelling.
Travel with confidence – enjoy your trip knowing you have a backup plan.
We’re excited for you to embrace this travel-rich decade ahead. Click Here for a “travel insurance checklist” you can use next time you book a big trip.
Here’s to your next great adventure — with peace of mind built in.
Disclosure:
Strategic Financial Services does not endorse or recommend any specific travel insurance provider mentioned in this article. The information provided is intended solely for general informational purposes and should not be construed as an endorsement, recommendation, or solicitation for any product or service. Clients are encouraged to carefully review policy details and consult directly with insurance providers or licensed professionals to determine the coverage most appropriate for their individual circumstances. Portions of this article were prepared with the assistance of artificial intelligence and reviewed by Strategic Financial Services for accuracy and appropriateness.