Top 7 Things to Do When Planning an Extended Retirement Trip

Retirement opens up a new chapter of life — one where your time is finally yours. For many, that means turning travel dreams into long-term adventures. Whether you're planning a months-long van journey, house-swapping across Europe, or a tropical escape, a little planning goes a long way in making your trip smooth, stress-free, and unforgettable.

Here are the top 7 things to do when planning an extended retirement trip:

1. Define Your Travel Goals

Start by asking: What do I want from this trip?

Are you looking for relaxation, adventure, cultural immersion, or a mix of all three? Having a clear purpose will help you shape your itinerary, choose destinations, and manage your time effectively. Maybe it's ticking off a bucket-list destination, visiting family abroad, or finally taking that cross-country campervan road trip.

2. Sort Out Finances and Budgeting

An extended trip requires a flexible yet realistic budget.

✅ Plan for daily expenses (food, transport, attractions)

✅ Include travel insurance, emergency funds, and unexpected costs

✅ Consider slow travel and off-season stays to stretch your budget

Many retirees fund travel through pensions, savings, or passive income — but also explore house-sitting, volunteering, or remote work to help cover expenses.

3. Prioritize Health and Travel Insurance

Health doesn't take a holiday.

Before departing, schedule checkups, refill medications, and check if your healthcare provider offers international coverage. Travel medical insurance is essential, especially for long stays. Choose a plan that covers emergency care, cancellations, and any pre-existing conditions. Check out World Nomad

Also, pack a small first aid kit, a list of medications, and digital copies of important documents.

4. Choose the Right Accommodation Style

Your comfort and mobility needs may influence where you stay.

Some popular long-term travel options include:

• House sitting or home swaps (cost-effective and homey)

• Extended-stay hotels or serviced apartments

• Renting RVs, campervans, or using a TentBox

• Short-term rentals through platforms like Airbnb or TrustedHousesitters

Pro tip: Look for lodging with laundry, kitchen facilities, and walkable surroundings.

5. Pack Smart and Light

When you're gone for weeks or months, overpacking is tempting — but it'll slow you down.

✅ Choose versatile, weather-appropriate clothing

✅ Use packing cubes and compressible bags

✅ Include tech for connectivity and charging

✅ Bring travel-sized essentials and refill on the road

Most importantly: don't forget your passport, travel insurance docs, and digital backups of all critical information.

6. Stay Connected and Safe

Before you leave, sort out how you'll stay in touch and online:

• Portable Wi-Fi devices or local SIM cards

• Power banks or portable solar chargers (like Bluetti power stations)

• Use location sharing with trusted friends or family

• Keep a copy of your itinerary accessible to loved ones

Apps like Google Maps, WhatsApp, and language translators are handy tools on the go.

7. Leave Room for Spontaneity

Planning is crucial — but so is flexibility.

The joy of extended travel lies in taking things slow, adjusting plans when needed, and enjoying the surprises along the way. Don't overfill your itinerary. Embrace local experiences, take rest days, and allow your adventure to evolve naturally.

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Final Thoughts

Extended retirement travel is more than a holiday — it's a lifestyle shift. With thoughtful planning, it can bring freedom, joy, and deep personal fulfillment. Whether you're chasing sunshine, family memories, or personal growth, the world is waiting.

Ready to plan your journey? Become a member of Golden Age Travellers Here. It's FREE!