Going Rogue: Traveling in Retirement

Susan Rose and I went “travel rogue”.

Both of us just got back from a non-traditional church mission trip. In somewhat of a last-minute decision, we flew into Havana, gave our Cuban Presbyterian partners gifts from our church to theirs, and returned home. Four suitcases of abundant and readily available items for us in America, but scarce and hard to get for them in Cuba.

We left on a Friday and came back on a Sunday. It is part of us embracing a lifestyle that affords more flexibility, spontaneity, and yes – service.

As a retirement lifestyle planner, I often hear from clients who are wondering what they should do with their newfound free time. Which is why they come to me.

Travel Strategy

Some people are eager to start improving their golf game or enjoy a slower pace for a while. Others are not sure what they want to do next. If you’re in either camp, I encourage you to consider a formal travel strategy – whether for enjoyment, mission, or service.

Here are just a few of the benefits of travel for retirees:

  • Staying active. Travel can help you stay active both physically and mentally. When you’re traveling, you’re constantly on the go, exploring new places and meeting new people. This can help to keep your mind sharp and your body in shape. Lugging four suitcases, 50 pounds each, I can attest.
  • Learning new things. Travel is a great way to learn about different cultures and ways of life. When you travel, you’re exposed to new foods, customs, and traditions. This can help you to broaden your horizons and become a more well-rounded individual.
  • Making memories. Travel is a great way to make memories that will last a lifetime. When you travel with loved ones, you create shared experiences that will bond you together for years to come.

In just a short period of time, I have an entirely different view of Cuba based on my personal experience. No longer is my knowledge of Cuba just about what I read or see in the news.


If you’re thinking about traveling in retirement, there are a few things you need to keep in mind.

  • First, it’s important to plan ahead (but do not be afraid to do something on the spur of the moment). Planning will help you to make the most of your trip and avoid any surprises. We had to invest a lot of time getting ready for our short trip, in a short period of time. Susan spent a lot of hours on WhatsApp and email.
  • Second, be sure to budget for your trip. Travel can be expensive, so it’s important to have a plan for how you’re going to pay for it. We had people donate their time and resources to make this trip affordable for us. What a blessing.
  • Finally, don’t be afraid to ask for help. There are many resources available to help retirees plan and budget for their trips. Without outside help, we would not have been able to make it work going to Cuba.

If you’re looking for a way to stay active, learn new things, and make memories, I encourage you to consider travel. It’s a great way to enjoy your retirement years (and before) and make the most of your newfound free time.

A Couple Of Things

Here are a couple of additional tips for planning a successful retirement travel trip:

  • Pack light. The less you have to carry, the easier it will be to get around. Pack only the essentials and leave the rest at home. We needed to do this, because of the gifts we brought.
  • Be flexible. Things don’t always go according to plan when you’re traveling, so it’s important to be flexible. If your flight is delayed or your hotel is overbooked, don’t get stressed out. Just go with the flow and make the best of it.

With a little planning, you can have a wonderful retirement travel experience. So what are you waiting for? Start planning your trip today!

Plan Your Post-Career Lifestyle Today

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The Post-Career Lifestyle Planning Audio Series

Do you want to take your travel to the next level? Join me on Thursday May 25th for another episode of our Post-Career Lifestyle Planning Series, A New World, A New You: The Benefits of Living Abroad. I’ll be joined by Emily Bron, International Lifestyle Consultant who will give us all advice on what it takes and what it is like to live in another country in retirement.

Additional Resources

Start your post-career lifestyle planning by taking the Retirement Time Analysis and get a complimentary summary report.

Test your general approach to time management through the Time Management Analysis, and also get a complimentary summary report.

What is your purpose? Get the Life Purpose Statement (LPS) Worksheet today and figure that out.

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