OneTravel - Book cheap flights, hotels and cars!

How to Plan a Trip After You’ve Retired

Senior couple vacationer having genuine fun on tropical Koh Lipe beach in Thailand
Written by Suzy Guese

This blog post was updated on October 4, 2019.

You’ve finally decided those cubicle days and hours in rush hour traffic are at long last behind you. Once you retire, the world is your oyster. Many retirees take advantage of their newfound free time by traveling the globe. However, before you head off to see the pyramids in Egypt or on that Alaska cruise, your first trip after retirement warrants a bit of planning. We’ve rounded up some key aspects to traveling post-retirement you’ll want to consider when plotting your trip.

Prioritize Your Dream Destinations

Elderly couple visiting Alsace region, walking on the streets of Kaysersberg town.

When you sit down to plan your first trip post-retirement, you probably already have a list of places you want to visit. Now is not the time to be restrained or conservative. If you have always dreamed of seeing Petra, prioritize that trip over some other destination that you’re less than enthusiastic about. While it can be intimidating to dip into your savings to hit the road, you also don’t want to regret years later not that dream trip at the top of your bucket list.

Planning that perfect bucket-list getaway? Just take a look at these cheap flights to hundreds of destinations!

Focus Your Travel Dates During Shoulder Seasons

Happy romantic senior African American man and woman couple on a deserted tropical beach

One of the biggest advantages to retirement travel is that you aren’t confined to standard workplace time off for when you can take a vacation. You can go when you want to go. When you are planning your travels after retirement, try to focus your dates around shoulder seasons. For example, Rome in the middle of summer can be a zoo. Instead, try to visit in the fall or spring when there are fewer crowds and prices are lower.

Figure Out Your Medical Insurance

doctor talking to her male senior patient at office

If you retired in your senior years, you know just how important your medical insurance is to your lifestyle. However, when you travel, specifically abroad, you aren’t always covered by your plan at home. Before you plan your trip, check to see where you are covered. If you are headed out of the country and you’re not covered, you’ll want to review travel insurance policies with medical plans. Find one that is right for you. Sometimes these plans must be purchased within days of booking your trip, so be sure you know all the rules to have your coverage in place. In addition to medical insurance, now is also the time to figure out what medications you’ll need while traveling. It’s always wise to know the generic drug names for any prescriptions you do take in case you find yourself in a foreign pharmacy.

Ask About Senior and Retiree Travel Discounts

Excited senior mature couple surprised by good unbelievable deals online

Before you retired or turned a certain age, you probably never thought to ask for discounts on certain areas of travel, from train tickets to car rentals to flights. However, now that you have hung up your working shoes, you might be entitled to some large discounts on your travels! Whenever you are booking transportation, hotels or even just showing up to a museum to visit on your trip, be sure you ask about any retiree or senior travel discounts. Since you’ll probably be on a budget, these discounts can help you stretch your trips even further so you can travel more in retirement.

Consider Accessibility

Man caretaker pushing elderly people in wheelchair in the airport

For those retirees past a certain age, accessibility can be an issue while traveling. In your younger days of travel, you might have taken multiple connecting flights with carry-on luggage, checked into the cheapest hotel with no elevator, or rented a car without worrying about your age. However, now you have to consider how accessible your trip will be. Rather than going carry-on for all of those connecting flights, consider checking a bag so you don’t have to lug it through several airports. Be sure you book accommodations that offer accessible rooms if you need them. Look for amenities like elevators, rooms on the ground floor, and walk-in showers. And if you are renting a car, you might be surprised that some countries place restrictions on your age. If you’re past a certain age, some companies won’t rent to you. To avoid a disaster while on your post-retirement trip, always consider accessibility in the planning stages from where you are staying to how you’ll get around.

Don’t Overschedule Yourself

Happy senior male tourist hiking in forest

All too often, retirees sign up for group travel tours and packages that have them scheduled for every minute of the day. If it has been a while since you last traveled, you might notice your energy levels are a bit lower than they once were. Traveling can take its toll on all ages, but if you are in your senior years, it can be especially exhausting. In order to make the most of your trip, don’t feel as though you need to see it all in one day. Avoid tours that don’t allow for free time to rest and explore. If you are planning your trip on your own, don’t bite off more than you can chew. Now that you have the time to travel, it’s time to embrace a slower pace to see the world.

Brush Up on Airline Rules and Regulations

senior wife and husband are standing with suitcases at international airport and looking at flight tickets

If you haven’t flown in a while, chances are flying will look quite different to you in retirement. A trip through the airport can be stressful when so much about air travel has changed. When you book your flight for that retirement trip, be sure you know all of your airline’s rules and regulations. Some fares won’t give you a seat assignment while others will offer free checked bags. Along the same lines, you’ll want to brush up on airport security rules. Know what you can and can’t bring on board the plane and just how you need to pack everything.

What other planning tips would you add to the list? Share your tips with us in the comments below!


About the author

Suzy Guese

Suzy Guese is a travel writer from Denver, Colorado. She caught the travel bug after taking her very first flight at just three months old—she was headed for Disney World—and has been a total travel junkie ever since. From family car trips across North America to stints abroad in Europe, Suzy travels the globe with her redheaded temperament in search of sarcasm, stories, and travel tips to share with anyone willing to listen. She blogs about her travels at