They learned these lessons the hard way, but you don't have to.

By Patricia Doherty
Updated March 13, 2020
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Travel is high on the list of plans for many retirees. With time available for longer trips, retirees want to explore new places, visit family, and spend time with friends. Even experienced travelers encounter problems along the way, many of which are unavoidable. For those new to taking extended trips, cruises, or international journeys, there can be a lot to learn.

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Travel + Leisure heard from retirees across the U.S. who shared stories about difficulties they encountered on trips, with the hopes of saving someone else from making the same mistakes. Here are a few of the lessons they learned the hard way.

Mistake #1: Not Arranging for a Wheelchair When Needed

"I am able to walk, so I didn’t think of requesting a wheelchair on a recent trip. The walk to the plane was so long, as was the wait in the security line. Then, there was an unexpected shuttle bus ride to the departure gate and a fairly uphill ramp into the terminal. I was exhausted by the time I got to my seat. A wheelchair would have made it so much easier." — Mike B. of La Quinta, California

Lesson Learned:

If you’re not comfortable walking more than 10 minutes or so, arrange a wheelchair for the airport. Terminals seem to be getting larger these days, and you might have a long walk to your gate or the baggage claim area.

Mistake #2: Forgetting to Factor in Medical Insurance

"While I was on a group tour in a quaint European town, I tripped on the cobblestone street, twisting my ankle and injuring my wrist. I needed medical care and went to an emergency room for X-rays and bandages. Luckily, nothing was broken, but the charges had to be paid immediately, putting a dent in my travel budget." — Barbara C. of Burbank, California

Lesson Learned:

Be sure your medical insurance will cover expenses when traveling outside the U. S., or arrange an additional policy. Medicare does not cover expenses incurred outside the country.

Mistake #3: Not Allotting Enough Time to Get to the Airport

"On a recent trip, my friend and I missed our flight. Between traffic, checking bags, the security line, and a long walk to the departure gate, we got there about two minutes too late. It was frustrating and expensive to rebook on a later flight." — Linda L. of Long Island, New York

Lesson Learned:

Leave plenty of time to get to the airport. When they suggest two to three hours, believe it. Besides, there are high-quality restaurants, interesting shops, airline lounges, and even nail salons, massage chairs, and comfortable places to sit, read, and charge devices.

Mistake #4: Signing Up for Every Single Shore Excursion on a Cruise

"On my first ocean cruise, I enthusiastically signed up for just about every shore excursion. They all sounded great, and I didn’t want to miss anything. Once I was on the ship, I learned a few things. It was lovely just relaxing on my balcony or in one of the ship’s lounges. It’s [also] possible to arrange private tours as some other guests did. They were able to see exactly what they wanted that way." — Eleanor N. of Redondo Beach, California

Lesson Learned:

Choose shore excursions carefully when planning a cruise, and consider arranging private tours or just enjoying time on the ship. You might overspend if you sign up for everything before leaving.

Mistake #5: Not Planning Ahead

"I waited in a few long lines on a recent trip, using valuable time being bored and getting tired. I didn’t plan ahead or find out about what was available to make better use of my time. And it’s not only the time; it’s tiring to stand for an hour, and sore feet detract from the enjoyment when you finally get where you’re going." — Nancy B. of Rockville Centre, New York

Lesson Learned:

Buy front-of-the-line tickets or book tours with special hours to avoid wasting time in long lines. It’s worth the extra money.

Mistake #6: Packing Uncomfortable Shoes

"Looking good and being fashionable should not have been my priority when I was shopping and packing for my trip. My feet were killing me after the first half-day of walking. Low heels with padding and support would have been a better choice. You can find shoes that are both stylish and sensible." — Gail W. of Palm Springs, California

Lesson Learned:

Be sure to pack comfortable shoes and break them in before going on your trip.

Mistake #7: Choosing the Wrong Travel Companion

"The sister of a good friend — another single woman like me — was planning a cruise and asked if I’d like to join her. She was experienced at cruising and I was not, so I thought it was a good opportunity. It turned out that we had little in common, and she had several annoying and embarrassing qualities (loud, abrasive, and a complainer). Although we had separate staterooms, we were seated together at dinner and booked into the same tours." — Eleanor F. of Chicago, Illinois

Lesson Learned:

Know the person you plan to travel with before you go on a trip with them.

Mistake #8: Leaving Your Money Belt at Home

"I was very careful with my purse because I had been warned about pickpockets, especially in crowds. A nice young girl stopped to ask me a question, and when I stopped, someone bumped into me. No big deal at the time, but a little while later, I discovered that my wallet was gone. Luckily, it was just some of my cash, but it could have been worse. Glad I wasn’t carrying all of my money or passport." — Stephanie H. of Seattle, Washington

Lesson Learned:

Use a money belt or some type of inside pocket or hidden place for carrying money or valuable papers.

Mistake #9: Forgetting to Check Any Flight Changes

"I booked a trip well in advance — about six months — for my husband and me. On the day we were leaving, we noticed that we were not seated together even though we had selected seats when we made the reservation. Apparently, there was a change in the type of plane and our seats were reassigned. If we had noticed sooner, we might have been able to fix the problem. Also, sometimes departure times change, so it’s a good idea to watch your flights by using the technology." — Irene A. of Beverly Hills, California

Lesson Learned:

Use the airline’s website or app to check your trips periodically, in case if there have been any changes in departure times or aircraft.

Mistake #10: Not Signing Up for TSA PreCheck, Global Entry, or Clear

"I noticed on my vacation that security lines were shorter and faster for travelers with TSA PreCheck and Clear. Anything you can do to save time waiting will make your trip better. I will be ready for my next trip." — Susan N. of Bonita Springs, Florida

Lesson Learned:

Apply for TSA PreCheck, Clear, Global Entry, or other available programs to make travel easier and more convenient.

Mistake #11: Carrying Only One Credit Card

"I was in a European country, and I used an ATM to get some cash when I was running low. My card never came out of the machine, and of course, it was a Saturday afternoon, so I couldn’t do much about it. I had to borrow money for dinner, which was embarrassing, and it took a few days to get another credit card from my bank." — Mary C. of Hempstead, New York

Lesson Learned:

Be sure to have more than one credit card with you when you travel.