10 Must-know Tips for Traveling Solo After You Retire

As a travel journalist, a baby boomer, and an enthusiastic fan of seeing as much of the world as I can, I’ve flown, cruised, and driven a few million miles over the past 50 years or so. I’ve traveled with couples, friends, journalist groups, my husband, and most recently, I’ve taken a few trips on my own. 

While at some point in my life, I may have eschewed the idea of solo travel, I now find it a very pleasant way to go. For others like me who still have the urge to schlep through airports with a packed suitcase and spend hours strapped into an airplane seat to see new places, solo travel can be an exciting experience. 

I understand that some others from my generation, and even younger folks, prefer to sign up with group travel companies that plan their itineraries, book their flights, reserve their hotel rooms, and arrange their meals and sightseeing tours. And I do recognize that certain trips, like adventure travels, are best taken with a guide and group. But I suggest taking a truly solo trip for the exhilarating experience of feeling independent and free to wander. Here are some suggestions for making the most of traveling solo after retirement.

Plan ahead.

After deciding on my destination, I make the basic arrangements for flights and hotels. Some solo travelers like to play it by ear without making room reservations in advance—it’s part of the adventure for them—but I suggest at least booking a room for the first night. We all arrive a bit tired, and it’s pleasant and safe to have a destination to start with. As far as flights, airfares vary by day of the week, airline, and connections, so it’s worth spending some time researching to save some money. The same goes for hotels. Check booking sites and compare their deals by contacting the hotel directly.

Join a tour if you want, but be selective.

If you want to join an organized tour at some point during a solo trip, be sure to choose the right tour for your needs and priorities. On a trip to Rome, I naturally wanted to see the Sistine Chapel and Vatican Museums—but so do thousands of others, every day, especially during the peak travel months. So, I signed up for a morning tour with City Wonders after learning that the company’s official Vatican Museums partnership enables its groups to use a special no-wait entrance. (Though, keep in mind, even skip-the-line groups often wait up to an hour.)

On another solo trip to London, I booked a walking tour of the West End with Lookup London. A private tour fit my schedule, and we visited the theater district, Oxford Street, and St. James’s Church (a Bridgerton filming location), where an afternoon piano recital was taking place. I loved having my own tour guide, but I also enjoy small groups where there’s interaction among the other guests and a chance to meet other travelers. 

Seek out new experiences.

By new experiences, I’m not suggesting bungee jumping or zip-lining across a rain forest canopy, although I know many senior travelers who would strap in without hesitation. And while I admire them for it, I’m thinking along the lines of a cooking class that includes visiting a market, shopping for ingredients, and then cooking with an entertaining chef, as I once did in Florence.

In London, I visited the posh Burlington Arcade, one of London’s most historic shopping destinations. A beadle in a delightfully British uniform greeted me with a bit of information about the arcade. From there, I went to the cosmetics boutique Code8, where a personalized lipstick shade was created for me. Then, my next new experience was having my boots polished by a charming gentleman as I sat on a vintage shoeshine stand and watched shoppers walk by. I know—it’s not exactly skydiving, but they were a few of my novel experiences. You can choose your own.

Make a to-do list.

In big cities like Rome, Paris, or London, it’s easy to make a long list of attractions you want to see. Sometimes, it’s just not possible to do everything, so you may need to prioritize. “Save something for the next time,” is what I always say. 

If you’re a foodie whose “to-do” list involves restaurants, make reservations well in advance, especially if you’re after Michelin-starred dining spots or those receiving lots of attention. Your list will also help you decide where to go based on the neighborhood you’ll be in. In London, I combined a matinee at a West End theater with dinner at Sketch, a unique restaurant I wanted to experience.  

Keep an eye on your phone battery.

I relied on GPS to guide me around London on my solo trip, and I strolled around with the confidence of a local—until that low battery warning appeared. After a day of taking photos, texting, and using Google Maps, I had just about drained my phone. Fortunately, it was time to hop into one of those adorable black cabs, have a chat with the driver, and return to my hotel.

Since then, I’ve learned to charge up before I leave the hotel and always carry a battery, knowing that a day of sightseeing is about all my phone can handle. When you want to call an Uber or find directions back to your hotel, you’ll be glad you brought a portable charger.

Let someone at home know your travel plans.

For your security and to give the folks back home some peace of mind, let someone know your itinerary. You don’t have to compromise your independence, but it’s smart to let a friend or relative know what you’ll be up to. I leave my husband with a printed copy of my itinerary, whether I’m on a group trip with other writers or traveling on my own. And, of course, I text or call every day, although I admit once in a while I’m having such a good time that I forget. 

Another safety tip: If your home will be empty while you’re traveling, hold off on posting Instagram photos that let the world know you’re out of town. Better to be cautious and share your experiences when you get home.

Be polite, but don’t be a pushover.

For your safety, always be aware of your surroundings and alert to what’s happening around you. If you’re uncomfortable in a place or with someone who approaches you, follow your instinct and find a way out of the situation. Sometimes travelers feel pressured to take a tour, go to a club, or accept a handout from someone on the street who then strikes up a conversation. If it doesn’t feel right, just move on. Travelers often worry about coming off as rude or offending someone, but your personal safety is foremost, so trust your gut.

Beware of pickpockets and scams.

AARP warns of the creative ways criminals take advantage of travelers. It can be easy to get distracted or become overly trusting of strangers, but being prepared will help you avoid thieves.

On my first small group trip as a journalist, my wallet was stolen from my purse at a major tourist site in a European city. This can happen anywhere, even at your local shopping mall. I was unwise to carry my cash, credit cards, and wallet in a shoulder bag around town, but at least my passport was safe in the hotel at the time. Now, I carry only what I need for the day in a secure crossbody bag or a hidden wallet. Some people prefer to use money belts for cash.

Be prepared.

Make sure you carry some of the local currency, in small denominations, in case you encounter cash-only shops or cafes. And be prepared to tip if it’s customary, including any hotel staff who help with your bags or provide other services. 

Do your research before the trip. I went to a town in Italy that was so small there were no taxis, Ubers, or public transportation options to get to the nearby beach. Fortunately, my hotel found a driver to take us (and also fortunately, he came back to pick us up later). Naturally, that was a cash transaction, and I was glad to be prepared.

Lastly, consider buying travel insurance. Flight cancellations, baggage losses, accidents, and illnesses happen, and you’ll appreciate the comfort of knowing you’re covered. 

Travel light.

As a confirmed carry-on traveler, I consider myself a pretty good packer, but sometimes that 22-inch suitcase can get very heavy. That’s my sign to reassess—do I really need those dress shoes? Or all those cosmetics? Probably not. Boarding a train, bus, or plane at a small airport without jet bridges requires carrying our own bags, so I make sure mine are manageable. While I appreciate it when another passenger helps me heave my bag into the overhead bin, I don’t count on that happening. (And it’s not the flight attendant’s job.)

I also always limit myself to two items. That way there’s no problem boarding a crowded flight where the gate agents check how much you’re carrying. Just as important, it’s easier to keep track of only two bags so nothing gets left behind. I do often start out with a purse, but I make sure there’s enough space to cram that into my personal item.

With these preparations, suggestions, and warnings, you can now proceed to plan your solo trip—hopefully, the first of many.