Prepared for Your Next Big Trip? Here’s a playbook to help

Oliver Wendell Holmes, Sr., American physician, poet and essayist, once said: “A mind that is stretched by a new experience can never go back to its old dimensions.”

 

Many seniors who are retired or have cut back on their work hours find Holmes’ statement to be true. They want another adventure in their lives and are traveling to destinations on their bucket list, especially to far-away places with diverse cultures, sights, foods and languages, from South Africa to Japan, the Arctic and Easter Island, to name a few. 

 

These places and others require long flights and lots of stamina to tour churches and game parks, walk glaciers (with poles), master steep stairs and navigate cobblestone roads, lie on beaches for hours (with sunscreen, a hat and maybe a mocktail Piña Colada in hand) and stay up past our normal bedtime for good theater, music, food and camaraderie.

The joys of breaking out of routines can be limitless. However, careful travel planning is critical. We know of two groups of travelers: the planners who start months and even a year ahead and the procrastinators who do everything at the last minute. For a start, know which group you are in.

 

But, if you haven’t traveled long distances for more than a few days in years, it takes thought. You wouldn’t throw a party without good prep or take an exam without studying. Air, train, bus and sea travel is vastly different than stuffing everything in your car and zooming off.

 

If you’ve booked your next trip, get ready, get set and go. To help you plan and enjoy your getaway more, here’s our pre-planning playlist.

 

Research your destination well. Buy or borrow a guidebook for the area or destination; consider online maps or the ones you carry with you; estimate after you read up on the sights you want to see, but leave some wiggle room for what you hear when you're away. Also ask friends for ideas. One couple we know always likes to take a cooking class or food walking tour in different destinations; another wants to see modern art and architecture; and someone we just heard took a tile class in a city where tiles line many facades. But get over the notion that you must see every church and monument; taste multiple croissants and sweet custard tarts from the bakeries everyone is touting; or imbibe all local beers. We’re at the age when soaking up culture, sights and vibe can be sufficient, and moderation is smart. But it’s just a fact: You’ll see and eat more than you did by staying home.

 

Decide if you’ll do the trip on your own or with a group. Are you a master researcher who feels comfortable and safe alone or with a friend or partner and possibly hiring local guides in advance or through a hotel concierge? Or do you like the safety of numbers in a group? If so, how big is a group? Some can be small; some quite large. Also, check out the expertise of guides available locally, whether you book them yourself or through the group. A knowledgeable guide who knows the area and its sights can boost your enjoyment quotient.

 

Consider using a travel agent. Most do not charge because they are reimbursed by hotels, etc. Someone who’s been to the area saves you time and often money planning what flight to take, what airline to use, what location or neighborhood to stay in, what hotel works best for your budget and taste and what local activities are worthwhile, such as cooking classes; which tour guides are worth hiring for an overall view of the area or special sites; which restaurants to book, plays to see, and more. Some specialize in certain countries or cities, which you can find online. Two sources are platforms like kimkim, which connects you with local experts for multi-day itineraries, or The WOW List from Wendy Perrin for vetted, high-end destination planners.

 

Pack in advance and sometimes with a list you’ve written out. We’re older, slower and tend to forget things—a passport and other travel documents such as TSA or Global reentry, chargers, getting vaccines for a certain destination, all the right clothing (and extra bags for dirty clothes), from layers to stay warm to rain gear with hoods to stay dry to comfy, broken-in shoes and hats for cold or warm weather. Someone suggested the smart idea of putting together outfits monochromatically for easier mix and match. Those black leggings can be dressed up and down, same with a button-down white blouse and pretty scarf. Remember to add sweaters or shawls. Air conditioning may be strong, but some countries don’t use lots of AC or any at all! And slip in a collapsible umbrella and one pair of old sneakers or old shoes for rainy days; you can leave them behind at the end of the trip if worn out.

 

Know how to pack. Some like to roll garments, some like hanging bags, some like smaller plastic containers to separate socks from undergarments and scarves. Have the right bags and luggage tags so if lost they’ll come back to you or purchase on Amazon luggage trackers or Bluetooth luggage tags, small electronic devices you place inside your suitcase, bag, or other valuables, and connect via Bluetooth to your smartphone’s tracking app or network. Condé Nast offers helpful tips at its site, https://www.cntraveler.com/story/the-golden-rules-of-packing. Some also like to put a business card or other piece of paper inside each suitcase with name, address and phone (or maybe just first name and phone so you’re not sharing too much information) so it comes back to you if lost, though that shows our age rather than the hipper electronic variety.

 

Consider your age. If a piece of luggage is too heavy to lift, leave it home, even if on rollers. Not all places have elevators, so lugging that big case up and down steep steps or even on and off escalators is harder than when we were young. This goes back to our packing list suggestions: pack lighter. So, what if you repeat outfits? In many cases, you’ll never see the people in your group again! And many cruise ships no longer have fancy dress nights or require a tuxedo. Find out in advance! One of us learned we’re only taking carry-on luggage next time!

 

Do more research. You have an idea of what you want to see. But again, be realistic if you’re in a city for three days or a week. That unusual monastery or museum may not work for this trip. Know your limits. If you fall asleep early, plan for a matinee rather than a show or play at night that ends at 11 p.m. If not an early riser, don’t book a sightseeing outing for 8 a.m. You don’t want to come home exhausted and feel you need another vacation from the vacation.

 

Ask AI for more help with anything. Need an itinerary? Ask Claude. Feed it the right information--dates, times, preferences, your age, number of days, destination, specifics of transportation—and presto, you have a plan/list. It’s pretty accurate and can be as specific as suggesting how to pack, what to put in a checked bag versus the carry-on.

 

Know airline rules. It will dictate the size of checked bags and the number you can check before you get charged extra. Also, know how many carry-on or personal items you can tote, like a purse or backpack. Medical devices like a sleep machine don’t count. You don’t want to get to the airport and find you must unpack and repack stuff. Check carriers regarding limits on suitcase number, dimensions and destinations for checked bags without charges. Ditto for checked bags and sizes since overhead compartments on certain airlines may be smaller. You don’t want to fight your seatmate for space above seats.

 

Know also what not to pack in a carry-on. No liquids (and that includes bottled water) over 3.4 ounces (100 ml); more than that amount, you must put it in your checked bag; and never pack any sharp objects like knives and box cutters, tools longer than 7 inches and self-defense items like pepper spray. Carry-ons can also be great if you put what you need in them, such as medications, makeup and maybe one change of clothes in case your checked luggage is lost.

 

Gather your electronics: cords, laptop, phone, tablet. There are carry-on cases for some of these items, and know what you always want with you. Keeping them together helps avoid search missions and unpacking them all.

 

Load on your Smartphone Google Translate or a similar app if you’re going to a country where English isn’t spoken. It’s easy. You type in a statement in English, and, in a nanosecond, it’s translated into another language. Just click the “Listen” button, and you can hear the pronunciation. You can also adjust the audio speed to normal, slow or slower in the settings. This can save embarrassment; for example, in Portugal, use its language rather than Spanish, a common faux pas. Also know how to say, “how much?” and “where is the bathroom?” “How do I get to this destination?” “What is this food?” and other crucial phrases.

 

Contact your network phone provider to check on its international coverage. It will share whether roaming is included in your plan or will cost extra, such as $100 for a month.

 

Gather reading material or load lots of books on your tablet if there is no Wi-Fi on the plane, cruise ship, bus or it doesn’t work. Guidebooks, books, magazines, a journal or notebook of favorite destinations, restaurants, shops and more¸ can all be stuffed in your purse or carry-on bag. Very few airlines offer printed magazines anymore; few hotels and cruise ships also do. Bring a few pens and a small pad of paper or notebook to take notes.

 

Update your passwords in a master list and alert your bank or credit card companies that you’re leaving so you can use your charge cards. Take photos of your passport and credit cards; take one set with you and leave one at home or with a family member. Bring another set of keys for a car if you drive yourself to the airport and even your house. Items get lost in trays at check-in lines and other places!

 

Decide if you want to have some U.S. dollars. American Express dollars no longer exist! Know if you want to bring some currency for the country you’re visiting and exchange a few dollars into that currency before you leave. Certain banks can do this, mostly the larger ones. Know whether to have purchases charged in dollars or the currency of the country to get the best exchange rate. But also know that most destinations take credit cards; have a check or two with you just in case. Shop smartly. Do you really need another dish, tchotchke such as a snow globe, kitchen towel or replica in miniature of Big Ben or ANYTHING at our age? If it’s an important memento, go ahead and sometimes even splurge on that gorgeous handwoven scarf. But don’t get caught up in buy-mania. Do you really need to bring home gifts for friends and family; your safe return should be a big present.

 

Remember prescription meds and more. Bring your Medicare and Medicare Supplement cards along with a list of all your medications. Be sure you have meds for your entire trip and then for a few days if you get stuck. Know what other related needs you want to cover—your dental care products, batteries for your hearing aids, makeup, nonprescription meds like aspirin, Band-Aids, nail clippers, shampoo, tweezers and again, put liquids into the right-sized bottles if you’re not checking your bag. Don’t forget the right adapters and plugs for these items, such as electric toothbrushes and water flossers. And binoculars can be handy for certain sights and events. It’s up to you if you’ve taken travel insurance in case of a catastrophic illness or disaster; it’s expensive but useful. Have that insurance info with you as well.

 

Be considerate of your travel mates. Don’t bring a smelly sandwich to eat even if you know you’ll dislike the food served on board the plane, bus or train. Eat before or choose a croissant, muffin or innocuous turkey sandwich. Do not remove your shoes unless you’re flying first or business class and have your own compartment.

 

Dress comfortably for the flight, long train or bus ride. That again may mean layers of leggings for women, a top, sweater or jacket or all of these and a pair of compression socks for a long flight or bus ride. Some bring a U-shaped neck pillow, which makes it more comfortable to sleep sitting up. And do not remove your shoes again; it’s rude.

 

Know that you can always contact an embassy or consulate in the country you’re visiting. Problems do happen: you lose a passport; you get sick and need a doctor and so on.

 

Be affable. Bring along your friendliest, cheerful personality. You want to help be an ambassador for our country; be polite in shops, be kind to hotel staff and servers, don’t talk too loudly and dress appropriately. You also may meet lots of strangers if on a group trip. Again, business cards come in handy if you meet others you like and want to stay in touch with them or take down their information on your phone. Be kind to those traveling alone if you’re with a friend, partner or spouse. Include those who come alone at your table if you’re in a group. You don’t have to become best buds, but inclusion is so kind. And if you don’t like someone in a group, become a great actor. It’s also kind; you probably will never see them again, thank goodness!

 

Check in on your computer or phone 24 hours ahead of your scheduled flight time, which most airlines require. This will avoid extra time at the airport, but you’ll still have to access your boarding passes and luggage info, if you’re checking bags, on a portal. If you’re not techy, you may want to have someone nearby help you, such as your teenage grandchild. If you make purchases in certain countries, you will want to secure your VAT or other refund, so you’ll need more time at the airport before heading home. Everyone seems to be traveling, so long lines require time to get through. Bring your patience!

 

Get through security as quickly as you can. If a TSA PreCheck cardholder, make sure the number is included on your ticket. And always have your Real ID or passport on hand.

 

Take photos. You may want to post online from your trip or make a photo book when home or both, using Shutterfly, Mixbook or other online platforms. Again, we’re old, so remembering what we saw and did and who we met is easier with a visual reminder. Postcards are also a good inexpensive way to do so.

 

Reassess once home and rested. We always learn about our likes and dislikes, even at our age. Thought you were a “cruise person,” maybe not anymore since you won’t see destinations in depth if you're going to one city or spot and staying put for days. You may be more of a city than country mouse, too. One trip can help you plan the next. If you love a certain destination, put it on your go-back-to list and add it to a new place that works well with it. Also weigh days away; some love to be gone for weeks; others find six days or a long weekend enough. Of course, that may depend on where you’re going. Write reviews of hotels, cruise lines, travel groups, tour guides; it helps them all do a better job, but try to be kind and helpful rather than nasty. Reviews also help others plan and make choices.

 

Don’t forget a master to-do list before you leave home. Cancel newspapers, mail delivery, shut off your computer, unplug some energy-sucking electronics, turn off your air conditioning or lower the heat, alert a family member, friend or neighbor to check your home just in case or to water your plants. You may also want to leave a house or car key with a family member or neighbor in case you lose yours on the trip.

 

Bon Voyage. Have a wonderful time, and again don’t forget to post some photos if you like to share, since who sends postcards anymore? But maybe don’t write, “Wish you were here!” since some aren’t as lucky to go away. And know that many will want details of your trip but may not want long, detailed replays, so read your audience before you recite every detail.