Since retiring from my career as a school principal, I have had the privilege of traveling extensively—often five or six times a year—and helping others make the most of their own travel time. Along the way, I have learned that retirement travel is not about doing less; it is about traveling with more freedom, better judgment, and a pace that lets you truly enjoy the journey.
These are the principles I use for my own travels and share with my clients.
USE IT BEFORE YOU LOSE IT
If there is a big, active trip on your list—a safari, a trek through hilly cities, an itinerary full of cobblestones, or a destination with long sightseeing days—my advice is simple: do it while it still sounds exciting.
Many travelers in their sixties are energetic, curious, and fully capable of taking on more challenging adventures. Ten years later, the same trip may still be possible, but it may not be as enjoyable. That is when ocean cruises, river cruises, and destinations with less walking can become especially appealing.
One reason I often recommend river cruising is the ability to choose your own pace. Depending on the cruise line and itinerary, guests may have choices ranging from gentler walking tours to more active hikes and bike rides.
TRAVEL WHEN OTHERS CANNOT
For years, when I was working in schools, family travel had to happen during summer vacation and school breaks—the most crowded, costly, and often hottest times to travel. Retirement changed that completely.
Now, I plan many of my own trips in March, April, May, September, October, and November. These shoulder-season months often offer a much better experience: smaller crowds, more reasonable hotel prices, more comfortable temperatures, and easier access to guides, restaurants, and attractions.
I also enjoy winter travel, provided it is not over Thanksgiving, Christmas, or New Year’s. But I always check the local holiday calendar first. A destination may be quiet during an American school break but bustling because of a European holiday, a major festival, or a regional vacation period.
GO SLOW ENOUGH TO ENJOY IT
One of the biggest changes I made after retiring was giving up packed, hour-by-hour itineraries. I have learned to build in a recovery day after a long international flight and to allow unscheduled time throughout the trip.
That extra time is never wasted. It may become a long lunch with a view, a neighborhood stroll, a visit to a small museum, or an unexpected recommendation from a local. Some of the best travel memories come from moments that were never on the original itinerary.
SPEAK A LITTLE OF THE LANGUAGE
I am fortunate to speak fluent Spanish, which has been surprisingly useful in many places around the world. But Spanish does not solve everything, so before each trip I still learn a handful of local words: hello, please, thank you, excuse me, and perhaps “where is the restroom?”
My Turkish, Hungarian, French, or Vietnamese may not be elegant, but the effort matters. I have found that people appreciate travelers who show respect for their language and culture, even when the conversation quickly returns to English.
LET THE CONCIERGE HELP
I have long believed that a good concierge is one of the best reasons to select the right hotel. A knowledgeable concierge can make a trip smoother and more memorable—especially when you need a last-minute restaurant reservation, a private guide, tickets, transportation, or advice on what is truly worth doing.
Over the years, I have learned that the best concierges know their cities exceptionally well. They often know which restaurants are genuinely good rather than simply fashionable, which tour operators are reliable, and which experiences are right for a particular traveler.
LOOK PAST TRAVEL BUZZWORDS
I am cautious when I see words like “authentic,” “artisanal,” “bespoke,” and “immersive.” They can describe something wonderful—but they can also be marketing language without much substance behind it.
After traveling throughout Europe, Asia, and South America, I have learned to look closely at what an experience actually includes, where it takes place, how large the group will be, and what recent travelers have said. This is also where having trusted suppliers around the world makes a real difference. I can help clients distinguish between a genuinely special local experience and one that only sounds special in the description.
CHOOSE EXCURSIONS CAREFULLY
This is a topic my cruise clients hear from me often: do not assume the cruise line’s excursion is always the best option. Cruise excursions can be convenient, but they may also be expensive and involve large groups.
Depending on the port, I frequently recommend carefully vetted independent providers that offer smaller groups, more personal service, better pricing, and a back-to-the-ship guarantee. Still, there are ports where the ship’s excursion is the smartest choice because of distance, traffic, or timing. The right answer depends on the ship, the itinerary, the port, and the traveler—not simply on the price.
TURN A LAYOVER INTO A DESTINATION
I have written before about making a layover part of the vacation rather than simply an inconvenience. With the right airline and routing, it can be possible to add a memorable city without substantially changing the airfare.
Istanbul is one of my favorite examples. Turkish Airlines offers eligible international passengers connecting through Istanbul the opportunity to arrange a stopover, with complimentary hotel accommodation available under certain fare, routing, timing, and advance-booking conditions.
Iceland is another excellent possibility for travelers heading between North America and Europe. A stopover can turn a connection into a chance to see Reykjavík, the Blue Lagoon, waterfalls, or the dramatic Icelandic countryside.
CHOOSE YOUR HOTEL LOCATION WISELY
I have friends who book a hotel far outside a city center to save money, only to spend valuable vacation time—and much of the savings—on taxis, trains, and long commutes. That is rarely my preferred strategy.
I encourage clients to stay in the part of town that suits the way they want to travel: near the museums, restaurants, historic center, waterfront, or transportation that matters most to them.
Hotels are deeply personal choices, but I often find that a well-run boutique hotel offers a level of charm, location, and individual attention that a large chain property cannot duplicate.
Having recently traveled in Asia, South America, and Europe—and with Australia and New Zealand ahead—I continue to update my hotel recommendations. There is no substitute for seeing destinations firsthand, returning to places over time, and knowing which hotels and experiences truly deliver for different kinds of travelers.
ALSO, ONE MORE THING TO ADD
This is not something publicly advertised, but my company gets “special” pricing on Holland America and Celebrity, not all sailings, all the time, but if something is of interest to you, ask me and I will check if the additional discounts are available.