Planning the Perfect Retiree Vacation
Your golden years are rife with opportunities. After all, you now have the freedom to set sail toward all the new sights your heart desires—no need to stockpile paid time off or pack your work laptop beside your beach towel.
However, with retirement often comes the challenges of advancing age, requiring you to take a little more care with your planning. Equip yourself with the following tenets of postretirement vacationing, and you can make the most of your liberties while still traveling smart.
Book offseason
Folks navigating busy career and school schedules tend to prefer summer and winter, but as a retiree, you can leave these overcrowded and overpriced dates to others. Opt instead to take your trips during “shoulder seasons”: periods just after peak seasons, typically in spring and autumn. “The special advantage that retired people have when it comes to travel is flexibility,” says Lynn Farrell, president of Foremost Travel Group. “Vacationing in shoulder season often means the weather is better and the crowds are gone.”
Note that congestion times may vary by location, though. For example, a beach resort may be just as busy in spring as in summer due to spring break and Easter, and some New England towns may welcome bustling crowds in fall to witness the changing foliage. Do your research before you choose a spot to ensure that you don’t wind up getting stuck among too many other tourists.

Insure your trip
Travel insurance might seem like an unnecessary money grab—something you scroll right past when booking a flight or hotel online. But in actuality, securing such coverage may be just short of a lifesaver, helping protect your investment in all sorts of scenarios. For one, it could grant you the freedom to arrange health-based cancellations without penalty. And, just as important, it may cover emergency medical expenses like hospital or doctor visits during your trip so you won’t feel the financial burden of an unexpected health scare.
While you can purchase a policy from an agent during the planning process, you could also seek out an independent travel insurance company. Shop on websites like SquareMouth to compare multiple plans and customize your coverage, or buy directly from a reputable option such as Travel Guard or Faye. As for the cost, you can expect to pay between 4 and 10 percent of your total travel expenses, though cancel-for-any-reason coverage may hike the price by an additional 40 percent. Even still, this investment could be more than worth it for the peace of mind it will bring.

Choose senior-friendly destinations
Your ideal vacation destination may look different in your golden years than in your youth depending on your current health status and how your preferences have shifted. For instance, if walkability and accessibility are a concern, you’ll want to avoid cities with older cobblestone streets, such as Rome, or steep hills and numerous stairs, such as San Francisco. Research each potential locale’s ordinances for ramps, railings, elevators, and other like infrastructure, and assess its public transportation for efficiency and ease of boarding. Places that succeed in both these areas will make it easier for you to explore the sights without putting excess strain on your body. And be sure that car travel is always an option in case you need to get off your feet.
Meanwhile, if you’re looking to treat yourself with relaxation after the hustle and bustle of your work life, you may want to choose an all-inclusive resort. Look to Travel + Leisure’s top recommended destinations for seniors, each of which offer a bevy of outdoor, health, and wellness activities. From Suncadia Resort in Cle Elum, Washington, to Lone Mountain Ranch in Big Sky, Montana, you can hit the putting green, indulge in a spa treatment, or take a low-impact exercise course such as outdoor yoga, all within steps of your hotel room. For more retiree-friendly vacation ideas, reach out to a travel agent or consult resources such as AARP’s travel hub.

Take it slow
As raring as you may be to get going, it’s crucial to adopt a slower approach. Primarily, this means being intentional about building an itinerary that suits your capabilities rather than jam-packing it with as many activities as possible—Farrell warns that overscheduling your trip could lead to burnout, especially for older retirees. “We recommend ‘packing your patience’ when traveling,” she says. “Vacations can be tiring as we age.”
In this vein, don’t feel the need to hit everything on your bucket list all at once. Farrell adds, “I recently worked with a couple to create a five-year travel plan,” she says. “They are very mobile now, so we are starting with Peru and Machu Picchu, then planning their future travels to accommodate less-active trips in five years.” And if you do decide to include multiple stops in one trip, pace yourself by staying at least three nights per setting; too many consecutive days of transport via plane, train, or automobile could wear on you and drain the joy out of your journey.

Leave your judgments behin
Whether you consider yourself a youthful and able-bodied retiree or experience some health-related challenges, feel free to see the world as your oyster, embracing rather than resisting the thrill of exotic travel. Farrell notes that one of her agency’s specialties is accommodating plans to their clients’ abilities and limitations alongside their interests. “I recently assisted a client in a wheelchair with booking an African safari with her children and grandchildren,” she says.

So shed your hesitation and design a trip around activities you’ve never had the chance to participate in, such as swimming among tropical fish or taking an international cooking class. To prepare, conduct a little research into a destination’s customs, language, accommodations, and activities via tourism books or vlogs. Or take the stress of planning out of your hands entirely by working with a travel agent, who can help you explore all the options at your fingertips as well as arrange guided tours, translators, and other support. While you may have certain hindrances as a retiree, modern travel resources are more numerous than ever, which means that your only true limit is your imagination.