To gather the ultimate guide to navigating midlife getaways, we spoke with top travel experts who specialize in planning trips for women in their 50s—including advisors from Virtuoso, Bluetail Travel, and Why Not Roam. Here are their top non-negotiable tips for going solo, protecting your peace on group trips, and packing like a pro.
Taking the leap into solo travel for the first time can feel intimidating, but the industry has evolved to meet women right where they are.
For a smooth transition into going solo, consider a European destination with built-in social options. "Lisbon and Porto alone offer plenty to explore independently," notes Sheree Holt, founder and chief roaming strategist at Why Not Roam. "You’ve got food tours, wine experiences, workshops, and small-group excursions that make it easy to meet other travelers... I would book a centrally located hotel and arrange a few social experiences in advance, then leave part of the itinerary open. That gives the option of having plans and potential company without committing to being with a group every minute of the trip."
2. Pre-Arrange Your Airport Transfers
Arriving in a foreign country after a long-haul flight with heavy luggage can immediately throw you into stress mode. Elevating your security and comfort right out of the gate starts at the arrivals gate.
Whether you are organizing a 50th birthday celebration or bringing three generations together, women are almost always expected to play party planner, itinerary wrangler, and tour guide—often at the expense of their own vacation.
Cruises can also serve as a built-in safety valve for group dynamics. "A cruise is often the ideal way to travel as a group, too: everyone's in the same place, but with the freedom to explore different excursions during the day before all meeting up over a lively dinner to share stories," Kilbreath adds.
4. Give Yourself Permission to "Slow Travel"
"Remember that you don't need to please everyone all of the time, and you don't need to see every landmark," says Schlegel. "After all, you are on vacation, so enjoy some relaxation, build in unhurried moments, and allow for serendipity in your exploration of a new destination."
Related: 8 Carry-On Essentials Every Over-50 Traveler Needs
"As a travel advisor who just turned 50 herself last week, my biggest tip is to be completely unapologetic about doing what you like when you travel," says Kilbreath. "Build in time to just soak up a place instead of always being on the go. Splurge on the business-class seat or the room upgrade, we've earned a little extra comfort. This is a new chapter, so lean into what actually excites you now... You're not the same person you were a decade ago, so take the trip that fits who you are now and don't feel guilty about it."
6. Seek Out "Comfortable Adventure"
"Arenal, Costa Rica, is one of my favorite recommendations for women who want adventure but have zero desire to rough it," shares Holt. "You can hike near the volcano, walk the hanging bridges, visit waterfalls, go rafting or zip-lining, then return to a beautiful resort for a spa treatment, a great dinner, and a soak in the hot springs. In Arenal, you can spend the day doing something that challenges you and end it wrapped in a robe with a view of the volcano. (That’s my preferred version of adventure)."
"A pashmina or, in winter, an oversized knitted shawl," recommends Schlegel. "You never know when you might encounter chilly air conditioning, a frigid airplane cabin, or cold weather, so it's important to remain warm and comfortable. A pashmina can also dress up an outfit for dinner, so you might as well bring a couple in different colors to maximize your travel wardrobe."
Related: After 20 Years Away, I Returned to Providence and Found The Secret Spots For Those Over 50
8. Rethink Your Luggage and Shoe Prep
"My favorite is a top-opening suitcase like Biaggi rather than a clamshell, as it saves space in tiny hotel rooms and lets you pack more," Kilbreath shares. She also reveals an inexpensive packing hack: "My cheapest insider trick: disposable shower caps. Slip them over the soles of your packed shoes and the rest of your carry-on items stay clean."
"Bring along a couple of travel sink laundry packets (for example, Tide) as well as two to four clothespins," suggests Schlegel. "You never know when you might need to rinse out an item of clothing, and this makes it easy. Bonus: the clothespins can clip a hotel curtain that may be letting in an annoying chink of early morning light."
10. Pack Extra Grace and Flexibility
"The practical one people forget is a universal travel adaptor... But the real thing to pack is your grace and flexibility," Kilbreath emphasizes. "Travel is never perfect. Flights get delayed, the restaurant you had your heart set on is closed, it rains on the one day you needed sun. The women who have the best time traveling are those who can roll with it, who treat the detour as part of the adventure instead of a ruined plan. More often than not, the hiccup becomes the story you tell for years."
Related: Lisbon Is the Perfect European Escape for Solo Women Over 50—and Here’s Why
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