Drea The first time I booked a solo trip in my 50s, I sat with my finger over the confirm button for a full ten minutes. Not because I couldn’t afford it, and not because I couldn’t swing the time. Because a small voice said women my age don’t do this. But we both know that that voice is a liar, and solo travel in your 50s is proof of that.
That voice saying women my age don’t do this is a liar.
It’s ok not to be coupled up, not to have kids of your own. Friends may or may not want to travel and that’s ok, because you can go it alone. Solo travel in your 50s isn’t a wobble or a consolation prize. It’s the good part, because you’re worth it, and I’ll show you six ways to do it.
For my full guide to solo travel for women over 35, start here →
Travel Lighter – Your Back will Thank You
If turning 50 taught me anything, it’s to pack lighter (I’m shedding all baggage, including my own!). My free custom checklist is the system I wish I’d had years ago. You’ll also get travel tips, inspiration, and the inside scoop when a new article drops.
Why Solo Travel in Your 50s is the Good Stuff
I have more clarity, more means, and less to prove than I did at 30, and that changes everything about traveling alone. In the past it was about hitting every sight on the list and maximizing every dollar. Today, I’m ok skipping something if it doesn’t call to me. And I’d rather have one great meal than three forgettable ones.
It’s nice to be able to put money where it actually matters to me now. An upgraded plane seat, the nicer neighborhood, or a private airport transfer. There’s a confidence and ease that comes with knowing who you are, what you like, and what feels right to you. I don’t need anyone to co-sign my itinerary anymore. I make it my own.
That debate over whether to book this first solo trip in my 50s? I had to remind myself that it’s ok to treat yourself a bit, I’m worth the splurge on a hotel in Beverly Hills, and that a weekend on my own so close to home wasn’t frivolous, it was self-care. That made booking a breeze, and as I write this from that very same swanky Beverly Hills hotel, I have zero regrets.
How to Choose Your Kind of Solo Trip (Not Someone Else’s Bucket List)
When you’re considering what type of solo trip to take in your 50s, the key is to match the trip to what you need right now, instead of copying a list. Whether you’re brave or tired or curious, there’s a trip out there that will help you make the most of not just the vacation, but this stage of life.
If you’re running on empty, you want structure, not logistics. The last thing you want is to figure out every detail and have a ton of decisions to make. Your dream trip is just to show up and bask in the relaxation.
On the flip side, if you’re itching and eager for something new, you want a stretch that surprises you.
Are you the nervous nelly, concerned about what could go wrong? You need a place that’s easy, not somewhere that pushes every comfort zone and then some. That private airport transfer? Suddenly it’s not just comfort, it’s a sense of safety that someone already knows you’re arriving, will meet you as you exit into baggage claim, and will help calm that part of your brain that starts to worry.
Once you reframe trips, or parts of a trip, this way, you start to see solo travel through a whole new lens. That’s why when I’m figuring out what kind of solo trip to take in my 50s, I think of a trip theme first. What do I want to feel there, and when I return home? That becomes the filter I use, and below are some prime examples.
6 Kinds of Solo Trips to Take in Your 50s
Here’s a look at six types of solo trips, all with their own intent, vibe, and outcome. Because the best trips aren’t the ones that are great when you’re there. They’re the ones that change you somehow when you come home, and stay with you long after the trip ends.
Which Trip Type Fits You Right Now?
1. The Reset Trip, for When You Need to Come Back to Yourself
The reset trip is for the woman running on empty who wants the structure built in and never has to eat dinner alone unless she wants to. Whether you want a mind, body, or overall reset, a solo wellness retreat works wonders here.
With plenty of structure built in (fitness options, wellness classes, and spa treatments, etc), there’s always something to do. You can also do nothing and feel right at home. When I went to BodyHoliday St. Lucia solo? I never once felt like the odd one out. Some days I did a ton of activities, other days my activity involved drinks, a book and the beach. And through it all, I met lovely people and shared meals, laughs and memories.
Recommended spots for a reset trip: BodyHoliday St. Lucia, Miraval Austin
2. The Freedom Trip, for When you Just Want to Feel Light
A freedom trip is for the woman who wants sun, fun, and zero agenda. You can chill, drink, dance, and relax. Deep thoughts aren’t needed, your main decision is the pool or beach, and which bikini to wear.
When I think of a solo freedom trip, I immediately think of Cabo. Warm weather, true vacay vibes, and zero judgement anywhere. Cabo San Lucas gives a bit more energy, while San Jose del Cabo gives off a more mature older sister feel. Either way, when I just need a break from it all and don’t want to think about a thing and feel free as a bird, I’m Baja bound.
Maybe life has thrown you some curveballs, maybe you’re in the midst of bodily changes (TYSM persnickety perimenopause), or maybe you just feel tied down by all the adulting at home. Whatever it is, a freedom trip lets you say eff it, I’m having fun. Even better if you can bottle up that feeling and bring it home with you (if you figure it out teach me how!).
Recommended spot for a freedom trip: Los Cabos
3. The Bucket-List Trip, for the One You Keep Putting Off
We all know about bucket list trips. Those once-in-a-lifetime destinations that seem so big and life-changing that they go on a list that may or may not be tackled. These are for the woman ready to finally book the big one.
For me, Japan was one of those places. It seemed so big and so different from where I had been, and yet that made it all the more intriguing. That moment I sat at a counter in Tokyo slurping soba by myself? I cherished every minute of it.
These bucket list trips have a way of imprinting on your soul more than some other trips do. Perhaps it’s because it felt so unattainable and then wham, there you are doing the thing. The places I visited, the food I ate, so much of it is still so vivid in my mind. If you’re ready for a bucket-list moment, now’s the time to just go.
Recommended spot for a bucket list trip: 5 Days in Tokyo, Japan
4. The Eat-Pray-Love Trip, for Slow Mornings and Long Dinners
When I went to Italy for three months, everyone said it was the start of my eat-pray-love journey, and I laughed. But looking back, I think they were right. I was searching for something, reconnecting with myself, rediscovering what I liked and what I didn’t. That took time, space, and a place that allows it all to happen. Italy did that for me.
An eat-pray-love trip is for the woman who wants to feel things and rediscover their love of life and wander with no one to answer to. Breakfast at your own pace, quiet walks and local discoveries, and leisurely dinners enjoyed with wine.
That time I spent in Italy? It was when I stopped waiting for company to enjoy the view, and instead found the beauty in being by myself (I’m biased but I’d say I’m a pretty good travel companion). And in that, I knew myself a bit more, and came home knowing what I wanted (and didn’t want) to do, and to this day I’m grateful for the trip and the time to make that happen.
Recommended eat-pray-love destination: 3 Months Solo in Italy
5. The Comfort-Zone-Pushing Trip, for When You Want to Surprise Yourself
Are you ready to push your own boundaries? To try something new? A comfort-zone-pushing trip is for the woman who wants a real challenge. It could be a trip with an uncomfortable moment. Or a trip to somewhere that seems just a bit more out of your norm. And even a solo adventure travel trip that gets your endorphins flowing.
For me, hang gliding over Queenstown, New Zealand was a moment I had dreamed of and also had slight nervousness about. I spent about two weeks solo in New Zealand before and after an adventure group trip there, and didn’t want to wait for the adventure travel part to start.
What I proved to myself out there is that I can do anything I put my mind to, and I’m open to new experiences even if they’re a bit scary. If you want to do the same, I highly recommend a solo adventure travel experience. The high from the trip will keep you flying when you land back at home.
Recommended destinations to push your comfort zones: New Zealand (coming soon), Galapagos, Mont Blanc
6. The Weekend Getaway, for the Solo Trip You Can Book on a Tuesday
If you want to travel solo but don’t want a lot of hassle, go for the weekend getaway. It’s for the woman who wants a reset without a passport. You can drive or fly, pack a weekender bag, and get a little taste of solo travel without all the decisions or tons of time off.
When I want a weekend getaway, Palm Springs is a perfect solo weekend. With its food scene, spa scene, and nature scene, there’s a little bit of everything. Morning hikes or pickleball, afternoon pool or spa, and evenings with a delicious meal and a classic martini.
A weekend gives you a chance to breathe, a second to relax, and a few beats to yourself. You can close that door and no one is going to be knocking on it in five minutes asking you a question (moms I’m looking at you). It’s down time, it’s your time, and it’s high time.
Recommended solo weekend getaways: Palm Springs, Palm Springs vs Palm Desert, Sedona
Whatever type of trip you’re looking for, there’s a place and experience that can give that to you. Every one of these worked for me as a solo traveler because the destinations are safe, they embrace solo female travelers, and they each have something special that makes me breathe easier, deeper and leave with a greater sense of peace than when I arrived.
Staying Safe and Sane When You Travel Solo at This Age
However safe a place is, it’s always smart to keep your wits about you as a solo female traveler. Here are a few habits that let me relax instead of white-knuckling it.
- My non-negotiable arrival-day routine: Private transfer from the airport if I’m not driving; time to check in and relax at the hotel before a quiet dinner out. Nothing crazy, this is my settling in day.
- How I handle dinner alone without dreading it. Pick a place with a little energy. It could be a bar seat, or a place with a patio or street seating. Somewhere where being solo feels normal or mysterious, even, not out of whack.
- The check-in habits I actually use. I always share my location with at least one friend back at home, and will do regular text/WhatsApp check-ins with friends and family while on the road. If you have kids or a spouse, schedule regular times to check in so they feel a part of it and can see how much brighter and lighter you are with your own time.
- When I book a guided day and when I go fully independent. I go guided when the logistics are complex, the location is remote, or the activities add a lot of risk. Hang gliding? Definitely guided. Hiking around Mont Blanc? Definitely guided. Spending a week in Cabo or a weekend at Miraval Austin? Independent all the way.
For more on staying safe when traveling solo, read Scared to Travel Alone
Solo Dinner Survivor Kit
Book the bar seat or a patio table, where a party of one feels normal.
Bring a book or your journal for a little company, or just people-watch.
Go a little early, when the room is calmer and the staff has time for you.
Order the thing you actually want, and a glass of wine while you’re at it.
Chat with the bartender, or don’t. Either way, you’re exactly where you should be.
The Planning Part I Finally Stopped Doing Myself
I love taking the trip, and I’m a rare bird that also loves the planning involved in making a trip happen (perhaps that’s why I became a travel advisor). I love learning about a new destination and its unique neighborhoods, crafting the right itinerary that fits the traveler’s needs, and figuring out where to stay.
One thing I have learned through this process, though, is that I can still get joy in this without having to do all the work. Partnering with an advisor can pull you into the dreaming and scheming, while they do the heavy lifting for you. You can give feedback and craft the trip you’re looking for without having 40 browser tabs open at all times. You get days of your life back, an itinerary you really want, and someone to make sure things go smoothly while you’re on the road.
I’m doing that as part of a larger Japan trip I’m taking. I have a network of partners on the ground in every country, and I’m relying on them to craft the days with heavy travel and lots of connections. What would have been two lost travel days are now amazing touring days seeing sights many overlook because they’re not directly off a shinkansen line. That’s the beauty that can come from partnering with a pro. This is exactly what I now do for the women I plan for. If you’re interested in planning your own trip, give me a shout.
FAQS
Conclusion
Ready for a solo trip but weren’t sure where to go? Hopefully this helps you pick the type of trip that matches where you are right now. Tired? book the reset. Curious? Book the comfort zone stretch. Not ready to go far? Book the weekend. The finger-over-confirm moment is the last hard part, and then it’s just you and a trip that’s entirely yours. Remember, solo travel in your 50s is less about finding yourself and more about enjoying the self you already are.
Solo travel in your 50s is less about finding yourself and more about enjoying the self you already are.
Have your trip type identified but need help locking in a location? Reach out and let’s make your solo travel dreams a reality.
Wherever you go, however you do it, I want you to have a trip to remember.
Happy travels, kindreds!
RELATED POSTS
Ready to plan your solo adventure? Start here:
- Planning Tips
- Wondering if you need a travel advisor to travel solo? Here’s how to decide
- Everything You Need to Plan Your Solo Trip
- Ready to plan? Take a look at my 2026 planning framework in How to Plan Your Best Travel Year.
- Solo Travel Confidence
- International Destination Inspiration
- US Destinations
HELPFUL LINKS
Ready to book? Here are my go-to resources:
- Work With Me
- Need help planning your 2026 travel? Contact me here for personalized itinerary assistance!
- Want more information on the benefits of using a travel advisor? Learn more here
- Planning Resources
- Government Advisory Page to check the safety status of any destinations you are considering
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