12 Solo Date Ideas to Build Confidence Before Your First Solo Trip // 173
If the idea of solo travel feels exciting—but also a little intimidating—this episode is for you. Cheryl shares 12 simple solo date ideas to help you get comfortable doing things on your own, build confidence, and prepare for your first solo adventure.
12 Solo Date Ideas to Build Confidence Before Your First Solo Trip
Have you ever thought about traveling solo—but something about it feels just a little too uncomfortable?
Not because you don’t want to go.
But because you’re not quite used to doing things alone.
If that sounds familiar, you’re not alone.
For many women, especially in midlife, the idea of solo travel isn’t just about logistics—it’s about learning to feel comfortable in your own company again.
And that’s where solo dates come in.
Why Solo Dates Matter Before Solo Travel
Before you ever board a plane or take a solo trip, there’s something even more important to build first:
Comfort with being alone.
When you practice doing everyday activities by yourself, you begin to:
- Build confidence
- Trust yourself more
- Enjoy your own company
- Let go of fear around being alone
Think of solo dates as training for solo travel.
Each experience strengthens that confidence muscle.
12 Solo Date Ideas to Build Confidence
Here are 12 simple and meaningful ways to start enjoying time on your own.
1. Visit a Cozy Café or Bookstore
Find a quiet café or bookstore where you can sip coffee, read, journal, or simply people-watch.
2. Explore a Museum or Art Gallery
Take your time moving through exhibits at your own pace—no rushing, no compromise.
3. Go Thrift Shopping
Browse secondhand shops and let your creativity wander. You might find inspiration—or a hidden treasure.
4. Walk Through a Farmers Market
Enjoy fresh food, local vendors, and a relaxed environment that’s perfect for solo exploring.
5. Have an Inner Child Playdate
Do something playful—paint, ride a bike, write poetry, or revisit a hobby you loved as a child.
6. Take a Walk or Hike Somewhere New
Explore a new park, trail, or neighborhood and enjoy time in nature.
7. Treat Yourself to a Spa Day
Book that massage or facial you’ve been putting off and give yourself time to rest and recharge.
8. Take a Creative Class
Try a painting, pottery, or jewelry-making class and tap into your creativity.
9. Attend a Cooking Class
Learn something new, meet people, and enjoy the experience of creating a meal.
10. Be a Tourist in Your Own Town
Visit the places people travel to see in your city—but you’ve never explored yourself.
11. Visit a Botanical Garden
Take in the beauty of nature and enjoy a peaceful, reflective environment.
12. Create a Vision Board at Home
Spend a quiet evening dreaming about your future and creating a visual reminder of your goals.
Building Confidence One Step at a Time
Each of these solo dates may seem small.
But together, they build something powerful:
Confidence.
The more you practice being on your own, the more natural it feels.
And over time, that confidence carries into bigger experiences—like traveling solo.
This Is About More Than Travel
Learning to enjoy your own company isn’t just about preparing for a trip.
It’s about reconnecting with yourself.
It’s about discovering what you enjoy.
What brings you peace.
What makes you feel alive again.
And that’s a beautiful place to begin.
If solo travel is something you’re exploring but aren’t sure where to start, this is something I support women with through 1:1 travel coaching.
Together we can explore your travel dreams and create a thoughtful plan that fits your life right now.Learn more here: https://cherylbeckesch.com/work-with-me
