Picking Your First Destination

How to Pick Your First Solo Travel Destination Without Feeling Overwhelmed

You’re ready to take your first solo trip (YES!), but there’s just one little problem…

Where should you go?!

The world feels huge when you’re planning a trip for one, and it’s easy to spiral into questions like:
“What if I choose the wrong place?”
“Should I go far or stay close?”
“What makes a destination solo-friendly?”

Take a deep breath, you’re not alone. Here’s how to take the stress out of the process and actually enjoy choosing where your solo adventure begins.

Step 1: Ask Yourself What You Need From This Trip

Before you open a dozen tabs and scroll for hours, pause and check in with yourself:

• Do you want rest or adventure?
• Are you craving culture, nature, or a change of pace?
• Do you want to be social or have more solo time?

Your mood matters. A beach weekend in California hits different than a museum-hopping week in D.C. There’s no “right” choice, just the one that fits you right now.

Step 2: Start Simple (Especially if It’s Your First Time)

For your first solo trip, choose a destination that’s:

• Safe and walkable
• Easy to navigate (bonus if there’s public transit)
• Language- or culture-familiar, or at least easy to get around in
• Known for being solo-travel friendly

Great beginner solo destinations in the U.S.:

• Charleston, SC – walkable, beautiful, foodie heaven
• Santa Fe, NM – artsy, peaceful, stunning desert vibes
• Portland, ME – charming coastal town with amazing seafood
• Savannah, GA – laid-back, historic, very photogenic
• Austin, TX – music, tacos, and solo-friendly energy

Want to go international? Try:

• Lisbon
• Tokyo
• Reykjavík
• Amsterdam

Step 3: Consider These “Solo-Friendly” Factors

Look for destinations that offer:

• Walkable downtowns or public transit
• Things to do solo (museums, markets, food tours, bookstores, hikes)
• A safe, inclusive vibe (check traveler reviews and solo traveler blogs)
• Plenty of daytime activities so you’re not stuck wondering how to fill time

Pro Tip: Cities with good coffee shops, food halls, and waterfronts = great for solo exploring.

Step 4: Think About How Long You Want to Go

Your first solo trip doesn’t have to be 10 days across the world. You can absolutely:

• Take a solo weekend getaway within driving distance
• Book a 3- or 4-day staycation with a hotel in your own city
• Do a slow solo trip to one town and really dig in

Ease into it. Once you’ve done one, you’ll feel way more confident planning the next.

Step 5: Make a Short List (Then Go With Your Gut)

Narrow it down to 2 or 3 destinations that hit your criteria. Do a quick vibe-check:

• Which one excites you most?
• Which one feels do-able right now?
• Which one are you already imagining yourself in?

That’s your sign.

Quick Tip: The Best First Solo Travel Destinations Are…

✔️ Easy to get around
✔️ Safe and solo-friendly
✔️ Full of stuff you already love doing
✔️ Not overwhelming to plan
✔️ The one you are most curious about

Ready to Pick Your Spot?

Check out our Get Inspired ideas for solo-friendly picks, whether you want local, abroad, staycation, or something a little in between. And remember: your first solo trip doesn’t have to be perfect. It just has to start.

Let it be fun. Let it be yours. Just go solo!