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The more you do it the easier it gets. If you like people, find group tours or meet up events.
Part of the fun for me was in planning all the things I wanted to do and kind of grouped it into ‘must do’ and ‘depending on time and what I feel like’. Then I could take a look and try and break it up, like, let’s do a walking tour with other people, or why don’t I book a tasting tour that has small group limits. That way I knew there would be some socializing, but no pressure, and I also knew what I wanted to do/see with the time I had and everything else was a bonus. Kept my days filled up and I had a purpose rather than being aimless which for me makes me feel more awkward.
Think about why you want to travel alone and what you want to do
Stayed at hostels which helped :) highly rated ones are a must because people will go there for the same reason and seek out that interaction but def still need a plan for yourself to stick to otherwise you’ll feel disappointed
I spent a month backpacking solo through Australia and, while the awkwardness never FULLY goes away, it helped me to remember that people aren’t focused on you (people mostly think about themselves), and they aren’t judging you for eating alone or doing an activity solo. And if they are, who cares, you’ll never see them again. Embrace the benefits to solo travel (getting to do whatever you want, at your own pace, with no conflict) and also try to get out of your head and focus on the places and experiences. It seems like forever when you’re in it, but then it ends and you’ll be back with people you know, so enjoy the time solo while you have it! I can’t wait to do it again.
Also, I agree with the hostel recommendation but my personal favorite is staying at AirBNBs where you can rent a single room and get to know the people living there. I feel like I have a “home base” and friendly faces in each city I visited.
Bring a book or journal that way you can fill some “awkward” time if you see fit.
Bring a journal with you and write how you feel. The awkwardness is normal until you learn more about yourself.
If you really want to meet people, try organized events for singles or try staying at a hostel to meet other people
Making an itinerary is the biggest thing for me. For me the toughest thing is trying to fill empty time in the day, so if you plan it out in advance the structure can help.
Obviously nothing ever goes 100% to plan, so figuring out what there is to do should give you ideas for other things in case whatever you’re trying to do is cancelled, sold out, or unavailable.
Being open is key. I just spent 2+ months in Colorado and New Mexico solo. Chat up other diners in restaurants and people working in stores. Also, hire a guide if there’s somewhere you want to go but don’t feel comfortable going alone. Meetup is a good resource for certain activities as well.