Solo Trekking through Concreate Jungles

The picture above was taken from my favorite view of the Manhattan skyline by a complete stranger because I went to New York City by myself in the middle of a particularly boring Oklahoma fall. And between all the mistakes I made, like staying in the middle of Times Square because the hotel threw in a free shuttle from the airport, I learned a lot about solo traveling. Like the fact that a shuttle does not cost that much.

I stayed for one week, smack in the middle of Times Square with a bucket list of activities, a credit limit that couldn't even cover my hotel, and seven good outfits. I had one moment of hesitation when my plane was descending over the glowing outline of the Manhattan island. I had never taken a taxi and didn't plan any outfits that go with subway gum on them. But I did have a portable charger and a drive for a good story. I walked through the JFK airport, immediately overtaken by excitement and suddenly couldn't care less about taxis vs subways. I was in the greatest city in the world.

Here's everything that I learned about solo, city traveling.

1. Do (at least some) research.

My personal opinion here is to do more rather than less, but I respect the element of spontaneity. In cities where there is so much to do, it can be hard to make well-informed decisions in the moment to make the most of your trip. I find it helpful to create lists or guidelines, if you're not a full-blown itinerary traveler, to see the things you care about instead of just the tourist traps that grab your attention. If you have time during the days leading up to the trip or the flight over, try to get together a list of restaurants, shopping, attractions, and picture/viewing spots. A few ideas in each category can make a great jumping-off point for your trip, you will always have that to fall back on.

2. Don't make a list of attractions/restaurants, make a Maps guide.

Now that you have a few ideas, creating a guide on Google Maps takes your bucket list from bullet points to a scavenger hunt around the city with all your top spots. You can group areas of the city to save money on transportation and keep one day's worth of activities within a walkable distance. Or you can prioritize attractions and know what things you can save to pass by on your way home from dinner.

3. Plan to walk or try ridesharing.

When you're traveling alone, the cost of an Uber for one is not much different than the price of an Uber for four, which can add up quickly. Either bring good walking shoes or the courage to rideshare with other solo travelers or small groups. I opt for walking shoes because strolling between districts and streets is a great way to explore new spots and restaurants. Please see the left for a delicious midday sangria on my afternoon walking through Little Italy on my way from Soho to cat yoga (not pictured because cats can't sign photo release forms).

4. Walk near groups or families when possible.

As mentioned, I wouldn't recommend staying in the heart of Times Square. While the hotel was a great experience and a fun splurge, walks home from dinner or around Central Park at night were not always a walk in the park. While you shouldn't go into your trips with a sense of cynicism about the people you will meet, I do suggest knowing how to stay safe when your gut says something is off. Following groups, families or couples closely gave me peace of mind when I found myself obsessively checking over my shoulder.

5. Order to go!

If you're a restaurant window shopper like I am, you understand the intense disappointment of having to pass up a little snack or an entire second bowl of pasta when you pass a good dish on the walk home from dinner. It's like finding that same pair of shoes you just bought on sale during the walk from the register to the next store. So don't pass it up. Especially not when you're in culinary powerhouses like so many cities are. Order something shelf-stable or re-heatable and save it for when you don't have plans for your next meal or need a midnight snack.

6. Drink where you sleep.

Going out for a nightcap alone can be intimidating. But if you have the budget for a hotel, go for one with a bar attached and try that before braving a late-night walk back in a new city after a few drinks. Many hotels in major cities will have rooftop bars that give a great view of the city at night, not to mention nighttime entertainment. Just because you aren't stumbling home from the bar doesn't mean no one is. This is also a great way to meet people who might be visiting and see if there is any room for plans to overlap.

7. Find the freebies.

Traveling can be expensive. But most major cities have a lot of free buildings or areas that you can explore. Libraries are a great place to enjoy that to-go snack you picked up and rest your feet. Places of worship have some of the most beautiful architecture and are always open to view and often open to respectfully explore. Graveyards and cemeteries, while eerie at night can be a peaceful and interesting stroll. Many sites have landmarks, like one I walked through in Edinburg that had the gravestone of Thomas Riddle. Some museums also have free or discounted admission. And if all else fails, malls and markets, train stations, or landmarks are always great places to walk around and explore the city centers with no financial commitment.

8. Try foods you don't like.

New cities may have the same dishes, but they also have different ingredients. Try dishes you've had and not loved and see if the difference in locally sourced ingredients can change your mind about your future ex-least favorite foods. Or, if you want better odds for a surprisingly good meal, look for unique foods and cuisines that give the city its claim to fame. For example, I grabbed a cactus taco in New York. While that ended up being the bad ending of a new food-testing, the New York-style bagel I got after more than made up for it.

9. Job search if you're open.

New cities are a great way to make new connections and explore possible career opportunities. You don't need to throw business cards or resumes around, but finding the headquarters of major corporations can be exciting and hiring managers take lunches at surrounding restaurants too! If you have time to plan, you can always reach out to connections in the area and ask to catch up if they have time.

10. Take time to enjoy life there.

It's great to maximize your time in new cities and get the most out of any trip. But it can also be nice to just enjoy what life is there. You can visit a local grocery store just to see and pick up some cheap snacks, do some passion work in a coffee shop, buy your favorite candy and enjoy a relaxing night in, find a park and take a walk, the city is your oyster.