GUIDE: Traveling Alone

One of my most asked questions is how I travel all by myself. Not necessarily a safety aspect, but bridging that socially awkward gap of eating alone, walking around all by yourself with just your thoughts. I will be honest, it took me a longggg time to get to where I am comfortable doing so much on my own— I like to attribute it to my perpetually single life and the fact that all my friends have “real jobs” and can’t just buy a plane ticket on a whim and go somewhere for a week or a month which I have been known to do on several occasions.

Even though I didn’t exactly just jump right into the deep end, the first time you travel alone is absolutely terrifying and you forget everything you’ve ever done by yourself.

But let’s take baby steps. Even though there really is only a couple of steps before heading right to the deep end.

First up: Coffee shop

Grab your computer, a pen and paper, whatever it is you need to work on, or even just go browse on Facebook for an hour, grab a coffee at the bar and settle in. This is so normal for people to do you’ll automatically feel comfortable.

Next up: Movies

I do this all the time and some of you guys brought this up a few times asking how I do it. It is the easiest thing ever because it’s not like you actually talk to your friends who you are in the movie with. It is much more natural than you think and a lot easier than you think. I also love the movies. If you don’t love the movies, still do this because you need to take yourself out of your comfort zone.

I suggest picking a good movie, don’t pick a kids movie because you’ll be self-conscious the entire time that people think you are a creep in a kids movie.

Step Three is a Bar

Go sit at the bar and have a drink. Take a book at first, please don’t be anti social and take your phone, even though it is like an extension of your hand now, just read a book or a magazine, or even your computer.

I am currently sitting in a restaurant with a black bean burger, a beer, and writing on my computer.

Every time you go spend less time reading or on your computer, talk to the bartender. Coming from a retired bartender, I always made sure the solo person at the bar felt comfortable.

You might even see other solo drinkers and, now the next thing I’m going to ask you to do is crazy, TALK TO THEM. Be your mom and just randomly say something to them, who cares if they think you’re weird, you’ll never see them again and they probably won’t think you are weird its just in your head.

Step Four: Eating alone!

You’re in the big leagues now, it’s time to go to a restaurant. I suggest starting with something easy like an order at the counter place before you jump right into having a server.

Read this next line very carefully,

NO ONE WILL THINK YOU ARE WEIRD

People can’t spend every minute with friends and you' can’t always have food in your fridge, you also don’t always have to take it togo, IT IS NORMAL!

Now, remember how I said you’ll eventually have to jump in and just bite the bullet? Now is that time. Buy the plane ticket.

My strongest suggestions from here is to stay in a hostel so you can meet other solo travelers. Before you know it you won’t be doing anything alone, you’ll make so many new friends you’ll be begging for a solo night at a restaurant where you don’t have to talk.

But, if you aren’t a hostel kinda kid, stay in a hotel, but get out there. Go on tours, and be awkward and talk to people!

The moral of the story is to try not to think so much, you care more about what people think about you than what they are actually thinking. Don’t let your fear of being alone keep you from experiencing something amazing!

The Wellborn Hotel

This past weekend I had the pleasure of spending the weekend with The Wellborn Hotel! This is Orlando’s newest boutique hotel and it is truly a hidden gem.

First of all, this hotel is made up of 3 historic buildings, the Norman-Parry Inn and the original Wellborn hotel.

Now, when you come off the exit of the 408 towards Orange Ave, you come around the ramp and just to your left there is a hotel that looks like it stepped right out of the 70s and that is the site of this weekends shenanigans.

When you walk into the Norman-Parry Inn to check in, you will be immediately impressed with the decor. There is a giant scrabble board on the wall spelling out their coffee menu, and they hand you an actual key to your door, not an electronic key, a real life key. Not to sound too millennial but I loved it.

They showed me through the front Inn, there is a day-room up front and a sun-room in back as well as a library, all are available for guest use. This is also where you get your complimentary continental breakfast in the morning.

We walked out the backdoor and stepped onto a brick pathway covered in market lights. The path opened up into a gorgeous courtyard filled with mix-matched tables and chairs, a small fountain, and, my absolute favorite, a cocktail cart! You all know how much I want Trudy to be a cocktail truck so this was a dream come true to see. I will warn you that we had a tropical depression pop through this weekend so unfortunately the truck wasn’t open due to rain but it was still cute.

At the back of the courtyard was the third historic house in the bunch with a large porch with giant Jenga and connect 4 (if it is giant is it still connect 4?) When you walk through the french doors there is a grand piano and sitting area with couches and chairs all in the 70s style. If you head up the staircase, you’ll head into the restaurant. The bar sits in the middle of the room and each room has low 70s couches and funky chairs, there is an old fashioned record player in the corner and soft music plays over the stereo. It is like being in an old Key West house, with bay leaves decorating every corner, that soft hint of pink, and a retro stain glass window in the bar.

Now, I have to tell you about the bathrooms, there are two on either side, one with pink and white balls and other with blue and white balls filling the bathtubs! It makes for awesome pictures, and I even got over my ball pit fear to get these photos. I have a great story about getting these pictures but I’m saving that for Thursday’s post.

After the tour I grabbed my stuff and headed up to my room. The room was nothing like what I expected. High ceilings with exposed wood beams, a gorgeous wood-framed bed with great carving detail, a bar in the corner (they know me so well) and a reading nook underneath the wrap around windows that gave us a panoramic view of the front and courtyard. The bathroom was down right adorable with pink and white tile, and the best lighting you’ve ever seen.

I will give you a heads up, there is no closet. So, if you have things to be hung up, I always pack my own hangers because I’m a weirdo, but you’ll have to use the coat rack.

After unloading all our things we set out to take pictures, obviously. Stephanie directed me around the courtyard for the best picture spots and let me tell you, the entire freaking hotel is Instagram central!

We headed back to the room to get changed for dinner, where my parents joined us for our evening at the Wellborn!

The restaurant is tapas and small plates but all delicious and shareable. They have a great happy hour too. I will get more into that on Saturday’s food post.

The Wellborn is walking distance from central Downtown Orlando. Now, ya’ll know I’m not big on going out Downtown, but hey, when in Rome, right?

The owner of the Wellborn also owns some of the hottest bars and clubs in downtown Orlando, like Mathers, and the newest addition to downtown, The Robinson Room. So we had to go there!

I had never been to Mather’s and everyone keeps telling me I was missing out and I have to say, it was truly a super cool bar.

You walk into an office building where you are greeted by Paul’s Poems who will write you a poem to be ready for you when you walk out. It’s pay what you want so I paid too much and then lost it in my Uber. I would like to say I did it on purpose for someone else to find this super happy poem about Brittany in Wanderland, but I didn’t and I’m still a little bummed about it.

Anyway, after a great night at both bars we headed back to our hotel room where Stephanie, Madison, and I and a few friends played Jenga on the front porch drinking wine. It was quite easily the most perfect summer night.

I would love to get into more details about our next nights out, but I have to leave you hanging right? Stay tuned for more on The Wellborn Hotel and our incredibly fun adventures downtown!

P.S. If you are in the Orlando area, make sure you check out The Wellborn for drinks and appetizers, either for happy hour or for dinner, it is a great date spot, girls night out, and your Instagram will love you.