Solo trips have become the inevitable combination of your desire for exploration outgrowing your circle. Most of us have been through it. You find an amazing deal for two people or four people and you start calling your friends but life is lifie’in, they can't get time off, their money is funny, or they can’t find a sitter for dem kids. Whatever the case may be, you find yourself wishing you had someone to go with you. I know it can be scary, especially if you are used to traveling in groups, but there's no reason you can't take the leap on your own.
I remember my first solo trip like it was yesterday. Dave Chappelle had just come out of retirement/back from Africa and was doing a residency in New York at Radio City Music Hall. I love me some Dave! He is easily one of my top three greatest comedians of all time! So I knew I had to be there, plus, the way that Virgo gave the entire industry the finger, this might have been my only chance to see him live before he did it again lol. The tickets that fit my budget were on a Wednesday night and the line-up featured Ice Cube, The Roots, Common, Vince Staples, and another comedian. I sent a group message to my friends and family to see if anyone was down to roll but after a day or two of, “I’ll let you know”, “I have to work”, and general crickets, I purchased my 5th-row seat, MegaBus ticket, and booked myself a room on Airbnb. ANNNND, I’m glad I did because yesterday’s price is definitely not today’s price!! I had the time of my life and was officially bit by the solo travel bug.
Traveling solo has transitioned from being viewed as something people do because they don’t have friends or family, to a preference for those seeking more out of travel than just parties and pictures for social media. People seeking a deeper travel experience for personal or professional development reasons can greatly benefit from solo trips.
Solo travel provides a freedom that really can't be put into words, it just has to be experienced. There is something powerful and freeing about being completely on your own time. Don't get me wrong, we all love creating memories with family and friends but, the group dynamic can sometimes be a bit much. Accommodating everyone's food, entertainment, destination, budget, and mode of travel preferences can turn into a very stressful part-time job, especially if you aren’t using a travel agent. The memories are great but the challenges are REAL.
If solo trips are something you've always wanted to do but haven't pulled the trigger yet, I'm here to help. The best way to get over any obstacle is to start small. Try planning a short trip to someplace close by, or somewhere you've already been but never alone. Consider a two or three-night getaway or a staycation several hours from your home. It could be a different state or a new part of your state that you’ve never explored. You can even start with baby steps like going to the movies alone or eating dinner by yourself. This will help you get comfortable with traveling alone and getting over what YOU think people might say or how it might look. It doesn't have to be elaborate, the goal is to get comfortable navigating the world by yourself. Making sure you are comfortable in your own skin is crucial to your solo travel journey. I call these confidence-boosting activities “Soft Launches”. Their goal is to take you a bit outside of your comfort zone without removing all your lifelines.
Here are a few of my favorite soft launch destinations:
First of all, there is no day that you can go to New Orleans and intentionally or unintentionally run into a festival. The city is always alive with something exciting, eclectic, historical, and colorful to offer visitors. New Orleans is a guaranteed good time with 24-hour bars, soul food, fine dining, amazing art, rich culture, and live music.
Maine, in a word, is Simply Beautiful. It doesn't matter if you are in the city of Portland or by the coast in the small town of Camden, the state is just breath-taking. AND, might I add, has some of the friendliest white people I have ever met in my entire life. I'm guessing recreational marijuana has something to do with that and I'm not mad. This is a place for nature enthusiasts, seafood lovers, wine lovers, history buffs, and people who enjoy mild summers. Oh, and did I mention LOBSTER?! The title of “world's best lobster” is well deserved and if you don’t like lobster, Maine will make you a believer! I don't know what happens when it gets shipped all over the world but it really doesn't taste the same. So much so that I only eat lobster when I’m in Maine lol.
Vegas is more than a “what happens here stays here” town. There's always something fun and a little quirky for you to get into. You can catch a show, hit the casinos, chill at the pool parties, walk the strip, zipline, visit one-of-a-kind museums, or see the Grand Canyon. Whatever you're into, you’ll find it in Vegas. I feel like it is the perfect soft launch destination for people who aren't quite sure what they want to do but want to be someplace with a lot of options. Also, you can always find amazing deals on flights and hotels to Vegas.
I mean… does it really need any introduction? There is shopping, Michelin-star restaurants, unique museums, the theater, comedy clubs, and a limitless amount of urban subcultures. I look at NYC as an Urbanite’s Disneyland because, no matter how many times you visit, there is always something new and amazing.
This is one of my favorite low-key getaway destinations because it has the perfect mix of old-world charm, walkability, convenient transportation, entertainment, and of course amazing food. The National Harbor and MGM Grand Hotel and Casino are just a water taxi or ferry boat ride away. So, you can enjoy the hustle and excitement of the Harbor and retreat to the other side of the river for more intimate venues with live music or catch an opera singer doing their thing on the street. If that isn’t enough to keep you occupied, Washington D.C. is less than 15 minutes away.
The Chi is just a vibe! It has its own very unique swagger that cannot be imitated or duplicated. It’s a place for people who love to visit cities where each culture has carved out its own identity and embraced the fusion of cultures. It has a nostalgic glamorous mafioso kind of feel. Chicago checks the box for people who love architecture, ethnic and cultural food tours, speakeasies, eclectic nightlife options, live entertainment, and amazing festivals. Deep-dish pizza is just the tip of the iceberg lol.
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