Try a Solo Trip

Jan 19, 2020 | Living, Travel

“At first you feel awkward…then after a while you just begin to live.” At 24, I’ve traveled alone twice journeying to Mexico and — most recently — Cuba. Traveling alone means that in the most practical ways, you don’t have the luxury of depending on someone familiar to you. Simple things like having your picture taken or needing a trustworthy eye to keep sight of your belongings make you get creative or devise a strategic plan ahead of time. 


Traveling alone may also bring about unsolicited remarks from others pondering why you are solo. You may notice a tinge of judgment in instances where you’re dining out and the waitress questions, “Oh…just one?” The question — and sympathy settling on her face — confirm what you already suspected: eating alone in public is…awkward. While traveling alone can seem scary or uncomfortable at first, it can also be a transformative experience. 

Here are five things I did to prepare for Cuba:


Safety should always be a concern, although it shouldn’t stifle how you live. Taking time to actively be aware of your surroundings, research destinations, and share your daily itinerary with a trusted source should bring peace of mind. A huge key while traveling solo is sharing your location in real time via cell phone with a friend/loved one back home. 

Proper Documentation

You will need a passport. In addition, you’ll need a visa, which can be purchased at the airport. 

Political Awareness

Many believe that Americans can’t travel to Cuba. This is incorrect. As of June 2019, U.S. citizens can travel to Cuba, but the reason must satisfy a travel category such as “Support of the Cuban people.” 

Currency Exchange

Take cash! Cuba doesn’t recognize American credit or debit cards. Research currency rates and decide which conversion will be most inexpensive. I exchanged my American dollars (USD) to Canadian money (CAD) in the U.S., and then upon arrival to Cuba I converted to Cuban Convertible Peso (CUC). 


My lodging was accommodated through Airbnb, and it made my experience a breeze. My host provided me with airport pick-up/drop-off, a cell phone, breakfast, and walking tour. Additionally, through Airbnb I was able to book group trips and sightseeing experiences — such as spending the day in Viñales, overlooking a breathtaking valley while having lunch with other travelers. This is a great way to naturally socialize with others. Traveling alone doesn’t mean traveling isolated.

As I played water frisbee at the Santa Maria beach with my newfound friends, I felt content. There I was all alone immersing myself in a new culture unbothered by the noise of my high-pace life awaiting me back home.

P.S. Plan a solo getaway to Vermont in the spring.