Valentine’s Day is here, which means plans for romantic dinners, gifts, and travel are underway. Valentine’s Day is often advertised as a day for lovers. However, as a single woman, I like the idea of normalizing singles to get in on the action. Allowing the holiday to be a day to celebrate self-love and enjoying your own company. With that, I thought it would be a great idea to list a few trips that are fun (and safe) options for the solo traveler. I gathered up a few of my own experiences and polled some friends on our best solo trips to put this list together. Are you in a relationship? No worries! These trips are also great for you and your partner!!!

*Disclaimer: I think this goes without saying but, be sure you are practicing safety when traveling alone. Unfortunately, we live in a world where merely taking a stroll alone at night is almost impossible without any sort of threat (especially for women). Be sure you pay close attention to your surroundings, make sure your loved ones know where you are, and follow your gut! If something doesn’t feel right, do not do it!* 


Chicago is actually one of my favorite cities. From the architecture to the food and the people, I LOVE everything about Chicago! I’ve been to Chicago twice on solo trips, and each time I had such a blast. 

Both times, I stayed in LondonHouse Chicago, a Hilton hotel located Downtown on Wacker Street. It has excellent views of the Chicago River and Lake Michigan and a really nice rooftop bar. I was able to walk pretty much everywhere in the city, from the hotel to sightsee, partake in attractions, and discover great food. 

When I needed to venture further out, I took Uber, and the drivers were all friendly. While walking around the city, I met some really great locals who had great food recommendations, and I met other tourists who volunteered to take pictures for me. 

I was here for a week-long each time, so I covered a lot of ground. Some top things I recommend are: 

  • Boat tours that take you down the Chicago River and through Lake Michigan. 
  • An architectural biking tour where guides lead you on a bike ride around the city while giving you the history of each building. 
  • The Sky Deck at Willis Tower (also known as the Sears Tower) is fun if you aren’t afraid of heights. 
  • Anywhere that serves deep-dish pizza. 
  • Perhaps dinner at Michael Jordan’s Steak House (it is a little pricey, but I’m a fan, and the steak and wine were delicious).
  • The Chicago Bean because who wouldn’t want a cool photo under this platinum sculpture?
  • A Chicago Cubs game. Wrigley Field is a historic stadium, and the fans are passionate!
View during lunch at the Corner Bakery right next to my hotel.
The Chicago Bean
I went during a time when getting your sunglasses in front of objects was cool
From the top of the Willis Tower. It was a long way down!
Had some really nice tourists help me out with photos

Seven Magic Mountains

Seven Magic Mountains was a recommendation I received from my friend who took a solo trip to Vegas and tried to find anything other than gambling to take part in. This popular attraction and art installation is only a 20-minute drive from the Vegas strip and worth it! 

It is a really cool place for photos and a fantastic work of art to stop and appreciate. It consists of 7 painted boulder totems that stand up to 35 ft tall. Done by the Swiss artist Ugo Rondinone, this piece of art demonstrates the midway point between the natural and the artificial (deep!). The natural being the vast mountain range and the artificial being the interstate taking you between Las Vegas and Los Angeles. 

I can stare at pictures of this attraction all day, and I definitely plan to visit myself soon!

© Seven Magic Mountains Official Website

Getaway House

You have probably seen these trendy tiny homes popping up in cities around the country on social media. The Getaway House delivers the promise stated in their name, the ability to get away. I went to one in my home state of Georgia with two friends, but I definitely plan on going back alone. This place is perfect for the solo traveler who wants a weekend away with a great book or to get some writing done. I quickly imagined going to focus on creating new content and complete new projects. If you are creative with a bit of a block, I definitely think heading out here will get your juices flowing again. 

The natural light and comfy bed will cure anyone’s writers block
There is a small stove top in the cabin but I mostly cooked everything on the outdoor fire.

Washington, D.C. 

Adding DC to the list as this city is a super easy solo trip for travelers who love museums and history. All of the Smithsonian Museums are pretty much free and within walking distance from each other, and finding food is extremely easy (not to mention delicious). You may even find some food trucks to indulge in. 

*Update: Many of the Smithsonian museums are temporarily closed due to COVID-19, so add this one to your list for later :)*

Cool art at Donald W Reynolds Center for American Art and Portraiture. This was one of my favorites.
I live
Needs no introduction
Reflection Pool at the African American Museum


Yep, a staycation is a great way to spend time with yourself. You can even rent an Airbnb in your own city for the weekend and take yourself out to dinner while at it. A friend did it for herself recently, and she said it was probably the most relaxing thing she’s ever done. Go ahead, treat the number one person in your life to a staycation! 

Again, I want to normalize singles celebrating Valentine’s Day with just as much love as anyone in a relationship. Yes, we all desire companionship at the end of the day. Yet still, one thing I’ve learned throughout my journey in this lifetime is, you will not find fulfillment, genuine love, nor wholeness until you are pleased and in love with yourself. Love comes from within, love is around you, YOU ARE LOVE! 

To all my singles and those in loving relationships, Happy Valentine’s Day!!!

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