Expert Advice

The One Where We Fly Solo

What if the best solo vacations are more than just "vacations"?

Jessica M

I know, I know.

You’ve read all the best solo vacation articles and blogs. You follow the famous solo travelers on Instagram. What else possibly could be said on the topic?

Here’s something: Hilton Grand Vacations adds unique opportunities for the best solo vacations.

I’m in my early 30s, single, and I love to travel. I guess that’s obvious, considering I’m writing for this blog and an Owner with Hilton Grand Vacations!

Yes, I love to see the world with my family and friends, but I also love to travel by myself.

Many times, the people who want to explore more of our big, beautiful world are not able to take those adventures with others because of conflicting schedules, personal interests, wanting to see different places, or even getting the same time off.

You often hear about families taking their entire family on trips with Hilton Grand Vacations: kids, grandkids, aunts, uncles, parents, and even grandparents.

If you’re looking into Hilton Grand Vacations and wondering if it works for singles—yes, it does. I want to help you embrace the solo travel life—especially with HGV.

I fell into solo travel.

I had a work trip to Chicago several years ago and decided to add the weekend to my trip to explore the city. All my friends know me as someone who loves being with people and share moments and memories. They all kept asking why would I want to go by myself—wouldn’t I get bored or lonely or go crazy being by myself?

If I’m being honest, it hadn’t occurred to me.    


I hadn’t been to Chicago in years, and this seemed like the perfect time to explore. But, after my friends said all those things, I got nervous that all of them would be true.

So, it made me glad it was only going to be two nights. After all, I was sure I could handle two nights.

That trip was a learning curve; however, I LOVED it!

I was pretty wiped from the work trip so I could move at my own pace. I could explore neighborhoods and go to restaurants that I wanted to.

A couple of meals I ate at the bar because I could get a seat right away, and I ended up having some enjoyable conversations with people who were in the same boat as me.

We even traded recommendations.


The fun thing about solo travel is that there are Facebook groups of Owners who will post that they are at a specific property and ask if anyone else is there to get drinks or hang out together.

The next trip I take by myself, I plan on doing that. What a fun way to meet other owners and still have people to hang out with on your solo vacation.

As I’m writing this, I’m taking the train home from a weekend with my dad at West 57th by Hilton Club (which was fabulous, in case anyone is wondering).

He had to leave a day before me, so I had time by myself to make sure I got the best bagel sandwich I’ve ever had for the third time because I could.

Sure, not everyone wants to eat a lox bagel sandwich three days in a row, but I do. And when I’m by myself, I absolutely can!

Hilton Grand Vacations Explorer, Jessica M.

Jessica M

Returning Explorer and Owner since 2019, Jessica says, “based on the way I traveled, vacation ownership just made sense." She enjoys the opportunity to use her ClubPoints to travel with family and friends, but you'll also find her flying solo. 

She says, "I love inspiring people to travel, and I'm excited to help young, single people think about vacation ownership and traveling in different ways than is often presented." Always one for adventure, you can find her off the beaten path to experience local culture, try regional foods or on the water enjoying watersports of all kinds. 

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