Solo Trip

My First Solo Trip: Orlando, FL

By nature, I’m an introvert. I typically travel with my family, just my husband, or even friends. While I’ve taken solo trips to visit family, I had never traveled completely on my own—booking the flights, staying alone, dining solo, and planning activities independently. For a while, I wanted to challenge myself with a true solo trip, and in August, I finally did it.

As a school teacher, the start of the school year is always stressful, and this year, I was transitioning into a new role for 2024-2025. I found a small window—three days between when my children started school and when I did—to take a quick solo getaway. I chose Orlando, FL, for its warm weather, ease of travel from Chicago, and reasonable prices. While I was excited for this challenge, I also felt a bit of guilt and wanted to be mindful of how many points and miles I used.

Flights

I flew Southwest Airlines, using miles to minimize out-of-pocket costs. Since Southwest has limited direct flights from O’Hare, I flew out of Midway International Airport to Orlando International Airport. The outbound flight cost 3,389 miles + $5.60 in taxes, and my return flight, which landed at O’Hare, cost 3,543 miles + $5.60 in taxes. If I had paid in cash, the round-trip ticket would have been $127—a reasonable price, but using miles saved me $115.80.

Hotel

I stayed at the Hyatt Regency Orlando, a large property attached to the Orlando Convention Center, with multiple restaurants, bars, a spacious pool, and a spa. It’s a Category 4 Hyatt, meaning award nights range from 12,000-18,000 points per night. My three-night stay cost 39,000 points, and I used a Club Access Award to enjoy the Club Lounge—one of the main reasons I chose this hotel. As a solo traveler, I liked having a comfortable space for breakfast, snacks, drinks, and even dinner. The cash price for my stay would have been $948.46, so using points was a great value.

Another reason I picked this hotel was its location on International Drive, a lively area with restaurants and entertainment, perfect for exploring without needing a car.

Activities

Day 1: Arrival & Unwinding

I arrived in the evening, but by the time I checked in, the Club Lounge snacks were already put away. I grabbed a quick sandwich from an on-site café, enjoyed a glass of wine, and headed to bed.

Day 2: Rainy Day Bliss

I woke up to a gloomy, rainy morning, but I wasn’t going to let that ruin my relaxation. After a Club Lounge breakfast (eggs, pastries, fruit, juice, and coffee), I booked a 50-minute massage at the hotel’s spa. I then spent another two hours enjoying the indoor hot tubs, saunas, steam rooms, and lounge areas. The staff was incredibly kind and invited me to return the next day to use the outdoor facilities since the rain had closed them.

After my spa session, I grabbed a snack from the lounge and briefly relaxed by the pool before another round of rain sent me back to my room for a nap and some reading.

That evening, I checked out the Club Lounge’s evening spread, which had enough variety for me to make a meal out of. The lounge also offered discounted wine, so I settled in with a glass while enjoying the view of downtown Orlando. As I sat there, I struck up a conversation with a sweet family celebrating their daughter’s birthday. Engaging with new people was exactly what I had hoped to push myself to do on this trip, and we ended up chatting for several hours. Afterward, I returned to my room to binge-watch some TV and get to bed early—after all, this trip was all about rest and relaxation.

Day 3: Sunshine & Solo Time

The next morning, I woke up to bright, sunny skies. After another Club Lounge breakfast, I returned to the spa’s outdoor area, where I spent four blissful hours reading in total solitude. I was the only one there the entire time, and it was pure tranquility.

Feeling refreshed, I decided to explore International Drive on foot, walking around and soaking in the energy of the area. After some time in the hot sun, I stopped at Hampton Social and sat at the bar for a drink and an appetizer. Then, I headed back to the hotel for dinner in the Club Lounge, where I once again found enough snacks to make a full meal.

That evening, I had another great conversation—this time with another solo traveler. We chatted for a few hours before I called it a night, as I had an early morning flight back home.

Final Thoughts

This trip was everything I needed—relaxing, refreshing, and a personal challenge to step outside my comfort zone. I had always thought I’d feel awkward traveling completely alone, but I found so much joy in doing things on my own timeline, indulging in spa treatments, and engaging with people when I felt like it. The Club Lounge access was a game-changer for a solo trip, giving me a comfortable space to unwind and meet new people without feeling too alone.

Even better, this trip was extremely cost-effective:

• Points & Miles Used: 45,932

• Cash Paid: $11.20

• Total Saved: $1,064.26

This may have been my first true solo trip, but it definitely won’t be my last!