How I Solo Travel: A Room With A View

Discover the insider secrets to booking the perfect hotel or Airbnb/VRBO accommodations for your next trip. Learn the tips and tricks I use to find the best deals and most comfortable stays.

How I Solo Travel: A Room With A View
My room at the Hotel 48LEX in New York City - taken February 2023

We all plan and execute our solo travels differently. Some of us have whiteboards, some of us use templates, some of us just haphazardly plan on the fly. There’s no right or wrong way. We all have our ways of making this happen. This guide series is meant to explain my process of planning a solo trip from start to finish.


I first began solo traveling almost a decade ago. It all started with a visit to my friends in Tampa, FL. Little did I know, this trip would be the beginning of my journey to becoming a seasoned solo traveler. I hopped on a flight to Tampa and rented a car, but my friends kindly offered me a separate bedroom to stay in. Although I had my own bathroom, we shared the kitchen and living room. While I truly appreciated their hospitality, I couldn't help but wonder what it would be like to have my own hotel room or even a whole house or apartment to myself. I've always preferred not to inconvenience others, although I don't believe I was a burden to them. After that experience, I decided to take matters into my own hands and booked my own hotel stays. After all, if I can live on my own, why couldn't I make it work while traveling? In this guide, I’ll lay out my strategy on accommodations.

low-angle photo of Hotel lighted signage on top of brown building during nighttime
Photo by Marten Bjork / Unsplash

Do Your Homework

When I decide to visit a city or destination, one of the factors that influences my decision is where to stay. Depending on the timing of my visit, I usually begin by using Google Maps to search for hotels near the city.

Example of a typical Google Maps search

Sometimes, I filter the results by specific hotel brands, but most of the time, I base my filter on reviews. Reviews play a crucial role for me, and I become skeptical if I come across only positive or negative reviews. In such cases, I actively seek out the "bad" reviews. I wonder if the reviewer is simply seeking an answer to a question or if they are generally a negative person. Generally, I rely on my intuition when it comes to these reviews because where there's smoke, there's fire.

Additionally, I thoroughly examine the rooms and the overall hotel through the photos shared by other guests. I pay attention to the layout and design, cleanliness, and the condition of the bathroom. Does it appear to be well-maintained or does it require some work? I also consider the quality of the shower and the appearance of the fitness center, even though I don't plan on using the pool. How clean does it look? I also take into account the public areas of the hotel. It's important to remember that not all hotels are the same.

When it comes to renting houses or apartments, I rely more on the pictures and reviews within the app. However, I also conduct a Google Maps search to verify that the location matches what is stated in the app.

Hotel, Motel, Holiday Inn

I consider the hotel to be the centerpiece of every trip, it is my “hub” for the destination I’m visiting. I usually prefer hotels located near a city but not right in the midst of it. Typically, I opt for hotels near airports or highways, although occasionally I enjoy staying in hotels situated within shopping centers or adjacent to malls. I appreciate having some activity around the hotel, but I also value the convenience of easy access in and out. When searching for a hotel, I prioritize those with complimentary parking (since many city hotels charge for it) and even free breakfast (after all, I'm already paying a significant amount, so why not enjoy some morning fuel!). Recently, I've been specifically seeking hotels with an on-site bar or restaurant, as I cherish the opportunity to unwind with a delightful adult beverage at the end of a long day of exploration. It would be wonderful if the hotel also offers an outdoor seating area with a cozy fire pit, and if it has been recently remodeled or is brand new, that would be an added bonus.

I typically stick to specific brands, mainly Marriott or Hilton, but I also consider staying at Hyatt or IHG properties. It's more of a personal preference based on my past experiences with them. Since I am a member of their rewards programs, I often receive special incentives like "double points" or my personal favorite, "double night credits." This allows me to move up to higher reward tiers and enjoy better perks. I always prefer to book directly with the hotel. Luckily, most of the hotel chains I work with allow me to add my AAA number, which gives me a 10% discount. Sometimes, I can even use my employer's travel discount for an even bigger savings, depending on the hotel chain. When booking a room, I usually go for the AAA rate as it guarantees the price in advance. Although it may be slightly more expensive than the prepay option, it offers the flexibility to change plans if needed. On hotel apps, I try to filter for hotels with free parking and breakfast, although it's not always available. I also take the time to carefully inspect the hotel and rooms on the app, comparing them to Google Maps for any inconsistencies. As for housekeeping, I usually opt out and only request fresh towels when necessary. I take pride in keeping the room clean myself, treating it as if it were my own residence and being respectful of the furniture. Additionally, I prioritize security and make sure to protect my belongings.

Weekend at Bernie's

I typically avoid staying at Vrbo or Airbnb's. It's not that I have anything against them or those who choose to stay there, but I do have some concerns. Working in insurance, I've noticed that the industry's response to underwriting these stays can be quite inconsistent. Additionally, I've seen hotel chains step up their game in response to Airbnb's, offering nicer rooms and features that houses and apartments just can't match. However, I do see the value in these accommodations, especially when staying with friends at a destination. For example, last fall, a friend from the west coast visited me and I booked a house for us to stay in. We each had our own bedroom and bathroom, but shared the kitchen and living room. Splitting the expenses made it a decent experience. Generally, what you see is what you get with these rentals. I usually opt for "superhost" listings and prioritize full privacy - I prefer not to stay with other people and look for listings with "instant booking." Since these accommodations require prepayment, I also make sure to secure travel and liability insurance in advance, just in case. While I do find these accommodations to be a bit less secure and offer fewer rewards compared to hotel apps, they still hold value for me.

Accommodations To Consider...or Not

If you have noticed, i'm not really into staying at shared accommodations like hostels. They just don't seem worth it to me, and I don't feel safe staying in them either. The money I save by staying there doesn't outweigh the loss of privacy. Apart from hotels, houses, and apartments, I'm not really interested in camping or glamping either. I enjoy having the windows open to let in fresh air (with a screen, of course) and sitting outside, but I prefer to sleep indoors, in a clean and comfortable room. That's just my preference. Security is also a big concern for me, as I wouldn't want anything to be stolen. However, I would consider renting an RV. In fact, one of my solo trip goals is to rent an RV and explore the Dakotas and the Rocky Mountains. The idea of having a mobile place to stay and being able to drive it around really appeals to me. Of course, I would need to do some research on parking locations to see if it's worth it or not. It's definitely a possibility!


Closing Thoughts

As I sit here and reminisce about all the places I've stayed in throughout the years, I've come to realize that solo traveling was something that unfolded naturally for me. You can either ease your way into it like I did or dive in as if it was a sweet hotel pool. In any event, I like having a nice, clean and comfortable room to come back to. There's something satisfying about waking up in the morning and heading downstairs to the gym for a workout. And having a delicious hot breakfast included in my rate means one less thing to worry about in the morning. While staying with friends is enjoyable and has its perks, as a solo traveler, my advice is to treat yourself and invest in a nice hotel room. As a normally inquisitive person, and someone who works in insurance, I question just about everything and that mindset applies to where I stay. After all, I believe the accommodation is the most important part of any trip away from home, because it's acting as your temporary home. It's where you sleep, relax, shower, exercise and eat. It needs to be clean and comfortable. It doesn't have to be luxurious, though that would be nice!

We covered the planning, the financing, the flight, the road trip and now the hotel stay. But how do I get around?? Find out next time!