How I Solo Travel: Moneyball

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.

One of my favorites movies is Moneyball. It’s the story of Billy Beane, who was the General Manager of the Oakland Athletics in the early 2000’s, who was given the unfortunate task of building a baseball team with a budget that dwarfed other Major League Baseball teams. Baseball fans know that not much has changed in Oakland, but the lessons are still the same. It emphasizes the importance of making the most out of the resources you have. Some may see it as a challenge to overcome, while others may find it overwhelming. Personally, I lean towards the former. I thrive on challenges. I also have a unique approach to budgeting and financing my travels, which sets me apart from others. In this guide, I will share how I typically finance my solo adventures.

Financing a solo trip for me usually starts with the flight. As previously mentioned last time, I pick out a specific date or range of dates, choose a few potential destinations, and then start comparing flight costs. My top choices usually include American, Delta, Jetblue, and Southwest. Lately, I've been leaning towards Southwest because their prices tend to be more budget-friendly, although I'm aware that it's just the base fare. I also make good use of my American Airlines, Southwest Airlines, and Delta Airlines credit cards for purchases, which helps me rack up plenty of airline miles. As for when to actually book the flight, ThriftyTraveler suggests booking relatively close to your departure date:

We always encourage travelers to book flights at least 30-45 days in advance. Don't wait until a few days or weeks before departure thinking you can score a last-minute deal. Airlines typically hike up flight prices in the days and weeks before departure – when they know business travelers and desperate flyers will pay whatever it takes to get where they need to go. You're much more likely to see savings when you book further out.

As I tend to book with miles, I make sure to plan way ahead. I often book my flights 3-4 months in advance and regularly check for any changes in prices on the app. The best part about booking with miles is that I can always rebook at a lower price (and fewer miles) later on, which has worked out well for me in the past. It's not necessary to constantly check, just a quick glance once or twice a day during meal times or before bed. It's like trying to outsmart the system, which can be both exciting and nerve-wracking. Personally, I find it quite enjoyable! Since the flight is mostly covered by points, my only expense is the taxes, which usually amounts to the cost of two Cold Brew coffees at Starbucks.

Once I get the flight booked, now it’s onto the hotel or accommodations. I typically make reservations through the apps of Marriott, Hilton, IHG, or Hyatt. However, if I opt for an apartment or house, I turn to Vrbo. These services have consistently provided me with positive experiences. Before confirming my booking, I always check for special deals on these apps, particularly for hotels, as they are my top choice. These deals often involve earning additional points for specific stays at certain times, which can help elevate my status. I also make sure to input my AAA membership details to see if there are any available discounts. Price is not the only factor I consider when booking a hotel. I conduct thorough research, utilizing Google Maps to explore the neighborhood and inspecting the hotel's interior and exterior. I pay close attention to the cleanliness of the bathrooms and rooms, as well as read through reviews and examine photos to make an informed decision. While my judgment may not always be accurate, this method has proven effective for me. When it comes to payment, I prefer to choose the higher rate option that allows me to pay upon my stay rather than prepaying. In instances where prepayment is required, I always opt for insurance, which is typically offered at the time of booking through the hotel or accommodation platform I am using. As mentioned last time, I tend to book hotels close to airports and highways to allow for quick transportation, and it is also much less expensive.

I usually make sure to book my rental car in advance, and my go-to choice is Enterprise. Their app makes it super easy to book, but I'm open to trying out other rental car providers as well. Personally, I prefer to book my car exclusively at the airport. Yes, it may be a bit pricier, but the convenience and time saved by simply walking from the baggage claim to the rental car garage is totally worth it. Nowadays, many airports even allow you to check in, provide some basic information, and choose your desired rental car from a designated row based on the tier you selected during reservation. Typically, I opt for a midsize or intermediate car, although occasionally I'll go for the largest option, like a crossover SUV. I treat rental cars with the same care as I do my own car. Before returning it, I always make sure to fill up the gas tank, not only because it's cheaper, but also because it's the responsible thing to do.

On the trip itself, I usually have a good idea of where my money is going and make an effort to budget wisely. Upon arrival, I typically head to the supermarket to stock up on travel essentials and snacks for my stay. I enjoy trying out local fast food spots, food halls, and food trucks, in addition to dining at nearby bars and restaurants. I also factor in the cost of planned activities, considering options like city passes for insight into museum and attraction prices. Supporting my local historical society grants me access to the North American Reciprocal Museum (NARM) program, which allows me free entry to various museums nationwide, leading to significant savings. I often explore local parks and attractions based on recommendations from fellow travelers on different platforms.

OK, this is all well and good, but how do I finance? Simple. I use credit cards that offer the option to split my purchases into monthly installments. Most of my airline credit cards provide this feature, and they offer different choices. I can choose to divide the payment over 6, 12, 18, or 24 months, each with its own installment amount and associated fees. It's a small price to pay considering that I only use this method for hotel and rental car expenses, while the rest of my trip is already budgeted for the month. I make sure not to overspend at the grocery store and usually select hotels that include breakfast in their rates. This way, I only need to worry about lunch and dinner. Activities can be affordable depending on what I want to do. The worst thing you can do is over-plan, so spend a few hours at each destination and that will give you 1-2 attractions per day, you don’t feel so rushed, and it also keeps costs down too.

The trip is finally happening! Now what? Flight, road trip? How do I get there? That will be next time.

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