Vacations are Hard Work

Vacations are fun, but it’s a job to plan a successful one. You need to set a budget, decide where you’re going, find lodging, figure out what you want to do, pack for your trip, and prepare your home. That’s a lot of things you must do before you depart on your vacation. 

In this article, I’ll describe how to plan a vacation for 2 people who live in the United States. You will need to adjust your own planning based on how many people you’re taking. I’m going to assume a few more things: 

  1. You’re planning this vacation months in advance, because that’s going to play a major role in how much you save on the 2 largest expenses on your journey: travel and lodging. 
  2. You aren’t traveling in peak or holiday seasons, because travel and lodging will be expensive no matter how far in advance you book everything. 
  3. You’re leaving your pets at home. 
  4. You aren’t renting a car.


So, you want to go on a vacation. What’s your budget? 

What! You don’t have one?! 

A budget is the most important part of planning a vacation. It dictates your entire experience from: where you can go, to how long you can stay, to what you can do while you’re there.  

Check your bank account now to see how much money you can throw at a travel experience. Okay, it looks like you have $2,000 to put toward a vacation. That’s awesome! We can work with that[1]

Now, where can you go with that kind of budget? 

Almost always, the largest expense is traveling to and from your destination. With our budget, you could theoretically travel to Europe[2], but the airfare alone will consume your funds and you won’t be able to do much when you get there. Realistically, you should be able to purchase round-trip flights to any major city in the continental United States for only $200-300 per person. 

If you want to travel somewhere inside your state or in a neighboring one, then you should consider driving your own car[3]. That could be a great cost-saving option for you, but we’re going to proceed with the assumption you’re going somewhere far away from home.

Pick a city, any city… Seattle, Houston, Washington DC, Los Angeles, Tampa, New York, etc.

Use your phone to check airfare rates from your city and save that info for later. This will help you decide how long you can stay at your destination. 

TipDo not use your phone to book airfare later. The travel websites save your personal data and use it to charge you more later, when you’re ready to make a purchase. 

Now that you’ve picked a city and recorded possible flight dates and pricing (including the return trip), use this information as the basis for the rest of your vacation. The next step is to figure out where you’re going to store your stuff and sleep. 


Using the flight information as a guide for your vacation, you need to find out where you want to sleep. You can find lodging for as low as $20-30 a night if you use a hostel. That’s not an option for most people. Especially, if you’re not very trusting when it comes to leaving possessions in a communal bunk room… even if there’s a locker. Another thing to consider, is you won’t know what your roommates are going to be like until you meet them… and try sleeping over their snores.

And then, you need to worry about their Covid-19 vaccination status. 

Let’s assume you want a private room, in a reputable hotel. One can be had for about $100-150 per night in most downtown hotels. Hotel rooms get cheaper the further away you get from tourist attractions. 

An alternative to hotels and hostels is Air BNB. Air BNB hosts can have pricing which is just as competitive as a hotel, and they can be located anywhere. Just like hotels, room prices increase the closer they are to attractions.

Deciding When to Travel

Chat with your traveling partner and decide when you want to travel and where you want to stay each night. You can expect to pay about $100-150 per night, for a private room in a nice hotel (or the Airbnb equivalent). I’d recommend staying no more than 5 days on a $2,000 budget. 

Now that you know the cost of airfare and lodging, go ahead and book your flights and hotel (remember not to book using the same device you did your research on). The days you travel may be dictated by the cost of airfare, which means you’ll need to be flexible with your outbound and return flights. Thankfully, hotel prices won’t change much from day to day.  

Tip: When booking your hotel, the facility will require your credit card information, but will not charge it until after you check out. That means you must save that money and account for it as a floating expense.

So don’t spend it.

Fun & Games

With airfare and lodging booked, you should have about $1,000 left over to play with. I like to do a Google search asking for “things to do at [CITY NAME]”. The results almost always take you to the city’s tourism page, which is a great starting point to building a list of things to do when you’re there.

While you’re looking at the city’s tourism page, be on the lookout for monuments and tourists attractions. These are either free, low/medium-cost, or expensive. Examples of each are:

  • Free: monuments, statues, parks
  • Low/medium-cost: Museums, tours, local experiences (like an observation deck)
  • Expensive: Shows, plays, popular or exotic activities, extra-city excursions such as: a wine tour, a helicopter flight, or going to the Hoover Dam (Las Vegas)

Tip: I recommend making a list of interesting things in a Word document or Notepad (Notepad removes all formatting and link info). Be sure to record the daily hours of operation[4] and the price of each activity for 2 people.

If you’re making a list of things to do, share that list with your traveling partner to eliminate any activities they have no interest in. This also gives your partner an opportunity to add things they want to see or do. 

Another source of activity ideas can be found in a travel guidebook. I mention guidebooks now, because I prefer to have a list of activities long before the trip starts and the book is used to supplement what I’ve already planned. I normally buy my city books a couple weeks before our departure date, to build more excitement prior to our journey. Any tips or new destination ideas found in the book can be worked into the existing schedule. 

One of the brands I’ve used in the past is “Lonely Planet”.


Once you agree on a list of activities, you must plan the logistics of how you’re going to get to all of these locations. It doesn’t make sense to go to each destination based on how they appear on your list. 

You MUST have a plan… or plan to miss out on fun activities! 

The easiest tool you can use with logistics planning is Google Maps, on driving (car) mode. Don’t worry about how you’re going to get to these locations yet. This will work even if you intend to use public transportation. 

Use your hotel as the starting location, and add each destination to the directions. You may need to use a few browser-tabs. Click and drag each destination on the map to create an orderly route from one point of interest to another. Here’s an example:

You may notice that some of your activities are located further away from others. Be sure to dedicate extra time to travel out to those destinations, and if there’s a time-crunch, you may need to reconsider how important those activities are to your vacation. 

I like to use multiple tabs to plan out my days, with each Google Map representing 1 day of travel. I recommend organizing your days like this: 

Day #1 Airport >> Hotel (check-in & drop your stuff) >> Attraction 1 >> Activity 2 >> Dinner with friends[5]

Day #2 Hotel >> Attraction 3 >> Activity 4 >> Attraction 5 >> Activity 6. 

Day #3 Hotel >> Attraction 7 >> Activity 8 >> Attraction 9 >> Activity 10.

Day #4 Hotel >> Attraction 11 (near hotel) >> Hotel (check-out) >> Airport.

Some attractions require that you to book a time to visit, so be sure to organize your activities with that in mind (example in Figure 1). 

Tip: While we’re on the subject of scheduling paid activities, you may need to be flexible with the order which you go to these destinations. I’ve found that most companies do not allow you to book your activity more than 2-3 weeks ahead of your trip.

Tip: You can “save” your activities by sharing the map via email or text. This is useful because you can resume or edit your plans simply by clicking on the link.  

Calendar the Activities

Now that you know the proper order of each activity and destination, put everything onto a calendar. Be sure to allot an appropriate amount of time for each activity. For a statue or a small monument, 30 minutes should be enough time to look at it and snap a picture or selfie. However, plan to stay at least an hour in a museum or at a popular tourist attraction. I like to divide each activity with hour-long spaces to ensure I have plenty of time to travel between each location.

Be sure to add the destinations to each calendared activity. If you’re using Google Calendar, it will give you a notification reminding you to catch a bus to reach your next activity on-time. 

Pack, Clean, and Pets

Now that the hard part is taken care of, it’s time to get everything ready for the trip. 

First and foremost, make sure your pets are taken care of!

Find a friend you trust enough to feed them, and give them a copy of your house key. If you don’t have anyone you trust, and you’re only going to be gone for a few days, you should evaluate weather your pet’s food and water will last the entirety of your trip. Consider boarding your pet if you aren’t confident in how long the food will last. 

Pack your bags and clean your house a few days before leaving. Having a clean house will prevent any embarrassment when your friend visits to care for your pets. When packing your bags consider a few things:

  1. The climate and weather of your destination – Be prepared to dress in warmer clothing if traveling to a northern state in the fall or winter.
  2. The number of days you’ll be there – Pack individual outfits for each day. I like to fold my shirts and pair them with a pair of pants/shorts, and then add socks and underwear. I’ll fold them all together to make it easier to grab an entire outfit and dress each day. 
  3. What you’re allowed to carry onto the plane – Normally, airlines limit you to one small briefcase and one smaller carry-on item. I can fit my 5 outfits into half of a small briefcase, with enough room for my traveling companion to do the same. Don’t pack like you’re moving there, pack what you need (Clothes, toiletries[6], and entertainment).


All that’s left is to travel and enjoy your vacation!

I’ve used this planning method for most of my vacations and it’s served me well over the years. So much so, I’ve been able to plan a complex, multi-city vacation without a hitch. It started from Houston, travelling to Chicago, then we boarded a train and traveled to Seattle, and then travelled back to Houston again… all with full itineraries of activities at each city.

That’s how good planning works! 

[1] Budget: A travel budget can be as low as a few hundred dollars, and you can still have a good time. If your budget is on the lower end, you will need to be creative and find free or low-cost things to do.

[2] Europe: I’m also assuming that you have a passport. If you don’t have one, then you may not be able to book passage or leave the airport.

[3] Intra-state Driving: If you don’t own a car, consider renting one and factor that added cost into your budget.

[4] Activities: Some cities are harder than others to plan for. The hours of their attractions may seem to be random. Some places aren’t open on days you’d think they should be open.

[5] Friends: It’s easier to schedule diner with friends who may live in the city you’re visiting on the first day you’re there. You get that social nicety out of the way, and can focus on doing everything else on your activity list. If you like to maximize your time on vacation, you probably will plan to do a couple things after you check into your hotel and shouldn’t be tired when you see them on the first day.

If you don’t have friends in the city you’re visiting… Great! No distraction. 

[6] Toiletries: Toothbrush, hairbrush, small cologne bottles, toothpaste, shaving supplies.

Exploring Dirt Roads

How many people can honestly say they’ve had the privilege (or horror) of driving on a dirt road? It’s hard to come across roads such as these in our paved and urban society. Let’s assume you have a car and want to go on a day trip out of the city, how would you encounter a dirt road? To find such a road, we must drive out of civilization and into the wilderness just for a chance to find a dirt road, which isn’t someone’s driveway.

No, you can’t drive into the first town 20-30 miles out of civilization with the expectation of being able to drive down a dirt road. Just because these people live so far outside the loop[1], it doesn’t make them savages. You’ll need to drive a little further out to be sure you can encounter a dirt road. I’d recommend driving as far as 50 miles, and then get off the main interstate or highway.

Don’t bother searching the nearest town for a dirt road because they tend to have enough money to build paved roads. Instead, start driving on the side roads between towns, through the county[2]. Use the green city and mile directional signs to guide you to a village you’ve never heard of. You’ll almost certainly find a dirt road to drive down around one of those small villages, and you may even find something interesting or unique inside one of these tiny communities. Villages tend to have flea markets, which are large outdoor resale malls and may have rare treasures or hard to find items. You may also encounter a historical marker in your travels.

Wherever you may encounter such a road, be sure to drive safely:

  • Don’t drive on dirt roads marked as private property or designated as a construction site. These roads are clearly marked. Trespassing aside, driving into a construction site or other privately owned property can be hazardous for you, your vehicle, and the owner’s property. You will be responsible for any and all damages.
  • Slow down and don’t drive like you’re on a freeway, even if it seems fun. Your dust can make it hard for other drivers to see. People tend to live off dirt roads and it’s not a neighborly thing to zoom by so fast your dust covers those homes. Also consider the possibility that the road comes to a dead end, and you may have to drive back and have an angry asthmatic granny shaking her head and wagging her finger at you in disappointment as you drive by her house again.
  • If you happen to find yourself in a “Road Runner’s” dust trail, turn on your lights so oncoming traffic can see you.
  • Dirt roads tend to be narrow, so be prepared to stop for oncoming traffic.
  • Watch for pot holes, dips, humps, bumps, and large rocks. The road is made of dirt, and will easily get weathered away by rain or fast cars.

I happen to enjoy going on road trips, just for the fun of it. I’ll turn on an audiobook and drive out to a random destination to discover what that small town or village has to offer. Oftentimes, I’ll need to drive down a dirt road to get to my destination. I guess I’m weird like that, which is why I don’t recommend you go on a road trip solely to find a dirt road to drive on. That’d be pretty boring. However, I do recommend that you pick a general area to explore, and just be aware of the different kinds of roads you take to get there.

It’s a cool feeling when you notice you’re doing something you don’t normally do. It’s refreshing to see the beautiful landscape of a dusty road cutting into the woodlands. Fans of horror films may laugh nervously as they continue to drive past mobile home after mobile home after trailer, and notice the country people staring at the outsiders driving a city-car as they sit on their front porches. Thrill-seekers may enjoy encountering a flooded creek and feeling that rush of panic as you see a local forge through and decide to risk it (I personally like the relief in deciding to “turn around, don’t drown”).

The thought of driving on a dirt road may not sound very appealing to most people, but I hope this story helps motivate you to step out of your normal routine and go explore someplace outside of your city. Who knows, maybe you’ll fall in love with going on road trips. Maybe you’ll make a hobby out of it as a historical marker pilgrim. Or maybe you could be a successful American flea market “picker”.

You never know unless you get out there and explore.

[1] “Inside/Outside the loop” is a common phrase used by city snobs. The act of leaving the innermost zones of a major metropolis is akin to leaving civilization itself. The distance a location may be from the heart of the city can be classified as the following:

  • Civilization = Everywhere within a freeway “loop”, that typically surrounds the inner core of a major city (like Loop 610 in Houston, Texas). Almost every major city or metropolis has such a loop.
  • The Fringe = Everywhere outside of the freeway “loop”, but inside any outer “loop” some major metropolises have (Houston’s Beltway 8 is an example of an outer “loop”).
  • The Wilderness, also known as “The Middle of [Fucking] Nowhere” = Anywhere outside of the outer “loop”. If the city doesn’t have an outer loop, the middle of nowhere pretty much starts 15 miles outside of the heart of that city’s downtown.
  • Might as well be on another planet! = Located in another city, or at least 30+ miles away from a major metropolis.

[2] County – Some people who’ve lived in a metropolis their entire live don’t actually know what a county is. If they live in a city as huge as Houston, which basically takes up all of Harris County and spills over into some of the neighboring counties, then it’s understandable that these people wouldn’t know the difference. To them, the county courthouse is just another name for a courthouse in the “Law” district of the metropolis.

A county is a large region in a state, which serves several administrative functions. Depending on how poor the county is, those services may be the bare minimum of recording marriages, deaths, and property transactions. Or if it’s a rich county, it may administer recreation centers, hospitals, and even airports (mostly small non-commercial airports). There normally are several villages, towns, and cities within a county.