Every once in a great while, I'll send my wife a message like this:
Don't plan anything this weekend & try to not bring any work home.
My wife, being who she is, will immediately want to know what I have cooked up. Usually, it's a weekend getaway of some kind that I've whipped up on the spot, something that she'll almost assuredly like.
Whatever it is that I've come up with, though, isn't breaking the bank. It's usually surprisingly cheap.
Here's how I do it.
Identify Target Dates
The first part of this equation is to simply watch the calendar for weekends that are free - or relatively free - of conflicts. These types of getaways work best for us in the late fall and the early spring, for example, because those weekends rarely have any sort of conflict going on, or if they do have a conflict, it's minor.
If I'm really eyeballing a particular weekend, I'll throw something on our shared calendar that indicates that the weekend is busy. I'll usually make up some reason for it, but the goal is to keep the weekend locked down while I plan out the other details of the trip. If it doesn't work, I'll just delete that event from the calendar.
I usually end up identifying six to eight weekends a year where this might work out, of which one (at most) ends up working out due to the other elements involved in the planning. I just keep an eye on the calendar for the coming month or two and try to lock down a weekend every once in a while.
What you need to do: Choose a few upcoming weekends that might work for a getaway, but don't peg all your hopes on one particular weekend. Don't overplan and make it essential that you find a deal on a particular date.
Clear Child and Pet Care
We have three relatively young children. They're old enough that I feel okay leaving the oldest in charge while I go to the grocery store, but they're nowhere near old enough to leave at home alone for an extended period of time. Thus, child care is a requirement, and I need inexpensive options.
My first option is to check with grandparents. Both my parents and Sarah's parents are supportive in this way and are quite happy to have the grandchildren visit for a weekend every once in a while. My first step, if a weekend is looking clear, is to check with both my parents and Sarah's parents to see if they're willing to watch the grandchildren for the weekend. I can also check with one of Sarah's sisters - the "cool aunt."
If that doesn't work, we do have a couple of friends in the area who would be willing to have our kids over for the weekend; we've reciprocated in similar circumstances. I'd also check with them, but I'd be more likely to want to leave that kind of favor for a genuine emergency.
It is not a cheap getaway if I'm having to pay for child care, so if our only option is some sort of paid child care, a weekend getaway is out of the question.
In the next few years, this will become a much less important option as our children become old enough to be able to stay at home alone. The reality is that our oldest is approaching high school and his younger siblings are nipping at his heels.
It's also worth noting that we have a couple of pets that need care while we're traveling, but we have neighbors who will step up and help in those situations. Feeding and checking on pets a few times over the course of a weekend is a favor we constantly trade back and forth.
So, our first objective is to find free child care. This eliminates a significant cost of the weekend for us.
If you don't have access to such care, start building relationships with people you trust that might lead to this type of care. Offer to take care of their children/pets, and swap child/pet care with them for gradually lengthening periods of time until such a request becomes feasible. This is the value of having a strong social and familial network.
What you need to do: Make sure that you have plans for any ongoing responsibilities, ideally plans that don't involve significant additional expense. Is there care for your children? Is there care for your pets? Is there care for any other people you may be responsible for?
Consider Getaways within Driving Distance
Before you move on, consider whether or not there are any weekend getaway locations that are within driving range of your home. This is often the most frugal option for a weekend getaway.
If I'm considering driving for a weekend getaway, I'll start looking at options within five hours of home, because we can and have driven five hours on a Friday evening in order to enjoy a little getaway. What kinds of points of interest are available to you within a four or five hour driving radius?
Google can be a great tool for this. Just Google for day trips or weekend getaways from your location (or, preferably, the metro area closest to you) and see what turns up. For example, over the years we've mined this list of weekend getaways in Iowa, along with some great places not on that list such as Honey Creek Resort on Rathbun Lake.
What you need to do: Look for interesting getaway locations within a few hours of your home, one that's drivable on a Friday evening after work. You might be surprised at the options available if you do some searching!
Look for Travel Deals
If I have a weekend blocked out and I know child care is available and I want to go somewhere further away than the driving radius, I start by looking at cheap last minute flight options. I will start hunting for these several weeks out, but I won't lock anything in until I either find a really good deal or we're down to the last week, in which case I either find a pretty good deal or I give up on the plan.
At this point, I am not concerned at all about the destination. What I'm looking for are cheap round trip flights to anywhere, ideally departing from Des Moines (the only decent-sized airport near us), but flights departing from Minneapolis are also okay.
This is where price comes first. What's a cheap flight that departs in the evening on Thursday or Friday (depending on the specifics of the weekend) and arrives back home on Sunday or Monday (again, depending on the specifics of the weekend)? Most of the time, I'm looking at a late Friday flight and a mid-day Sunday flight, but that can vary if there's a special weekend coming up in terms of our personal schedule.
Believe it or not, if I'm careful with the hunting, I can often find last minute flights well below $100.
I use a number of tools for this, including Kayak, Hipmunk, and FlightScanner. I just check them regularly and have them set to give me alerts if cheap flights pop up in my search criteria. These sites all have smartphone apps that will pop up alerts for you. When I've identified a good potential weekend, I start searching all of these sites and a few others all at once.
In terms of planning flights, include all airports that you could reasonably use for a weekend getaway, not just the one that's closest to you. For example, I know that Minneapolis flights are cheaper for us but a bit logistically harder, while Des Moines flights are going to cost a little more but be logistically easier. I'll watch for deals from both airports, though.
Also, don't lock onto a particular destination. You're looking for deals on any flight, and you'll want to choose among the least expensive options that appear. My recommendation is to scoop flights that are less than $100 to an interesting destination, with perhaps even a lower threshold if you have several airports nearby.
What you need to do: Once you have a weekend in mind, use airline search tools to start finding cheap flights for that weekend to anywhere from any airport near you. Don't obsess over a particular destination - let serendipity rule here.
Look for Housing Deals in Possible Target Areas
As soon as a cheap flight pops up or you've decided on doing a more local getaway by car, immediately start looking for cheap lodging in that area for the weekend. I usually aim for anything that's low cost that doesn't have disastrous reviews associated with it - the cheapest price I can find on a hotel or Airbnb that doesn't have reports of bedbugs or other significant problems.
Again, I use a variety of tools for this. I use Hotels.com, Airbnb, Kayak, and so on. If I'm going to a remote destination, I look for anything that's in that metro area. If I'm using the radius around us, I usually have a handful of possible places in mind and look for housing deals near any of them to see what's inexpensive and available.
Yes, sometimes I'll find that everything in an area is booked up or the few rooms that are available are super expensive. Guess what? I just don't go to those destinations that weekend. It's okay. A big part of all of this is flexibility, and that means dropping plans if they don't work out.
This actually doesn't take very long at all once I have a destination or two in mind. Since I'm usually doing this just a week or two in advance (or sometimes less than a week), I usually find that either an area seems to be highly booked up, or else at least a few lodging options are offering really cheap rates for the weekend. If everything's booked up, I move on; if not, then I've got a cheap hotel.
If you find a bunch of great deals, look at the extra perks offered by the lodging options. A continental breakfast is a huge perk, as one can utilize that for brunch and take some fruit along with you, drastically reducing food costs on the trip. A true bed and breakfast is similarly nice.
Another option, of course, is to consider camping as a weekend getaway, but this likely reduces the range of travel as you're going to have to be able to set up camp at your destination in the dark if you go too far. This might not be a problem for some, but could be a deal breaker for others.
What you need to do: Once you have a cheap flight (or you've decided to drive to the weekend getaway), start looking at a wide variety of housing options. Airbnb should always be considered, along with hotel searching tools like Hotels.com. A hotel with a continental breakfast or full breakfast at no noticeable additional cost is a big perk, as you can use that as brunch and take some fruit with you.
Look for an Interesting Centerpiece, and a Deal Associated with That
You have low cost transportation to a low cost destination. Great. Now, what are you going to do when you get there?
This is the time to start researching the area you're planning to visit. There are a lot of different tools for this, starting with the tourism guide for the area, but also using tools like Atlas Obscura.
When you're doing this, prioritize cool things that are free or extremely low cost, especially if they're irregular events. Maybe there's some kind of free concert or free arts festival going on in the area that weekend that you can check out. Maybe there's a special exhibit at an art museum or something like that, or perhaps there's a limited time art installation in a park. Look for things that you'd both be interested in that fall into this category.
What I've found is that, if I find two or three things like that, that's good enough. Those things serve wonderfully as the centerpiece of a weekend getaway. The rest of the time, trust in serendipity. Go there, get up without a plan other than visiting a particular park at a certain time or something, and then wander to your heart's content.
One challenge on such a trip is food. What we usually do is eat at one or perhaps two cool restaurants in the area and go super cheap on the rest of our eating. I really like hotels with continental breakfasts, as we'll often eat at them fairly late in the morning and treat it as a brunch, put a few fruits in our bag that we take out for the day, maybe have one small treat from a street vendor during the day, and then eat somewhere cool for dinner.
Thus, I'll typically try to figure out a good deal on one interesting meal in that city or area. Check out sites like Restaurants.com or BlackboardEats.com for bargains on dining if you're flexible. You're probably not going to end up going to a hot and mega-exclusive restaurant this way, but you'll probably find something good and interesting at a very good price. Try to target something vaguely near your hotel or near the area where you've found something interesting to do.
What you need to do: Scour travel guides for low cost or free cool things to do in the area, particularly ones that only happen that weekend. Let most other things happen by serendipity, but check out restaurant deal websites for at least one planned meal at a discount.
Don't Sweat Transportation Unless You're Getting Out of the City
One thing I've discovered is that, unless you're getting out of the city, you're far better off simply using mass transit to get around rather than the expense of renting a car. Most of the interesting things you're going to want to do can be reached easily on foot from a mass transit stop, so, assuming the destination city has a decent mass transit system of some kind, I just rely on that to get around.
In a pinch, I'll use Lyft or a taxi service to get back to our hotel or something like that if we're out late, but mass transit usually takes care of all of our travel needs.
There's an additional factor in that, if you're planning on an out-of-the-city destination that also requires a flight, you're likely leaving yourself rather little time for a weekend getaway. I prefer either a drivable destination or one where I can fly and then rely on our feet and public transport along with a Lyft or two.
What you need to do: If you're flying to a remote city, study the public transport in that city and use that if at all possible. Focus on activities that are walkable from your hotel or are easily accessed via public transportation. Try to avoid getaways that require both a flight and a car rental.
The thing to remember about a weekend getaway is that most of the fun of such a getaway really boils down to exploring a new place with a loved one along with time for romance, away from the distractions and challenges of your everyday life. It doesn't have to involve an expensive resort or a perfect weekend. Just focus on finding cheap travel options, then plan around wherever that cheap travel option takes you. You can make memories and romance almost anywhere you go.