The Secret to Picking the Perfect Place For Your Vacation Home
Location is everything, but it can also be the hardest decision to make.
Reading Time: 4 minutes
Location, Location, Location
In the post Should You Buy Your ‘Second Home’ First?, I laid out an argument (based on my personal experience) for buying a ‘second home’ before your primary. Here, I want to tackle the next most common question: Where should I buy?
For some people, the answer is obvious. My in-laws, for example, have been vacationing in York Beach, Maine, every summer since they were kids. Once they were adults, they started to bring their children to the beach every year, and now, the grandkids have joined the crew. If they were doing this exercise, York Beach would top their list, without hesitation.
For my husband and me, it was always Lake George in upstate New York. Nicknamed the “Queen of American Lakes,” it’s a sentimental place to us. Early in our relationship, we camped there every summer with our beloved dog—grilling three meals a day, sleeping in a tent, and enjoying the simple pleasures of the outdoors. But at some point during each trip, surely missing hot water and electricity, I always thought, wouldn’t it be nice to own a house here someday?
Not everyone has a location that immediately pops to mind, though—and that’s okay. Maybe you’re excited to take this first step onto the property ladder, but you don’t know where you want to do so. Or perhaps you already own your home but want to invest in a second property—one that builds equity and, ideally, generates a profit while someone else pays your mortgage—but you haven’t considered where that would be. Don’t worry—we’ll tackle this together, and by the time you’re done reading this, you’ll have the clarity you need to move forward with confidence. (Or at least, set up a Zillow alert.)
No, your vacation home doesn’t have to be in the middle of nowhere… unless you want it to be!
(Photo: Trout Landing by @EmilyElizabeth_)
A Random (But Relevant!) Tangent
When my husband and I first got engaged, I found it surprisingly difficult to plan our wedding. While I had a lot of experience planning events, I had never been someone who dreamed of getting married. In fact, I was (and still am, to some extent) a bit of a commitment-phobe. Every time we toured a wedding venue, I left feeling the same way: it was beautiful, but was it perfect? Was it what we wanted?
I eventually realized that my hesitation was caused by a lack of clarity—I didn’t know what ‘perfect’ meant when it came to our wedding. Sure, part of my struggle was the aforementioned fear of commitment, but more importantly, we hadn’t defined what we were looking for. We didn’t know what a ‘successful’ Katie and Joe wedding meant, aside from leaving it married, of course. Without a clear vision, each beautiful venue left me more confused than the last.
That realization allowed us to step back and rethink our approach. Back at home, over a glass of wine, we paused our frantic search to ask the critical question: what does our perfect wedding look like? Only after we defined what we wanted could we begin to make meaningful progress towards a wedding that felt like us.
The same principle applies to buying a vacation home. With millions of stunning properties available, it’s easy to get swept away by charm or discouraged by price. But without a clear vision, it’s hard to know if you’re looking at the one. Owning a vacation home isn’t just about wishful thinking; it’s about defining your vision in concrete terms and aligning it with achievable goals. So let’s start by dreaming! Nothing is off the table (yet). Allow yourself the freedom to imagine your perfect retreat and later, we’ll ground that dream in reality.
The Sticky Note Exercise
Whether you know exactly where you want to buy or find yourself at the confused crossroads I faced when wedding planning, this straightforward Sticky Note exercise will help you figure it out. (And yes, we did use this exact same method to tackle wedding planning—how people are capable of making decisions without Post-It notes or Excel will always baffle me.) So grab yourself a pack of sticky notes and ask yourself the following questions:
How often do you plan on using your vacation home?
Is it a weekend retreat or a seasonal escape?
What seasons do you envision being there—winter ski trips, summer lake days, or year-round visits?
How far are you willing to travel?
Would you prefer to drive, or are you comfortable flying there?
What types of settings do you like—coastal, mountain, countryside, urban centers, etc.?
What contrasts are you seeking? If you live in a city, do you crave nature and solitude? If you’re in the suburbs, is walkability key?
What activities matter most to you? Beaches, skiing, hiking, wineries, or proximity to cultural attractions?
As you look over your sticky notes, brainstorm possible destinations that fit your criteria. Consult maps, search Google, or ask ChatGPT for ideas. Be as specific as possible, like:
Coastal towns within a three-hour drive of New York City
Walkable ski destinations within a four-hour flight of Boston
Lakes near golf courses within a six hour drive of Chicago
Create a shortlist of the places that fit your needs. In future posts, we’ll review how to check each area’s short-term rental regulations, as well as the average home price in the neighborhood, tourism demand, a review of the local competition and more.
This was all about narrowing in on the perfect destination. And now, you’re that much closer to pinning down where. Next up, figuring out the what.
Next Up...
Once you’ve shortlisted destinations, it’s time to dream about the house itself. In the next post, we'll use the Sticky Note exercise again, but this time, to figure out what attributes your dream vacation home should have (aka what do you want it to look like)? You’ll then take your findings from this post, plus your findings from the next, and create the ultimate Vacation Home Vision template. This document will help you capture your ideas in one place, providing a personalized guide for you to vet properties through when the time comes.
Like what you read today? Have a question? Just want to say hi? I’d love to hear from you. Email me at Hello@BuyYourSecondHomeFirst.com or message me on social media @BuyYourSecondHomeFirst. I personally read and respond to every single note.
*The content shared on Second Home First is for educational and informational purposes only. Please consult a licensed financial advisor before making any investment or financial decisions.