it’s just priced and marketed incorrectly.
Owners argue about this constantly: is shoulder season worth fighting for, or is it just dead time you plan around? We put the question to David Kuperberg, Majestic’s Managing Director of Real Estate. His take: the mistake isn’t the season, it’s how owners talk about it.
The pattern he points to is a familiar one. A property has a strong peak season, a predictable off season everyone plans around, and then this in-between stretch that nobody wants to touch. Rates get slashed. Marketing goes quiet. Staff gets cut. The property just waits it out until the calendar turns back to “real” season. That’s not a strategy. That’s giving up on three or four months of the year and hoping the rest of the calendar covers for it.
Kuperberg’s first example is Palm Springs. For decades, summer in the desert was treated as dead time there, something to survive rather than sell. Then, starting around the pandemic, the destination noticed something: a real customer base actually wanted the heat, as long as they had a pool, a lounge chair, and air conditioning waiting for them. So the market repositioned. Campaigns like “Play for Days” and “Born to Chill” reframed summer around exactly what people were already doing: pool days, spa time, discounted luxury stays, and events like VillageFest that only make sense once the sun goes down. Same weather. Same months. A completely different spin, and a completely different customer.
His second example is Costa Rica. Nobody wants to book a “rainy season” vacation. But rename it the “Green Season” and suddenly you’re not describing a problem, you’re describing rainforests at their most alive, rivers running full, waterfalls actually worth photographing. The rain didn’t change. The story around it did.
That’s the part Kuperberg thinks most owners miss. Shoulder season isn’t a scheduling problem. It’s a positioning problem.
A slow period only stays slow if nobody redefines it.
Every destination has a version of this. Somewhere in the calendar there’s a stretch of weeks that gets treated as filler, when it might actually be a distinct product waiting for the right story and the right guest. Maybe it’s a quieter, more affordable version of the peak experience. Maybe it’s a completely different traveler than the one being marketed to the rest of the year. There’s no way to know until the demand actually gets studied instead of assumed away.
To be clear, Kuperberg isn’t saying every shoulder season has a “Born to Chill” campaign hiding inside it. Some slow periods really are just slow, and that’s fine. But most owners never get far enough to find out, because the default move is to discount and wait rather than dig into who’s actually still traveling during that window and why.
For owners sitting on a stretch of the year they’ve mentally written off, that’s exactly the kind of question Majestic’s Strategic Advisory team gets into first: market assessments, positioning, and feasibility work that tests whether there’s real demand hiding in a period assumed to be dead. Sometimes the answer is that the assumption was right, and the slow season stays slow. Often, it isn’t.
Reach out to the team to find out which one your property is.