When Your Destination Isn’t Ready for the Guests You Brought

The real work of shoulder season isn't filling rooms. It's filling gaps.

You saw the potential. Guests were willing. Your calendar had availability. The math made sense.

But now you're spending half your time doing work that isn't yours.

You're printing "what's actually open" sheets because the visitor bureau's website still lists July hours. You're apologizing for the museum that closed two weeks ago without updating Google. You're explaining that yes, the trail is open, but no, the shuttle that gets you there isn't running yet.

And underneath all of it: guilt. Like you tricked guests into coming. Like their disappointment is your fault, even when it isn't.

This week's Destination Sunday piece reframed seasonality: it's not a demand problem. It's a planning problem. Destinations that only plan for peak leave operators improvising.

When the destination's coordination doesn't match your operating window, where do you spend the most time filling the gaps?

That's the real cost of shoulder season. Not empty rooms. Rooms you filled, and then had to apologize for.

Why October's Problems Get Made in January

Shoulder season coordination fails because the decisions that shape October get made in January—when no one's thinking about October.

Marketing budgets are locked before anyone asks what information will be current in the fall. Staffing plans are finalized before anyone considers who'll answer visitor questions in the slow months. Event calendars? Built for peak. Then left to rot.

The destination's website promotes beaches when the leaves are turning. The visitor center has reduced hours or closed entirely. The "things to do" page lists attractions that shuttered weeks ago.

And it's not just DMOs. OTAs are part of the problem too. Booking.com and Expedia show "nearby attractions" that haven't been updated in months. Guests book based on listings that promise a farmers market, a sunset cruise, a restaurant that closed last spring. You don't control those listings. But you're the one who explains why they're wrong.

DMOs and platforms get credit for shoulder-season marketing without bearing the operational cost. Operators absorb the downside privately.

The destination promotes October. You deliver October. When October disappoints, you're the one at the front desk. The DMO doesn't get that phone call. Booking.com doesn't get that look of disappointment. You do.

I watched a couple check in last October. They'd driven three hours. They had a whole day planned. Winery, sunset kayak, dinner at the place they'd read about online.

The winery had switched to weekends only. The kayak rental closed at 3. The restaurant was shuttered until spring.

They didn't yell. They just put their phones away and looked at each other. Deflated.

I spent 20 minutes rebuilding their afternoon. Found them a vineyard that was open. Called a friend who does informal kayak tours. Gave them my personal dinner recommendation.

They left happy. That's 20 minutes I didn't bill for, repeated several times a day, hours every week spent cleaning up someone else's system.

Where Your Time Is Really Going

Most owners I talk to underestimate how much shoulder-season labor goes to fixing other people's mistakes—because it feels like hospitality, not work.

But there's a difference between hospitality and compensation.

Hospitality is recommending your favorite restaurant. Compensation is explaining that the restaurant the visitor guide recommended closed for the season, and here are three alternatives that are actually open.

Track it for one week. Note every guest question that required you to correct information the destination should have provided.

Or use the shortcut: At the end of each shift, write down the one question you answered most often that wasn't about your property. Thirty seconds. Do it for a week.

Most operators find: 10–15 minutes per guest, several times a day. Across a month, that's 10+ hours of unpaid work.

Then build what the destination didn't:

• Level 1: A 15-minute weekly update. A printed half-sheet. "Here's what's open this week." Saves 30–60 minutes of front-desk conversations weekly.
• Level 2: A shared doc with one or two operators you trust—not the whole chamber. When she hears the museum changed its hours, she adds it. When you learn the shuttle stopped, you add it. Start small. In some destinations, trust is thin. Don't build a coalition. Find one person who's shown up for you before.
• Level 3: A simple page on your website. "What's Open in [Destination] This Fall." Link it in pre-arrival emails. Guests arrive already oriented.

Each level reduces front-desk time, repeat explanations, and the slow drain of apologizing for things you didn't break.

Why Fixing Expectations Beats Marketing Harder

Not every shoulder-season problem is the destination's fault. Some of it is yours:

• Your website listing hours or amenities that aren't current
• Pre-arrival emails that reference activities not available off-peak
• Staff who don't know what's open because no one briefed them

One unfixed gap on your website can cost you a negative review. One negative review in shoulder season—when you have fewer bookings to dilute it—can shift your rating for months.

Fix your gaps first. Then you've earned the standing to push the destination to fix theirs.

Set honest expectations before booking. A simple reframe in your listing or pre-arrival message:

"October in [destination] is quieter than summer—which is part of why we love it. Some seasonal attractions and restaurants will be closed, but here's what's open and worth your time this month..."

Guests who book after reading that are the right guests for shoulder season. They arrive without the mismatch that leads to disappointment, bad reviews, and discounts you shouldn't have to give.

Prep your staff before shoulder season starts. A 15-minute briefing:

• Here's what's closed or has reduced hours right now.
• Here's our "what's open" sheet—hand it to anyone who seems confused.
• When a guest is disappointed about something we don't control, acknowledge it ("That's frustrating") but don't apologize like it's our fault.
• Don't offer discounts without checking with me. Instead, offer late checkout, a local recommendation, or the wine in the fridge.
• If someone's really upset, come get me or write it down so I can follow up.

You're not training them to be therapists. You're giving them permission to be helpful without carrying guilt that isn't theirs—and without giving away margin.

What to Stop Apologizing For

When a guest is at your front desk, frustrated because the kayak rental closed early, they don't care whose fault it is.

Acknowledge without owning: "That's frustrating—I'd be annoyed too. Their hours have been unpredictable this fall."

Pivot to what you can do: "Here's what I'd suggest instead..."

Don't discount for destination failures. The pressure is real. The guest is upset. You know they might write a review.

But discounting your rate for someone else's mistake trains guests to expect compensation for things you don't control. It eats your margin. And it doesn't fix the problem.

Instead, offer something that shows care without costing cash:

• A late checkout
• A bottle of wine or local treat
• A personal recommendation on a card: "Here's my favorite sunset spot—most visitors don't know about it"
• A follow-up text the next day: "Hope the rest of your trip came together"

These say "I care" without saying "this was my fault." Most guests feel the difference.

When the Destination Won't Change

Some of you have been bringing data to chamber meetings for years. Nothing changes.

Three options:

Accept that you are the visitor bureau now. Stop waiting. Build your own orientation layer. Operate as if destination-level coordination doesn't exist—because for your guests, it doesn't.

Band together with other operators. A WhatsApp group. A shared "what's open" page multiple properties link to. Sometimes, when operators start doing the DMO's job visibly, the DMO gets embarrassed enough to step up.

Decide shoulder season isn't worth it. If the dysfunction costs more than you earn—labor, emotional energy, reputation repair—it might not be worth staying open. That's not failure. That's math. Run the numbers without shame.

What a Better October Looks Like

A guest arrives. They already know the shuttle isn't running. You told them in your pre-arrival email. They've seen your "what's open" list. They're not expecting peak. They're expecting October.

You hand them a printout with your favorite spots. They smile. They head out.

No apologies. No scrambling. No guilt.

Shoulder season feels like what you hoped it would be: quieter, calmer, sustainable.

Not because the destination figured it out. But because you stopped waiting for them to.

Destination Sunday sets the lens. Monday helps you apply it.

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Postscript: A 10-Minute Audit

Use this now to find one thing to fix this week. Or save it for your end-of-season debrief.

10-Minute Shoulder Season Friction Audit — AI Prompt

I run a [hotel / inn / vacation rental / tour operation] in [destination].
We stay open during shoulder season, but guests often arrive with outdated or incorrect expectations about what’s available.

I want to quickly identify where friction is coming from and what I should fix first.

Step 1: Ask me questions first.

‍Ask only the minimum number of questions needed (no more than 6) to understand:

• The most common guest questions that require me to correct information they found elsewhere (visitor bureau, Google, OTAs, or my own website)
• What I find myself apologizing for most often
• Where my staff struggles most when guests are disappointed

Step 2: Synthesize, don’t lecture.

‍Based on my answers, summarize the patterns you see in plain language.

Step 3: Categorize the friction clearly.
Sort the issues into:

1. Destination / OTA gaps (outside my control)
2. My gaps (things I can fix)
3. Expectation-setting opportunities (things I could address before arrival)
4. Staff training gaps (things my team needs clearer guidance on)

Step 4: Prioritize for impact.
Identify:

• The single issue causing the most repeated friction or time loss
• The one fix I can realistically implement this week that would reduce guest confusion, staff stress, or unnecessary apologies

Step 5: Extend the insight.
Suggest:

• One simple way to share this pattern with other operators or my DMO (without sounding like a complaint)

Keep your tone practical and specific.
Avoid generic hospitality advice.
Optimize for clarity, time saved, and fewer front-desk apologies.

‍

Pick one gap. Fix it this week.