The 2026 Shoulder Season Playbook: Why The Smart Planner is Abandoning Peak Season (And How to Do It Without Getting Burned)

Look, here's the reality: The Points Guy just dropped their 2026 trends report, and buried in the data is a stat that should wake up every guy who's ever been stuck organizing the group trip: 16% of Americans are actively avoiding peak season. Not because they want to—they're doing it because peak season has become a logistical nightmare of crowds, price gouging, and the kind of friction that ruins friendships.

I've been saying this for years, but now it's official: Shoulder season is no longer the "budget alternative." It's the tactical advantage.

The Data Doesn't Lie

According to TPG's research, flight prices drop roughly 30% in fall compared to summer. Search volume for smaller airports—places like Bozeman Yellowstone International (BZN) and Yampa Valley Regional near Steamboat—has doubled year-over-year. People are done fighting through Denver International like it's the running of the bulls.

But here's what the trend pieces won't tell you: Shoulder season success requires a completely different playbook. You can't just show up in October expecting July conditions with fewer people. That's how you end up in a closed restaurant, in the rain, with four hungry guys staring at you like you planned this disaster.

The "AI Planning" Trap

The report also notes that AI tools can reduce planning time by 50-80%. Sounds great, right?

Wrong.

I've tested these tools. They'll spit out a "perfect" itinerary that includes a hike on a trail that's snowed in, a restaurant that closed six months ago, and a "highly rated" hotel that's actually a converted motel with a rebranding budget. AI doesn't know that the shuttle you need stops running October 15th. It doesn't know that the distillery you bookmarked requires reservations 90 days out in shoulder season because they cut staff.

AI is a research assistant, not a planner. The Planner—the human who understands the group's dynamics, budgets, and risk tolerance—still matters. Don't outsource your competence to an algorithm.

The Play: 2026 Shoulder Season Destinations

Based on the data and my own intel, here are the tactical moves for The Planner in 2026:

1. Portugal in April/May

Lisbon is averaging sub-$500 flights for spring 2026. The weather is 65-75°F, the tourist hordes haven't arrived yet, and the wine country (Douro Valley) is entering its most beautiful season. The Play: Fly into Lisbon, spend two nights, then rent a car and base yourself in Porto for three nights. Day-trip to the Douro. Total per head including flights: ~$1,400 if you book now.

Logistics Note: Portuguese restaurants often close for extended lunch (2-5 PM) and many smaller spots shut entirely on Sundays. This isn't a "wing it" destination. Make reservations.

2. Montana in Late September

The Bozeman airport search volume doubling isn't a fluke. September in Montana is dry, the summer crowds are gone, the aspen are turning gold, and the elk are bugling. This is the sweet spot for a High-Low trip: hike the Beehive Basin Trail in the morning, soak in a natural hot spring in the afternoon, then hit Open Range in Bozeman for a $65 bison ribeye that rivals anything in Manhattan.

The Marcus Move: Book the Beehive Basin shuttle by August 1st. They cut runs after September 20th, and if you miss the window, you're looking at a 4WD rental minimum.

3. New England Coastal Towns in October

Everyone thinks October in New England is peak season, but here's the inside track: the second and third weeks of October see 40% fewer visitors than the first week, and the foliage is actually better. The summer coastal crowds are gone, the leaf-peepers have moved inland, and the lobster shacks are still open but you can actually get a table.

The Play: Base in Portland, Maine. Day-trip to the White Mountains for hiking, then back for dinner at Eventide Oyster Co. (get the brown butter lobster roll, trust me). Intensity Level: 3. Interest: Seafood, Whiskey, Light Hiking.

4. Japan in November

Tokyo made TPG's shoulder season list, and November is the move. The typhoon season is over, the autumn colors are hitting their peak, and the tourist crush of cherry blossom season is a distant memory. Plus, the dollar-yen exchange rate is still favorable for Americans.

Critical Logistics: Japan requires more pre-planning than any destination on this list. The JR Pass pricing changed in 2023, and it's no longer a no-brainer. You need to calculate your exact route before purchasing. I've got a calculator spreadsheet—DM me if you need it.

The Gear Adjustment

Shoulder season demands a different packing list. You need layers that handle 30-degree morning swings, waterproof shells for unpredictable weather, and—I'm serious about this—merino wool base layers. (I wear Smartwool 150s; Darn Tough socks are mandatory for any trip I plan.)

The "Dave" Test for shoulder season: That guy who shows up in shorts and a hoodie for a November hike? He needs a gear intervention before the trip. Send the packing list two weeks out, and check in three days before departure.

The Financial Framework

Here's the math that matters: A shoulder season trip typically saves 25-35% on flights and lodging. If you're planning a 5-guy trip with a $2,500 per-head budget, that's $625-$875 per person back in the pot. That's the difference between a standard Airbnb and a lodge with a hot tub. That's the difference between "whatever's open for dinner" and the chef's tasting menu.

The Splitwise Rule still applies: Set up the group expense tracker before the first Venmo request. Shoulder season savings disappear fast if you're splitting bills manually in a group chat at 2 AM.

The Warning Signs

Not every destination works for shoulder season. Avoid:

• Caribbean in October: Hurricane season peak. Not worth the gamble for a bachelor party.
• Alaska in April: Mud season. Everything's closed, nothing's accessible.
• European beach towns in October: Sad, shuttered, and the restaurants that are open are serving the dregs of summer inventory.

The Bottom Line

• Shoulder season isn't "settling"—it's strategic. 30% cheaper flights, half the crowds, and better availability at the restaurants that matter.
• AI won't save you. It'll generate a pretty itinerary that falls apart on contact with reality. Do the research yourself.
• The destinations: Portugal (April/May), Montana (September), New England (mid-October), Japan (November).
• The gear: Pack for 30-degree swings. Merino wool. Waterproof shell. Darn Tough socks.
• The math: 25-35% savings = upgrade budget for experiences that actually matter.

Look, Chief—peak season is for people who don't know any better. The Planner who masters shoulder season isn't just saving money; he's delivering a better experience with less friction. That's competence. That's respect. That's how you keep the friend group intact for the next trip.

Get the spreadsheet ready. The window for April Portugal bookings is already closing.

- MV