Beating the Crowds

Six vacation markets you'll wish you bought into two years ago

When I was a kid in the ‘90s, my grandfather used to tell a story about three beachfront lots in Loveladies on Long Beach Island.

“It was the 1950s, right after a hurricane… a guy at the bar offered him all three lots for $10,000 each… he passed… those lots are worth millions today.”

I remember thinking he squandered the best real estate deal of all time. And then blamed him that we weren’t rich.

We all have those stories: the friend or uncle who almost bought in Montauk in the ‘80s, looked at Park City before the Olympics, Aspen when it was a mining town, yada yada.

The pattern is always the same: a place that was underbuilt, underknown, or had just been through something terrible. A catalyst arrived, and the window closed.

Here are six places where that window is still open.

Driggs, Idaho

The place. A ranch town in Teton Valley on the west side of the Tetons, ten miles from Grand Targhee Resort, which gets 500-plus inches of snow a year.

What makes it great. Fly fishing on the Teton River. Mountain biking. Yellowstone next door. A growing food and brewery scene. Targhee’s powder is consistently ranked among the best in the country.

What’s happening. Grand Targhee Resort is expanding: 50 new cabins, new lift infrastructure, new terrain. The average single-family home in Jackson Hole hit $10.7 million in 2024. Driggs median is $525,000 to $795,000. That’s one-sixth of Jackson. Teton County added 35% more jobs between 2017 and 2023, population up 14% in five years.

Sandpoint, Idaho

The place. A lakefront town on the shores of Lake Pend Oreille in northern Idaho, home to Schweitzer Mountain, the state’s largest ski resort at 2,900 acres.

What makes it great. Lake and mountain in the same town. Schweitzer has a 2,400-foot vertical drop. Downtown punches well above its weight in restaurants and breweries. Year-round recreation from skiing to wakeboarding.

What’s happening. Alterra acquired Schweitzer in 2023 and added it to the Ikon Pass. Every resort that joins Ikon sees a visitation spike. New chairlift already installed. Population up 29% since 2020. Median home around $450,000 to $589,000, correcting from pandemic highs. Sun Valley is $1M-plus.

Taos, New Mexico

The place. A high-desert arts town in the Sangre de Cristo Mountains, 70 miles north of Santa Fe, with a world-class ski area that averages 305 inches of snow.

What makes it great. One of the best art scenes in the American West. UNESCO World Heritage Taos Pueblo. New Mexican food people fly across the country for. Expert ski terrain with $300 million in renovations over the past decade.

What’s happening. A $5.4 million airport terminal is opening this month. JSX already flies direct to Dallas and Denver. The bottleneck in Taos has always been accessibility, not desirability, and that bottleneck is being removed. Median home around $599,000 versus Santa Fe at $750,000 to $900,000. Buyer’s market with 7.6 months of supply.

Gunnison, Colorado

The place. A university town 28 miles south of Crested Butte, sitting at the confluence of the Gunnison River and Blue Mesa Reservoir, Colorado’s largest body of water.

What makes it great. World-class fly fishing, backcountry skiing, mountain biking. Western State gives it year-round energy. Less precious than Crested Butte. More the kind of place where people actually live.

What’s happening. Crested Butte prices are roughly three times Gunnison’s. Condo and townhome prices in Gunnison have surged 73% as buyers shift south. The Driggs-to-Jackson dynamic, playing out in real time, 28 miles apart.

Gulf Shores, Alabama

The place. Thirty-two miles of white-sand Gulf Coast beach between Mobile Bay and the Florida Panhandle, anchored by Gulf Shores and Orange Beach.

What makes it great. The beaches are legitimately beautiful. Gulf State Park covers 6,150 acres. Deep-sea fishing charters leave daily. The seafood is better than most of the Panhandle. One of the few Gulf beaches where you can still buy for under $500,000.

Also home to my favorite bar in the world - Florabama.

What’s happening. Visitor spending hit $4.7 billion. Nearly 8 million visitors a year. A thousand new lodging units added in the last 18 months, another thousand coming. Median home is $458,000 to $515,000 versus 30A at $800,000 to $2 million. Vacation rentals average $43,700 a year.

Mexico Beach, Florida

The place. A small Gulf Coast town in the Florida Panhandle, halfway between Panama City Beach and Apalachicola.

What makes it great. Hurricane Michael leveled it in 2018 as a Category 5. The town has been rebuilt almost entirely from scratch: modern, elevated, storm-resilient homes on a stretch of Panhandle beach that feels like old Florida. No high-rises. No strip malls.

What’s happening. The housing stock is brand new. The prices reflect disaster recovery, not the quality of what’s been built. Median is $350,000 to $525,000 versus 30A at $800,000 to $2 million. That window closes once the last lot develops and the narrative shifts from “recovery” to “destination.” Insurance is a Panhandle-wide headwind, but this construction was built to current code.