She’s spent decades crisscrossing the country, and it’s not the big cities or buzzy resorts that stick with her—it’s the slower, sweeter places where charm comes easy and the crowds never found their way in. “These towns remind you what travel’s really about,” Brown says. “Connection, character and a little surprise around every corner.”
Related: 7 of the Biggest Travel Trends to Watch for Summer 2025, According to Getaway Guru Samantha Brown
1. Corning, New York
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Its location also makes it a great base for wine tasting. Just a short drive away, on the southwestern hills of Keuka Lake, lies Dr. Konstantin Frank Winery. Founded in 1957 by a Ukrainian-born plant scientist who pioneered the use of European vinifera grapes in New York’s cool climate, the winery is still run by his family today. “You’re not just tasting wine,” Brown says, “you’re tasting history.” Sample sparkling wines, Gewürztraminer, rosé and more at what’s now the state’s most award-winning vineyard.
As for where to stay, the Inns of Aurora are a favorite in the Finger Lakes. Though located about an hour away on the shores of Cayuga Lake, the scenic drive pays off for this fun fact: the five-inn property is owned and lovingly restored by American Girl creator Pleasant Rowland.
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2. Beaufort, North Carolina
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Walkable and historic, Beaufort’s downtown is lined with 18th- and 19th-century homes, weathered churches and waterfront paths where sailboats drift by. “There’s such a connection to the sea here,” Brown notes, pointing to the North Carolina Maritime Museum as a must-see for maritime buffs. Right across the street, you can also watch boatbuilders handcraft wooden vessels at the Watercraft Center—“a true labor of love,” she adds.
Come nightfall, Beaufort offers one more surprise: “It’s an International Dark Sky destination,” Brown says, “so the stargazing is phenomenal.” With little light pollution, the skies over Cape Lookout explode with stars, making this quiet seaport feel even more like a hidden gem.
3. Flagstaff, Arizona
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Perched at 7,000 feet, Flagstaff offers a refreshing contrast to the desert heat found elsewhere in Arizona. Summers here are blissfully mild—think 80s by day and sweater weather by night. “It’s one of those rare places where you can hike through a ponderosa pine forest in the morning and be dining at an independent art-forward restaurant by night,” Brown notes.
One of Brown’s favorite stops is the Lowell Observatory, where Pluto was discovered in 1930. “The new visitor center is phenomenal,” she says. “It makes space feel tangible—like you’re a part of the exploration.” Nightly stargazing sessions with powerful telescopes give you a front-row seat to Arizona’s famously clear skies as well. A perfect end to an active day.
Related: The U.S. Travel Destination Everyone Should Visit at Least Once, According to Getaway Guru Samantha Brown
4. Traverse City, Michigan
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Located along the shores of Lake Michigan, the small city is best known as the cherry capital of the world—home to the National Cherry Festival in June—and a launchpad to Sleeping Bear Dunes National Lakeshore, where sandy trails and scenic overlooks meet sweeping views of the lake. “It’s absolutely stunning,” Brown says, recommending it for both drives and dune climbs.
Wine lovers can sip their way around the region, but Bonobo Winery, founded by TV personality Carter Oosterhouse and actress Amy Smart, is a standout. “They really poured their hearts into it,” Brown says.
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5. Route 66 Mini Road Trip: McLean, Illinois
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Start in Joliet at the Old Joliet Prison—yes, the one from The Blues Brothers. “What better place to kick off a Route 66 trip than a prison?” Brown jokes. Touring the site with the former warden from the movie shoot gave her a front-row seat to behind-the-scenes stories about Belushi and Aykroyd. Though it closed in 2002, the Gothic structure now draws visitors with its pop culture cred and fascinating history.
Finally, cruise into McLean, where a local entrepreneur is reviving small-town Illinois with a vintage arcade empire. “It’s a dream for anyone who grew up in the '80s,” Brown says. With more than 3,000 playable games—from Galaga to original pinball—Arcadia and Pinball Paradise are pure joy. You can even stay overnight in retro-themed apartments, some with private arcades. “It’s one of those places you never expect to fall in love with,” she says, “but you absolutely will.”
7. Madison, Wisconsin
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Brown especially loves how seamlessly the city blends nature and culture. “It has this creative energy that makes everything—from the food scene to the public spaces—feel alive,” she says. Don’t miss the Dane County Farmers’ Market, one of the best in the country, or a meal at one of Madison’s many chef-driven spots celebrating Wisconsin’s deep culinary roots.
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