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What does AI dream of? Castles and hot-air balloons

A tourist takes a selfie in South Lake Tahoe. | George Rose/Getty Images

Looking for a quick getaway? Artificial intelligence may be able to help. A spate of new AI-assisted apps promise to make trip planning easier. But should travel influencers be worried that AI will make them go the way of the travel agent in the ’90s? 

We tested out, a ChatGPT-powered web browser application, to see how AI would plan out long weekend getaways to some of the Bay Area’s most popular destinations. Most of Roam Around’s suggestions link to travel tours offered through, which some have suggested is how Roam Around makes its money. Even bots, it seems, can’t escape the gears of capitalism. 

We used Roam Around to plan a theoretical three-day staycation here in San Francisco and asked for long weekend recommendations in Napa, Tahoe and Santa Cruz. Ultimately, the AI’s recommendations weren’t half bad—and some suggestions, like a hot air balloon ride or drinking wine at a Tuscan-style castle—were even slightly whimsical. While the technology struggled to account for drive times, the itineraries Roam Around offered were a solid starting point for DIY trip planning. So can travel influencers relax? Your job is probably safe … for now.  

San Francisco

Roam Around’s hit list for the City by the Bay included unsurprising icons and landmarks like the Golden Gate Bridge, Alcatraz Island, Fisherman’s Wharf, the Ferry Building and attractions in Golden Gate Park, like the Japanese Tea Garden and de Young Museum.

A screenshot of a three-day itinerary for San Francisco from | The Standard Staff

While not particularly unique travel suggestions, the AI hit some of San Francisco’s top tourist attractions—and even suggested a charming ferry ride to nearby Sausalito. However, if you’re looking for human-generated recs of what to see and what to skip in San Francisco, The Standard has put together a handy list of go-to and skippable SF tourist destinations. Verdict: Roam Around’s recommendations were generic but serviceable.   

Fisherman's Wharf is a recommendation from Roam Around for a three-day visit to San Francisco. | George Rose/Getty Images | Source: George Rose/Getty Images


Roam Around surprised our staff with suggestions to take a hot air balloon ride over Napa and a visit to a winery with a castle. Bonus points for creativity! The AI also suggested would-be travelers take in the natural wonder of Calistoga’s Old Faithful Geyser of California. That’s a 45-minute drive from Napa proper, so depending on your timeline it could be worth the drive or out of your way.

A screenshot of a three-day itinerary for Napa from | The Standard Staff

The Standard’s more seasoned travelers, however, were not as impressed with Roam Around’s suggestion to hit up the much-lauded, but lately much-maligned, Michelin-starred French Laundry. Not only does the famed restaurant’s tasting menu cost $350 per person, but also whether the meal is actually worth it has been much-debated lately. Verdict: Take up Roam Around’s suggestions for activities but skip its high-end restaurant recommendations.

Castello di Amorosa, a replica of a medieval Tuscan castle, in Calistoga in the upper Napa Valley is one destination recommended by Roam Around for a three-day stay in the area. | George Rose/Getty Images


Roam Around suggested some of Tahoe’s most scenic spots to hike or shred, including Emerald Bay State park for “spectacular views of the surrounding mountains and crystal clear water,” a tour of that area’s Vikingsholm castle and Heavenly Mountain Resort, which the AI sells as offering “panoramic views” and “4,800 acres of skiable terrain.” However, portions of Roam Around’s itinerary could have you driving in circles around Lake Tahoe.

A screenshot of a three-day itinerary for Tahoe from | The Standard Staff

The day three itinerary suggested starting off at Donner Memorial State Park to pay your respects to the ill-fated Donner Party in the morning, then heading to Truckee River for some river rafting or kayaking in the afternoon (current snowy weather conditions be damned), and ending your day at the Edgewood Restaurant in South Lake Tahoe. Even you if hit up a leg of the Truckee River around the park, it will take you a little over an hour to drive to the restaurant at the other end of the lake. Verdict: Check the travel distances before you go.

Heavenly Mountain Resort's Gondola is one recommendation from the AI-powered itinerary planner Roam Around. | George Rose/Getty Images

Santa Cruz 

Roam Around’s travel suggestions for Santa Cruz could be similarly spread apart. For instance, it doesn’t make too much sense to drive from Forest of Nisene Marks State Park back to The Buttery bakeshop in Santa Cruz proper or trekking out to the “ineffable, natural phenomenon” known as The Mystery Spot embedded in the redwoods outside Santa Cruz back to the Mediterranean restaurant Laili in the city’s downtown.

A screenshot of a three-day itinerary for Santa Cruz from | The Standard Staff

Aside from the obvious tourist destinations like the Santa Cruz Boardwalk, Roam Around did offer some interesting activities from taking a surf lesson at Cowell Beach to visiting the Monterey Bay National Marine Sanctuary. Verdict: Take the order of the itinerary with a grain of salt.

Among other seaside spots, Roam Around recommends hitting up the Santa Cruz Boardwalk during a three-day weekend stay. | Carol M. Highsmith/Buyenlarge/Getty Images

Maryann Jones Thompson contributed additional reporting for this story.
Christina Campodonico can be reached at