No planning required: a $2,500 romantic weekend adventure guided by an iPad

Where will this take us?
Where will this take us?
Image: Alice Truong/Quartz
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What happened to Talisman?

Here I was in Nicasio, California, a small town in Marin County popular with cyclists and Ferrari owners, looking for clues that might lead me to Talisman, a promising racehorse that mysteriously vanished the night before.

An hour after scouting out the town square, where we were chasing a lead (quite literally), my partner and I found a bloody ax under a hatch. Could this somehow point us to Talisman—or what remained of him?

headlands gamble nicasio marin county
A smoking gun?
Image: Alice Truong/Quartz

I’m not a trained private investigator, and neither is Mat, but we were dispatched by The Firm to look into the matter. Why? Believe it or not, this was supposed to be a romantic weekend getaway.

I didn’t fully know what was in store when I signed us up to beta test a weekend adventure billed as the Headlands Gamble.

Unlike how I usually operate, I did zero planning for this trip. I didn’t read any guidebooks, consult any online reviews, schedule any activities—hell, I wasn’t even exactly sure where we were going.

The only thing I had done was fill out a survey the week of my trip—and nag Mat, my life, adventure, and soon-to-be investigative partner, to do the same.

We were about to embark on a new type of experience, organized by First Person Travel, a concierge travel agency—an immersive-narrative travel startup, if you will—that promised to take care of all the details for what would prove to be a whirlwind weekend. All I knew was that we’d explore sleepy towns in Marin County, just north of San Francisco, in a convertible—oh, and role play as detectives solving some kind of mystery.

The concept

First Person Travel aims to provide a “one-button push to an amazing weekend,” says Gabe Smedresman, who with actor-writer Satya Bhabha (you might know him as Shivrang in Fox’s New Girl) co-created the Headlands Gamble. “Everything is taken care of for you—the car, hotel, meals. You just show up.”

The Headlands Gamble is by no means a passive experience, though. “I have zero interest in doing a bus tour,” says Smedresman. “I feel I’m much more independent. I’m self-driven, but also open to serendipity. This is what I want in travel.”

He took a gamble believing others wanted the same from their travels. Since July 2015, more than 30 couples (admittedly, still a small number) have put their weekends in the hands of First Person Travel. They’re guided by an iPad that dispenses instructions and directions, and it’s this device that allows the people working behind the scenes to track participants’ whereabouts, steering them back on track if they’re hopelessly lost (which happens to the best of us in mountainous Marin, with its notoriously spotty cell service).

headlands gamble nicasio marin county
It may look idyllic, but there’s something dark here.
Image: Alice Truong/Quartz

In some ways, this trip is set up like a real-life video game, and that’s no coincidence given Smedresman’s lifelong obsession with them and prior work as a game designer. ”What we’re trying to do is use technology to bring the best of video-game design into a real-world experience,” he says.”As life becomes more digital, the real world is something we’ll need more and more.” He, of course, recognizes there’s some irony in using tech to facilitate a trip designed to help busy people unplug.

Unplugging has become a major selling point for some niche travel companies offering quirky, off-the-beaten path vacations. Like the Headlands Gamble, they’re limited by how big they can scale, but that’s part of the charm. The CEO of Getaway, which rents out tiny houses in the Boston area, has referred to his company as “the anti-vacation.” It has raised $1.1 million from investors on an intriguing concept: to keep the location of its 200-square-foot, WiFi-devoid cabins a secret until 24 hours before—an attempt to force people to step back from their hectic, overplanned lives.

Once you add live theater into the mix, it’s apparent First Person Travel is in new territory. It takes inspiration from projects like Odyssey Works, which stages extended theatrical experiences lasting days to months for an audience of one. (Smedresman says he designed two of these experiences.) Odyssey Works spends months carefully crafting a narrative based on research into its audience. As a 2012 New York Times article described, it would “abduct” the participant the day of the performance and take him or her to a secluded location for a private show, complete with dinner and tent to spend the night in. But Odyssey Works was strictly an art project, and the Headlands Gamble is an attempt to commercialize that model by putting on two “shows” each weekend.

headlands gamble nicasio marin county
What’s on the other side?
Image: Alice Truong/Quartz

Originally, the Headlands Gamble was a $2,450 all-inclusive affair. That package came with a convertible, one-night stay at a seaside inn, and all meals and drinks. But the team recognized that was more than most people would pay for two days, so First Person Travel in March created a “basic” package, which for $1,650 includes the hotel but requires travelers to use their own cars and pay for meals out of pocket. It also added a luxe version for deep-pocketed Bay Area yuppies. At $3,250, the “perfecta” tier takes the all-inclusive package up a notch with gourmet meals and little flourishes that are tailored specifically for the couple.

Even at these steep prices, Smedresman insists “we’re making a very slim margin.” What might not be immediately obvious is that there’s lots of logistics and overhead involved, including hiring a set of four actors for each couple. “We always knew the Headlands Gamble was not a money-making endeavor,” says Smedresman. Instead, it’s a “proof of concept” that will be adapted into smaller-scale productions that take place over the course of an evening in San Francisco. First Person Travel started as a passion project for its creators, but they now see it as a viable business. ”We’re really hopeful and looking to get support from the world around us to say we want this kind of stuff,” adds Bhabha. “These experiences are valuable and exciting and worth it.”

Who done it?

So back to the missing racehorse. After a chauffeur whisked us away from our home in San Francisco to Golden Gate Fields in Oakland, a frazzled woman named Sarai explained that Talisman was last seen on this racetrack the night before following a stunning practice run.

headlands gamble nicasio marin county
The central figure in the Headlands Gamble.
Image: Alice Truong/Quartz

Sarai, who was brokering Talisman’s sale to an unknown buyer for $2 million, was depending on this deal to go through to avoid being sent back to the Middle East (like Talisman, all the characters we meet have incredibly rich back stories). “There’s a lot riding on this,” she tells us.

As we enjoyed a light breakfast overlooking the racetrack on this sunny Saturday morning, Sarai explained that Talisman was no ordinary racehorse. He lacked the pedigree of his peers, having been raised on a farm by a man named Herb. No one knew he could run like that—”as fast as American Pharoah, but his bone structure is better”—and, understandably, a lot of people in the horse world were not happy their thoroughbreds were losing to this nag. As far as motives went, it seemed everyone who knew Herb had a horse in the race.

headlands gamble nicasio marin county
A distressed Sarai, left, at Golden Gate Fields in Oakland.
Image: Alice Truong/Quartz

We quickly narrowed down our prime suspect to Vance Faraday, a prominent Marin horse dealer who was coincidentally at that moment leaving Golden Gate Fields. I felt like a real-life Sam Spade, the San Francisco detective in Dashiell Hammett’s Maltese Falcon, as we were in hot pursuit in a red Ford Mustang convertible—the keys of which Sarai conveniently handed us moments before (one of the perks of working for a sheikh, apparently). Before we left, Sarai reminded us to “always refer to the tablet.” From here on out, we’d communicate using this device.

Our chase took us to Nicasio. We didn’t track down Vance, but our sleuthing led us to a bloody hatchet that belonged to her. (Not only was her name on the ax, but The Firm’s forensics department independently verified that fact with fingerprint analysis based on a photo we sent via the tablet.)

After we gathered our evidence, we headed to Point Reyes to meet Herb. Though Station House Cafe was a busy local hangout, we were able to skip the line and find Herb, a scruffy, white-haired man with a slight country twang, nervously gulping down his coffee at a table. He’s clearly distraught. Talisman was more than just a horse to him—he called him a “a sign from God”—but Herb felt he had no option but to sell the horse to help care for his terminally ill wife, Ann.

We were fascinated, but also famished, and as if on cue, Herb said he needed to take care of some business. He urged us to order, eat, and leave when we’re ready. “The bill’s on me,” he insists. Logistically, this was magic. There was no wait for a table or for the back-and-forth with the check afterward. There should be a startup that does just this.

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Herb at the trail.
Image: Alice Truong/Quartz

Before he went about his way, Herb suggested a few local spots to scope out as part of our investigation and then to check in with him afterward. How lovely he suggested we meet at a trailhead that would take us through an easy but scenic hike.

A clue left behind by Herb.
A clue left behind by Herb.
Image: Alice Truong/Quartz

As I picked up a menu, I noticed a slip of paper left behind by Herb with names of what appeared to be ranches and numbers scrawled next to them. Scarfing down a burger, I pondered what this list could mean. And didn’t Sarai hint at some scandal involving Talisman? Did Herb think Vance could be behind this? Did he have reason to suspect Dustin, the jockey he regarded as his son who was known to hang out with the wrong people? Was Sarai involved? Who was her buyer anyway?

The script

As a condition for letting me experience and write about the Headlands Gamble, Smedresman asked that I not reveal too much of the story.

I get why he’s so protective. He’s trying to build an immersive-narrative company, and it’s the story that’s at the heart of everything. He and Bhabha, who were both in the same class at Yale and later got to know each other through mutual friends, had spent two months researching the history of the area and crafting this intricate storyline.

“I live in LA, but was in San Francisco almost for the entire of last year,” says Bhabha, who also directed the Headlands Gamble. “I was not interested in creating something that was like a sort of choose-your-own adventure where if you think the butler did it, it turned out the butler did it.”

headlands gamble bolinas marin county
Our sleuthing took us to Bolinas, California, a beach town known for not being the friendliest to visitors.

In developing his characters, he paid close attention to Marin. “The environment the travelers are placed into is such a major character in a piece, if not the major character in the piece,” he says.

Knowing that the Gamble would explore Marin, Bhabha had mulled on a few themes, including ecoterrorism and the West Coast slave trade. But after chatting with locals, he said “immediately it was very clear to me that story about horses and farmhands and the changing economic landscape in that area was most organic.” He continued his research at the UCLA library, “check[ing] out everything I could get about horses, about racing, about horse mysteries.” Sherlock Holmes’s The Adventure of Silver Blaze was one source of inspiration for the noir theme.

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One of the local gems in Bolinas, California: a pay-what-you-want bookstore.
Image: Alice Truong/Quartz

Even after the script was written and actors cast, he continued to refine the story based on feedback from participants. The version I experienced on the last weekend of February “is pretty much locked down,” says Bhabha, noting the ending was dramatically different from that first performance in July. (Smedresman adds that the team is working on building out side missions and personalizing the trip for couples.)

That’s not to say everything went off without a hitch. By its nature, the Headlands Gamble has a lot of moving parts, and it was not immune to the occasional snag—like when we were handed the key to the wrong car, or when the cabbie couldn’t find us at the end because the team changed the location of the final scene.

Though I went into this journey with a little bit of cynicism, I must admit the actors, who never broke character (even Dustin during the 20-or-so minute lull while waiting for the cab to show up), managed to draw us in. In between the meals, hikes, and sightseeing, we couldn’t help but reexamine the clues we collected and each person’s motives. Having pieced together the puzzle before the grand finale, I do wish I got the satisfaction of explaining, in Sherlock-style deduction, exactly what happened to Talisman in one big a-ha moment. But alas, it was played out before us in the final scene where the actors revealed everything, to the point where it felt like we were being hit over the head with it.

In the end, everything was surprisingly well executed, even if there were some hiccups along the way. They don’t call it a beta test for nothing. For the days following, I continued thinking back to the sights I would’ve otherwise passed on my way to Muir Woods or Point Reyes National Seashore, to Talisman and the other characters, to the logistics, to the story, and to the tidy ending, which left no loose strings hanging.

Still, were it not for the special “rush” pricing offered by First Person Travel to fill up its weekend slots, I’m not sure I’d take the Gamble. There’s certainly an audience here in the Bay Area, but I’m not the type to pay $9 for green juice, let alone drop what’s essentially the cost of rent for two days of travel.

What I can say is that the Headlands Gamble gets me excited for the San Francisco spinoff to come, which hopefully will be attainable to plebeians like me.