Terrible experience. The all inclusive price ~($1500/person) was obscene compared to what you get and the sub par execution. 1. Day one, our pickup was an hour late. So we are just sitting in our hotel lobby with our bags waiting. 2. 90% of the driving is through areas with little to no cell/internet service. The iPad app with the driving instructions often didn't work and would only show 1/2 of the instructions, without being able to scroll to the other 1/2 of the instructions. We had to call the office multiple times to resolve. Ultimately we used our personal phones (which HG advises you don't bring) to figure out the gaps 3. The 'hotel' they arranged was an old dirty musty Air BNB type cabin in the woods with years of caked on dust and dead bugs fully covering all windows. Most of the windows had no curtains. The plumbing appeared to be installed by a toddler/amateur with the resulting water flow as if you put your thumb at the end of a water hose. And there were no lights or paved roads on the last mile to get to this disgusting smelly cabin. 4. Second day..the staff member that was to bring our breakfast just didn't show up. We were notified 5 mins before he/she should have arrived and that we could get our own breakfast (at our expense) until our next activity. 5. Our next activity was an hour drive away (I get the impression HG thinks driving is fun and we should really enjoy this) but when we get there the establishment has NO IDEA what we are doing and there is no one from HG staff there to meet with us to discuss the case (as was noted would happen per the itinerary). But no worries..when we call HG they are 'deeply sorry' and we just need to make the hour drive back to where we just came from for our next adventure. 6. We get back to the town we started in and we now have 2 hours to burn it until we hear from another character. 7 min call, now another 1.5 hours until we meet another character. 5 min meeting then 20 mins car ride and another character with an unsatisfying 2 min resolution to case...20 mins car ride..20 mins ferry ride...it's 6pm and experience is over. Literally a wasted day driving for hours. In summary, if this cost $200 per person, I would have no complaints. However, $1500/person is unacceptable. And the whole operation has sub par unprofessional execution. I would highly recommend you spend your $3K on a better company and experience. Stay away from Headland's Gamble!!!!!!!!!!! read more

I wish I could give The Headlands Gamble 10 stars! My friend and I truly had the time of our lives. This incredibly immersive experience was unlike anything I've ever done before! I don't want to give anything away, but our weekend of adventure and mystery truly defied all of our expectations. Driving from place to place with our custom playlist all while chasing clues to try and find a missing horse felt like being in a real-life Nancy Drew novel! How cool is that?! One of my favorite parts was getting to know all of the incredible characters and actors throughout the weekend. Each of them were well-cast and completely convincing. They have a very difficult job and totally delivered. Again, I don't want to give anything away...but we really appreciated our gift from Dustin ;) The bed and breakfast was perfectly adorable and cozy. I never wanted to leave (except we had a mystery to solve!) It was such a nice touch to have our favorite drinks waiting for us in the room, along with fine bread and cheese. We truly felt like queens! We traveled to areas of the Bay that we had never been to before even though we've lived in the area for a combined 25+ years! If you are from out of town...do it. If you are a local...do it. If you are anyone...do it! Headlands Gamble is an experience that is unlike anything you've ever done before. The memories are well worth the price! Good luck finding talisman! read more

"What did you do last weekend?" That would be a tough question to answer. Let's just say we were hired as private investigators to solve a case. Yup. That was it. Headlands Gamble is an unique adventure. Trust me. If you were to participate, the less you know about it the more interesting your experience would be. Resist the temptation to google anything before your trip. All you need is just an open mind to embrace everything that comes. Learn to play and have fun. You won't be disappointed. read more

We had a great time, and my expectations were exceeded. I hope they come up with a new story line soon so that we can return. Someone below mentioned that they take your car without any notice, however, I was alerted to that immediately after I signed up so it was no surprise to me when it happened. They may have just started adding that note. I loved all the little details and appreciate that the customer service didn't stop once the game was finished. I asked for some additional pictures, and a very specific horse toothpick that I was sad to lose and I received them in the mail. The only snafu was that we couldn't find our rental car in San Fran after the actress gave us our keys (and per the games request our phones were in the glove box) but we found a payphone and someone with the game came and took care of us. It ended up being somewhat close to where we thought it was, but across a busy street. These things happen, it's just a learning experience to make it better for the next group. read more

The Headlands Gamble is a weekend of fun, mystery and unbelievably gorgeous sights. From the start of our adventure, my partner and I weren't exactly sure what to expect, but by Sunday evening our expectations were most definitely exceeded. The blend of technical elements, great characters and mind boggling logistics made for a once-in-a-lifetime experience. First Person Travel was exceptionally accommodating and professional, while maintaining a truly personal touch. If you are looking for something more than the same old boring date or anniversary ideas, or if you and your bff just want to try something different, look no further. The Headlands Gamble is worth every cent. A quick caveat: if you use assistive devices to get around, be up front about that, as there were definitely non-ADA friendly portions during the weekend. I'm confident First Person Travel would be able to make things work smoothly, but I figure a heads up is warranted. As a slightly mobility-impaired person I struggled a little, but it was absolutely worth it. tl;dr - 10/10 would adventure again! read more

What a wondrous and memorable weekend! Jonathan b. and Darcy N. describe the experience well, so rather than just repeat their comments, I'll add that... The Headlands Gamble was unlike any other trip I've taken. In addition to the engaging and exciting experience of being a main character in an intricate and compelling piece of interactive theater / real-world game, it was also a totally unique *travel* experience. The best way I can describe it is that it's like being on a roller coaster - not in the usual sense of abrupt highs and lows, but rather that it felt like we were being pulled from one beautiful vista, fantastic meal, or novel experience to the next with no knowledge of what was around the corner, and when it was over we felt exuberant and happy. Highly recommended! read more

Spent the weekend with my girlfriend crisscrossing Marin and exploring small towns that time seems to have forgotten. What for, you ask? The Headlands Gamble, a fully curated weekend for two, solving a mystery. It was an absolutely astonishing feat of choose-your-own-adventure storytelling, with sumptuous experiences around every corner, including lodging, real-life characters, and clues everywhere. Its been impossible to try to describe to friends what the weekend was like and yet I wish I could! First of all, its a secret. Second, this kind of experience is so new: its hard to to explain how you feel *in* it more than any other kind of performance. One of the best aspects, which helped my girlfriend relax, is that while there are amazing characters who we interacted with, we didn't have to act like anyone other than ourselves. The tour agency made us feel at home being ourselves, which actually freed us up to engage everything more fully. Last thing: its also a culinary treat. The dishes and drinks were compelling. I think we had (almost) as much fun meeting the real residents/servers/barkeeps of these hidden away places as solving the mystery. Big hells yes. read more

Absolutely phenomenal! I was given this experience as a gift, and was quite nervous - I previously have worked in theater and often times get caught up on how a show might work, never stopping to enjoy the actual production. However, this WAS NOT the case. I was quickly swept up into a fast paced world of horse racing, mystery, and adventure! Within the first hour, I was grossly concerned about the well being of the characters and what was to come. If you're looking for a weekend getaway - this is it. My friend and I felt taken care of throughout the weekend! Additionally, we were provided times to really relax and take it all in. The story was very plot driven, but not overwhelming. It is maneuvered in a way that's lets you know when it's okay to sit back and when it's more important to jump in. I have not stopped talking about this trip and find myself scrambling for new & better ways to describe it. read more

I'd been dying to do Headlands Gamble for ages (I have a game-design crush on Gabe Smedresman) and it totally lived up to expectations. Would strongly recommend to couples who want to have an adventure while seeing some of California's natural beauty. I think my favorite part was the balance of game and travel, which I would describe as 50-50. One of my friends said she would have preferred it to be more like an escape room where you are really diving headlong into the content and the pressure is on. Me, I feel like escape rooms are everywhere and you can do them any time you want. I enjoyed the opportunity to sleuth and to solve, and to do it without having to feel like we were rushing through our relaxing weekend trip. To me, it became clear pretty early that this isn't the kind of game you can be particularly good or bad at, and that was just what I was in the mood for. Believe me, I can be as competitive as the next person - and we did get stats at the end of our game that gave us some points of comparison between our group and other players - but I don't need to race through my vacation at a breakneck pace. So I really appreciate the opportunity to participate in the story and how it wasn't at the expense of the sightseeing. Given that we did not pay for the all-meals-included option, they still provided us with a generous amount of food. At the end of the journey (no spoilers) when the fate of the Maguffin is revealed, I was quite emotionally invested. There were lots of good surprises and a great level of attention to detail. We felt incredibly well taken care of and grateful to have experienced something so special. If you are the kind of person who thinks the Headlands Gamble might be a good fit for you, you should definitely book it. You won't be sorry. read more

This is a fun and creative idea for a couples getaway to Marin, but I felt the execution didn't warrant the high price. Particularly troublesome is that at one point (without advance warning) they ask you to turn your car keys over to members of their team and they drive your car away while you are doing something else. This seems problematic depending on how much you care about your car, or the insurance details of your personal or rental vehicle. Their staff left our car parked on the streets of San Francisco with the key inside the gas cap (which was visibly open), rather than returning the key directly to us, which I frankly found very irresponsible. read more

Had a fantastic time! Engaging storyline and incredible amenities. Highly recommend.

My boyfriend and I just spent the most magical, memorable , zany birthday weekend being Private Investigators to crack a case . This experience was perfectly conjured up with just the right mix of mental gamesmanship, physical adventure , laughter and travel wonderment. We saw places we would have never found on our own. We met "characters" galore and we also whipped up a little romance . These two days were so well executed . Every need taken care of. So easy !!!! One price and you then just enjoy the rocking ride. So many layers of fun. I have now recommended it to EVERYONE as the trips are tailored you. You can go with just your honey or just a pal. It would make a fun family adventure as well as a perfect venue to pop the question or simply to celebrate the mystery of life. I travel all over the world ...who knew I could experience this much adventure this so close to home. Bravo Headland Gamble ! read more

If I could, I'd erase my memory so I could do this over again. If you're a visitor to the Bay Area, this tour/game/immersive theater experience will allow you to see the best of the beautiful West Marin area in a way that's both leisurely and adventurous, always filled with pleasure. We have lived around here for decades and know this area well, and it opened up all kinds of new experiences, so it's a fantastic getaway for locals, too. The storyline for this interactive weekend of theater and puzzle-solving is ingenious; the performance by the various characters you'll meet is so professional that at times we forgot they were acting; the whole experience is stage-managed behind the scenes with attention and also great wit--you always know it's a game, and you always know they will take good care of you. And it's true immersion; even familiar places take on new dimensions as their/your story unfolds. It's incredibly relaxing to put yourself in their hands. The level of the mystery-solving is just right, not frustrating ever but challenging enough to be gratifying when you figure something out. Along the way you'll get classic West Marin experiences--in our case, a cocktail hour picnic, time by the ocean, a sunset horseback ride, plenty of walks, exploring some great small towns, good meals. Many surprises along the way. It has real warmth to it, none of the heady coldness I associate with some puzzle/escape room kinds of experiences, but you'll feel pride when you make progress in understanding what's going on. It would be fun to do with kids old enough to help solve the mystery, or with friends, but I think it might work best as it did for us, a romantic couple's, honeymoon-ish splurge. Hey, it might even work as couple's therapy, the experience is so intimate and so designed to please. There was just the right balance of competition (we found out a little about how well we did at the end) and safety net--you can't blow this experience, they'll make it work for you. If you don't choose the higher-end version, you end up staying the night in a place that's pretty charming but can be noisy, so either upgrade if you can or be sure to look for the earplugs on the bedside table! I'm sure the location you get if you pay more is amazing. Really, this is worth every penny. The best weekend getaway I've had in decades of Bay Area living. And one of the very best theater experiences I've had, anywhere, as well. Standing ovation for the cast and crew and designers--thank you, Charles, whoever you are. read more