Inspirato Mission, Accomplished. Family Trip to Los Cabos.

Sophie and Rebecca playing, laughing and experiencing some beautiful freedom together!

To inspire lasting memories and relationships by changing the way family and friends experience the world.” There it is. That is the Mission of Inspirato. Now, please hold that thought for a minute if you would…

The last couple of weeks I’ve been trying to think of an angle for my trip report from Los Cabos. I have not felt inspired to write a long, detailed trip report about our week at Casa Ola, even though our week was full of blog fodder considering all the fun we had on a daily basis. But, even with an incredible trip like we had in Los Cabos, a long narrative report can be a bit boring for the reader, and for the writer as well. So, I’ve just sat with my thoughts for a few weeks.

You may not be too surprised to hear that I am/was a huge fan of Anthony Bourdain. I watched his shows and read his writings religiously. He was a genius of humanity, able to transcend cultures and languages to connect with people, utilizing travel and cuisine to create stories and build friendships. It was never exactly about the destination. The destinations just created the context for the stories he told us. Stories that we initially weren’t a part of. We were outsiders. He brought us in. He gave us a seat at the table and invited us in to hear and be a part of some beautiful narratives around the globe. The trip itself was merely the foundation, the scaffolding that facilitated the creation of an experience, a story, a place where relationships were birthed or grew in new ways. Oh, how I miss his storytelling and humanity.

Our Fishergirls…My youngest actually had a huge Sail Fish on the line and lost it, her first “the one that got away” story

That brings me back to the mission of Inspirato. It starts out with, “Inspiring lasting memories and relationships…”. With our group of 12 (9 extended family and 3 friends that became extended family) in Los Cabos, Inspirato nailed this part of their mission. But here’s the deal. It was not the incredible Casa Ola residence itself that inspired the lasting memories. Nor was it the incredible concierge service or the super delicious in-residence breakfast preparation. It wasn’t even the enhanced cleaning protocols that made us all so comfortable while traveling during these strange times. All of those things are the tools, the hardware. They are the means to an end, with that end being “inspiring lasting memories and relationships”. As with the travels of the aforementioned Anthony Bourdain, all of what Inspirato provides is the foundation, the scaffolding on which we all can create beautiful, lasting memories. I guess its a partnership between Inspirato and their members. They cover everything you could imagine to create the perfect vacation framework. But, then it’s on us to make the investment and join Inspirato, plan the time away from work, make sure the kids are free (probably the hardest part right at this life stage!), and include other family and friends when possible. This partnership leads to inspired memories and relationships. And more often than not, many of those most inspired and beautiful memories end up being the most simple, relaxed times. This was definitely the case with our trip to Los Cabos. A few of our most inspired memories from Cabo…

This scene was a nightly occurrence. Us dads were happily relegated to the pool

Evenings at home, outdoors. Hours and hours…and hours of time were spent together in the pool and jacuzzi every singe night. Sharing Stories. Learning about each others’ lives. Sharing some of life’s struggles. So many hours of simple conversations, the stuff that builds and deepens relationships. And without fail, at some point each night, we’d find ourselves looking at our watches in disbelief, realizing that it was already past midnight (yet once again) and everyone was still awake and hanging out together, young and old alike. These times are gifts. There is investment and sacrifice involved in making these kind of big trips happen. It’s in these moments where you have no doubt that it’s worth every penny spent and every hour sacrificed.

Our default hangout spot at Casa Ola

The kitchen island. It must have been originally created and designed by a relationship building genius! Every single kitchen island has some type of magnetic force at work within it. They have their own gravity system. They pull all beings toward their core, causing its victims to sit and chat (and snack) for hours and hours. Casa Ola’s kitchen island must have had a uniquely dense core as its pull was often irresistible. Whether it was the moms cooking dinner, the girls baking cookies, or the dad’s prepping appetizers, the balance of the group seemed to show up to take part in both the activities and the conversations. After all, there was connection to be found around that island, something I guess we are often hungry for. (Funny side note…As I write this while sitting in my home office right now, there are about 12 teenage girls sitting around the kitchen island in our home chatting away. It’s a beautiful SoCal evening. They could be hanging out by the pool, or in the girls’ rooms, or the family room, living room, etc. But no, they have been sucked in by the draw of the kitchen island. It’s force strikes once again).

Not only were there lasting memories created and relationships built around that island, there was some seriously delicious food that sprung forth from the more functional aspects of the kitchen island. My favorite was the tuna ceviche that we made with the tuna we had caught earlier that morning (I guess I was enjoying too much to capture a photo). That was some fresh ceviche! There were also the traditional oatmeal chocolate chip cookies that our girls always bake on vacations, no matter where our travels may take us. The seared tuna was also spectacular. We caught three tuna total on our day out fishing, gave one to the crew, and still had an incredible amount of fish for the 12 of us to make our way through. And behold, we managed to finish every last bite.

Conversation, connection, and great food. That’s what makes the kitchen island such a special place.

Seared Tuna…same day it was caught!

Best Dinner, Cheapest Dinner. Early in the week, I texted Paco, our concierge and said, “Can you recommend an excellent taco place where the locals go, not one of the tourist places?”. Paco delivered big time! We had dinner at Tacos El Paisa. For my non Spanish speaking friends, Paisa, short for paisano, is a word a bit tough to translate into English, but means something like countryman, fellow citizen, but is very much slang in form. I’m realizing I don’t think we have a word like Paisa in English. Okay, that’s not really important. What is important is that these tacos were other worldly. So, so good. This was the most simple of locations. A concrete block building. The heat and humidity only slightly muted by the singular large fan overhead. But, those tacos! El Taco Macho cambió mi vida. I’d never experienced a taco with a fresh chile poblano resting on the tortilla as the base layer, creating something of a hand held chile relleno. It was glorious. If you happened to have read this previous post, you’re right, I think I probably gained back five pounds just in this one evening. But, no judgement please! It was worth every mile of running that was required to eliminate these calories. And by the way, our bill that evening came out to about $6 per person. That is serious value!

“Taco Macho” on the right. See the chile under there?

But remember, it’s never just about the food. The taco, albeit a powerful and most wonderful bit of sustenance, does not, in itself, deepen relational bonds between people (although I would absolutely respect arguments rebutting this claim). But sitting there at Tacos El Paisa, our Tacos Machos led us to a place of great conversation. This particular evening, we all shared about our quarantine experiences of the past few months. So many conversation seem to end up there these days. But, it was therapeutic. The five cousins shared funny stories about Zoom classes, the stress of online classes, and of course about missing Prom and other high school rites of passage. The adults at the table mostly enjoyed an evening of listening to our teenagers reflect on their experiences during a historic global pandemic. Our girls hadn’t seen their cousins in four years, and they live 1,000 miles apart, but it was fun to hear how many shared experiences they had had during such a strange past few months.

Cousin Pool time and great photo op

So those are some of our lasting memories and relationship stories, and I’m realizing right about now that my goal in avoiding a long post may be proving to be quite unsuccessful. Nevertheless, let’s get to the next portion of Inspirato’s mission, “by changing the way friends and families experience the world”. Yeah, Inspirato nailed this part of their mission as well. Our friends and our family experienced the world in a new way, a changed way.

Family Picture…Casa Ola exterior was beautiful!

The most dramatic change in the way we experienced the world was that, on this trip, we actually experienced the world alongside our friends and families as a group of twelve. When you have a six bedroom home in Los Cabos, you are able to do that. Once again, Inspirato is there to provide that foundation you need to make this happen. Without Inspirato, we could have done a nice family vacation in Cabo. And it would have been fun and a special family time. But, we sure wouldn’t have gone through the trouble, nor the expense, to seek out a wonderful six bedroom home. In this case, it was no trouble at all and the cost was simply included in our Inspirato Pass membership. Inspirato had us covered. It provided the framework for our intentionality in putting this trip together. And that led to seven nights with a very special group of 12 people. My wife’s uncle’s family is a family we love, but with all the busyness of life, and the distance between us, we just don’t connect as much as we’d like to. But, this week the five cousins forged a depth of relationship that may just last a lifetime. They now have an active group text. They “Snap” each other regularly. That’s what maintaining long distance friendships looks like in this day and age. I like to believe that a week long vacation with friends/family can be the relational equivalent of years of sporadic get togethers. It just feels like that’s true. It sure seemed to be true for this trip.

Photos at dusk

Perhaps the most unique change to the way our family and friends experienced the world was that, due to having so much space in our Inspirato Residence, we were able to invite along some dear friends that are professional photographers. They stayed in the beautiful casita at Casa Ola that had it’s own private entrance and kitchenette area. It worked wonderfully well for them and their adorable little daughter, who had such a blast with all of her older “cousins”. She was four going on fourteen for the week. My wife and I are now her “aunt and uncle” and we so happy to have gained a new “niece”. It’s crazy how friends can become more like family after just a week of living together on vacation. And having a professional photographer with your group at all times is incredible. All of the girls were able to do individual photo shoots and they had a blast taking turns and helping do hair and makeup for one another. Even that turned out to be a totally bonding experience for all of them.

I’m quite certain we’ll be bringing these friends along on more future Inspirato trips. What a blessing when you realize that you travel so well with your most talented photographer friends!

My girls with Mia, their newest little “cousin”

So yes, Inspirato’s mission was accomplished on this trip…as with countless other trips that its members are able to enjoy. Inspirato provides its members with the scaffolding required to create and build beautiful vacation experiences and memories. The wonderful Inspirato Teams that help make your initial reservation, the Destination Concierge, the incredible Inspirato Residences themselves, the in-residence chefs, enhanced cleaning protocols, all of these things lay the foundation. But upon our return home after this vacation, I asked my girls what their favorite part of their trip to Cabo was. Their answer, “It was so fun just hanging out with our cousins and Mia”. So simple, so profound. All of the incredible service, luxury, comfort, and convenience are very intentionally taken care of by Inspirato so that we, their clients, can “just have fun hanging out with our cousins and Mia”. That right there is how Inspirato inspires lasting memories and relationships by changing the way family and friends experience the world.

Underwater fun with my girls at Playa Chileno

And I do want to leave a few recommendations for those who travel to Los Cabos with Inspirato:

  • Take advantage of the in-residence breakfast. It’s delicious, reasonable, and starts your day off in a wonderful way. They clean everyone all up also! Chilaquiles were our favorite dish!
  • Go fishing! Cabo is world famous for deep sea fishing and there’s nothing like eating your same-day fresh catch for dinner. What a treat! Reach out to me and I can “hook you up” (Dad-joke intended) with a day out on the Reel Deal, a beautiful 55′ Viking owned by a friend who mentioned he’d be open to having Inspirato members charter it once in a while. (Private boat, not available to public as charter)
  • Professional Photos: If you have a friend that’s a professional photographer, take them with you! 🙂 Having this trip so well documented will be a lasting blessing. I’m sure your concierge can recommend great options. Or feel free to reach out to our friends. They are a lot of fun and super talented!
  • Tacos Paisa: Get yourself a couple of “Tacos Machos”. You’re welcome.
  • Playa Chileno: We loved our day at Playa Chileno. Your concierge can set you up. Many beaches in Los Cabos aren’t great for swimming, but Chileno is fantastic! Danny Boy Tours was our transportation/guide and highly I recommend them.
  • Flora Farms: Before visiting, I thought it was a bit over-hyped as it was universally recommended. I understand why now. You’ll be happy you spent at least one evening here.
  • Plenty of un-scheduled chill time: Inspirato Residences lend themselves so very well to just hanging out…at the pool/patio, the kitchen island, wherever. Just relax and enjoy.


Just a quick update on how we continue to get incredible value out of Inspirato Pass. We used our one-time Guest Pass to send some dear family friends to a villa at the Pelican Hill Resort a couple of weeks ago. They had a blast and we loved being able to share the Inspirato magic with them! And next up for me is a trip to Aspen at Inspirato’s Buckhorn residence in October. I’m going with a group of guys for a strategy retreat for a non-profit we’re preparing to launch. I look forward to sharing all about it in a month or so. Stay tuned!

Safe and happy travels my friends!

And as always, please say hello if you have any questions or comments. I enjoy hearing from so many of you!

As much fun as we had with the group of 12, we’re looking forward to getting away soon as a group of just 2 ; )

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