Our Cabo Playbook
From someone who’s been over 30 times
I didn’t discover Cabo on Instagram or through a travel blog. My parents owned a house there when I was growing up, so Cabo has always felt less like a vacation destination and more like a familiar rhythm in my life. I’ve been more than 30 times at this point, which means we’ve done the sightseeing, the excursions, and the long lists of “must do” activities. Now, when we go, it feels different. It feels like returning somewhere that already knows us.
Planning your own Cabo trip?
We put everything we actually use—where we stay, what we book, what we pack—into one simple guide.
One of the reasons I still love Cabo is because it’s easy. It’s an easy international flight from the West Coast, the weather is consistent year round, and from a hospitality standpoint, I’ve rarely experienced service like I have there. Restaurants genuinely care about the experience they’re creating. Resorts operate at a high standard. There’s an attention to detail that few places I’ve been truly compare. After decades of going, there’s something grounding about knowing exactly what you’re walking into.
Now I get to bring my girls. That part feels full circle in a way that’s hard to put into words- maybe a little nostalgic.
What Most First-Timers Don’t Realize
If you’re planning your first trip, the most important thing to understand is this: you don’t go to Cabo for the beaches or for all day ocean swimming.
Cabo sits on the Pacific side, and the undertow can be intense. The currents are strong, and while there are swimmable beaches, this isn’t a calm, turquoise Caribbean destination where you float for hours without thinking about it. The ocean is beautiful, but it deserves respect.
What you do go to Cabo for is the weather, the food, the golf, and the pace. It’s the kind of place where you can slow down without feeling like you’re missing out on something. And if you only stay in the main tourist area near the marina in Cabo San Lucas, you’re only seeing one version of the story.
San José del Cabo is one nearby city we always make time for.
San José feels quieter and more artsy. It’s more old school and more family oriented. The downtown is charming, the coffee shops are excellent, and the farm-to-table restaurant scene is some of the best we’ve experienced anywhere. It has a refined feel without being flashy, and we genuinely love spending time there.
Where We Stay and Why
When we travel with extended family, we prefer staying together rather than booking separate hotel rooms. For us, the best setup has been staying in a private home within a resort community like Quivira Los Cabos or Diamante Cabo San Lucas. This is the exact Airbnb we stayed at this last trip. It is brand new and we had zero complaints. Our daughter thought the bunk room was awesome!
That combination gives you your own pool and private space, while still having access to resort amenities like cabanas, water parks, and on-site restaurants. At Diamanté, they will even deliver room service from the restaurants directly to your house, which feels like the best of both worlds. You can cook when you want to, order in when you don’t, and still enjoy restaurants like Nobu Los Cabos without leaving the property.
It allows everyone to spread out, but still come together easily.
Why We Always Rent a Car
Cabo is more spread out than people realize, especially if you want to explore beyond your resort. For us, renting a car has always been worth it.
We use Cactus Rent A Car, and we’ve had consistently good experiences with them. They pick you up from the airport and it’s a quick drive to their office, which avoids the long waits and aggressive upselling you can sometimes encounter with other rental companies. We’ve had those nightmare rental experiences in the past, so finding a company that is straightforward and efficient makes a big difference. When it’s time to head home, they drive you back to the airport, which feels almost like valet service. Ask for our guy Luis Cesena - he will take excellent care of you! This is one of those small decisions that makes the whole trip feel easier.
If you’re staying in an Airbnb or plan to explore San José regularly, having a car gives you flexibility that’s hard to beat.
Traveling With Littles
Traveling with young kids can feel overwhelming, which is why we’ve used Baja Baby Gear the past two years.
They deliver everything directly to your rental, including a crib, high chair, changing table, diaper genie, and books. They even asked for the girls’ ages and brought an entire tote of toys, from building blocks to a baby doll. Not having to pack those items or stress about whether they’ll be available changes the entire tone of the trip. You show up and it’s already handled. Both times they coordinated with property managers and had the items delivered and set up prior to arrival as well as retrieved after we left. Truly white glove service.
What a Normal Cabo Day Looks Like for Us
This is the part people don’t always see—Cabo feels easy for us now, but it didn’t start that way. We’ve just figured out a few things we do the same every time.
Cabo mornings usually start early, this trip especially because Indie wasn’t sleeping particularly well. Four people in one bedroom is always an adventure, but we’ve learned to embrace it. Not because there wasn’t room but because our kids are little leeches - they love us. haha
We wake up and head to the pool. Tinsley is usually in the water almost immediately. Broc and sit out by the pool and catch up on calls or emails, because being entrepreneurs means work doesn’t pause just because we’re in Mexico. We often plan our days around Tinsley’s online homeschool classes, which adds a layer of structure to our mornings.
Food plays a big role in how we move through the day. Cabo does fresh, flavorful food exceptionally well, and we genuinely plan around meals. Sometimes we order breakfast in. Other times we make reservations and/or head into town. It’s a balance of slow mornings and intentional outings.
Where We Love to Eat
Fiore is one of our favorite spots for breakfast and coffee when we want to go into town for something quicker. The avocado and burrata toast for breakfast is incredible, and the steak baguette is always a win for lunch. Their coffee is also excellent.
Flora's Field Kitchen in San Jose is somewhere we go every single trip. The Cabo area has embraced farm-to-table dining in a way that feels genuine, and Flora’s does it beautifully. El Huerto Farm to Table offers a similar concept but in much closer proximity to the City of Cabo. Both Flora’s and El Huerto offer gorgeous grounds and space for kids to play.
La Dolce has been a staple since I was a child. If you go, order the filet gorgonzola with a side of fettuccine Alfredo and thank me later. The dress is more casual Cabo. Chambao Los Cabos is another favorite when we want something a little more elevated- it’s located in San Jose and the vibes are immaculate. Craft Kitchen is also another really nice option and family favorite- they have locations in Cabo and San Jose, although the Cabo location is rooftop resort and recently shifted to adults-only so keep that in mind. These are just a few of our top favorites but the food scene in Cabo is top tier.
Packing Thoughts
Overpacking is usually the problem, not under packing. If you’re staying somewhere with laundry, there’s no need to bring an outfit for every possible scenario. I prefer packing a capsule wardrobe with versatile staples and then changing things up with accessories like a hat or a bag.
Evenings can cool off slightly, so a light jacket is worth throwing in. And having good luggage makes airport days smoother than people expect. We travel with Tach luggage because it’s simple, functional, and easy to maneuver. People literally run to us at the airport just to take a picture of the luggage brand. Good luggage is one of those things you don’t think matters… until it really does.
If your rental doesn’t include a golf cart and you’re staying inside a resort community, you can typically rent one, which makes getting around easier.
Is Cabo Safe?
In our experience, Cabo feels no different than any other major city. You use common sense, stay aware of your surroundings, and avoid putting yourself in questionable situations. In all the years we’ve been traveling there, we’ve never had an issue.
If You Only Have a Few Days
If your trip is short, I would prioritize spending a half day in San José, booking at least one farm-to-table dinner, and doing whale watching if you’re there during the season. A boat tour to Land’s End is also worth it at least once.
Beyond that, I would choose accommodations that allow you to relax. Cabo is best enjoyed when you’re not trying to check off every possible activity. Eat well. Slow down. Let the days breathe.
And yes, the golf is legit. Broc would insist I mention that the golf courses are truly excellent. Quivira Golf Club and Diamante Golf Club are both stunning, but there are also great courses at a range of price points.
Why We Keep Going Back
The word that always comes to mind is consistency.
We know what we’re going to get. We know the restaurants we love, the neighborhoods we enjoy, and the general rhythm of our days there. There’s something comforting about returning to a place that feels predictable in the best possible way.
Now my girls are building their own memories in the same place I once did, and that continuity is something I don’t take lightly. Cabo isn’t just a vacation for us. It’s a return to something familiar, steady, and meaningful.
If you’re planning a trip to Cabo…
We put everything from this post (and a lot more) into one place so you don’t have to piece it together.