Our Winter Getaway to Cabo

As you know, winter in New England can be brutal. And if you follow my Instagram, you know I recently ran away from old man winter and escaped to much fairer weather in Mexico! I’ve learned that the secret to every Bostonian’s happiness is to go somewhere warm to recharge at some point during blizzard season.

In truth, the winter hasn’t been all that bad this year (knock on wood, since it is definitely not over yet), so I feel a little guilty saying we needed an escape. But not guilty enough to regret a damn second of any of it. This trip was bliss. Shall we vicariously bask in Cabo’s sunbeams through these photos? We shall…

Will and I have been hustling, moving from city to city following different career opportunities for each other, and living on a tight budget for the past eight years. All of a sudden, we looked up and realized we hadn’t taken a REAL vacation since our honeymoon eight and a half years ago (!)—so it felt like high time for us to enjoy a true stay-at-a-hotel vacation (rather than crashing with friends on an air mattress) with nothing else on the calendar but pure relaxation.

Why Cabo?

First of all, if you are asking “Why Cabo,” I see you and I hear you. All I knew of Cabo was what I’d seen on Laguna Beach; judge if you must. But after weighing our decisions, Will and I both decided that we wanted to go somewhere warm, sunny, and slow paced so we could relax and unwind without pressure to take advantage of too much sight-seeing.

Do I want to travel to Paris, seeing every museum, stroll along Montmartre, and hit every back alley flea market? Absolutement. Do I want to experience the culture of Morocco, Greece, Thailand, India, Italy, etc. etc.? Yes. But we knew if we did those trips, it wouldn’t necessarily be a restful visit but one that we wanted to pack in a lot of activities. And honestly, after medical school for Will and running my own business for six years with zero restful escapes or vacations within those experiences, we decided to prioritize R&R over a grand adventure. We have more life to live and can do those things later…and if I’m honest with myself, I’m a lazy traveler! I want to sleep in, lounge like a cat in a hammock, drink, eat, read books, sleep, and repeat.


Cabo delivered.

I mean, look how happy and tan and well-rested we are! GOALS ACHIEVED.

Will is in his residency, so his schedule is the toughest to coordinate around now that I’m no longer tied to my own storefront. (By the way, love on all your local small business owners! Retail is always expected to be open, with even longer and crazier schedules on holidays that other people usually get off from work.)

Having designated, real vacation days in our work schedules is a newfound joy for us both, we were PUMPED to bask in its amazingness!

One of Will’s assigned vacation weeks was at the end of January, and it was honestly the perfect time to be in Cabo. It was only us and a couple other families at the resort, so on top of it being rather quiet, the resort ended up giving us a complimentary upgrade to a nicer suite because they weren’t fully booked. It was such a nice gift and complete surprise that we really appreciated.

What We Did

Like I said before, we were’t looking to pack in a lot of sight-seeing or off site adventures. But there was plenty to take advantage of without having to over-schedule our days!

Every night we went to sleep with our patio doors open and woke up to a clear view of the sunrise. We’d make espresso in the room and go lay on loungey beds on the attached patio and take it all in.

After a lazy morning in the room, we’d mosey on down for a long breakfast on the water at the resort. It was their best meal and I honestly still crave the huevos rancheros. SO. GOOD. That dome in the center—which Will and I affectionately named “Stickgloo”—was another bar and restaurant but also just looked like a beautiful contemporary sculpture. I swear none of this is sponsored (I wish, haha!) but we chose our resort wisely and barely ever left.

When we did leave and go into town, we borrowed one of these cute cruiser bikes and peddled around like we were in The Notebook. Honestly, it was adorable as hell and super fun and if you give me a bell I WILL ring it.



Most times, we just put our swimsuits on (I wore the same one everyday so that I didn’t have a mixed bag of tan lines…and because I make it a rule to only bring carry-ons and pack light) and headed down to the beach and/or pool.

A couple other highlights include a couple’s massage at a gorgeous spa where Will discovered he loves and I hate steam rooms (REAL PANIC SETS IN WHEN I AM CLOSED IN THAT ROOM).

We also rode horseback on the beach which sounds so annoyingly bougie and I guess was, but I absolutely loved that and would have kept riding for another hour.

Here are more photos of us being blissfully happy. I think that was wind blowing Will’s hair, he doesn’t usually sport the Sonic the Hedgehog look 😉

Now that I’m looking at it all, we did walk away with a decent amount of photos that we can look back on and remember all the memories we made, but we were also very conscious of leaving our phones off and camera behind ninety percent of the time so we could be present and enjoy our time together.

There were a couple people there with drones and cameras being hardcore about filming and photography and documenting the place in the most aspirational light, which felt excessive and intrusive to us and I hope I’m never that person. It’s a fine line of feeling creative and wanting to capture some moments, while also making sure to turn everything off and unplug.

I got to finish a whole book, start to finish, and got plenty of quality time with my handsome hubs talking about life, how far we’ve come, and new dreams and goals we have with each other. We only really wished our crazy little wombat General Gazpacho was there 😉

The details

We stayed at this gorgeous San Jose del Cabo resort. All of this is completely unsponsored, I just loved our experience and many of you were asking for details so we wanted to share! It was a trip we saved up for and splurged on and we were so happy with the service, the amenities, and the room. I would hands down would go back a million times over.

At the end of the post I’m sharing links to what I wore and packed (and similar options for vintage or locally found in Cabo pieces). Quick tip: I mix and matched ASOS swim bottoms with that Marysia swim top to stay on budget and the textures worked perfectly together! 😉

I wore the below swimsuit everyday and loved it! The large brim hat is vintage and I am selling that exact one out of my closet over on my Poshmark page if you’re interested!


Alright guys, that’s everything! Let me know if you had any questions that I didn’t get to, or if you’ve been before and have suggestions for people that I didn’t list!


This post is not sponsored but does contain affiliate links. When you shop these links I may make a small commission on a sale at no additional cost to you. Thank you for supporting the time and love that goes into these Millay posts by shopping our links! As always, all opinions are my own.

Join the conversation and share your thoughts!

  1. Jane says:

    Love love love this so much ! We are all now drooling and dreaming !!! Much much deserved . Xxoo

    • Mary says:

      Aw Jane, thank you so much! We feel so lucky that we got to spoil ourselves a bit…turns out I will float around in a heated pool all day, every day if you let me 😉 Missing you!

  2. Looks lovely. Glad you guys enjoyed your time away.

    • Mary says:

      Thanks so much Carolyn, it was gorgeous! We were lucky that we had amazing, clear and sunny weather the whole time too! One day of cooler, overcast weather, but still relaxing. Still pinching myself that we got to experience this trip 🙂 xoxo

  3. I am dying over these beautiful editorial-like photos! I love this recap and really want to make a trip to Cabo now…for the R&R as well. Also, let me fix one sentence in your post….”We only really wished our crazy little wombat General Gazpacho AND BESTIE/SISTER JESS were there”

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