If you haven’t noticed yet, there’s a theme to where we’ve been staying in Puerto Rico, geographically that is. Our last stay was in the mountains at a former coffee plantation so if you’re guessing we stay close to the beach next, you’re right. 

The drive down the mountain was much more enjoyable than going up. With the rest of our drive being on flat highways, it was pleasurable. I guess not so much for Emily but that’s not because of the road conditions. She started to feel a little under the weather the night before our departure, but luckily a quick stop at the pharmacy helped her feel better. Knowing she would soon have her feet in the warm white sand, ocean breeze through her hair, and warm Caribbean Sea wrapped around her body helped her mentally.

As we pulled through the gates at Villa Montana we were both excited to spend a few days sprawled out on the beach. After checking in at the front office, it was time to settle in our room. We followed the directions provided by the staff, our personal villa awaited.


This was another establishment that told us they had wheelchair accessible rooms but I’d have to get up three steps to get into the room. Confusing, I know. 

So, you can imagine our delight at finding out the room was exquisite and wheelchair accessible! Not even one step. Not sure why they originally mentioned steps, but it was wheelchair accessible so no complaints here. Our room came with a kitchen, washer and dryer and air conditioning.


Long trips like we’re doing make us grateful for easy laundry! Our room at the coffee plantation was nice, but very basic. Air didn’t circulate so it was kind of muggy in the room. Our villa on the other hand, could freeze a steak. Speaking of steak, Emily and I were planning on taking a trip to the grocery store so we could use our fancy kitchen but... Our plans quickly changed when Emily suddenly received fantastic news. 

If you didn’t already know, this vacation was planned around Emily’s exit from her role at PlanGrid. She had just resigned and wanted to take some time to decompress and mentally prepare before she started her new role at Castlight. Shortly after arriving at Villa Montana she learned the company she just left was acquired for almost a billion dollars. The news was extremely exciting, so we skipped the grocery trip and hit the hotel restaurant and bar to celebrate. 


Emily worked her tail off for over 4 years. Working for a start up is laborious but rewarding. It can be positive in many ways. She had the opportunity to build an amazing team and she clearly did. They kick ass and will continue to perform well because of the foundation that was created for them by Emily and her other leaders. These people mean the world to her and it was tough leaving them. In addition, she became a female leader in construction tech which isn’t an easy task. Construction has been dominated by men for years. Barriers have been broken. Start ups often offer shares instead of cold hard cash during the beginning of their existence. Employees do well when the company goes public or when it’s sold. For Emily, well, she will be reaping her reward soon. I’m amazed by her attitude. She’s humble. She’s one of the people, not overzealous or braggadocios. 

The following day we went to Harina Bakery for breakfast. Owned and operated by a local gentleman. The food was delicious and the service was superb.  


After breakfast we went grocery shopping at Econo 5.

econo 5.jpg
econo 5 store.jpg

It’s always great to prepare your own food. Not only does it save money it makes me feel like I’m home. We’ve been away from home for awhile now and are moving often. I can’t help but feel a little lost from time to time. Cooking helps me feel a little settled and eases my soul. 

When we got back from the store we packed our beach bag and made the short walk to the beach. Getting on this beach was simple. Getting off the beach... it was a site to see. I had to crawl up a steep embankment while Emily held my legs. We stayed on the beach for most of the day.


The beach had super comfortable love seats placed perfectly under palm trees.


I sat and watched the waves for hours. I felt peace in its purest form. 


When we got back to our room I put my chef hat on and started prepping dinner. A small stove top and limited cooking utensils didn’t stop me. I was able to whip up chicken breast, fresh squash ravioli, stir fry and fresh salad. Don’t worry, it wasn’t a Romaine salad. 


We went to the beach early the next day. We enjoyed soaking up the Caribbean sun rays all day. Emily has some great melanin and her breathtaking tan is the proof. I’m dating a babe!


What about my tan you’re probably asking? Well, I don’t really tan. No matter if I dunk myself in a sunblock tank, I always turn red. I mean fire engine red that is. A few days later I do what comes naturally. I shed like a reptile and a new transparent Matt arises. 

After the beach we showered and went to the hotel restaurant for Thanksgiving dinner. Speaking of thanksgiving, do you know why the first thanksgiving was celebrated? It’s pretty gruesome but I think every American should learn about it. I’m sure the details are still up for debate but you can’t hide the fact that this happened. Lincoln turned a new page in the book of thanksgiving. He made it about family and love which is much better than celebrating...well you’ll know if you click here.

I’m thankful to be alive. I’ve seen “life’s” opposite...there’s nothing there, so everyday that I’m still here I feel lucky. My family has a thanksgiving tradition which is probably similar to most families thanksgiving traditions. During dinner we get to tell each other what we’re thankful for. Most people keep it short but I like to be different. I usually write a speech. Some love it and some hate it but what everyones has in common is that they have to listen to it. Emily and I kept the tradition alive by shared with each other what we are thankful for. 

With age, holidays sure have changed a lot. Families grow, move, and start new traditions. This was my second thanksgiving away from family. I love and miss them but I’ve spread my wings. I’m gliding high through life and couldn’t be happier. I’ve always wondered why we need holidays to remind us of loving our families. We should love them unconditionally everyday. 

We left our beach front villa the day after thanksgiving. Exactly a week before we board a plane back to California. We stay in the capital, San Juan, for our last week in Puerto Rico. Our last week is filled with exciting activities. nightlife, adaptive recreation, hiking and more beaches. 

But until then, follow us here

Matt Facebook & Instagram

Emily Facebook & Instagram