A Work Trip Turned Into Something More
Recently, Micheal and I had the opportunity to visit San Diego around a work trade show I was attending. One of the biggest perks of my role is being able to turn work travel into something more—covering my flight and extending the trip by bringing Micheal along and adding a few extra days together. We wanted to share our San Diego travel itinerary for others who may find themselves with a few days to spare in this beautiful city.
This trip felt especially meaningful.
Micheal completed his Navy boot camp in San Diego years ago and had only been back once or twice since. He wanted to revisit the place where that chapter of his life began—and I was excited to experience that part of his story with him.
So we spent a full week in San Diego, blending work, exploration, and a little bit of everything in between.
🍸 Downtown San Diego & First Impressions
We kicked things off downtown near the convention center, where I was staying for work at the Manchester Grand Hyatt.
Our first night was simple and perfect:
- Cocktails by the water at Sally’s
- Dinner at Puesto (one of my go-to spots for incredible tacos and appetizers)
- A sunset view over the bay that reminded us instantly why people love this city
It was the kind of evening that sets the tone for a trip—easy, beautiful, and full of anticipation.
⚓ A Walk Through Micheal’s Past at Liberty Station
The next morning, we went to what used to be the RTC, Recruit Training Command—where Micheal went through boot camp. This is unique to our personal San Diego travel itinerary, but it was a great experience and I highly suggest checking it out if you’re in the area.
Today, it’s known as Liberty Station.
What once was a highly structured military environment is now filled with:
- restaurants
- shops
- walking paths
- families and dogs enjoying the sunshine
But for Micheal, it was something entirely different.
He pointed out:
- where he used to stand in line for the chow hall
- where the barracks once were
- the areas where he trained.
It was surreal—watching someone walk through the same physical space while seeing something completely different than what exists today.
🌊 La Jolla, Coastal Drives & Our Ongoing Debate
From there, we made our way to La Jolla and up the coast.
We explored:
- UC San Diego’s campus
- a cozy Italian spot where we split pasta and pizza
- the coastline, stopping wherever we could to walk and take it in
Eventually, we found our way down to the water where people were gathered around tide pools and seals.
And this is where our personalities really show up.
I’m fascinated by sea life—but also can’t help thinking, “What would this taste like?”
Micheal, on the other hand, is completely captivated by the beauty of these animals and sees them as something to admire, not eat.
So while he’s in awe, I’m over here mentally building a menu… and he’s looking at me like I’m the villain in a Disney movie.
🍽️ Food Highlights (Because Let’s Be Honest… This Matters)
San Diego absolutely delivered on food.
A few standouts:
- Dinner at Water Grill (seafood, of course)
- A bucket list visit to Nobu where I finally tried sea urchin and their famous miso cod
- More oysters, cocktails, and “we should probably stop ordering” moments than I can count
Micheal kept it balanced with things like fish and chips… while I leaned fully into the experience.
🛶 Slowing Down at Kona Kai Resort
After my work portion wrapped up, we shifted into full vacation mode at Kona Kai Resort on Shelter Island.
This was our reset.
- We kayaked around the marina (I wanted to go further out… Micheal vetoed due to sharks)
- Relaxed by the adults-only pool
- Ordered food and drinks straight to our lounge chairs (highly recommend)
It was the perfect contrast to the busier start of the trip.
🍝 One of the Most Memorable Dinners
One of the most unique moments of the trip was dinner at Solare in Liberty Station.
For me:
- a Michelin-recommended restaurant
- incredible spiny lobster pasta
- a full, indulgent dining experience
For Micheal:
- sitting in the exact place where he once went through boot camp
That contrast made the whole experience unforgettable.
🌺 Our Final Night & A Perfect Ending
We wrapped up the trip at Bali Hai on Shelter Island.
- Happy hour drinks
- A sampler platter (plus an extra order of ribs for Micheal)
- More oysters for me
After dinner, we walked along the water and sat watching the bay.
And then—one of those moments you don’t plan for—
A group of dolphins swam alongside a ship coming into the harbor.
🌿 Final Thoughts
San Diego gave us a little bit of everything and thanks for checking out our San Diego travel itinerary. We were able to explore:
- history
- perspective
- incredible food
- time to slow down
But more than anything, it gave us the chance to experience a place that meant something deeply personal to Micheal—and to create new memories in that same space.
That’s the kind of travel we’re always chasing.