San Diego Adventures: Family, Fun & A Wedding on the Bay

I just returned from a whirlwind trip to San Diego, California, with my brother, Chad. If you’ve never been, let me tell you—San Diego is one of the best places in the U.S. for its weather alone. The climate is nearly perfect year-round, making it a dream destination for weddings, vacations, or just a quick getaway.

This time, our trip wasn’t just for fun; we were there to celebrate love! Our cousin was getting married to a Marine helicopter pilot she had fallen madly for, and they had planned the most stunning rooftop wedding on Harbor Island, just next to our hotel—the Sheraton Bay Tower & Marina, conveniently located just minutes from the airport.

Traveling With a Reality TV Villain (aka My Brother)

For those who don’t know, my brother, Chad, was a reality TV personality—some may even say villain (TV’s words, not mine). He first rose to fame on The Bachelorette, and from there, his TV career took off in various wild directions. Let’s say his time on reality television has made my life… interesting over the years.

But for this trip, it was just Chad and me, siblings on an adventure to celebrate family. We had planned three nights together, which seemed simple enough… until a massive ice storm threw a wrench in our travel plans. More on that later.

Where We Stayed: Sheraton Bay Tower & Marina

The bride recommended that we stay at the Sheraton Bay Tower Hotel & Marina. Situated nicely on Harbor Island with multiple buildings spread along the marina, this hotel had it all, and we couldn’t have been happier with our choice. Some of the wedding party stayed in the Marina Tower, but it was just a short walk or shuttle ride over there if needed. A few things I learned about this hotel:

• The Marina Tower has been recently renovated, but perhaps doesn’t have quite as nice of a view. We chose the Bay Tower for the marina view and larger rooms. 
• The Bay tower was closer to the wedding venue, so we planned to walk from one to the other. 
• The Marina tower has the restaurants/bars that seem to attract the most attention from folks.
• The Bay Tower was much more of a peaceful, quiet experience.
• Request a balcony! The view is superb.
• The Bay Tower Lounge is excellent for a late-night visit & cocktail.
• The quesadillas at the Marina Tower restaurant were delicious, and the venue had a nice, lively vibe to it. 
• In the mornings, there is FREE yoga by the Lanai Tower. It was beautiful. I enjoyed Kelly‘s class. 
• Perfect resort for morning or evening strolls. With a convenient bakery and sandwich shop on the walk, it’s perfect to grab a cup of coffee to enjoy the boat views and California sun.
• There are wonderful chairs, fire pits, and tables that face the marina out for us, and we thought that was awesome. Just needed some more time to enjoy these. Maybe next time.
• Doordash conveniently delivers to the hotel and directly to your room! Score! 
• Bicycles for use on the grounds – your first hour is complimentary for staying at the resort, and after that, it is $10/hour.

The Wedding: A Rooftop Dream with a Hip-Hop Twist

The wedding was situated on a rooftop on Harbour Island, just next to our hotel, the Sheraton Bay Tower Marina in San Diego. It was conveniently located just four minutes from the airport. The venue, Harbor View Loft, was a rooftop that overlooked the marina and made for a dreamy view at sunset. San Diego can be stunning this time of year, and we were in luck.  It was about 70 degrees out, and the theme was beach formal. The bride and guests wore plumeria flowers in their hair, which added a lovely tropical touch to the evening.

The venue not only had a beautiful outdoor rooftop with a scenic view, but it also had a stunning indoor area with floor-to-ceiling windows all around that made the perfect setting for a 75 +/- wedding. There was a DJ included, of course, that the bride & groom had requested only rap/hip hop music…and it turns out that was a fantastic call! We enjoyed a champagne toast on the rooftop, and several cocktails with friends and family while celebrating our new family member, whom we welcome with open arms. Cheers to them both.

Exploring San Diego: Good Food, Good Drinks, and a Cool Brewery

For our first evening in California, our family had arranged a rehearsal dinner at Stone Brewing World Bistro & Gardens at Liberty Station. Be careful, as there are multiple locations! So, know where you are heading. We were booked at Liberty Station, which used to be a former Marine fort turned brewery & restaurant. This was the perfect setting and vibe for my first evening in town. Chad was arriving later in the day so I was solo for my first San Diego adventure. At Stone Brewing, there was an open-air area that the family had reserved for the evening. Very casual, easy, come and go. In the courtyard, there was a bartender available for included beverages, and a bocce ball set up for our use on 2 large playing fields.  Of course, I must mention the delicious food, which included multiple choices of flatbread pizzas, hummus, Ahi tuna, wontons, and more. It may sound weird to suggest this, but I also highly recommend visiting the restroom at this brewery. It is unique! 

My favorite place we dined at, though, was a short trip from our hotel at the end of the marina. We chose to walk, which I also highly recommend. The setting was at a waterfront restaurant called Island Prime. For lunch, we sat on their beautiful patio, enjoying the sunshine and view of the water while we devoured an Ahi tuna and fresh crab tower with fried plantains, as well as mahi-mahi tacos, black beans, and a fresh tuna poke bowl. The crab tower and ahi tuna tower were one of my favorite things, I do believe that have come across my plate. You may hear me say a lot, but that means I loved it! There was also a Mexican restaurant next door that looked perfect for a meal, but we were unable to make it over this visit. 

One evening, the wedding party decided they needed a night out! So we headed to Moonshine Flats for some late-night line dancing and cocktails. I must say it’s been some time since I’ve ventured out with the 20 and 30-year-olds to a dance club, but Chad and I had a blast watching our cousin and her friends learn the dances, laugh, chat, and just really cut loose! 

Since my brother’s goal for the year is to purchase a yacht and relocate to Florida, we thought it would be a fun idea to get on a boat here in Cali! So Chad did some digging and located the Flagship Cruise line to take us on a dinner sunset cruise! The cost came out to be $250 for both of us, plus appetizers and alcoholic beverages. The ship, California Spirit, held about 175 guests who were excited for an evening on the water, touring the stunning harbor. We enjoyed braised short ribs, jumbo prawns, mashed potatoes, and green beans! This ship has multiple decks, with the rooftop being perfect for sightseeing. What we realized after arriving on the cruise was that most guests were couples. So, brother and I made it a point to let people know we were not dating by making comments like “Hey, brother, want to go outside for some fresh air?”

“Yes, sister, let’s go admire the view.”

The day after the wedding, while Chad was resting and consuming massive quantities of Shake Shack that he had donated to the hotel, I decided to explore La Jolla. The wedding guests had all raved about it the night before, so I thought it was the perfect time to get out and explore solo while Chad got his much-needed relaxation time alone. With a quick 30-minute Uber ride, I was able to find a nice drop-off spot that put me close to Richard Walker’s Pancake House. In more recent years, I have begun to crave a nice hot coffee and breakfast whenever I can! Which is ironic since this is what we have always made fun of our father for. He MUST have his breakfast and coffee every morning, most of the time at the same place every day, eating the same meal, otherwise, his day is ruined. Hopefully, I don’t get that obsessed with it, but today seemed like the right fit. After enjoying the patio, people-watching, coffee, and some pancakes with peanut butter, I decided to get on the move and walk around this area. The cute streets and stores led me eventually to La Jolla Cove and Children’s Pool, where I was able to watch the adorable seals and sea lions with their babies frolicking… slowly, of course, in the sand and water. What a treat! You won’t have any trouble finding these areas, fortunately, as there are hordes of people around with their cameras that have the same idea! A must-see for sure.

As I mentioned, my brother was a late joiner to this Cali trip, so we were on different flights. Myself coming in through Dallas, and my Brother is coming in through Phoenix. With arrival and departure times pretty well lined up,  we were having a seamless, relaxing time on our weekend getaway. We used Uber and Lyft to get around and walked when possible. Biking the area is also a must! Convenient and easy are two words I would use for San Diego. That is, until it was time to head home to Oklahoma.

Getting Home: A Wild Ride Through the Ice Storm of 2025

Now, onto the not-so-glamorous part of the trip—getting home.

A massive winter storm was expected to hit Oklahoma and surrounding states predicted to be the worst since 2011. Chad and I were racing the clock to get back before the snow and ice took over.

Long story short:

• Multiple flights got canceled.
• We ended up stuck in Dallas overnight, with a 7.5-hour layover.
• The airline thankfully put us up in a hotel, since my first flight was delayed due to maintenance, causing me to miss my second flight.
• In a weird twist of fate, I ended up on the same flight as Chad to Phoenix (Thanks, Mom! I truly believe she had a hand in keeping us together for this travel mess).
• After striking out with rental cars, we finally found one, thanks to a kind worker at Enterprise who came through for us when every other company left people stranded.
• The drive home? Four hours of pure anxiety. Ice, sleet, snow, and my windshield wipers struggling to keep up.
• Chad saved the day with his navigation skills and some strategic wiper de-icing.
• But we made it home safely around 2:30 PM—just in time to hunker down for an Oklahoma snow day with my fur babies.

Final Thoughts: Another Trip, Another Adventure

This trip had it all—love, laughter, great food, family time, and a travel disaster that (thankfully) ended well.

Would I do it all over again? Absolutely.

Would I rather avoid another snowstorm nightmare? Also absolutely.

But at the end of the day, memories like these are what life’s all about. Cheers to my cousin and her new husband, to another unforgettable adventure with my brother, and to making it home in one piece!

Until next time, San Diego!

❤️ Tiffany