“Stay Classy, San Diego”: Trip to SoCal for Delicious Food, Breweries & Half Marathon

“Stay Classy, San Diego”: Trip to SoCal for Delicious Food, Breweries & Half Marathon

“Veronica Corningstone: For the entire Channel 4 news team, I’m Veronica Corningstone.
Ron Burgundy: And I’m Ron Burgundy. Go f**k yourself, San Diego.”

– Will Ferrell (Ron) & Christina Applegate (Veronica) from Anchorman: The Legend of Ron Burgundy

When thinking of cities in the United States, few places have impressed me more than San Diego, California. The beer, food, and entertainment make it one of my favorite cities. I wrote about my time there before, but that post took a cursory look at my experience. Therefore, today, I am heading back to 2017 and my trip to San Diego. In so doing, I will survey what I did, all in support of a Rock ‘n’ Roll Half Marathon, but this time I wasn’t running with my brother Jeff, nor was I running alone. While my wife Corinne did not, nor would she ever, participate in the 13.1 miles of scenic fun, her sister, Kaitlyn, did. The three of us took a nearly week-long trip to SoCal, and the rest is history.

Bonding Over Movies with Hilarious A$$h•les

“Dale Doback: Why do you have Randy Jackson’s autograph on a martial arts weapon?
Brennan Huff: ‘Cause I bumped into him and all I had on me was this samurai sword. And you’re not gonna not get Randy Jackson’s autograph, right?
Dale Doback: I would’ve done the exact same thing.”

– Will Ferrell (Brennan) & John C. Reilly (Dale) from Step Brothers

My sister-in-law Kaitlyn is awesome. I remember the first time we met nearly two decades ago. She was newly out of high school and preparing for college in New York. She worked hard, graduated with a communications degree, and, after professional highs and lows, got a job working for a major radio station and professional sports team. Of course, for me, this meant free tickets to sporting events and frequent trips to NYC to see her. Recently, she got married and, more recently, gave birth to a beautiful baby girl. Kaitlyn’s grown up in the years I have known her, but she will always be, no matter what, my movie buddy when it comes to quoting scenes from filmmaker Adam McKay’s comedies, like Step Brothers, The Other Guys, and Anchorman.

She has an adult job and an adorable daughter, but Kaitlyn still loves a foul mouth comedy. On the other hand, Corinne is not a fan of Adam McKay comedies like Step Brothers. Instead, she enjoys his uniquely styled films The Big Short and Don’t Look Up. Sure, I like those too, but his earlier cinematic work is profoundly hilarious. I love to quote those earlier films way, and while my wife might not roll her eyes externally, she does voice her wish to pivot topics and discuss Food Networks The Kitchen or Wentworth on Netflix! I am nearing 40 years old, and as Corinne says after I drop perfect movie lines, “You have a Ph.D.,” but I love making people laugh. Sure, I can be profound and, yes, an adult, but I love making those around me laugh.

Kaitlyn is super fun and this is nice when you have few friends as I do. Even so, she lives far away, so when Corinne and I get to see her, at least before the pandemic, we jam a lot into a short amount of time. Whether it’s Halloween in Salem, a brew tour in Boston, ax throwing in Brooklyn, or a speakeasy on the lower east side of Manhattan, we have fun when we get together, and yes, I constantly make Kaitlyn laugh, as I would my little sister. That is why, over the years, movie quotes or scene recall has become “our” thing. If something is said or met with a subtle reminder, one of us will break into character, and laughter will ensue. More often than not, we reference Step Brothers.

The night before Kaitlyn got married, Corinne and I spent time with her at my in-law’s home in New York. While sitting at the kitchen table, we enjoyed a moment of rare silence. We had pizza, New York pizza, so we were in a food coma. Anyway, while sitting at the table, I played a scene from Step Brothers on my phone. When John C. Reilly, Dale, sings and uses some rather crude lyrics. The scene is just shy of three minutes, and when I hit play, not five seconds later, Kaitlyn broke out into song and, verbatim, sang with the clip performing a perfect mic drop performance. Immediately after, we endlessly quoted other scenes before Corinne put an end to our comedy “routine.” Moments like this are why Corinne refuses to let me sit near Kaitlyn at functions.

The first time I watched Step Brothers, Kaitlyn visited Corinne and me in Salem. She suggested it and acted dumbfounded when discovering I overlooked watching it. We sat in the living room, rented the film, and quickly hit play. Holy shit, the film was hilarious and all over the place, in a good way. As someone who loved Wedding Crashers, Anchorman, Old School, and 40-Year-Old Virgin, the fact that I refrained from watching Step Brothers for so long was odd and somewhat distressing. I immediately thanked Kaitlyn! It was, therefore, no surprise when I asked Kaitlyn to join me to run in San Diego; she responded, “I don’t know how to put this, but I am kind of a big deal.” Suffice to say; she was on board.

Background of Trip

“Hello? Who’s there, I’m talkin’? Hello? Who is this? Baxter… is that you? Baxter! Bark twice if you’re in Milwaukee… Is this Wilt Chamberlain? Have the courage to say something! Hello?”

– Will Ferrell (Ron) from Anchorman: The Legend of Ron Burgundy

What did I know about San Diego before choosing it as a trip destination? Sadly, very little. What I learned about the city was picked up from Anchorman, and my mistaken assumption Saved by the Bell was set there. I knew it was beautiful with incredible restaurants, breweries, beaches, and an exciting atmosphere. It wasn’t until I noticed a Rock ‘n’ Roll Running Series event being held in San Diego that I contemplated a trip to the west coast. I have discussed several half marathons I have run organized by the Rock ‘n’ Roll Running Series. Races in Brooklyn, Denver, Nashville, DC, and New Orleans have proved fantastic experiences and fabulous vacation destinations. When Kaitlyn expressed interest in a half marathon, I knew the Rock ‘n’ Roll San Diego event, held in early June, was a perfect choice.

San Diego immediately makes me think of Anchorman, so once I texted Kaitlyn, and after going back and forth quoting the film, we discussed whether this trip was possible. I should note this was not purely out of the blue. On more than one occasion, Kaitlyn expressed interest in running a half marathon. Her love of San Diego and the fact she had a friend living there was, honestly, a slight surprise. As soon as I asked her, Kaitlyn responded with an unequivocal “YES.” Unsurprisingly, Kaitlyn was nervous about running 13.1 miles and wondered whether she could “actually” do it. After convincing her she could, she signed up, and I did the same. I had already chatted with Corinne to gauge her interest, but this trip included her baby sister, so she was supportive of a trip to SoCal.

With five months to train, I knew I would get the miles in and trusted Kaitlyn would try her best, which she did and more. With a running plan in place and a promise to Kaitlyn, I would start the race with her; no matter her pace, Corinne and I began booking flights, accommodations, and “entertainment,” meaning everything other than race-related activities. We ended up booking a perfect flight with Sun Country Airlines, departing from Boston, with a layover in Minneapolis, and direct from there to San Diego. I despise flights with stops; just read My No Good, Horrible, Very Bad Travel Adventure for clarity. No matter, the flight was inexpensive.

Corinne and I decided against Airbnb. We weren’t opposed to it, but we wanted to stay in the Gaslamp Quarter, adjacent to the San Diego Convention Center, Coronado, and Petco Park, amongst other significant attractions we planned to visit. With most Airbnb’s in the area a little out of our price range and lacking a pool, Corinne and I decided on Hotel Indigo San Diego-Gaslamp Quarter, an IHG Hotel, an incredible hotel. With our flights booked, hotel reserved, and race training in progress, we read over a few tourist guides to gain insight into eateries, breweries, and forms of fun. Doing so allowed Corinne and me to get a good feel of the area around our hotel.

Kaitlyn’s friend, Stephanie, lived in Pacific Beach, and she offered to drive us around, or we could use Uber, which was inexpensive in San Diego. Therefore, we refrained from renting a car which was, spoiler alert, wise. As the weeks went by, our excitement only intensified. I think all three of us were ready to let loose and escape our everyday lives, even for five days. Sure, I would run a half marathon, but between 2015 and 2016, I ran eight half marathons. My body had begun telling me to slow down, but I prepared for the San Diego course, and I wasn’t trying to “PR.” Instead, I wanted to help Kaitlyn accomplish her goal, running 13.1 miles, which she harbored doubts she could do. I felt the same when I ran my first race in Walt Disney World, but I knew she could do it.

Welcome to San Diego

“Terry Hoitz: Your farts aren’t manly.
Allen Gamble: Are you serious?
Terry Hoitz: They sound like a baby blowing out birthday candles.”

– Will Ferrell (Allen) & Mark Wahlberg (Terry) from The Other Guys

We arrived in San Diego on a cloudy but warm June afternoon. Kaitlyn met us after we arrived; her flight from NYC landed an hour before Corinne and me. After collecting our bags, we headed to the Uber pickup, located outside the main terminal and in a well-signed area. We quickly picked up an Uber and headed downtown. Our hotel, situated in the Gaslamp Quarter, one block north of Petco Park, home of the San Diego Padres, was about fourteen minutes from the airport, or roughly four miles. Our driver was pleasant and shared insights into what we should see and experience. With five days to enjoy the city, we appreciated our driver’s advice and took his suggestions to heart.

We were not disappointed when we arrived at our hotel, Hotel Indigo San Diego-Gaslamp Quarter, an IHG Hotel. Located on Ninth Ave, the hotel has a beautiful contemporary flair and is close to everything, including a brewery across the street. Corinne checked us in, and we made our way to our 7th-floor room. The three of us shared a room, which helped keep the cost down and included two queen-size beds, plenty of space, and a well-designed bathroom. Honestly, we wouldn’t spend a tremendous amount of time in the hotel, so this worked. The hotel has a splendid rooftop bar serving cocktails and spectacular views, including Petco Park, a vantage point allowing visitors to see gameplay. One problem, the hotel didn’t have a pool. Wait, what?

Yes, you read that correctly. Our hotel, which we selected for pool access, did not have a pool. We chose it because of its location. So, what did we do? Well, the hotel had an agreement with another hotel, roughly two blocks away, that allowed guests of our hotel to use their pool. Our decision might be strange, but it worked out fine. That hotel had a 4th-floor rooftop pool that was stellar and offered excellent accommodations, like a cabana, drink service, and hot tubs. We didn’t care one iota that our hotel lacked a pool. The other hotel’s pool was incredible. After checking in, inspecting our rooms, and exploring the hotel, we left downtown. I learned something imperative that night; the food and brews in San Diego are freaking amazing!

Highlights: Eateries, Breweries & Baseball

“I’d like to be pimps from Oakland or cowboys from Arizona but it’s not Halloween. Grow up Peter Pan, Count Chocula.”

– Owen Wilson (John) from Wedding Crashers

I can’t keep this post manageable if I provide a daily breakdown. Instead, I will cut to the chase and explore where we ate, which breweries we visited, and what fun we had in San Diego in the days before the Rock ‘n’ Roll Series Half Marathon. San Diego is a foodie city with tons of options, and most, if not all, of these options, are fantastic. We had terrific tacos, brilliant burgers, and mouth-watering southern California fried chicken. We washed those types of dishes down with incredible craft beers at numerous breweries, of which we visited a handful. Sadly, there was, nor will there ever be, enough time to see them all, but those we visited were fantastic. We ate well, drank a lot, and did what we could, including watching a baseball game where we ate and drank more!


The food; oh my god, the food. Kaitlyn, Corinne, and I left San Diego far happier than when we arrived. We were satisfied, and the food options helped make our trip a thrilling experience. For the first couple of days, we tried a few incredible places. On our first night, we met up with Kaitlyn’s friend Stephanie and visited one of the largest San Diego breweries, Stone Brewing. After several drinks, we ate at Slaters 50/50 at Liberty Station, a fantastic area with many shops, restaurants, markets, and more. Slaters 50/50, “founded in 2009,” is an inspired burger eatery with unique dishes and a wonderfully Californian vibe that radiates throughout the restaurant. We all had burgers, fries, and even an “amped-up” milkshake.” Eating in San Diego began perfectly!

While our hotel offered breakfast, Corinne, Kaitlyn, and I were interested in visiting local restaurants. On more than one occasion, we went to Copa Vida. I love breakfast while on vacation. Suppose you read about my trips to The Big Easy or Nashville. In that case, you understand how important starting the day with a delicious breakfast and coffee is, especially on trips centered around a half marathon. I mean, Corinne doesn’t run, but she does drink coffee, so she often researches her options, and Copa Vida, only one block from our hotel and adjacent to Petco Park, was on her “go-to” list. Copa Vida is a beautiful cafe, offering roasted and brewed coffee options and unique breakfast dishes. I tried avocado and almond butter toast, with Corinne ordering smoked salmon and soft scramble toast.

Copa Vida was not the only place we visited more than once. We frequently visited Oscars Mexican Seafood, located on J St, close to Copa Vida and our hotel. This location is no longer open, but it was a gem. Vibrant, spacious, and the food, well, the tacos were the best. I tried the grilled shrimp, octopus, and smoked fish, which were fantastic. Oscars was a great find and offered quick counter service, a trend for most eateries. Order at the counter, sit down, and staff brings the food to you. Rarely did we have a waiter/waitress, so I imagine this is more of a California thing. Although that type of service is in Massachusetts, it’s more sporadic. The vibe of the establishment shined brightly that day.

Another eatery we tried for breakfast was during our trip to the beautiful peninsula of Coronado. We took an Uber there to check out the famous Hotel del Coronado. The weather was grey and cloudy, but we made the best of it and ate at Parakeet Cafe, which served excellent coffee and decent food options. I tried the salmon toast, and it was good. We spent time in Coronado strolling around after breakfast, even visiting MooTime Creamery for ice cream, but we left with a story and a cold treat. The ice cream was expensive, and I remember Kaitlyn ordering chocolate sprinkles and the “extra” cost nearly made her drop her cone. We soaked in the atmosphere as we walked to Centennial Park and then boarded a ferry to the Convention Center, where we went to the Rock ‘n’ Roll Expo.

Sure, we ate sushi and more tacos at a few other places, but the last two restaurants of note were Fairweather Rooftop Bar and The Crack Shack. We visited these eateries shortly after running 13.1 miles, as you will learn. We enjoyed lunch after the race at Fairweather Rooftop Bar, and there was no one there. We felt as if we had the entire outside bar area to ourselves, and it was outstanding. The rooftop bar is on the second floor and offers terrific views of Gallagher Square and Park at the Park, both of which are beyond the center field of Petco Park. It just so happened that there was an ice cream eating contest in the square, which doesn’t scream “yum,” but was entertaining.

To go back for one second, upon entering the eatery from the ground floor, the hostess directed us to the elevator to the rooftop bar. Corinne and I went to the elevator, and Kaitlyn asked to meet us at our table. When the elevator doors opened, Corinne and I jumped with fright and nearly ran away. There, in the corner, was a massive plastic deer, which one does not expect to see in this particular situation. Once we composed ourselves, we headed up to our seats and the first thing Kaitlyn said when she sat down a few minutes later was, “did either of you jump when elevator doors opened, and the deer sculpture appeared?” We had a good laugh and then enjoyed a delicious meal. I liked the burger and fries along with a craft beer. The price was great, the food was good, but the energy was incredible, but one restaurant was superior.

The Crack Shack is impressive. Located in Little Italy, The Crack Shack is an eatery serving up delicious southern fried chicken and incredible sides. We visited the restaurant for dinner the night after our race, so we were hungry, although we had superb lunch and had several beers at Ballast Point Brewing, a short drive away. We were not starving, but we were hungry, and the fried chicken was divine. The restaurant’s setup is communal, with large tables outside under lite up pergolas. We ordered at a window and sat near a fire pit. Celebrating the race with Corinne, Kaitlyn and Stephanie, was lovely, and The Crack Shack’s charm made a lasting impression. The building design, decor, and nearby street atmosphere enhanced the excitement of this stunning eatery.


The beer; oh my god, the beer. While we enjoyed some San Diego craft beer everywhere we went, like the Padres game, we enjoyed several visits to breweries, ones I selected based on popularity and location to our hotel. While I wasn’t a fan of the brewery closest to our lodging, Half Door Brewing Co., I was more impressed by three other breweries. It wasn’t that Half Door Brewing Co. was bad; it wasn’t. I wasn’t impressed by the beer, which seemed heavy on the IPA, not my favorite, and the wheat beer I did try, I didn’t finish. The esthetic of the place was interesting, and we had a seat overlooking the road, which allowed us to people watch and observe the activity at Petco Park, but otherwise, it was subpar. No matter, we still drank plenty, and the following three breweries were terrific for several reasons.

Stone Brewing World Bistro & Gardens at Liberty Station was impressive. Craft beers at Stone Brewing are national, and I might even say, internationally recognized. I observed their beers on tap in Shanghai at DAGA Brewing. The brewery’s design was impressive. The inside resembled an Italian Villa or French Chateau. Very spacious, beautifully decorated, and classy. But we drank our beer in the garden, which might be the best beer garden I have visited. Sure, the beer garden at Threes Brewery in Brooklyn was beautiful, but Stone was in a tier of its own. As we snapped photos, Kaitlyn, Corinne, and I sampled wheat, blonde, and, sure, an IPA or two. We had a glorious night and the fact that we were together, what else could we want.

Mission Brewery was the next brewery on our list, which offered a different feel but included no beer garden. Mission’s taproom was in a vast and spacious 1894 industrial building, located about one block east of Petco Park. I discovered Mission while researching San Diego breweries, and its location to Petco Park made it appealing. We had tickets to a game, so the three of us walked from our hotel and got a drink before going to the game. So, in other words, a place to “pregame!” Overall, I enjoyed the brewery, and we were able to taste different beers. Kaitlyn savored the Pilsner, Corinne ordered a stout, and I tried a blonde ale. Delicious flavors and the brewery had a large bar with an excellent logo/sign, offering us a fun hour of chatting and savoring another San Diego flavor.

Although we visited one more brewery, I did try a couple of local craft beers at Petco Park. Thanks to being registered for the half marathon, the Padres played the Colorado Rockies, and we snagged discounted tickets in advance. The stadium is incredible and probably my all-time favorite ballpark, thanks to its design, quality, and the fact there wasn’t a bad seat anywhere. We moved around, watching from varying vantage points, doing so as we ate and drank our way around the stadium. Corinne and Kaitlyn are stadium snack “monsters,” and I was pleased by the beer stands selling local beers for, weirdly enough, fair prices. Kaitlyn and Corinne, at one point, reminisced about the time I freaked out when I couldn’t find a pretzel at a Yankees game. It turned out fine; my mother-in-law Mary found one; the problem averted.

The last brewery we went to was the one I was most excited to visit. Ballast Point, in Little Italy, was marvelous. We descended on it, using an Uber before eating at Crack Shack, but we consumed and drank as airplanes flew over our heads and we sat in a cabana-style area in the beer garden. We spent a few hours at Ballast Point, and I tried several of their staples, making several family members back home jealous. Ballast Point was genuinely excellent, and the beer, even the Sculpin IPA, not my typical go-to, was fantastic. Kaitlyn’s friend Stephanie joined us, and we had a great time, sampling beers, eating appetizers, and, for me, selecting the Wahoo Wheat and California Kölsch, two unforgettable beers. Upon exiting the brewery, Kaitlyn surprised me with a Ballast Point t-shirt, a wonderful gift, and a reminder of this experience.

San Diego Half Marathon

“We’re here to f**k shit up!”

– John C. Reilly (Dale) from Step Brothers

I have written several posts on my half marathon travel. It should come as no surprise I enjoyed this race tremendously. What made it better was running with Kaitlyn. She was nervous, but let’s discuss the expo before getting into that. Like all Rock ‘n’ Roll expos, the San Diego event was massive, housed at the Convention Center, the same event space that holds San Diego Comic-Con. We arrived at around mid-day and shortly after our morning in Coronado. Picking up our bibs was simple, and there were tons of vendors – all of whom occupied two halls of the Convention Center. We took photos, bought supplies, and I think Kaitlyn felt positive. She trained hard, put in the miles, and in the days before our trip, experienced slight self-doubt but was ready.

The following day, race day, Kaitlyn, Corinne, and I took a charter bus, organized by the race, departed the Gaslamp Quarter, and headed to the starting line. The bus dropped us off at Balboa Park, where hundreds of runners had arrived. The energy was electric, and Corinne stayed with us for an hour before leaving to get coffee and return to the hotel. She promised to meet us at the finish line, a mile from the hotel, but she had time. I usually seek out races where it begins/ends closer, but staying in the Gaslamp was far too important. San Diego required a little more pre and post-race navigation. We walked around Balboa Park before getting into our corral. Corinne took some photos as we waited and then headed off, but not before offering Kaitlyn some parting words of advice; to have fun.

When the horn went off, Kaitlyn and I were in the front of our corral, so we took off. We ran through Balboa Park, alongside the world-famous San Diego Zoo and beautiful neighborhoods like University Heights and Normal Heights. The scenery was spectacular. There was never a dull moment, and thousands of spectators cheered us on, offering shots of alcohol and mixed drinks along the way. I have run over a dozen half-marathons, but there is a reason I consider this my number two favorite race. It had everything, and the weather was terrific. As planned, I stayed with Kaitlyn for the first three miles, ensuring she maintained a slow and steady pace. I explained that if she needed to stop and walk, do it, and if she felt good, keep running. In the end, I confidently told her she would finish!

Those three miles are probably the most emotionally satisfying stretch of road I have ever run when all is said and done. Being able to run alongside my sister-in-law, enjoying the insanity, was a great memory. I wanted her to have her half marathon experience and conquer this goal without hovering. At the 5k marker, and noticing she didn’t need me and her pace excellent, Kaitlyn told me to go on ahead. The rest of the race was smooth, and my strategy well-planned. I completed the race in a near PR performance. When I finished the run, it was a madhouse. Even so, I grabbed snacks, water, and my fantastic finisher’s medal. I quickly located Corinne and, together, watched Kaitlyn finish the race strong! We took some photos and celebrated our accomplishments upon meeting up at the post-race party at Waterfront Park.

Bags are Packed, Not Ready to Go

“John Beckwith: You better lock it up.
Jeremy Grey: No, you lock it up!
John Beckwith: You lock it up!
Jeremy Grey: You lock it up!
John Beckwith: You lock it up!
Jeremy Grey: Lock it up!”

– Own Wilson (John) & Vince Vaughn (Jeremy) from Wedding Crashers

We left San Diego the day after the race, but it was an incredible trip from start to finish. The three of us talk about this trip often, and typically, no matter what we are doing, we suggest a return trip to the city. I am grateful for those San Diego memories of the three of us laughing over the cost of chocolate sprinkles, taking glamour photos of two sisters walking towards the water in Coronado, drinking too much craft beer, eating not nearly enough fried chicken, and dancing on the Padres Jumbotron. We made that 2017 trip right, and it acts as travel inspiration and illustrates how awesome it is to travel with family, and being there as a loved one accomplishes a personal goal. Kaitlyn may never want to run that distance again, but she doesn’t have to; she did it!

6 thoughts on ““Stay Classy, San Diego”: Trip to SoCal for Delicious Food, Breweries & Half Marathon

  1. First of all – Running next to San Diego Zoo and through University Heights sounds incredible!! I love so much that you did this race with your SIL and it’s so wonderful to hear how you two are clearly friends.

    Secondly – The is nothing short of a delight and now I’m dying to go back to San Diego to get it again. 😅

    Loved reading this!
    – Alli | On the Trip Side

    Liked by 1 person

    1. Hello Alli! Oh my, thank you so much for your lovely comment. I appreciate it, and it means a lot. Yes, you need to get back to San Diego! I plan on getting back soon, but I need to get to the Seattle area first! I registered for the Rock ‘n’ Roll Series race, and my wife noted many of the coffee shops you recommend on your blog, but the race has changed. Hopefully, I will see the Pacific Northwest soon. Thanks again for reading and the excellent comment!


  2. San Diego is one of my favorite places in the world! I spent three weeks there when I went and loved every minute of it. It’s such a beautiful area of the country with absolutely perfect weather. If only it wasn’t so expensive I would retire there.

    Liked by 1 person

    1. Hi Donna! Thank you so much for your comment. I can’t agree more. San Diego has so much to offer, and as someone from New England, the weather is a dream. I would love to retire to a part of the country where the weather doesn’t ruin my running schedule! Thank you for reading my post.

      Liked by 1 person

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