Travel Guide
Vibrant Culture & No Summer Crowds: Unveiling California’s Most Underrated City
Jul
As one of America’s largest states, California is home to some of the country’s biggest icons and, conversely, some tight-lipped secrets.
Whether it be fairytale beach towns, lush state parks, or major cities somehow flying under the radar, there’s no denying California’s appeal for all types of travelers.
As a 10-year “Golden State” resident, there’s one city I’ve always heard described as “boring”, but after a recent trip, I can attest it’s anything but… and may be even more enjoyable than San Francisco.
How could I know that, you might be wondering…
Well, I’ve visited both cities within a span of 3 months. Given their proximity and tinges of similarity, it’s only natural to compare.
So, get ready to slap your grandma in disbelief because I’m crowning none other than San Jose as California’s most underrated city.
With a surprising melting pot of cultures cultivating an insanely impressive food scene, a vibrant downtown that seemed virtually spotless for California standards, more laid-back vibes than you’d expect with its uppity reputation, and home to a historic hotel oozing so much charm and character I swear the walls were talking to me, I was left questioning what myself and others have been missing all this time.
I wish I had the answer because I feel foolish visiting the “The Bay” so many times and not even considering spending a day in San Jose.
I do feel better knowing the city is beginning to receive the attention it deserves. Believe it or not, TimeOut is backing me up by recently naming San Jose as a top 20 city in America.
Without further ado, let’s dive into what makes San Jose special, starting with local legend…
Happy Birthday, Hayes Mansion: 120 Years Looks Great On You!
Hayes Mansion, a Curio Collection by Hilton has quite an impressive resume. Dating back to 1905 (even further if you count the prior Edenvale Estate), the second-coming of what Hayes Mansion is today is a well-preserved time capsule with modern era amenities — lucky for you, you can score $120 in dining credits to celebrate!
The elegant aesthetics alone are why you’ll see so many weddings held here — fun ones too!
I didn’t pack a tux, so I probably missed my chance to pull off an epic Wedding Crashers moment!
That’s okay, though. Even traveling solo, I never had a dull moment with Hayes Mansion as my base to explore San Jose.
My spacious room was outfitted with a heavenly bed, a rainfall shower with perfect water pressure, and a separate living space to sprawl out on the couch and bang out articles for you folks.
Plus, the pool and hot tub were mere steps from my wide (yet shared) backdoor balcony, providing an easy shortcut to the place you can always find me at any luxe hotel.
The waters were sparkling clean, but keep in mind with so many wedding guests, some of the common areas are packed with people who not only lose their inhibitions, but common human decency to pick up after themselves — their fault, not Hayes’.
As such, I never had a chance to enjoy the only fire pit on-site at night, but the pool area stays open until 9 pm, and I had no trouble squeezing in a workout as the spotless, upgraded fitness center is open 24/7.
But…the reason a gym sesh was a priority this trip was not because I was too lazy to do laps in the pool or burn some cardio exploring the captivating maze of timeless hallways — it’s because Hayes’ lone restaurant Palm & Ember was simply too good to over-indulge for both breakfast and dinner.
Palm & Ember
I began each day with a velvety cappuccino and impressive spread of a breakfast buffet each morning from Palm & Ember, unable to overcome my will power to avoid second helping of the usual staples of sausage, bacon, and real scrambled eggs (not the gross pre-made goop you find at cheap chains).
I appreciated the array of fresh juices and smoothies too, and the fact that the buffet was endless.
You can be as healthy or indulgent as you want. Green juice balances out the cholesterol overload, right?
Dinner was even better. As someone who grew up 2 hours from Louisiana’s state line and has frequented New Orleans multiple times, whoever the chef is gets my tip of the cap for their take on Crawfish Etouffee — and the Burrata Meatball was the perfect app to hold me over while they crafted a flawless Cajun classic with their own twist.
It was equally as delicious (if not better) than any meal I’ve had in the Bayou. Not to mention, they sling a mean spicy marg capped off by family-size tiramisu for dessert.
See why I was doing sit-ups at midnight now?
Hotel Tip: To gain a better understanding of Hayes’ fascinating timeline, book a guided tour from Hayes family descendants!
Downtown San Jose: Arrive Hungry, Leave Happy
Before visiting San Jose, I would’ve told you it’s a decent-sized city with an NHL team and snooty Silcon Valley “Karens” acting like they’re better than everyone.
That couldn’t be further from the truth.
I quickly discovered, yes, San Jose does have Silicon Valley one-percenters, but you’d hardly never know it.
The city was so laid-back, welcoming, and friendly, you could be sitting next to a billionaire CEO or the neighborhood poolboy and you wouldn’t know the difference (well, except for Santana Row — more on that in a bit)
I couldn’t have been more impressed with downtown’s San Pedro Square, a lively district with a colorful pedestrian-only promenade lined with the city’s best bars and eats.
Even the Taco Bell has a bar. But, the last thing you’d want to do is waste stomach space with a Crunchwrap Supreme.
Start off perusing the San Pedro Square Market, a local favorite hangout with every type of cuisine you can imagine, but the newest addition will fuel your day.
Playback Coffee is San Jose’s newest coffee shop. Their Honey Matcha Latte was spectacular and exceeded all expectations of being just another matcha concoction piggy-backing off the latest drink trend.
Nope! They pride themselves using only premium ingredients straight from Japan. You can taste the difference. Sorry, Starbucks…
The Pressroom
It’s unlikely you’ll spend all day roaming downtown, but you should definitely come back for dinner at The Pressroom, just around the corner from the unmissable San Pedro Square banner.
Don’t let the glitzy aesthetics trick you into thinking they’re distracting you like a moth to a flame from so-so food— this place knows what they’re doing and that’s why I barely scored a seat.
I’m glad I did because it was undoubtedly the best overall meal in San Jose. I’ll be honest, ya boy is indecisive. Sometimes I like to ask for recommendations and the Pressroom couldn’t have delivered any better from their array of unique cocktails to again, a mouthwatering dessert giving New Orleans a run for its money (do I sense a theme here?).
Here’s exactly what you should order:
- A City Beat signature cocktail
- Ahi Tuna Poke Nachos
- Southeast Steak Salad
- Handmade Lemon Ricotta Agnolotti (I would fly back just to eat this again!)
- Beignets (with a trio of spreads)
And if you’re feeling like you wanna act like a local, tap into your Silicon budget and order a shot of rare 20-year Pappy to wash it all down.
Dr. Funk
Whether it’s Happy Hour or last call, Dr. Funk lives up to the name as a funky tiki bar. It can easily be where your night begins or ends — super fun vibes and waaay better than Tiki Pete down the street.
Better yet, they just released a new cocktail menu that I had the privilege of some sneak peek sips (it’s a hard job, but somebody’s gotta do it!).
Here are my 3 favorite cocktails at Dr. Funk’s and I believe they’ll soon be yours too:
- Espresso Oasis
- Three Dots & A Dash
- Phoenix Rising
A Melting Pot Of Delights: Peeling Back San Jose’s Surprising Culture
Did you know San Jose is home to one of only 3 authentic Japantowns left in the U.S.? It’s true, and it’s a really vibrant neighborhood to explore.
I was only here for a short while but parts really did feel like a slice of Asia. The sushi at Okayama was fantastic — and the $5 beer felt like a steal for a city where the average home price is pushing $2 milli.
There’s also Little Saigon, home to the largest Vietnamese community outside of Vietnam. I couldn’t squeeze it into my jam-packed schedule, but it’s first on the list next time!
With Silicon Valley’s global talent pool, Japantown, Little Saigon, and even a pint-sized Little Italy district, and almost unheard-of Little Portugal, you can’t help but notice how cosmopolitan San Jose really is.
10th Street Distillery: The ‘Wizards Of Whiskey’
While exploring Japantown, I booked a tour at 10th Street Distillery and met who I’m dubbing the “Wizard of Whiskey”, Virag Saksena who’s of Indian descent, living the “American dream” by quite possibly created the most impressive whiskey distillery in the world.
Very few times have I been blown away meeting someone, but Virag is a true mastermind. The man lives and breathes his passion for whiskey production and it’s contagious.
Now, I’m man enough to admit when I’m not qualified for something. It’s in your best interest to book an insightful tour like I experienced where you’ll look they first brew beer specifically for whiskey production and work their magic resulting in what’s been crowned the ‘Best Whiskey in the World‘, so make sure you order the “Dragon” and one of the best Old Fashions ever to grace my lips.
I loved this distillery so much, I bought my girlfriend (a picky Tennessee born-and-raised whiskey aficionado) a bottle of Peated Single Malt for her birthday by using their product map, and needless to say she loved it!
My Top 5 Favorite Places To Visit In San Jose
It’s time to put a bow on San Jose, one of the most pleasant surprises in my recent travels.
These are my top 5 favorite places to visit in San Jose:
- The Pressroom: enjoy elevated California cuisine and unique, newspaper-themed cocktails at this restaurant and bar, honoring its journalistic roots
- San Pedro Square: hosts a buzzing food hall and pedestrian walkway in downtown San Jose that offers a diverse collection of eateries, bars, and live music (including aforementioned Playback Coffee and Dr. Funk)
- Japantown: vibrant, authentic cultural district that proudly preserves Japanese heritage through its unique shops, eateries, and museums — and the behind-the-scenes experience 10th Street Distillery definitely capped off an unforgettable trip.
- Winchester Mystery House: a sprawling mansion known for architectural oddities, inspiring the Helen Mirren film, Winchester
- Santana Row: The “Beverly Hills” of San Jose with trendy bars and a vibrant boulevard of ritzy storefronts
**Travel Off Path was a guest of Hayes Mansion & Visit San Jose, who helped with the creation of this itinerary by hosting some of our accommodations and attractions. Our opinions, recommendations, and suggestions remain our own.**
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