For this blog post I partnered with bestie Brianna, who is a South Bay Native and she’s currently still live there working as a local real estate agent. She is truly an expert on all things San Jose!

When having friends that come visit the Silicon Valley, they typically just think of going to San Francisco but in reality, San Jose is a destination in its own right. In the past few years San Jose has been making a name for itself as a place to visit, I mean it is a major part of Silicon Valley!

I recently had a fun San Jose staycation with my blogger besties, hosted by Signia by Hilton San Jose. We stayed in a lovely luxury suite and our itinerary was jam-packed with local fun. Throughout our stay, we enjoyed lounging by the pool, a shopping spree in Santana Row, late night spa fun with the bubbly flowing, and then brunch in the morning.

I invite you to plan your own San Jose getaway, keep reading to see my top 10 favorite south bay hangout spots and so many Instagram worthy locations!

Weather in San Jose

San Jose, California has a Mediterranean climate, characterized by mild, wet winters and warm, dry summers. The city enjoys plenty of sunshine throughout the year, with an impressive average of 300 sunny days annually. In the summer months, temperatures typically range from the mid-60s °F at night to the mid-80s °F during the day. Which gives you plenty of gorgeous weather to be out and about outdoors.

Top Trendy Places to Eat and Explore in San Jose

Santana Row

I love this place! I have been strolling down this beautiful outdoor high-end mall since High School. It is a great place to meet friends for lunch, get some shopping done, and relax with a cup of coffee.

I would first stop by Cocola Bakery for some coffee and baked goods. Next stop would be H&M and Sephora! The Sephora location here is fairly new and not as crowded as the one across the street at Valley Fair. We also got to attend a cocktail party at Kendra Scott and we made some custom bracelets.

Then I would grab lunch at Mendocino Farms. The inside is bright and well decorated, perfect for that Instagram shot. For drinks, I would recommend El Jardin for margaritas or Vbar located inside Hotel Valencia. For our girls trip, we had dinner at Pizza Antica.

Anywhere you walk down Santana Row you can snap a great photo for Instagram but my favorite is the colorful wall with vintage bar window gates.

Westfield Valley Fair Mall

I know I mention this place can get crowded, but this is a pretty large mall. They have stores from Nordstroms, Mac, Quay Australia, NYX Cosmetics, and Forever 21. Plus a huge food court with some amazing places to eat like Sushirrito, Super Duper Burger, Din Tai Fung, Meh Oh Ramen, and Loving Hut (vegan-friendly). I love chilling in the outdoor terrace area. They have a nice fire pit and is a great place to actually just chat and relax with your friends.

Top 10 Instagrammable Places in San Jose - Rooftop pool at the Signia by Hilton San Jose — Rooftop pool at the Signia by Hilton San Jose

Winchester Mystery House

The Winchester Mystery House is a historic mansion located in San Jose, California. It was built by Sarah Winchester, the widow of William Wirt Winchester, the heir to the Winchester Repeating Arms Company. You may recognize the name because they made a popular TV show based on this family and the mansion.

Sarah Winchester was said to be haunted by the ghosts of people who had been killed by Winchester rifles, and she believed that the only way to appease these spirits was to continuously build onto her house. She also believed that the constant construction would confuse any vengeful spirits that might be after her.

Today, the Winchester Mystery House is a popular tourist attraction, offering guided tours of the bizarre mansion. Visitors can explore the many rooms, staircases, and secret passages, and learn about the fascinating history and legends surrounding the Winchester Mystery House.

The mansion is located very close to Santana Row and Valley Fair Mall. So it’s very easy to include in your itinerary after a day of shopping and eating.

Top 10 Instagrammable Places in San Jose - Winchester Mystery House — Winchester Mystery House

San Pedro Square Market

If I'm going to Downtown San Jose you can usually spot me at San Pedro Square. I love this area because you have a wide variety of food shops and drinks. You can get Mexican, Vietnamese, or Italian food and grab a drink at the bar on site. Alma Tequileria is the newest Instagrammable spot in San Pedro Square Market.

Top 10 Instagrammable Places in San Jose - Holiday brunch at the Signia by Hilton San Jose — Holiday brunch at the Signia by Hilton San Jose

Haberdasher

This is a speakeasy-inspired bar. I love all the crafter drinks here and it has vibes of the 1920s with a modern flare. This is a smaller bar so on weekends it can get packed and there are lines out the door, but the drinks are worth it. My favorite drink is the Watermelon Jive.

SoFA District

This part of San Jose you will find lots of street art, mainly because the SoFA District is the Silicon Valley Creative District in San Jose. Along 1st Street, it has amazing restaurants, coffee shops, and bars.

Some of my favorites are Academic Coffee and The Salad Planet. I also love the SoFA Marketplace because they have Drag Brunch on Sundays! Also Every first Friday of the month they have an Art Walk which showcasing local artist in the San Jose area. You can find soooo many amazing wall art pieces here too!

San Jose Museum of Art

I love coming here with my girlfriends for the San Jose Museum of Art special events. They usually have Third Thursday events where they have the museum open at night for extended hours and have live music and drinks available.

The Municipal Rose Garden

If you are in the area in the springtime, the Rose Garden is a must! There is a fountain in the middle of the garden and sooo many different types of rose hybrids and flowers. This is a great location for a picnic/bbq or to take family photos. Or in my case, some great spring photos for the blog.

Alameda Street

The Alameda street leads into downtown San Jose, it passes by the SAP Center where large concerts and the NHL Shark Tank is located. If you walk the down the Alameda you will find a great variety of local small business, chain stores and restaurants. Some of my favorite places in this area are Black and Brown (Clothing Consignment/ Thrift Shop), Recycle Bookstore (soo many used books!), Luna Kitchen (Mexican Food), and Zona Rosa (modern and trendy Latin food).

Japantown

I recently discovered this part of San Jose because a close friend of mine moved into this neighborhood. Just like the SoFA District, Japantown is full of local artists. You can find street art around every corner. Here you can find Japanese food such as ramen and sushi. They also have a cute local clothing shop called Classic Loot where you can find 80-90’s vintage pieces and other small business brand selling their merchandise. There is also a karaoke bar called 7 Bamboo which you will most likely find me singing there on the weekends.

Japanese Friendship Garden

If you love scenic walks you are gonna love this place. Similar to other Japanese gardens it is calm and serene with many koi ponds and beautiful bonsai trees. Perfect spot for photos, especially when the cherry blossoms start to bloom in the springtime! Plus it is free to enter.

Apple Visitor Park

Okay so this is not right in San Jose, but for all you Apple enthusiasts you will like this. Just a 15 min drive in Cupertino you can check out the Apple Visitor Center. They have a smaller Apple Store there and a cafe, so it is a nice area to get work done or enjoy a cup of coffee. Pus if you go to the top level you can see the newly constructed Apple Park HQ.

Guest Contributor: Brianna Ramirez of Design By Brianna.