Travel like a local.

Podcast, Reedy Press

Hiking Mt Um, Local Wines & Winchester Mystery House in San Jose, California

Best things to do in San Jose California - Cassie Kifer - Winchester mystery house

The Winchester Mystery House

I’m really excited to interview Cassie Kifer, author of “Secret San Jose: A Guide to the Weird, Wonderful, and Obscure” about San Jose, California. Cassie’s tips for the best things to do in San Jose are awesome because she’s lived in San Jose for 15 years and wrote a book on unique attractions in the city. She loves the diversity of people, the hiking, and the protected open spaces that are so close to the city.

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Best things to do in San Jose California - Cassie Kifer - Sierra Vista at dawn

Sierra Vista at dawn

San Jose, California

San Jose is in the heart of the Bay Area’s Silicon Valley. The city located in Central California just south of San Francisco and is nestled among rolling green hills. Although the city is a hub of modern technology, its downtown historic district is home to architectural landmarks, like the 1883 Italianate-style Oddfellows building and Spanish Colonial Revival structures.

Cassie says that the weather is perfect all year. It’s not too hot in the summer, yet the winters are very mild. San Jose is the warmest and sunniest part of the Bay Area, so you don’t have to worry about the famous San Francisco fog.

Throughout the year, there are numerous festivals to attend. Cassie’s favorites include the San Jose Jazz Festival and the Historic Japanese Obon Festival. Visitors can also take a detour outside the city limits to visit the wine region of the nearby Santa Cruz Mountains. One of the most popular wineries is the Ridge Vineyards. The Winchester Mystery House is also a popular attraction due to the unique architecture and claims of it being haunted.

We share a lot of resources and local suggestions in today’s podcast, but you should also check out Visit San Jose, the local visitor’s bureau. They are a wealth of information and can help you plan an itinerary based on your time, budget, and interests.

If you’d like to learn how to travel for free using airline miles and hotel points, check out my free 7-day email course.

Best things to do in San Jose California - Cassie Kifer - mural art 2

Mural art throughout the city

Getting around San Jose

The local airport is San Jose International Airport (SJC), which is a ten-minute drive to downtown.

Cassie says that renting a car is the best choice when visiting San Jose. Although the Bay Area has some of the best public transportation in California, you’ll need a car to explore many of the area’s best attractions outside the city limits. For the best offers, visit Avis, Budget, or Hertz.

Uber and Lyft are also excellent ways to get around if you are taking a short trip.

When you only need a car for a couple of hours, you can rent by the hour with Zipcar. Join now to get $25 loaded into your account.

Best things to do in San Jose California - Cassie Kifer - Orchestria Palm Court player pianos

Palm Court player pianos

Places we talked about on the podcast

Here is a map of all of the places we talked about on the podcast episode with Cassie Kifer about San Jose, California. You can zoom into the map and click on each dot to explore the city.

  • Red dots = best places to eat in San Jose, California
  • Green dots = best things to do in San Jose, California
  • Yellow dots = best places to stay in San Jose, California

Who is Cassie Kifer?

Cassie Kifer is a San Jose-based communications consultant, urban planner, and explorer. Her work has been featured in Delta Sky Magazine, National Geographic Travel, Fodor’s Travel, Thrillist, and on the website of the Santa Clara Valley Open Space Authority. Cassie released “Secret San Jose: A Guide to the Weird, Wonderful, and Obscure” in September 2020 with Reedy Press. You can find Cassie’s book and many others just like it at the Reedy Press online store.

When she is home, you can find her seeking out interesting food and cultural experiences and hiking the South Bay’s many parks and open spaces with her husband and rescued shelter dog, Riley. She also shares stories and photos about food and travel on her blog, Ever In Transit.

Best things to do in San Jose California - Cassie Kifer - headshot

Check out these articles that she wrote:

You can connect with Cassie on her website and on Twitter, Facebook, and Instagram.

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Best things to do in San Jose California - Cassie Kifer - Mt Umunhum

Views from Mt Umunhum

Stay tuned for our next episode

Best things to do in Panama City Florida - Jan Johnson on a pontoon boat

Jan on a pontoon boat

Listen to the next episode when Jan Johnson of Bayhouse Playhouse Vacations shares the best things to do in Panama City, Florida. Jan and I talk about the dog mayor of Mardi Gras, visiting Shell Island, and the annual Blessing of the Fleet. We hope you’ll join us when We Travel There.

What’s your favorite part of San Jose? Send us a Tweet, let us know in the comment section below, or continue the discussion in our Facebook group!

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To see which cities we’ve interviewed and scheduled, please visit If you’d like to be a guest on the show, please submit an application at

Related episodes

To learn more about California cities, listen to these other episodes: