Toasting the Moon in San Jose, California

Travel for 2 cost breakdown (at the time of writing this post):

  • Hotel De Anza: $250 per night
  • Food/Entertainment/Transportation/Souvenirs: $1000
  • GRAND TOTAL FOR 2 TRAVELERS – 4 days: $2000

***At this time, we are not endorsed by any outside affiliates. That said – when booking our trips, we have had a lot of success with, Skyskanner, and Tripmasters.


Toast the Moon always recommends using a passport. We also recommend TSA Pre-Check and Global Entry, because who wants to waste their vacation time in an airport line, am I right? Traveling around the United States is not difficult, but changes are in the air. Please be advised that as-of October 1, 2020 – basic drivers’ licenses will no longer be valid for identification in airports. Sign up for a passport or Real ID now to avoid complications later!

San Jose – Come Here for Work – Stay Here for Fun!

Chances are you haven’t placed San Jose, CA on your bucket list. In fact, you may not even know where to find it on the map. But, there is a good chance that if you work in the tech industry, you will find yourself here at some point.

Upon arrival, you may take a quick look to see how far you are from San Francisco, Santa Cruz, or Monterey. Maybe you want to see Big Sur or go to wine country. And, you could do all of those things. Each one is an easy day trip from San Jose.

However, I would argue, that you may have just as much fun not fighting the traffic and exploring what the South Bay has to offer. You might be surprised.

What To Do?

Explore Downtown!

Downtown San Jose has been growing! It rivals it’s Oakland and San Francisco counterparts with restaurants, markets, festivals, and live entertainment. You could find the SAP Center (or Shark Tank) and catch a concert or Sharks game. San Pedro Square Market hosts live events and houses 20 vendors ranging from craft beer bars to pizza to sushi to tapas and even home goods. You could have a Roaring 20’s weekend during jazz fest where you listen to great jazz, stay in a historic hotel (like De Anza Hotel listed above) and go to Haberdasher to role play your speakeasy dreams. You could aim for a staycation “abroad” by scouting out only Vietnamese spas and foods, German biergartens and restaurants, Japanese home goods and sushi, or Filippino markets. You could come for Christmas to explore Christmas In the Park – a FREE mini-themepark set in the middle of downtown with rides, crafts, cozy food, local entertainment, and Christmas trees and scenes as far as the eye can see. The opportunities are endless!

Downtown San Jose is a stew of cultures, things to do, and new places to see.

Let’s Play Ball!

San Jose is a great place for sports lovers! Check out the local minor league baseball team the San Jose Giants to meet Gigante, see some fireworks, and enjoy rooting against the beer/cider batter! Or, you could dress in teal and go see the Sharks! Recently, the San Francisco 49ers have also moved to San Jose’s neighboring city of Santa Clara. And the soccer team (ahem…football), the San Jose Earthquakes, is always fun to see! If you’re in San Jose – you will be able to find a game to enjoy!

Go See Museums – Parks – Shopping Centers – or Neighboring Towns!

San Jose also houses the Tech Museum, the Intel Museum, The Children’s Discovery Museum, The Rosicrucian Museum, The Winchester Mystery House, several Art Museums, and other historical museums of random interest. You could easily spend a weekend exploring history, arts, and culture through the museums.

Almaden Quicksilver park has a history museum discussing mining in the area as well as dozens of trails and hiking options. The Municipal Rose Garden is very near downtown and has picturesque blooms nearly all year long! Vasona Park is great for wildlife and photography, and there are also multiple bike paths and trails throughout the city.

Shopping in San Jose is a treat. Downtown and Willow Glen have many local artisans and shops for local goods. But, for big shopping adventures, head to the Westfield Valley Fair Mall and Santana Row. Not only will you find almost every major store you can imagine, you will also be able to check out really cool cars parked along Santana Row as well as the occasional celebrity sitings and top-notch clubs.

If you must leave San Jose, but you don’t have a lot of time to spare, neighboring communities such as Santa Clara, Fremont, Los Gatos, Saratoga, and Cupertino all have a lot to offer depending on your tastes and budget.

San Jose – We Came for Work – We Stayed for Fun!

I guess that this post has made it pretty clear that we have a thorough knowledge of the San Jose area. I just couldn’t keep it as short as the other posts. This has been our home for eight years now. It’s a wonderful place to visit and a wonderful place to call home. There is always something new to explore! We’ll never see it all!

Toast the Moon Rating:

  • Food and Drink: 9/10
  • Culture/Locals: 7/10
  • Things to Do: 9/10
  • Adventure Opportunities: 8/10
  • Cost: 8/10
  • Total: 8.2/10 – Cheers!

Enjoy your adventure!

Toast the Moon – Cheers,

Noah and Majhon

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