3 Days in San Jose, CA: Itinerary of the Best Things to Do in the South Bay

When you think of visiting the Bay Area, where comes to mind? San Francisco, definitely. Probably Oakland and/or Berkeley. Maybe somewhere in the North Bay like Napa or Santa Rosa in Sonoma County. Does San Jose come to mind? There are far more things to do in San Jose than you might think. San Jose is the final piece of the puzzle – the South Bay’s great weekend destination!

Whether you live in the Bay Area and need a new weekend getaway or are visiting the San Francisco area and want to explore beyond the city limits, spending a weekend in San Jose is a great option. I spent 3 days in San Jose in October 2019 and it was a perfect break from the bustle of the cities further north around the San Francisco Bay.

Read on for tips on visiting San Jose, the best things to do in San Jose, and a perfect weekend itinerary for San Jose. You’ll also find a few hotel suggestions to help you book everything and rest easy once you arrive. Read on for the ultimate guide for a weekend in San Jose!

In this post, I promote travel to a destination that is the traditional lands of the Tamien Nation, Ohlone, and Muwekma peoples. With respect, I make a formal land acknowledgment, extending my appreciation and respect to the past and present people of these lands. To learn more about the peoples who call these lands home, I invite you to explore Native Land.

This post was originally published in November 2019, and was updated in January 2023.

San Jose, California Travel Tips

Getting to San Jose

If you’re flying into the Bay Area, consider flying direct into San Jose airport. It’s the easiest option by far and several of the low-cost carriers operate here – including Frontier Airlines, Southwest Airlines, and Alaska Airlines.

San Jose airport is located about 10 minutes from downtown San Jose, and you’ll need to rent a car to get around. I recommend renting from Sixt or Alamo. They all offer budget rentals and run regular deals and specials. If you’re not sure (or not loyal to any particular car rental company), consider using a tool like Momondo or TripAdvisor to compare a bunch of options (yes, TripAdvisor does rental cars!).

Traveling Around the Bay Area

If you’re planning to visit San Jose as well as other cities in the Bay Area (San Francisco, Oakland, and Berkeley are the big three), you might wonder how to get around the Bay Area. Unfortunately, driving is your best option – but be prepared for traffic literally everywhere.

It can take 1-2 hours to get from San Francisco or Oakland to San Jose depending on the time of day and traffic. Plan ahead to give yourself plenty of time if you’re driving, especially on the weekend.

It is possible to take the Caltrain from San Francisco to San Jose too if you don’t want to drive a car. I’ve never done it, but you can find the schedule and fares on the Caltrain website.

Okay, now that you’ve got the basics set, it’s time to get to the fun part – the best things to do in San Jose for a weekend!

Day 1: Visit Lick Observatory & the San Felipe Hills

Whichever way you arrive for your weekend in San Jose, the first of things to do in San Jose is to leave… to the San Felipe Hills, that is! Actually, you won’t be able to do the activities today without a car, so opt to rent one at the airport in San Jose for the day even if you don’t use it for the rest of the trip.

First Stop: Space

The goal of today’s excursion is to visit Lick Observatory, a famous historic observatory nestled in the San Felipe Hills atop Mt. Hamilton. As you know, I’m a big space nerd, so I always love to visit spots like Lick – it’s also one of the best things to do in San Jose, so even less space-obsessed people might find the history interesting – and the post-visit dinner stop is worth for the journey it alone!

Speaking of the journey… Though the distance isn’t long, it takes about one hour to drive from San Jose to Lick. This is because of the winding two-lane mountain road you’ll be on.

Lick Observatory has two main public sights: the Great 36″ refractor (mentioned in the article linked above) and the Shane 3-meter telescope (a workhorse telescope used for longer observations) in a different complex. It’s a pretty easy 15-minute between the two observatory buildings. The only way to see the historic telescope is on a guided talk/tour; these are on the half-hour between 12pm and 5pm daily (so 12:30pm, 1:3pm, etc.). There’s also a gift shop you can browse if you’re waiting for a tour to start.

Dinner with a View

After admiring the two telescopes, make your way back toward San Jose. Along the way, stop off at the Grand View Restaurant. They have amazing farm-to-table food from their own farms as well as local suppliers. This restaurant has stunning views out across the Santa Clara Valley – you can watch airplanes coming in and out of the airport and the sun set behind the Santa Cruz Mountains.

We had a fantastic dinner of Italian food – zippy Padron peppers, a small bowl of Tagliatelle alla Bolognese the chef insisted we try, classic Pollo Parmigiana with tangy tomato sauce, a decadent Kabocha squash pyramid pasta drizzled in brown butter – followed by two desserts (Tiramisu and Butterscotch Budino). The two desserts only happened after all that food because we mentioned Watertable in Huntington Beach and the amazing three-dessert dinner we had there!

Stay until the sun goes down, then make your way safely down the mountain for the night. (I have a section on where to stay in San Jose at the end of this post!)

Day 2: Explore Downtown San Jose

Today it’s time to explore downtown San Jose – i.e. the real San Jose where people live and which you might miss if you only visit those fancy Venture Capital funds trying to get your cool tech idea the funding to become a ‘unicorn.’

(Don’t worry if that lingo made zero sense – it’s the last time I’ll speak “Silicon Valley” in this post!)

Catch the Vibe

Downtown San Jose feels like “where it’s about to be” in the Bay Area. It has the vibe of a college town on the edge of graduation combined with a city about to fill up with all the hipsters and tech bros that have made the San Francisco Bay Area one of the world’s most interesting places to live, eat, drink, and travel. This is because of San Jose State University, close to downtown (#collegebars) plus the fact that San Jose is one of the last major housing markets available for tech people moving from SF. It’s definitely about to “be” in San Jose.

Start your morning with a self-guided street art walking tour. (I personally did one that turned out to be space-themed! ?) San Jose is a grid city so it’s pretty easy to wander without a route; Google Maps obviously works well here too since their HQ is just up Highway 101 in neighboring Mountain View.

For lunch, grab a table on or near the patio at Olla Cocina. This cool Mexican restaurant is located in San Pedro Square and an easy walk from most downtown attractions. Order a horchata and the chorizo mac and cheese (or the fish tacos if you’re vegetarian) and people watch through the garage doors that are open most days.

Indoors vs. Outdoors

In the afternoon, check out the Tech Interactive. As the name suggests, this science museum shows off the best of what happens in the South Bay. But, it’s family oriented to make biotech, aerospace, and other fields way more accessible. It’s easy to spend a few hours exploring the exhibits, some of which require queuing up for, and it’s important to be patient if you want a chance to do any of the hands-on stuff… like the jet pack chair in the space section!!

If you’d rather be outside, consider taking a walk along the Guadalupe River Trail. This urban waterway has been heavily modified but the trails are nice and take you through some greenery. One notable stop on the route is Little Italy. This small cluster of buildings gives you a sense of old San Jose and some of the immigrant groups that helped shape the city in centuries past.

Dinner Options

For the evening, you could eat dinner and stay another night in downtown San Jose – or shift to Santana Row where you’ll be exploring tomorrow. (We did the latter.) If you decide to stay in San Jose, restaurants that catch my eye include Elyse, a French-Vietnamese restaurant, or Il Fornaio for Italian if you’re not tapped out from last night at Grand View. (You see now there’s still an Italian influence here!)

Day 3: Discover Santana Row

It’s time for your final day of this 3 days in San Jose trip! If you stayed in Santana Row last night, today is super easy; roll up and wander the main street (Santana Row) whenever you’ve finished breakfast at your hotel. If not, rise and shine to get parking before the crowds of day shoppers flood this fascinating combination of outdoor mall and self-sufficient planned community.

Get Lost … but Don’t Leave Yet

Beyond the flashy storefronts and hip restaurants and bars, the Winchester Mystery House is by far one of the best things to do in San Jose. I went in the evening for their Halloween tour; during the day they offer a history tour through a completely different part of the house. That is all to say you could definitely do their daytime tour plus any special nighttime events they might be offering based on seasons or holidays.

There are no photos permitted in the Winchester Mystery House, but on the tour you’ll learn about Sarah Winchester and her bizarre obsession with keeping the house – really, it’s a compound – in a constant state of construction. Be prepared for disorienting floor plans, functionless stairs and rooms, and the strange sense you’ve stepped into that house you get lost in when you have a nightmare… Okay, maybe you should only visit during the daytime!

Not to Be Morbid – Here’s Your Last Meal

After the Winchester Mystery House, finish your weekend in San Jose with lunch along Santana Row. There are a number of great restaurants in this area; all you need to do is choose one that sounds interesting to you. (The restaurant we ate at and which is pictured above – Sino – closed a few years ago, which is unfortunate as their fancy dim sum was delicious!)

Then it’s probably time to head home, sadly! Whether you need to fly home from San Jose or make your way back to SF to finish your trip there, your 3 days in San Jose have come to an end. You’ve had the chance to sample the city’s views, food, and innovation that makes this South Bay destination so compelling.

Where to Stay in San Jose

As you plan your weekend in San Jose, you might wonder where to stay. You’ll need to book two nights for a three-day weekend, so keep in mind which of these things to do in San Jose that you want to do, and where they are, when booking.

I was hosted at two properties in San Jose, split between downtown San Jose and Santana Row for one night each. This allowed me to sample the best of both areas in the city.

Hotel De Anza

The Hotel De Anza is located on the edge of downtown San Jose near Guadalupe River Trail – meaning it’s perfectly situated for however long you want to spend exploring the downtown core.

Their rooms are wonderfully large and the whole hotel maintains the traditional art deco vibe from the building exterior. (It reminded me a lot of the Hotel Lucia in Portland, Oregon.) We had a high corner room that offered great views of the streets below as well as planes flying overhead on their approach to San Jose airport.

Rooms at Hotel De Anza start from $120 per night. You can book on the hotel website, on Booking.com, or on Hotels.com.

Hotel Valencia

Located in the heart of Santana Row, the Hotel Valencia is deceiving from its exterior. You’d never know how much there is behind the facade at street level! Ascend to this Spanish-style villa property with a big beautiful courtyard, a small pool, and fantastic rooms.

Our room was an excessively large but delightful suite with everything we could have hoped for – a seating area, a table where I got a bit of work done, a huge King-size bed, and a balcony overlooking Santana Row and the San Felipe Hills. As Mr. V and I stayed here on the second night of our 3 days in San Jose, it seemed like the perfect bookend to look out over the city and hills we had just spent a weekend exploring.

Rooms at the Hotel Valencia start from $206 per night. You can book on the hotel website, on Booking.com, or on Hotels.com.

Have any other questions about the best things to do in San Jose and planning your weekend trip? Let me know in the comments!

My weekend in San Jose and this post were produced in partnership with Hotel Valencia and Visit San Jose. All recommendations for where to stay, what to do, and what to eat for a weekend in San Jose are made at my own discretion.

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