California is a big state, which means it is full of amazing places to explore! I grew up in San Jose, and so having spent 18 years there, I feel qualified to tell you exactly how to spend 48 hours there! So lets get started.

Where you’re staying:

San Jose has an airport, and a convention center, which means it’s home to a lot of chain hotels. But those aren’t very fun, so here are some alternative places to really enjoy your stay.

1. Hotel Valencia, Santana Row

355 Santana Row

For the bad and boujee out there, this is your place. Situated in the middle of Santana Row, you’re in dining and shopping paradise. With upscale boutiques, designer stores, and chains like Urban Outfitters and H & M there’s something for everyone. The hotel also sports a rooftop pool and bar that is ideal to enjoy in the California summer (or California and season). There is also complimentary breakfast, a bar and restaurant indoors and valet parking.

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2. Fairmont Hotel, San Jose

170 S Market St.

A classic gem of a hotel, I attended many bat mitzvahs and wedding receptions here. Their restaurant Il Fornio is top notch Italian food, and solid cocktails. And the downtown location is prime for night life, restaurants or a Shark’s game if you’re there during hockey season. You’e also right near down town attractions like the Tech Museum, Children’s discovery museum, Art Museum, and the Cathedral.

3. Dolce Hayes Mansion

200 Edenvale Ave.

The decor here is a little dated, and you’ll need a rental car to get around. But there’s a gorgeous pool to tan by, a fun list of cocktails, and they host a plethora of classy events like weddings! Their wifi is also fire, so you might not need to complain too hard about staying in.

4. Hotel Los Gatos

210 E Main St., Los Gatos

Los Gatos has always been one of my favorite areas within proximity of San Jose. It translates to “the cats,” but it’s actually an incredibly dog friendly city. Full of great high end shopping, an incredible bakery (Icing on the Cake) and great casual and fine dining, it’s a desirable but tiny town for a reason.

Where you’re Dining

For Brunch:

SF may have a stronger claim on San Jose brunch, but make no mistake, we’ve got some solid eats. Try these places for a mid morning pick me up.

The Table

1110 Willow St.

This spot has been a hit ever since it opened, serving fun twists on brunch specials like chicken and waffles, ricotta pancakes, and beignets. Their cocktails are equally tasty and inventive. Their space isn’t huge, so there will be a wait, but sip mimosas at the bar to kill time with no complaints. Their outdoor patio is heated, and its corner location provides prime people watching.

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Bill’s Cafe

Multiple Locations

A small, Bay Area centric chain, Bill’s cafe whips out specials that vary from decadent (think a deep fried and sugared cinnamon roll) to the health conscious (egg white omletes and granola). There’s something here for everyone, and you’d be crazy to pass on mimosas and bloody mary’s.

Mimosas Cafe

4660 Pearl Ave.

If you dream of mimosas the size of your head, you’ve come to the right place. They also have a tasty variety of normal sized mimosas from prickly pear and watermelon, to cranberry and grapefruit. They also offer eggs any way you could want them from scrambles, to omletes, to skillets.

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For Dinner

Orchard City Kitchen

1875 S Bascom Ave #190

This small plates focused restaurant is one of the best in town. You have to try the triple B: bacon, biscuits, and butter, it is to die for. Their cocktails are also inventive and tasty, and are sometimes themed, last time I was there each drink was named for a star wars character! So cool.

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Pizza Antica

334 Santana Row

This Santana Row spot serves so much more than pizza, but the pizza is undeniably good. Make sure to try their seasonal pasta, and pair with the strawberry basil lemonade, or a nice glass of rosé. And to those who think brocolli doesn’t belong on pizza, this place is about to prove you oh so wrong.

Siena Bistro

1359 Lincoln Ave.

This hidden neighborhood gem is not to be missed. Nestled in the back of a Lincoln Ave plaza, Siena serves traditional Italian food with a twist, a solid wine list, and offers a romantic outdoor patio, complete with heat lamps and twinkle lights. The head chef often will come out to check in on how everyone’s meal is doing. The desserts are standouts as well.

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For Dessert

Icing on the Cake

50 W Main St, Los Gatos

One of the best bakeries I’ve been to in my life, and that is saying something people, because I spent a week in New York and managed to go to Magnolia’s TWICE to get cupcakes that I didn’t share. I have no shame. But actually, all of the desserts here are to die for, and they have vegan as well as gluten free options so no one has to miss out.


1275 Lincoln Ave #1

Give it to San Jose to get hip on the rolled ice cream trend before SF, but this place makes some seriously tasty and stunning ice cream concoctions. My personal favorite is the cookie butter flavor, because, um, have you had cookie butter? Yeah, you get it.

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Susie Cakes Bakery

1109 Lincoln Ave

Another of my favorite cupcake spots, I first fell in love with the Marina location, and so my heart was sent a flutter when I learned they were putting one in my hometown suburb of Willow Glen. And it does not disappoint guys.

Milk and Wood

387 S 1st St

Instagram fans, this place has your feed covered. The ice cream pops here are tasty and pretty: choose from 25 flavors, add your toppings, take a pic, gram that ish, and dig in.

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For Drinks

Paper Plane

72 S. First St. 

This place combines a laid back vibe with creative craft cocktails for a perfect spot to end your night (or begin it…)

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43 W San Salvador St.

First Single barrel, and one of the first speakeasy bars on the scene, this spot has gained a new name, draft cocktails, and snazzy electic mixers, but held onto it’s old school vibes.

Roots and Rye

3055 Olin Ave #1005

Another Santana Row spot, this bar offers rustic chic decor with hand crafted cocktails that are worth the pretty penny they go for.

SP2 Communal Bar and Restaurant

72 Almaden Avenue

You know a place is a standout if they’re capable of overcoming a poor location to serve great drinks and bites to happy customers, in what is an airy and open space once you actually locate it in the alley way next to San Pedro Square Market, which leads into our next section quite well…

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What You’re Doing

Spending a Night at a Market

87 N San Pedro St

San Pedro Square Market is not in fact, where you should head for groceries. It is a place you should hit up for a night of tasty bites, and drinks, and meandering through two artsy/industrial chic spaces. It’s a solid place for groups too as there’s a little bit of everything to satisfy even the pickiest of eaters in your crew.

Hitting Up the Museums

There are multiple can’t miss museums in San Jose, but the classics are The Children’s Discovery Museum (otherwise known as the purple museum for its exterior color),

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The Tech Museum which features an imax dome, robots, a bobsled simulator, and so much more, and lastly, there is the San Jose Museum of Art, which is full of cool sculptures as well as fun rotating exhibits.

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Taking a Hike

San Jose provides many nature trails, whether you’re a biker, hiker, or just a nature enthusiast, you’ll find the hike for you, whether that’s at Penetencia Creek, Campbell, or Lost Gatos. Check out your options here:

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Going to a Game

Whether it is hockey, baseball, football, or soccer season, you can take in your game of choice in San Jose. The SAP center hosts San Jose Sharks hockey games for those who love the ice, with preseason games beginning in September, and the season running till April, depending on how well the team performs. And if you want to catch the Giants before they become household names in the city, check out a San Jose Giants baseball game in the summer. There are several colleges you can catch football at, and in the summer watch a San Jose Earthquakes game in the newly done Avaya stadium.

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So there you have it folks, now you know how to spend a long weekend in San Jose. Optional singing of “Do You Know the Way to San Jose” on the car ride there is allowed.

[featured image from The Crazy Tourist]

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