Cupertino

Cupertino (population 60,000 in 2020) is situated up against the foothills of the Santa Cruz mountains. It is something of an anomaly being the one city in the South Bay that doesn't have a distinct town center or main street, though there are concentrations of upscale development in the works. It has a highly-rated local schools system and quiet neighborhoods.

It's 15 minutes west of San Jose and 45 minutes south of San Francisco. The nearest railway, Caltrain (connecting San Francisco with Gilroy), stops in downtown Sunnyvale, about a ten-minute drive from the city center. Bus service is provided by VTA.

Cupertino has 2 major streets: De Anza Blvd., which runs north-south, and Stevens Creek Blvd., which runs east-west. The intersection of these two streets is in the center of Cupertino, and most of the businesses and shopping centers in the city are located in the area.

Highways 85 and 280 cross through Cupertino. These provide excellent access to the western cities in the South Bay, and to downtown San Jose (respectively).

Public transportation in Cupertino, as is the case for much of Silicon Valley, is very poor. The predominant form of transportation is personal vehicles.

Traffic is not much of an issue and major streets come with bike lanes, so biking is relatively safe.

Due to its consistent tangerine/beige colors and the amount of money local authorities probably spend in maintainance, Cupertino is actually quite beautiful, with a peculiar charm distinct to that of its neighbors. The contrast with San Jose outskirts, Sunnyvale or South Los Altos can be striking at city edges.

The northeastern quarter of Cupertino (including the "city center" at the intersection of De Anza Blvd. and Stevens Creek Blvd.) hosts a large number of Apple Inc. offices. This is unusual given that tech giants tend to set their headquarters in outlying urban areas—usually beyond a freeway—and rarely approach downtown. Apple employees can easily make up the vast majority of bystanders in these locations, especially at lunchtime, and may be seen wandering around with half-open MacBooks and openly discussing confidential matters.

• 🌍 De Anza College (intersection of Highway 85 and Stevens Creek Blvd). The community college for the area. It is one of the largest community colleges in the area, and has an excellent reputation. 
• 🌍 Apple Infinite Loop (Apple Campus), One Infinite Loop (intersection of Highway 280 and De Anza Blvd). The historical headquarters of Apple, Inc., still in use. Despite their overall lack of aesthetic quality, they were the most recognisable of all Silicon Valley headquarters until the construction of the Apple Park a mile to the east, and Apple fans do take selfies in front of the main entrance. You can go through the first door, up to the reception and before security check, and then take a peek through the glass panes at the rather scenic main hall, with banners featuring the company's latest product hanging in front of the inner lawn. 
• 🌍 Apple Park (between Wolfe, Homestead, Tantau and Junipero Serra Freeway). The headquarters of Apple, Inc., inaugurated in 2017. One of the largest buildings in the world (factories excluded) in terms of length and width, this $5 billion ring-shaped "spaceship" was built on the Vallco Park at the location of a historic barn, which was rebuilt on the north of the site. The Apple Park is near-entirely surrounded with a mound, trees and a fence, which conceal most of it from sight. In contrast, its glass walls are transparent enough to allow seeing the employees inside, and the sheer size of the place tends to give optical illusions on whether the walls are actually straight or curved. The Apple Park Visitor Center is a two-story building at the east of the headquarters. The ground floor includes a small Apple Store, exclusive merchandise, a café and an AR model of the site. Upstairs is a balcony with a view on the headquarters. Contrary to Infinite Loop, it is not possible to smuggle oneself through the entrance of the Apple Park. 
• 🌍 Cupertino Historical Society and Museum, 10185 N Stelling Rd, ☏ +1 408 973-1495. W-Sa 10AM- 4PM. free; donations welcome. (updated Mar 2018)
• 🌍 McClellan Ranch Preserve. Daily, dawn-dusk. Nature museum and blacksmith shop: Sa Su 11AM-3PM. On McClellan Rd. has an old farmhouse (with pigs!) and a short trail along the creek to walk. Cupertino also a bunch of suburban parks, notably Memorial Park on Stevens Creek Blvd. which has ponds with ducks. Free. 

Hiking trails can be found in the Fremont Older Open Space Preserve, with is connected with the Mid-Peninsula Open Space Preserve, offering even more options. Streets generally have bike lanes and (sparsely-used) sidewalks that can be good for jogging.

• 🌍 Euphrat Museum of Art, 21250 Stevens Creek Blvd (on the De Anza College campus), ☏ +1 408 864-8836. Tu - Th 11AM - 3PM (during exhibitions). Describing itself as "more than a museum" the Euphrat, it includes exhibitions and programs to engage kids in the arts. 
• 🌍 Rancho San Antonio County Park (Rancho San Antonio Open Space Preserve), 22500 Cristo Rey Dr, ☏ +1 650 691 2165. 8AM-sunset daily. A popular hiking location with over 25 mi (40 km) of trails. Good for biking and horseback riding as well. Features a farm called Deer Hollow Farm that offers tours and seasonal produce for sale. Arrive early if visiting on weekends as it can be difficult to find a parking space. Free. (updated Apr 2023)
• Tai Ji Men Qigong Academy - Cupertino Branch, 10590 S. De Anza Blvd, ☏ +1 408 283 0128. (updated Mar 2024)

Apple's two campuses, the Apple Park and Infinite Loop, both feature a "Company Store". They sell corporate merchandise not available either at the company's standard retail stores or on the Internet, and each store sells different swag. This includes t-shirts (usually in limited edition), mugs, notebooks, caps, and other small gifts. They are open M-F 10AM to 5:30PM, and closed on some public holidays.

• 🌍 Coach House Wine & Spirits (Liquor and Cheese), 1655 S. De Anza Blvd, ☏ +1 408-252-7141. 8AM - 8:30PM. Awesome local wine store and deli with tons of character. Has great selection of tequila, whiskey, scotch, and vodka. Cheap. 

Cupertino has a large Chinese population and so has a lot of Asian food choices. It doesn't have a walkable downtown and most of the restaurants are in smaller strip malls.

• 🌍 Cupertino Village (Homestead Rd. and Wolfe Rd.). A good place to find authentic Chinese food, with the restaurants and shops catering to mostly Chinese customers. There are a few Taiwanese, Cantonese, and other regional specialty places around. 
• 🌍 Alexander's Steakhouse, 10330 N Wolfe Rd (next to Vallco Shopping Mall), ☏ +1 408 446-2222. Amazing tasting steaks, but expect a bill in the 100s. (updated Jul 2015)

• 🌍 Picchetti Winery, 13100 Montebello Rd, ☏ +1 408 741-1310. 10AM-4PM. One of the oldest wineries in California, established in 1890. It is on a historic ranch in the Santa Cruz mountains and within the Midpeninsula Regional Open Space, with nearby hiking trails. Flight of 5 wines for $15, refundable w/ purchase at $5/bottle. (updated Jun 2019)

• 🌍 Cupertino Inn, 10889 North De Anza Blvd, ☏ +1 408 996-7700, toll-free: +1-800-222-4828. 
• 🌍 Juniper Hotel Cupertino, 10050 S De Anza Blvd, ☏ +1 408 253-8900. Check-in: 3PM, check-out: noon. (updated Jul 2015)
• 🌍 Courtyard By Marriott, 10605 North Wolfe Rd, ☏ +1 408 252-9100, fax: +1 408 252-0632. 
• 🌍 Hilton Garden Inn, 10741 North Wolfe Rd, ☏ +1 408 777-8787, fax: +1 408 777-8040. 
• 🌍 Hyatt House, 10380 Perimeter Rd, ☏ +1 669-220-3800. 
• 🌍 Residence Inn by Marriott San Jose Cupertino, 19429 Stevens Creek Boulevard, ☏ +1 408-777-0188. (updated Jul 2020)

The following hotels and motels aren't in Cupertino proper but are very close, in San Jose, Santa Clara, and Sunnyvale. Downtown San Jose is home to the finest hotels in the area.

• 🌍 Woodcrest Hotel, 5415 Stevens Creek Blvd, ☏ +1 408 446-9636, info@woodcresthotel.com. 
• 🌍 Aloft Cupertino, 10165 North De Anza Boulevard, ☏ +1 408-766-7000. (updated Apr 2020)

Be careful to check for ticks after hiking in fields in the bay area. There is a high rate of lyme disease transmission in the Bay Area. If a bull's-eye rash develops at the tick bite site, immediately seek medical help and treatment with antibiotics. There have been instances of mountain lion sightings in the western periphery of the city, in the foothills of the Santa Cruz mountains.

Cupertino is very safe, with violent crime virtually nonexistent. On the other hand, this means the local sheriff's deputies have little to do but hide behind bushes to catch drivers for moving violations. Be sure to obey traffic laws while in Cupertino.

• One of the city's strongest assets is its accessibility to the Mid-Peninsula Open Space Preserve (aka Rancho San Antonio) which extends up and down the Santa Cruz mountains.
• Not only is it one of the most accessible, Fremont Older Open Space Preserve is generally not as frequented as the other preserves on the peninsula, making for a quiet get-away very close to the heart of Silicon Valley.