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People viewing the giant refractor telescope at Lick Observatory

San Jose History Tour

Fun fact for the history buffs traveling to San Jose: the city predates California and was the first civilian settlement in what was then known as Nueva California. When the state of California was founded in 1850, San Jose became the first capital and has been an important place in California history since the city was founded in 1777. You’ll be delighted by the the vast historic experiences and sights waiting to be discovered, as San Jose’s vibrant past is celebrated by people, places and events throughout the city.

Day 1

lick observatory

Lick Observatory


Grab coffee and a French or German pastry at La Lune Sucree before heading to enjoy a day of sightseeing. After breakfast, it’s time for the first stop on your historical tour of San Jose: Kelley Park. Here, you can travel back in time to learn about San Jose’s origins. Nineteen different organizations, including History San Jose, the Portuguese Historical Museum and the Viet Museum, tell the story of San Jose through different cultural perspectives.


Continue your tour at San Pedro Square, the oldest district in San Jose. Here, you can explore the many stalls of vendors serving food and beverages from across the globe. This is the perfect place to relax, have a drink and enjoy the afternoon. San Pedro Square is adjacent to the Victorian-era Fallon House, which was owned by Thomas Fallon, one of San Jose’s early mayors, elected in 1859. Explore the fascinating history of Fallon, who was a frontiersman, and his wife, Carmelita, who was a daughter of prominent Spanish landowners. 


Cap off your day with beautiful sunset views from The GrandView Restaurant and enjoy seasonal cocktails, charcuterie, steaks and pastas, all made, cured and grown on their farm garden adjacent to the restaurant. After dinner, once the stars to come out, climb a little further up the mountain and spend a memorable night at the Lick Observatory. Since 1888, Lick has been at the forefront of astronomical research. During the summer, Lick features nighttime telescope viewings paired with live music and astronomy lectures, and daytime tours are offered year-round.

Day 2

Cathedral Basilica of St. Joseph

Cathedral Basilica of St. Joseph



Put on your walking shoes, because this morning is all about exploring the history within downtown San Jose. Before your first stop on this historical walking tour, start your morning with coffee and a freshly baked pastry from Bijan Bakery & Cafe. After fueling up, it’s time to walk across the street to Plaza de Cesar Chavez, the oldest public open space in California, and the site of California’s first state capitol. After exploring the park, it’s time for the next stop: the Cathedral Basilica of St. Joseph. This beautiful historic landmark wows downtown visitors with its angelic stained-glass windows and towering domes. Free tours are offered to guests during the day.

Just a block over, you’ll find the Bank of Italy building. This landmark is the one of the oldest skyscrapers in Silicon Valley, and until 1970, it was the tallest building between San Francisco and Los Angeles. The last stop of the morning is Peralta Adobe, one of the oldest remaining structures in San Jose. Its interior is decorated just as you would have found it centuries ago.

winchester mystery house


Be sure to spend an afternoon on a visit to one of San Jose’s most iconic buildings: The Winchester Mystery House. Dubbed the “house built by the spirits,” the mansion is the former home of Sarah Winchester, heiress of the Winchester Rifle fortune. This beautifully made, eerie home was built to confuse the spirits that Sarah said were the victims of her family’s business. A tour of the home and its beautiful grounds may leave you feeling in awe and slightly spooked.


The pioneers of the California wine industry were enamored by the vast microclimates in the Santa Cruz Mountains and Santa Clara Valley. They settled here and these regions have become two of California’s oldest wine producing regions. This valley brought Pinot Noir vines to California, made sparkling wine famous and claims the state’s fourth oldest continuously operating winery. Silicon Valley’s wine region has been touted by Wine Spectator as the “most underappreciated appellation in the world.” The history of this area’s wine industry is best experienced at The Mountain Winery, which was made famous by Paul Masson’s adage “sell no wine before its time,” and is credited with coining the term sparkling wine. Here you can enjoy concerts in a historic and serene setting in the Santa Cruz Mountains overlooking Silicon Valley.

Downtown Walking Tour Map

Download walking tour map here.

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