Big Sur and the Monterey Bay


This tour gives you a rich combination of the urban sophistication of San Francisco, the dramatic natural beauty of the California coastline and its unique Pacific marine wildlife, the laid-back “surf” culture of Santa Cruz, and the history of the old Spanish missions.

Start with a few days surrounded by the serene beauty of San Francisco, the City-by-the-Bay, then head south toward California’s central coast. This the famed Route 1. This stretch of scenic road, among the world’s most beautiful coastline, blends the sophistication of world-class wine regions with pristine coastal beauty and rugged mountain ranges. Small charming oceanfront communities, breathtaking scenic hikes, and innovative dining experiences are all part of the unforgettable experience of the region.   

From observing elephant seals and sea lions at Año Nuevo State Park to hiking along the rocky point at Point Lobos, catching a glimpse of Pinnacles National Monument from Salinas, the hometown of author John Steinbeck to walking the boardwalk in Santa Cruz, this is a breathtaking journey that the seasoned traveler and the casual adventurer will enjoy equally.

The suggested basic itinerary takes on the best of San Francisco and fuses it with a multi-day exploration into the vast beauty of the California coastline. But this is indeed only a suggestion. All year round, a multitude of seasonal activities and day-trips can make your visit ever more special. Let us tailor your travel time to your own tastes and interests.

Length of trip
10-12 days, easily extended to 14 days or more

Start-end points
San Francisco

Best time to travel
All year-long

Urban, rural and nature
History and culture  

Intensity level
Easy and relaxed

Suitable for
Independent or assisted travel
Couples, families and small groups


  • Immerse yourself in the diversity and vibrancy of San Francisco’s neighborhoods
  • Experience the sights and sounds of Chinatown’s secret alleys and Fisherman's Wharf marina
  • Explore the iconic landmarks of Coit Tower, Lombard Street and Golden Gate Bridge
  • Embark on a ferryboat adventure for a visit of the island and prison of Alcatraz
  • Enjoy San Francisco’s multitude of beautiful museums and art galleries
  • Explore San Francisco’s neighborhood in a go-car
  • Cruise the Bay and under the Golden Gate in the Bay Voyager
  • Enjoy a last drink at Heinhold’s Last Chance Saloon in Oakland

Suggested itinerary at a glance

Day 1-2 • The neighborhoods of San Francisco

Start your adventure with an exploration of one of the most beautiful, interesting and diverse places in the world. In spite of its reputation for hilly terrain, many of San Francisco neighborhoods are actually very accessible and easy to explore on foot.

Discover the hidden history of Fisherman’s Wharf and immerse yourself in the Bohemian culture of North Beach. Stroll along the Marina along the Bay of San Francisco to Fort Point underneath the awe-inspiring Golden Gate Bridge. If you are in an adventurous mood, walk across the Bridge to the Marin Headland side of the Golden Gate for breathtaking views of the North Bay on one side and the Pacific Ocean on the other.

Take a leisurely walk through the hidden alleys of Chinatown to learn about the past and current history of the” Benevolent Associations”, the Tongs and the Gangs. Immerse yourself in the sounds, smells and culture of this neighborhood where ancient history and modern politics intertwine.

Day 3-4 • The Mission District, Nob Hill, Golden Gate Park, Alcatraz

One of the oldest neighborhoods of the City, the Mission District has its origins in the Mission Dolores, established by the Spanish in 1776. Today, it is not only the center of the Chicano and Latino culture, it is also one of the liveliest and hippest neighborhoods of the City. Art galleries and music venues abound, alongside restaurants serving foods from around the globe.

Once a deserted hill in the middle of an expanding city, Nob Hill caught the eye of the five railroad barons. Learn about Nob Hill’s colorful history and feuds, how an earthquake and a fire wiped it out, and how it resurrected itself to become a grand setting for a cathedral and a Hitchcock movie.

For a stroll in a flatter part of San Francisco, take an exploration of Golden Gate Park, where beautiful green open spaces are the background to the renowned Academy of Sciences, the De Young Museum, the Conservatory of Flowers and the Japanese Tea Garden.

There is so much to see and to do in San Francisco, but a visit of the City-by-the-Bay will not be complete without a ferry-boat across the Bay for a visit of the Island prison of Alcatraz. For an unforgettable experience, if time permits, time the schedule of your ferry ride with the sunset hour. This is when the Golden Gate Bridge turns even more red and the building of the city shimmer in the glowing light.

Day 5 • San Francisco Day of Adventure

Today is your opportunity to explore the City at a different pace and from a different viewpoint: on the road or on the water.

On the road: Riding in a GoCar, an open two-seaters that is easy and fun to drive, you start the journey from Fisherman’s Wharf and continue to the Marina District, Crissy Fields, below and above the Golden Gate Bridge, along the ocean to Golden Gate Park and the Presidio. Of course, the tour is not complete without zigzagging down the crooked Lombard Street. This ian experience guaranteed to put a smile on your face.

On the water: Ride the open-deck Bay Voyager, a powerful 300 HP, 24 feet vessel under the expert navigation of Captain Charles. The scion of a long line of marine officers, Captain Charles shares his intimate knowledge of the Bay and its history while riding the swell. From secret alcoves around Treasure Island, to circling Alcatraz and zipping under the Golden Gate Bridge, this is an unforgettable experience.

And for a perfect ending to your journey, take an evening ferry to Oakland’s famed Jack London Square district to visit a place where history, culture and food mingle for a unique experience. From tiny saloons favored by the local firemen, to upscale hipster eateries serving fusion cuisine, there is something for every taste and budget. A drink at Heinhold’s First and Last Chance Saloon is an absolute must. One the oldest bars on the West Coast, it was Jack London’s favorite dive and where he wrote many of his adventure novels.

Day 6-8 • Down the Pacific Coast, Año Nuevo to Santa Cruz

It is time to start your road-trip along the famed Highway One! Over the next few days, you drive along the Pacific Coast through a region of small coastal towns, each with its own charming character. Experience the local flavors of Pacifica and Half Moon Bay, then head out to Pescadero. The Portuguese fishing family that established the town is still serving its famous artichoke soup with garlic bread at Duarte’s.

Año Nuevo State Park is located just south of there. Its low, rocky, windswept point juts out into the Pacific Ocean, where it hosts one of the largest mainland breeding colonies in the world for the northern elephant seal. In the company of an environmentalist guide, take an easy stroll through the dunes on the accessible wood boardwalk. It leads you to a platform above the beach where you can observe the colony of seals and sea-lions. Watch for the telltale puff of spray in the ocean as whales migrate in season along the coast. And of course, look out for a fin cutting through the surf. This is the natural habitat of California’s the great white shark.

Santa Cruz, the self-proclaimed birthplace of the California surf culture, is next on your itinerary. It is easy to agree to the claim when you visit the tiny, shrine-like Surf Museum overlooking the daredevil maneuvers of the wave riders at Cowell’s Beach and Streamer Lane. But there is more than surf in Santa Cruz. Its Beach Boardwalk (one of the last of the classic seaside amusement parks in the United States), pedestrian avenues lined with quintessential funky California stores, great restaurants along its piers and a vibrant music scene make it a place you want to explore further.

Day 8-9 • Monterey Bay, Carmel, Big Sur

Few places on earth can live up to their own mythology, but Monterey is a notable exception. No matter what you’ve heard or seen, nothing can prepare you for the jaw-dropping beauty along Monterey's fabled coast and village-like pedestrian thoroughfares. Start with a relaxed stroll on Cannery Row to the world-class Monterey Aquarium before heading out to the Fishing Pier for a meal of the freshest catch of the region. This is also where you may want to board a vessel to get close-and-personal with the whales playing in the Bay of Monterey.

Situated on the Monterey Peninsula, Carmel is known for its natural scenery and rich artistic history. It is also known for an abundance of designer stores, gourmet eateries and upscale art galleries that cater to its wealthy residents (including Clint Eastwood, a resident and the former Mayor of Carmel). After a stop at its local market, it’s only a short drive to Point Lobos and a hiking trail leading to an overlook above the ocean. This is one of the best places in California to observe marine wildlife. Great sharks, whales, elephant seals and sea lions all share this habitat.

The scenery in Big Sur, California is unmatched, leading to an almost unavoidable sense of well-being. Cliffs, rocks, redwoods and bubbly surf create an epic backdrop for recreation, romance and relaxed exploration. Big Sur has provided inspiration to photographers, painters, writers and musicians: Henry Miller, Jack Kerouac, Ansel Adams, and The Beach Boys, to name a few.

Not-to-miss Big Sur highlights include the Point Sur Light Station, which stands atop a dramatic volcanic rock just off the spectacular Big Sur Coast. Jutting out into the Pacific Ocean it stands as a silent sentinel to a bygone era. And naturally, your visit needs to include taking the wide and well-maintained trail through the majestic redwoods and up the side of a canyon to the waterfalls of Pfeiffer Park.

Day 10-11 • El Camino Real, Salinas and California Missions, Silicon Valley

On your journey back to the San Francisco Bay, you may choose to take the inland road and follow loosely what is known as “El Camino Real”, the King’s Road. Established during Spain’s reign of California, it connects San Diego on the south to Santa Rosa and the region north of San Francisco. Along its path, Spain created a network of twenty-one “missions”. While some retained only their core set of buildings (always a church and often a military outpost), many have grown into the cities we know today. San Francisco, Santa Clara, Sonoma are only a few. Take a journey through history.

The Mission San Antonio de Padua, nestled below the Santa Lucia Mountains in central California’s Valley of the Oaks, is the third mission established by the Franciscan Order. A bit off the main road, it is almost as isolated today as it was in 1771. But its isolation is also part of its attraction. The rose garden outside of church invites meditative strolls. Call in advance to reserve a place for dinner at the communal table and maybe even spend the night in one of the monk’s rooms. The myriad of stars in the unpolluted night sky is worth the detour.

If you have another few days

San Simeon • Sitting atop an “Enchanted Hill”, comprised of 165 rooms and 123 acres of gardens, terraces, pools and walkways, and showcasing a legendary art collection, Hearst Castle’s history begins in 1865. George Hearst purchased 40,000 acres of ranchland, and in 1919, William Randolph Hearst inherited thousands of acres around San Simeon, and purchased more. The spread eventually encompassed about 250,000 acres. Hearst Castle was designed by architect Julia Morgan, between 1919 and 1947, and donated to the State of California in the 70’s, becoming a Historical Landmark.

Morro Bay / San Luis Obispo • Sometimes called the Gibraltar of the Pacific because of its world-famous Morro Rock, Morro Bay is lined with miles of unspoiled beaches, nature trails. A state and national bird sanctuary, Morro Bay is a regular stop for sea otters.

Gilroy Outlets • Conveniently located directly off Hwy 101 and just 20 miles south of Silicon Valley, Gilroy Premium Outlets features the largest collection of designer and brand name outlet stores in Northern California. Shop more than 145 stores including 7 For All Mankind, Banana Republic, Columbia Sportswear, Kate Spade New York, Nike and many more.

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