16 days in California Itinerary

16 days in California Itinerary

Created using Inspirock California trip planner

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Route & dates

16 days in California Itinerary

Start: Chicago
Fly:  7​h 45​min
1
Manhattan Beach
— 5 nights
Drive:  1​h 30​min
2
Ventura
— 2 nights
Drive:  2​h 15​min
3
Pismo Beach
— 2 nights
Drive:  3​h 15​min
4
Big Sur
— 3 nights
Drive:  3​h
5
San Francisco
— 2 nights
Fly:  6​h 15​min
End: Chicago

5
nights
Manhattan Beach

Manhattan Beach ©
Manhattan Beach is a city in southwestern Los Angeles County, California, United States, on the Pacific coast south of El Segundo, and north of Hermosa Beach. You'll find plenty of places to visit near Manhattan Beach: Santa Monica (26-Mile Bike Path, Santa Monica State Beach, & more), Beverly Hills (Two Rodeo Drive & Mulholland Drive) and Malibu (The Getty Villa, Zuma Beach, & more). And it doesn't end there: enjoy the sand and surf at Manhattan Beach, don't miss a visit to Santa Monica Yacht Harbor Sign, and take in the waterfront at Redondo Beach Pier.

To find photos, other places to visit, and tourist information, read our Manhattan Beach road trip app .

Chicago to Manhattan Beach is an approximately 8-hour flight. You can also drive; or take a train. Traveling from Chicago to Manhattan Beach, you'll gain 2 hours due to the time zone difference. While traveling from Chicago, expect little chillier days and about the same nights in Manhattan Beach, ranging from highs of 76°F to lows of 65°F. Finish your sightseeing early on the 29th (Mon) to allow enough time to travel to Pismo Beach.

Things to do in Manhattan Beach

Parks Outdoors Beaches

Side Trips

Santa Monica, Malibu, Beverly Hills, Hermosa Beach Pier, Redondo Beach Pier
Highlights from your plan
Manhattan Beach ©
Manhattan Beach
Santa Monica Pier ©
Santa Monica Pier
Santa Monica State Beach ©
Santa Monica State Beach

2
nights
Ventura

Ventura, officially the City of San Buenaventura, is the county seat of Ventura County, California, United States. Start off your visit on the 30th (Tue): take in the waterfront at Stearns Wharf, steep yourself in history at Old Mission Santa Barbara, then admire nature's wide array of creatures at Santa Barbara Zoo, and finally stop by Fox Fine Jewelry. On the 31st (Wed), you'll have a packed day of sightseeing: take a stroll through State Street Underpass and then indulge your senses at some of the top wineries in the area.

For where to stay, reviews, and more tourist information, refer to the Ventura trip planning app .

Traveling by car from Manhattan Beach to Ventura takes 1.5 hours. Alternatively, you can take a train; or do a combination of flight and bus. In July, daytime highs in Ventura are 73°F, while nighttime lows are 62°F. Finish up your sightseeing early on the 31st (Wed) so you can go by car to Pismo Beach.

Things to do in Ventura

Tours Zoos & Aquariums Parks

Side Trip

Santa Barbara
Highlights from your plan
Wine Tours & Tastings
Old Mission Santa Barbara ©
Old Mission Santa Barbara
Santa Barbara Zoo ©
Santa Barbara Zoo

2
nights
Pismo Beach

Pismo Beach ©
Pismo Beach is a city in San Luis Obispo County, in the Central Coast area of California, United States. Start off your visit on the 1st (Thu): get some thrills on the water with a speed boat tour, then stop by Alapay Cellars, then look for all kinds of wild species at Monarch Butterfly Grove, and finally take in the waterfront at Pismo Pier.

To find photos, maps, reviews, and tourist information, read Pismo Beach holiday maker .

Traveling by car from Ventura to Pismo Beach takes 2.5 hours. Alternatively, you can take a train; or take a bus. Traveling from Ventura in July, you will find days in Pismo Beach are somewhat warmer (80°F), and nights are little chillier (56°F). Wrap up your sightseeing on the 2nd (Fri) to allow time to drive to Big Sur.

Things to do in Pismo Beach

Wildlife Parks Outdoors

Side Trip

Avila Beach
Highlights from your plan
Monarch Butterfly Grove ©
Monarch Butterfly Grove
Speed Boats Tours

3
nights
Big Sur

Big Sur ©
A sparsely populated area with stunning views, Big Sur attracts artists and tourists traveling California’s scenic Highway 1.
Big Sur is known for nature, beaches, spas, historic sites, and trails. Your plan includes some of its best attractions: tour the pleasant surroundings at Julia Pfeiffer Burns State Park, kick back and relax at Sand Dollar Beach, visit a coastal fixture at Point Sur State Historic Park, and immerse yourself in nature at Andrew Molera State Park.

To see photos, other places to visit, reviews, and more tourist information, refer to the Big Sur holiday planning tool .

Traveling by car from Pismo Beach to Big Sur takes 3.5 hours. Alternatively, you can do a combination of train and taxi; or take a bus. Traveling from Pismo Beach in August, you will find days in Big Sur are slightly colder (70°F), and nights are about the same (57°F). Wrap up your sightseeing on the 5th (Mon) to allow time to drive to San Francisco.

Things to do in Big Sur

Parks Nature Outdoors

Side Trip

Sand Dollar Beach
Highlights from your plan
Julia Pfeiffer Burns State Park ©
Julia Pfeiffer Burns State Park
Pfeiffer State Beach ©
Pfeiffer State Beach
Pfeiffer Big Sur State Park ©
Pfeiffer Big Sur State Park

2
nights
San Francisco

San Francisco ©
San Francisco is a top holiday destination featuring scenic beauty and great ethnic and cultural diversity.
Kick off your visit on the 6th (Tue): contemplate the long history of Golden Gate Bridge, then head off the coast to Alcatraz Island, and then take a leisurely stroll along Fisherman's Wharf. Here are some ideas for day two: look for gifts at Exploratorium and then walk around Golden Gate Park.

Before you visit San Francisco, use our trip planner to discover what you can do and see there.

Getting from Big Sur to San Francisco by car takes about 3 hours. Other options: do a combination of taxi and flight; or take a bus. In August, plan for daily highs up to 73°F, and evening lows to 59°F. Wrap up your sightseeing on the 7th (Wed) early enough to travel back home.

Things to do in San Francisco

Parks Historic Sites Shopping
Highlights from your plan
Alcatraz Island ©
Alcatraz Island
Exploratorium ©
Exploratorium
Golden Gate Bridge ©
Golden Gate Bridge

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