11 days in United States Itinerary

11 days in United States Itinerary

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Route & dates

11 days in United States Itinerary

Start: Chicago
Fly:  6​h 30​min
1
San Francisco
— 3 nights
Drive:  1​h
2
Sonoma
— 1 night
Drive:  2​h 30​min
3
Santa Cruz
— 1 night
Drive:  1​h
4
Monterey
— Few hours
Drive:  3​h
5
San Simeon
— 1 night
Drive:  4​h 30​min
6
Los Angeles
— 1 night
Drive:  2​h 30​min
7
San Diego
— 3 nights
Fly:  6​h 30​min
End: Chicago

3
nights
San Francisco

San Francisco ©
San Francisco is a top holiday destination featuring scenic beauty and great ethnic and cultural diversity.
You'll explore and learn at Exploratorium and Musee Mecanique. We've included these beaches for you: Marshall’s Beach and Fort Funston National Park. There's lots more to do: explore and take pictures at Alcatraz Island, take in the waterfront at Fisherman's Wharf, steep yourself in history at Golden Gate Bridge, and get to know the fascinating history of The Embarcadero.

Find out how to plan San Francisco trip without stress by asking Inspirock to help create an itinerary.

Chicago to San Francisco is an approximately 6.5-hour flight. You can also do a combination of flight and train; or drive. The time zone changes from Central Standard Time to Pacific Standard Time, which is usually a -2 hour difference. Traveling from Chicago in July, expect San Francisco to be slightly colder, temps between 73°F and 57°F. Finish your sightseeing early on the 24th (Wed) to allow enough time to drive to Sonoma.

Things to do in San Francisco

Parks Beaches Outdoors
Highlights from your plan
Golden Gate Bridge ©
Golden Gate Bridge
Alcatraz Island ©
Alcatraz Island
Fisherman's Wharf ©
Fisherman's Wharf

1
night
Sonoma

Set in the heart of one of the United States' most esteemed wine-producing regions, just 45 minutes from San Francisco, Sonoma boasts colonial Mexican architecture, including a mission.
Start off your visit on the 24th (Wed): indulge your taste buds at Food & Drink.

For reviews, other places to visit, photos, and other tourist information, read our Sonoma online attractions planner .

Drive from San Francisco to Sonoma in 1.5 hours. Alternatively, you can take a bus; or do a combination of subway and bus. Traveling from San Francisco in July, you will find days in Sonoma are somewhat warmer (81°F), and nights are a bit cooler (52°F). You'll have a few hours on the 25th (Thu) to wrap things up before traveling to Santa Cruz.

Things to do in Sonoma

Tours Shopping

Side Trip

Oxbow Public Market
Highlights from your plan
Wine Tours & Tastings
Oxbow Public Market ©
Oxbow Public Market

1
night
Santa Cruz

Santa Cruz ©
Santa Cruz remains synonymous with surfing, but this counterculture bastion offers plenty even if you don't plan to catch any waves.
Start off your visit on the 25th (Thu): see the interesting displays at Santa Cruz Surfing Museum and then take in the waterfront at Santa Cruz Wharf.

For reviews, ratings, and other tourist information, go to the Santa Cruz road trip site .

Traveling by car from Sonoma to Santa Cruz takes 2.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. When traveling from Sonoma in July, plan for little chillier days and about the same nights in Santa Cruz: temperatures range from 73°F by day to 55°F at night. Finish your sightseeing early on the 26th (Fri) so you can drive to Monterey.

Things to do in Santa Cruz

Museums
Highlights from your plan
Santa Cruz Surfing Museum ©
Santa Cruz Surfing Museum
Santa Cruz Wharf ©
Santa Cruz Wharf

few
hours
Monterey

Monterey ©
Monterey is a city in the U.S. To see maps, reviews, ratings, and more tourist information, use the Monterey trip itinerary maker tool .

Drive from Santa Cruz to Monterey in an hour. Alternatively, you can take a bus. In July, daytime highs in Monterey are 69°F, while nighttime lows are 55°F. Wrap up your sightseeing by early afternoon on the 26th (Fri) to allow enough time to drive to San Simeon.

Things to do in Monterey

Historic Sites

Side Trip

Pacific Grove Oceanview Boulevard
Highlights from your plan
Pacific Grove Oceanview Boulevard ©
Pacific Grove Oceanview Boulevard

1
night
San Simeon

San Simeon ©
When you arrive in tiny San Simeon, which lies halfway between San Francisco and Los Angeles, you can see why William Randolph Hearst chose this coastal locale for his famous hilltop castle.
To find photos, ratings, maps, and other tourist information, read our San Simeon online tour itinerary planner .

You can drive from Monterey to San Simeon in 3 hours. Alternatively, you can take a train; or do a combination of bus and car. While traveling from Monterey, expect much hotter days and about the same nights in San Simeon, ranging from highs of 94°F to lows of 56°F. Cap off your sightseeing on the 27th (Sat) early enough to go by car to Los Angeles.

Things to do in San Simeon

Shopping Wineries
Highlights from your plan
Hearst Ranch Winery ©
Hearst Ranch Winery

1
night
Los Angeles

Los Angeles ©
Surrounded by mountain ranges, forests, valleys, beaches, and deserts, the metropolitan area of Los Angeles is home to over 17 million people.
Kick off your visit on the 27th (Sat): explore the world behind art at Diorama-museum of Bhagavad-gita, then enjoy the sand and surf at Venice Beach and Boardwalk, then don't miss a visit to Abbot Kinney Boulevard, and finally shop like a local with Third Street Promenade.

For maps, ratings, reviews, and more tourist information, go to the Los Angeles holiday builder site .

Traveling by car from San Simeon to Los Angeles takes 4.5 hours. Alternatively, you can do a combination of bus and flight; or do a combination of bus and train. While traveling from San Simeon, expect slightly colder days and somewhat warmer nights in Los Angeles, ranging from highs of 83°F to lows of 66°F. Wrap up your sightseeing by early afternoon on the 28th (Sun) to allow time for the car ride to San Diego.

Things to do in Los Angeles

Shopping Museums Beaches

Side Trip

Third Street Promenade
Highlights from your plan
The Getty Center ©
The Getty Center
Venice Beach and Boardwalk ©
Venice Beach and Boardwalk
Abbot Kinney Boulevard ©
Abbot Kinney Boulevard

3
nights
San Diego

San Diego ©
Divided into neighborhoods with distinct characters and cultural heritages, San Diego sits just north of the Mexican border and offers visitors a blend of tourist attractions, including a lively nightlife, diverse cuisine, and a thriving musical scene.
Your cultural itinerary includes sights like USS Midway Museum and San Diego Air & Space Museum. Museum-lovers will appreciate Old Town Model Railroad Depot and Spanish Village Art Center. There's lots more to do: enjoy the sand and surf at La Jolla Cove, tour the pleasant surroundings at Coronado Beach, shop like a local with Gaslamp Quarter, and admire the striking features of Marston House Museum.

To find maps, where to stay, and more tourist information, refer to the San Diego day trip site .

Traveling by car from Los Angeles to San Diego takes 2.5 hours. Alternatively, you can take a bus; or fly. Traveling from Los Angeles in July, expect nights in San Diego to be about the same, around 68°F, while days are little chillier, around 77°F. You will have some time to spend on the 31st (Wed) before leaving for home.

Things to do in San Diego

Beaches Outdoors Parks

Side Trip

Coronado Beach
Highlights from your plan
La Jolla Cove ©
La Jolla Cove
USS Midway Museum ©
USS Midway Museum
San Diego Air & Space Museum ©
San Diego Air & Space Museum

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