27 days in California Itinerary

27 days in California Itinerary

Created using Inspirock California attractions planner

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Route & dates

27 days in California Itinerary

Start: Chicago
Fly:  6​h 15​min
1
San Francisco
— 4 nights
Drive:  1​h 15​min
2
Napa
— 4 nights
Drive:  2​h 45​min
3
Truckee
— 3 nights
Drive:  4​h
4
Yosemite National Park
— 5 nights
Drive:  4​h 45​min
5
Carmel
— 1 night
Fly:  4​h
6
San Diego
— 4 nights
Drive:  2​h 15​min
7
Los Angeles
— 5 nights
Fly:  7​h
End: Chicago

4
nights
San Francisco

San Francisco ©
San Francisco is a top holiday destination featuring scenic beauty and great ethnic and cultural diversity.
San Francisco is known for nature, museums, parks, nightlife, and shopping. Your plan includes some of its best attractions: snap pictures at Golden Gate Bridge, buy something for everyone on your list at Ferry Building Marketplace, head off the coast to Alcatraz Island, and get curious at Exploratorium.

For traveler tips, photos, and more tourist information, read our San Francisco online vacation planner .

Chicago to San Francisco is an approximately 6.5-hour flight. You can also do a combination of flight and train; or drive. Traveling from Chicago to San Francisco, you'll gain 2 hours due to the time zone difference. When traveling from Chicago in December, plan for warmer days and somewhat warmer nights in San Francisco: temperatures range from 59°F by day to 45°F at night. Wrap up your sightseeing on the 19th (Thu) to allow time to drive to Napa.

Things to do in San Francisco

Museums Parks Childrens Museums
Highlights from your plan
Golden Gate Bridge ©
Golden Gate Bridge
Alcatraz Island ©
Alcatraz Island
Fisherman's Wharf ©
Fisherman's Wharf

4
nights
Napa

Napa ©
Located just 80 km (50 mi) north of San Francisco, Napa sits at the southern end of the scenic Napa Valley, one of the world's major wine regions.
Explore the numerous day-trip ideas around Napa: Sonoma (MacLaren & Simraceway Performance Driving Center), Pride Mountain Vineyards (in St. Helena) and Healdsburg (Jordan Vineyard & Winery & Sapphire Hill Winery). The adventure continues: indulge your senses at some of the top wineries in the area, admire the masterpieces at The Hess Collection Winery & Art Museum, do a tasting at Taylor Family Vineyards, and look for gifts at Petaluma Seed Bank.

To see more things to do, traveler tips, ratings, and more tourist information, read our Napa holiday planning tool .

You can drive from San Francisco to Napa in 1.5 hours. Other options are to do a combination of subway and bus; or take a bus. Expect slightly colder evenings in Napa when traveling from San Francisco in December, with lows around 35°F. Finish up your sightseeing early on the 23rd (Mon) so you can travel to Truckee.

Things to do in Napa

Wineries Tours Museums

Side Trips

Sonoma, Healdsburg, St. Helena, B Cellars Vineyards and Winery, Petaluma Seed Bank
Highlights from your plan
Sapphire Hill Winery ©
Sapphire Hill Winery
Wine Tours & Tastings
Simraceway Performance Driving Center ©

3
nights
Truckee

Truckee ©
Truckee is an incorporated town in Nevada County, California, United States. Step out of Truckee to go to Tahoe City and see Hellman-Ehrman Mansion, which is approximately 38 minutes away. And it doesn't end there: ski along the peaceful trails at Tahoe Donner Cross Country, steep yourself in history at Rainbow Bridge / Donner Summit Bridge, hit the slopes at Tahoe Donner Downhill Ski Area, and don't miss a visit to Concours d'Elegance Lake Tahoe.

For ratings, traveler tips, photos, and more tourist information, read our Truckee online journey planner .

You can drive from Napa to Truckee in 3 hours. When traveling from Napa in December, plan for a bit cooler days and much colder nights in Truckee: temperatures range from 41°F by day to 15°F at night. Wrap up your sightseeing on the 26th (Thu) to allow time to travel to Yosemite National Park.

Things to do in Truckee

Winter Sports Outdoors Parks

Side Trips

Tahoe City, Emerald Bay State Park, Concours d'Elegance Lake Tahoe
Highlights from your plan
Emerald Bay State Park ©
Emerald Bay State Park
Hellman-Ehrman Mansion ©
Hellman-Ehrman Mansion
Rainbow Bridge / Donner Summit Bridge ©

5
nights
Yosemite National Park

Yosemite National Park ©
Massive granite mountains, towering waterfalls, groves of Giant Sequoia trees, and wilderness as far as the eye can see distinguish the landscape of Yosemite National Park.
Yosemite National Park is known for nature, trails, scenic drive, wildlife, and museums. Your plan includes some of its best attractions: take in the dramatic natural features at Glacier Point, don't miss a visit to Yosemite Village, get great views at Yosemite, Tunnel View, and take in the awesome beauty at Mt. Hoffmann.

For where to stay, maps, ratings, and more tourist information, go to the Yosemite National Park trip builder tool .

Traveling by car from Truckee to Yosemite National Park takes 4 hours. In December, daily temperatures in Yosemite National Park can reach 46°F, while at night they dip to 14°F. Wrap up your sightseeing on the 31st (Tue) early enough to drive to Carmel.

Things to do in Yosemite National Park

Parks Outdoors Nature
Highlights from your plan
Glacier Point ©
Glacier Point
Badger Pass Ski Area ©
Badger Pass Ski Area
Mariposa Grove ©
Mariposa Grove

1
night
Carmel

Carmel ©
Carmel-by-the-Sea, often simply called Carmel, is a city in Monterey County, California, United States, founded in 1902 and incorporated on October 31, 1916. Kick off your visit on the 1st (Wed): enjoy the sand and surf at Point Lobos, take a memorable drive along 17-Mile Drive, then get to know the fascinating history of Pacific Grove Oceanview Boulevard, and finally make a trip to Fairy Tale Cottages of Hugh Comstock.

To find traveler tips, photos, where to stay, and more tourist information, use the Carmel vacation planner.

You can drive from Yosemite National Park to Carmel in 5 hours. Alternatively, you can do a combination of car and flight; or do a combination of car, flight, and shuttle. When traveling from Yosemite National Park in December, plan for a bit warmer days and much warmer nights in Carmel: temperatures range from 62°F by day to 43°F at night. Finish your sightseeing early on the 1st (Wed) so you can travel to San Diego.

Things to do in Carmel

Outdoors Scenic Drive Parks

Side Trips

17-Mile Drive, Pacific Grove Oceanview Boulevard
Highlights from your plan
Point Lobos ©
Point Lobos
Pacific Grove Oceanview Boulevard ©
17-Mile Drive ©
17-Mile Drive

4
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.
Step out of San Diego with an excursion to Self Realization Fellowship Hermitage & Meditation Gardens in Encinitas--about 30 minutes away. There's much more to do: meet the residents at San Diego Zoo, immerse yourself in nature at Torrey Pines State Natural Reserve, examine the collection at Maritime Museum of San Diego, and let little ones run wild at Balboa Park.

To find other places to visit, ratings, and tourist information, you can read our San Diego trip planner .

Traveling by flight from Carmel to San Diego takes 4 hours. Alternatively, you can do a combination of shuttle and flight; or drive. Expect a bit warmer evenings in San Diego when traveling from Carmel in January, with lows around 51°F. Wrap up your sightseeing on the 5th (Sun) to allow time to drive to Los Angeles.

Things to do in San Diego

Parks Zoos & Aquariums Museums

Side Trip

Self Realization Fellowship Hermitage & Meditation Gardens
Highlights from your plan
San Diego Zoo ©
San Diego Zoo
USS Midway Museum ©
USS Midway Museum
Balboa Park ©
Balboa Park

5
nights
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.
Change things up with these side-trips from Los Angeles: Anaheim (Disneyland Park & Disney California Adventure Park). And it doesn't end there: get in on the family fun at Universal Studios Hollywood, examine the collection at The Getty Center, see the sky in a new way at Griffith Observatory, and explore the world behind art at Diorama-museum of Bhagavad-gita.

For traveler tips, maps, more things to do, and tourist information, you can read our Los Angeles trip planner .

You can drive from San Diego to Los Angeles in 2.5 hours. Other options are to take a bus; or fly. January in Los Angeles sees daily highs of 70°F and lows of 49°F at night. Wrap up your sightseeing by early afternoon on the 10th (Fri) to allow time for travel back home.

Things to do in Los Angeles

Theme Parks Museums Fun & Games

Side Trips

Anaheim, Santa Monica Pier
Highlights from your plan
Diorama-museum of Bhagavad-gita ©
Diorama-museum of Bhagavad-gita
Disneyland Park ©
Disneyland Park
Universal Studios Hollywood ©
Universal Studios Hollywood

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