29 days in California Itinerary

29 days in California Itinerary

Created using Inspirock California planner

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Route & dates

29 days in California Itinerary

Start: Chicago
Fly:  6​h 15​min
1
San Diego
— 4 nights
Drive:  2​h 15​min
2
Los Angeles
— 6 nights
Fly + Drive:  4​h 15​min
3
Yosemite National Park
— 4 nights
Drive:  4​h 45​min
4
Carmel
— 3 nights
Drive:  3​h 15​min
5
St. Helena
— 5 nights
Drive:  1​h 30​min
6
San Francisco
— 6 nights
Fly:  6​h 15​min
End: Chicago

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.
Get a sense of the local culture at USS Midway Museum and Maritime Museum of San Diego. Shop till you drop at Gaslamp Quarter and Africa and Beyond. There's much more to do: enjoy the sand and surf at La Jolla Cove, stroll through Windansea Beach, admire nature's wide array of creatures at San Diego Zoo, and let the kids burn off some steam at Balboa Park.

Plan my day in San Diego using traveler tips and tourist information provided by Inspirock.

Chicago to San Diego is an approximately 6.5-hour flight. You can also drive; or take a train. Traveling from Chicago to San Diego, you'll gain 2 hours due to the time zone difference. Traveling from Chicago in February, things will get warmer in San Diego: highs are around 68°F and lows about 53°F. Finish your sightseeing early on the 5th (Wed) to allow enough time to drive to Los Angeles.

Things to do in San Diego

Parks Beaches Outdoors
Highlights from your plan
La Jolla Cove ©
La Jolla Cove
USS Midway Museum ©
USS Midway Museum
Maritime Museum of San Diego ©
Maritime Museum of San Diego

6
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.
Shop till you drop at Montana Avenue and Hammer Museum. You'll enjoy a bit of beach vacationing at Venice Beach and Boardwalk and Santa Monica State Beach. Change things up with these side-trips from Los Angeles: Santa Monica (Third Street Promenade, Bergamot Station, & more). There's much more to do: take a stroll through Abbot Kinney Boulevard, hunt for treasures at Melrose Trading Post, get to know the fascinating history of El Pueblo de Los Angeles, and browse the different shops at The Grove.

To see other places to visit, photos, traveler tips, and other tourist information, you can read our Los Angeles holiday app .

You can drive from San Diego to Los Angeles in 2.5 hours. Other options are to take a bus; or fly. In February, daily temperatures in Los Angeles can reach 71°F, while at night they dip to 51°F. Cap off your sightseeing on the 11th (Tue) early enough to travel to Yosemite National Park.

Things to do in Los Angeles

Neighborhoods Shopping Beaches

Side Trips

Santa Monica, Two Rodeo Drive
Highlights from your plan
Abbot Kinney Boulevard ©
Abbot Kinney Boulevard
The Getty Center ©
The Getty Center
Santa Monica Pier ©
Santa Monica Pier

4
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.
Give yourself a bit of retail therapy at Yosemite Museum Gallery and Ansel Adams Gallery. Visit Big Trees Lodge, National Historic Landmark and Yosemite Cemetery for their historical value. On the 13th (Thu), spend an exhilarating day on the slopes at Yosemite Ski and Snowboard Area. The adventure continues: take your sightseeing to a higher altitude at Cathedral Beach Picnic Area, make a trip to Pothole Dome, tee off at Big Trees Golf Course, and hit the slopes at Curry Village Ice Rink.

For reviews, ratings, where to stay, and more tourist information, refer to the Yosemite National Park holiday planner.

Traveling by combination of flight and car from Los Angeles to Yosemite National Park takes 4.5 hours. Alternatively, you can drive; or do a combination of flight and bus. In February, Yosemite National Park is cooler than Los Angeles - with highs of 48°F and lows of 18°F. Finish your sightseeing early on the 15th (Sat) to allow enough time to drive to Carmel.

Things to do in Yosemite National Park

Parks Outdoors Winter Sports
Highlights from your plan
Cathedral Beach Picnic Area ©
Cathedral Beach Picnic Area
Yosemite Museum Gallery ©
Yosemite Museum Gallery
Ansel Adams Gallery ©
Ansel Adams Gallery

3
nights
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. Get some cultural insight at Pacific Grove Oceanview Boulevard and Gallery by the Sea Carmel. Your itinerary includes some good beach time at Point Lobos and Carmel River State Beach. Change things up with a short trip to Parsonage Winery Tasting Room in Carmel Valley (about 32 minutes away). And it doesn't end there: immerse yourself in nature at Asilomar State Beach, enjoy the sand and surf at China Cove and Gibson Beach, and tour the pleasant surroundings at Pacific Grove Shoreline Parkway Marine Refuge.

To find ratings, maps, traveler tips, and other tourist information, read Carmel online holiday builder .

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 February, plan for a bit warmer days and much warmer nights in Carmel: temperatures range from 63°F by day to 45°F at night. Wrap up your sightseeing on the 18th (Tue) early enough to drive to St. Helena.

Things to do in Carmel

Beaches Outdoors Parks

Side Trips

Pacific Grove, Parsonage Winery Tasting Room
Highlights from your plan
Point Lobos ©
Point Lobos
Pacific Grove Oceanview Boulevard ©
Pacific Grove Oceanview Boulevard
Asilomar State Beach ©
Asilomar State Beach

5
nights
St. Helena

St. Helena ©
The city of St.
Do some cultural sightseeing at Modus Operandi Cellars and Inglenook. Explore the numerous day-trip ideas around St. Helena: Healdsburg (Jordan Vineyard & Winery, Stephen & Walker Winery, & more) and The Hess Collection Winery & Art Museum (in Napa). There's still lots to do: learn about winemaking at B Cellars Vineyards and Winery, wander the wide-open spaces of Long Meadow Ranch - Rutherford Estate, take in the exciting artwork at Mumm Napa, and stop by Oxbow Public Market.

For ratings, more things to do, photos, and tourist information, use the St. Helena holiday planning website .

Traveling by car from Carmel to St. Helena takes 3.5 hours. Alternatively, you can fly; or do a combination of flight, subway, and bus. Plan for a bit cooler nights when traveling from Carmel in February since evenings lows in St. Helena dip to 40°F. Finish your sightseeing early on the 23rd (Sun) so you can drive to San Francisco.

Things to do in St. Helena

Wineries Museums Shopping

Side Trips

Healdsburg, Oakville, Rutherford, Calistoga, Napa
Highlights from your plan
Pride Mountain Vineyards ©
Pride Mountain Vineyards
Inglenook ©
Inglenook
Jordan Vineyard & Winery ©
Jordan Vineyard & Winery

6
nights
San Francisco

San Francisco ©
San Francisco is a top holiday destination featuring scenic beauty and great ethnic and cultural diversity.
Do your shopping at Ferry Building Marketplace and Union Square. Get a sense of the local culture at Fisherman's Wharf and City Lights Booksellers. Next up on the itinerary: head off the coast to Alcatraz Island, browse the eclectic array of goods at Ferry Plaza Farmers Market, shop like a local with Ghirardelli Square, and take a stroll through The Castro.

For reviews, traveler tips, ratings, and tourist information, read San Francisco trip builder app .

Traveling by car from St. Helena to San Francisco takes 1.5 hours. Alternatively, you can do a combination of bus and subway; or take a bus. Traveling from St. Helena in February, you can expect nighttime temperatures to be somewhat warmer in San Francisco, with lows of 48°F. Wrap up your sightseeing on the 29th (Sat) early enough to travel back home.

Things to do in San Francisco

Neighborhoods Shopping Historic Sites
Highlights from your plan
Alcatraz Island ©
Alcatraz Island
Golden Gate Bridge ©
Golden Gate Bridge
Fisherman's Wharf ©
Fisherman's Wharf

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