9 days in San Francisco Bay Area & San Diego Itinerary

9 days in San Francisco Bay Area & San Diego Itinerary

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Route & dates

9 days in San Francisco Bay Area & San Diego Itinerary

Start: Chicago
Fly:  6​h 15​min
1
San Francisco
— 3 nights
Drive:  1​h 30​min
2
St. Helena
— 2 nights
Fly:  3​h 45​min
3
San Diego
— 3 nights
Fly:  6​h 15​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.
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, head off the coast to Alcatraz Island, take in the waterfront at Fisherman's Wharf, and stroll around Golden Gate Park.

To see more things to do, ratings, maps, and more tourist information, read San Francisco trip planning website .

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. In September, plan for daily highs up to 76°F, and evening lows to 58°F. Finish your sightseeing early on the 24th (Tue) to allow enough time to drive to St. Helena.

Things to do in San Francisco

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

2
nights
St. Helena

St. Helena ©
The city of St.
Start off your visit on the 25th (Wed): learn about winemaking at Anderson's Conn Valley Vineyards, then learn about winemaking at V. Sattui Winery, and then savor the flavors at Food & Drink. Here are some ideas for day two: do a tasting at Pride Mountain Vineyards, then do a tasting at Jordan Vineyard & Winery, then learn about winemaking at Gracianna Winery, and finally learn about winemaking at B Cellars Vineyards and Winery.

To find reviews, where to stay, other places to visit, and more tourist information, use the St. Helena day trip tool .

Traveling by car from San Francisco to St. Helena takes 1.5 hours. Alternatively, you can do a combination of subway and bus; or take a bus. Traveling from San Francisco in September, expect nights in St. Helena to be slightly colder, around 51°F, while days are somewhat warmer, around 84°F. Finish your sightseeing early on the 26th (Thu) so you can travel to San Diego.

Things to do in St. Helena

Wineries Tours

Side Trips

Healdsburg, Wine Tours & Tastings, B Cellars Vineyards and Winery
Highlights from your plan
Anderson's Conn Valley Vineyards ©
Anderson's Conn Valley Vineyards
Wine Tours & Tastings
Gracianna Winery ©
Gracianna Winery

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.
San Diego is known for zoos & aquariums, museums, beaches, parks, and historic sites. Your plan includes some of its best attractions: get to know the resident critters at San Diego Zoo, sample the fine beverages at Malahat Spirits, immerse yourself in nature at Torrey Pines State Natural Reserve, and examine the collection at USS Midway Museum.

For more things to do, where to stay, maps, and other tourist information, you can read our San Diego driving holiday planning app .

Traveling by flight from St. Helena to San Diego takes 4 hours. Alternatively, you can do a combination of bus and flight; or drive. When traveling from St. Helena in September, plan for little chillier days and somewhat warmer nights in San Diego: temperatures range from 79°F by day to 68°F at night. Wrap up your sightseeing on the 29th (Sun) early enough to travel back home.

Things to do in San Diego

Parks Zoos & Aquariums Fun & Games
Highlights from your plan
San Diego Zoo ©
San Diego Zoo
USS Midway Museum ©
USS Midway Museum
Balboa Park ©
Balboa Park

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