14 days in San Francisco Bay Area & San Diego Itinerary

14 days in San Francisco Bay Area & San Diego Itinerary

Created using Inspirock California trip itinerary builder

Make it your trip
Fly to Sacramento International Airport, Drive to Healdsburg
1
Healdsburg
— 2 nights
Drive
2
Napa
— 3 nights
Drive
3
San Francisco
— 4 nights
Fly
4
San Diego
— 4 nights
Fly

S M T W T F S
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Healdsburg

— 2 nights
The quaint city of Healdsburg is one of northern California's wine capitals, serving as the meeting point for three of Sonoma's most important wine-producing regions.
On the 5th (Mon), savor the flavors at Food & Drink, then learn about winemaking at Alexander Valley Vineyards, then do a tasting at Gracianna Winery, and finally learn about winemaking at Stephen & Walker Winery. On your second day here, do a tasting at Jordan Vineyard & Winery, then take in the exciting artwork at Patrick Amiot, and then identify plant and animal life at Safari West.

Plan my trip to Healdsburg with suggested itineraries provided by Inspirock.

Kelowna, Canada to Healdsburg is an approximately 10-hour combination of flight and car. You can also drive. Expect a daytime high around 30°C in October, and nighttime lows around 9°C. Finish up your sightseeing early on the 6th (Tue) so you can go by car to Napa.

Things to do in Healdsburg

Wineries · Parks · Tours · Wildlife

Side Trips

Napa

— 3 nights

America's Wine Country

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: MacLaren (in Sonoma) and St. Helena (Anderson's Conn Valley Vineyards, Pride Mountain Vineyards, &more). There's still lots to do: indulge your senses at some of the top wineries in the area, learn about winemaking at V. Sattui Winery, look for gifts at Oxbow Public Market, and make a trip to Sonoma Plaza.

To find ratings, photos, maps, and more tourist information, you can read our Napa vacation maker site.

Traveling by car from Healdsburg to Napa takes 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. Expect a daytime high around 29°C in October, and nighttime lows around 8°C. Finish your sightseeing early on the 9th (Fri) to allow enough time to drive to San Francisco.

Things to do in Napa

Wineries · Tours · Parks · Shopping

Side Trips

San Francisco

— 4 nights

City by the Bay

San Francisco is a top holiday destination featuring scenic beauty and great ethnic and cultural diversity.
San Francisco is known for nature, parks, and museums. Your plan includes some of its best attractions: snap pictures at Golden Gate Bridge, stroll around Golden Gate Park, make a trip to Ferry Building Marketplace, and examine the collection at Musee Mecanique.

For where to stay, ratings, maps, and other tourist information, read our San Francisco trip itinerary maker tool.

You can drive from Napa to San Francisco in 1.5 hours. Other options are to do a combination of bus and subway; or take a bus. Traveling from Napa in October, expect a bit warmer with lows of 15°C in San Francisco. Wrap up your sightseeing on the 13th (Tue) to allow time to travel to San Diego.

Things to do in San Francisco

Parks · Historic Sites · Museums · Neighborhoods

San Diego

— 4 nights

America's Finest City

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.
Change things up with a short trip to Self Realization Fellowship Hermitage & Meditation Gardens in Encinitas (about 32 minutes away). There's much more to do: learn about wildlife with up-close encounters at San Diego Zoo, examine the collection at Maritime Museum of San Diego, immerse yourself in nature at Torrey Pines State Natural Reserve, and let the kids burn off some steam at Balboa Park.

To find traveler tips, photos, ratings, and tourist information, you can read our San Diego road trip site.

Traveling by flight from San Francisco to San Diego takes 4 hours. Alternatively, you can drive; or take a bus. Traveling from San Francisco in October, expect somewhat warmer with lows of 20°C in San Diego. Finish your sightseeing early on the 17th (Sat) to allow enough time to travel back home.

Things to do in San Diego

Parks · Zoos & Aquariums · Museums · Theme Parks

Side Trip