16 days in San Francisco Bay Area & Napa Valley Itinerary

16 days in San Francisco Bay Area & Napa Valley Itinerary

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Route & dates

16 days in San Francisco Bay Area & Napa Valley Itinerary

Start: Montreal
+2
Fly + foot + shuttle:  10​h 30​min
1
Monterey
— 2 nights
Drive:  15​min
2
Carmel
— 3 nights
Drive:  2​h 45​min
3
Napa
— 2 nights
Drive:  45​min
4
Calistoga
— 1 night
Drive:  45​min
5
Healdsburg
— 3 nights
Drive:  1​h 30​min
6
San Francisco
— 3 nights
Fly:  9​h 15​min
End: Montreal

2
nights
Monterey

Monterey ©
Monterey is a city in the U.S. Start off your visit on the 31st (Sat): savor the flavors at Pacific Grove Certified Farmers' Market. Keep things going the next day: get to know the fascinating history of Pacific Grove Oceanview Boulevard, look for gifts at A Taste of Monterey-Wine Market & Bistro, and then savor the flavors at Food & Drink.

To find other places to visit, reviews, traveler tips, and other tourist information, read our Monterey road trip planner .

Montreal, Canada to Monterey is an approximately 10.5-hour combination of flight and shuttle. You can also fly; or drive. You'll gain 3 hours traveling from Montreal to Monterey due to the time zone difference. Traveling from Montreal in August, expect Monterey to be slightly colder, temps between 24°C and 16°C. Wrap up your sightseeing on the 2nd (Mon) to allow time to drive to Carmel.

Things to do in Monterey

Shopping Outdoors Parks

Side Trip

Pacific Grove
Highlights from your plan

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. Do some cultural sightseeing at Ocean Avenue and Point Sur State Historic Park. Visit Carmel River State Beach and Point Lobos for some beach relaxation. Explore the numerous day-trip ideas around Carmel: Big Sur (Limekiln State Park, McWay Falls, & more).

For where to stay, photos, traveler tips, and tourist information, refer to the Carmel trip planner .

Carmel is very close to Monterey. September in Carmel sees daily highs of 26°C and lows of 15°C at night. Finish your sightseeing early on the 5th (Thu) to allow enough time to drive to Napa.

Things to do in Carmel

Parks Nature Outdoors

Side Trip

Big Sur
Highlights from your plan
Carmel River State Beach ©
Carmel River State Beach
Point Lobos ©
Point Lobos
Pfeiffer State Beach ©
Pfeiffer State Beach

2
nights
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.
Start off your visit on the 6th (Fri): take a memorable tour with Tours, then do a tasting at Robert Mondavi Winery, and then learn about winemaking at B Cellars Vineyards and Winery. Get ready for a full day of sightseeing on the next day: learn about winemaking at Robert Biale Vineyards, do a tasting at Trefethen Family Vineyards, learn about winemaking at Ma(i)sonry Napa Valley, then learn about winemaking at Jessup Cellars, and finally learn about winemaking at Hendry Ranch Wines.

Before you visit Napa, use our trip planner to discover what you can do and see there.

Getting from Carmel to Napa by car takes about 3 hours. Other options: do a combination of flight, subway, and bus; or take a bus. Traveling from Carmel in September, you will find days in Napa are a bit warmer (32°C), and nights are slightly colder (12°C). Finish your sightseeing early on the 7th (Sat) so you can drive to Calistoga.

Things to do in Napa

Wineries Tours Outdoors

Side Trips

Yountville, Oakville
Highlights from your plan
Balloon Rides
Robert Mondavi Winery ©
Robert Mondavi Winery
Robert Biale Vineyards ©
Robert Biale Vineyards

1
night
Calistoga

Calistoga ©
Indulgence is the name of the game in Calistoga.
Kick off your visit on the 8th (Sun): learn about winemaking at Anderson's Conn Valley Vineyards, learn about winemaking at Del Dotto Estate Winery & Caves, then learn about winemaking at V. Sattui Winery, then look for gifts at Dean & DeLuca, and finally do a tasting at Castello di Amorosa.

To see maps, traveler tips, more things to do, and other tourist information, read Calistoga holiday planner .

You can drive from Napa to Calistoga in an hour. Another option is to take a bus. September in Calistoga sees daily highs of 34°C and lows of 12°C at night. Finish your sightseeing early on the 8th (Sun) to allow enough time to drive to Healdsburg.

Things to do in Calistoga

Wineries Historic Sites Shopping

Side Trip

St. Helena
Highlights from your plan
Anderson's Conn Valley Vineyards ©
Anderson's Conn Valley Vineyards
Castello di Amorosa ©
Castello di Amorosa
Del Dotto Estate Winery & Caves ©
Del Dotto Estate Winery & Caves

3
nights
Healdsburg

Healdsburg ©
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.
Explore hidden gems such as Armstrong Redwood State Reserve and Williamson Wines Tasting Room. Step out of the city life by going to Salt Point State Park and Sonoma Coast State Beach. There's more to do: do a tasting at Mazzocco Sonoma and pause for some serene contemplation at St. John the Baptist Catholic Church.

To find more things to do, other places to visit, photos, and other tourist information, refer to the Healdsburg travel app .

Traveling by car from Calistoga to Healdsburg takes an hour. Alternatively, you can do a combination of taxi and bus. In September, daytime highs in Healdsburg are 34°C, while nighttime lows are 12°C. Cap off your sightseeing on the 11th (Wed) early enough to go by car to San Francisco.

Things to do in Healdsburg

Wineries Parks Nature

Side Trips

Iron Horse Vineyards, Sonoma Coast State Beach, Salt Point State Park, Armstrong Redwood State Reserve
Highlights from your plan
Armstrong Redwood State Reserve ©
Armstrong Redwood State Reserve
Sapphire Hill Winery ©
Sapphire Hill Winery
Stephen & Walker Winery ©
Stephen & Walker Winery

3
nights
San Francisco

San Francisco ©
San Francisco is a top holiday destination featuring scenic beauty and great ethnic and cultural diversity.
Step off the beaten path and head to Limantour Beach and Bolinas Beach. Get a sense of the local culture at Union Square and Fisherman's Wharf. The adventure continues: head off the coast to Alcatraz Island, don't miss a visit to Ferry Building Marketplace, take in the waterfront at The Embarcadero, and look for gifts at Z. Cioccolato.

To find reviews, traveler tips, other places to visit, and more tourist information, go to the San Francisco trip builder app .

Traveling by car from Healdsburg to San Francisco takes 1.5 hours. Alternatively, you can take a train; or take a bus. When traveling from Healdsburg in September, plan for slightly colder days in San Francisco, with highs around 28°C, while nights are a bit warmer with lows around 17°C. Wrap up your sightseeing by early afternoon on the 14th (Sat) to allow enough time to travel back home.

Things to do in San Francisco

Parks Outdoors Beaches

Side Trips

Bolinas Beach, Limantour Beach
Highlights from your plan
Alcatraz Island ©
Alcatraz Island
Fisherman's Wharf ©
Fisherman's Wharf
Union Square ©
Union Square

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