16 days in San Francisco Bay Area & New York City Itinerary

16 days in San Francisco Bay Area & New York City Itinerary

Created using Inspirock United States trip planner

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Route & dates

16 days in San Francisco Bay Area & New York City Itinerary

Start: Auckland
Fly:  15​h 30​min
1
San Francisco
— 3 nights
Drive:  1​h 30​min
2
Healdsburg
— 2 nights
Drive:  1​h 15​min
3
Napa
— 3 nights
+3
bus + subway + Fly + bus:  11​h 30​min
4
New York City
— 5 nights
Fly:  22​h 30​min
End: Auckland

3
nights
San Francisco

San Francisco ©
San Francisco is a top holiday destination featuring scenic beauty and great ethnic and cultural diversity.
Head to Exploratorium and Ghirardelli Squarefor some retail therapy. And it doesn't end there: buy something for everyone on your list at Ferry Building Marketplace, take in the views from Golden Gate Bridge, wander the streets of Twin Peaks, and take in the waterfront at Fisherman's Wharf.

To find traveler tips, reviews, more things to do, and other tourist information, read San Francisco attractions planner.

Auckland, New Zealand to San Francisco is an approximately 15.5-hour flight. You can also do a combination of flight and train. The time zone difference when traveling from Auckland to San Francisco is minus 20 hours. When traveling from Auckland in September, plan for much warmer days in San Francisco, with highs around 28°C, while nights are about the same with lows around 17°C. Cap off your sightseeing on the 18th (Wed) early enough to go by car to Healdsburg.

Things to do in San Francisco

Neighborhoods Shopping Historic Sites
Highlights from your plan
Ferry Building Marketplace ©
Ferry Building Marketplace
Union Square ©
Union Square
Exploratorium ©
Exploratorium

2
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.
Start off your visit on the 19th (Thu): take in the exciting artwork at Patrick Amiot, learn about winemaking at Stephen & Walker Winery, then learn about winemaking at Jordan Vineyard & Winery, then do a tasting at Gracianna Winery, and finally look for gifts at Petaluma Seed Bank. Here are some ideas for day two: take in the exciting artwork at Sebastopol Center for the Arts, do a tasting at Sapphire Hill Winery, then learn about winemaking at Bella Vineyards and Wine Caves, and finally enjoy the sand and surf at Sonoma Coast State Beach.

Use Inspirock's suggestions to plan your Healdsburg trip and find the best activities and attractions for your vacation.

You can drive from San Francisco to Healdsburg in 1.5 hours. Other options are to take a bus; or take a train. Traveling from San Francisco in September, expect nights in Healdsburg to be a bit cooler, around 12°C, while days are somewhat warmer, around 34°C. Cap off your sightseeing on the 20th (Fri) early enough to go by car to Napa.

Things to do in Healdsburg

Wineries Beaches Parks

Side Trips

Sebastopol, Petaluma Seed Bank, Sonoma Coast State Beach
Highlights from your plan
Gracianna Winery ©
Gracianna Winery
Sapphire Hill Winery ©
Sapphire Hill Winery
Jordan Vineyard & Winery ©
Jordan Vineyard & Winery

3
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.
Head to Mumm Napa and Oxbow Public Marketfor some retail therapy. Appreciate the collections at The Hess Collection Winery & Art Museum and Imagery Estate Winery & Art Gallery. You'll find plenty of places to visit near Napa: Benziger Family Winery (in Glen Ellen), Schramsberg Vineyards (in Calistoga) and St. Helena (Anderson's Conn Valley Vineyards, Pride Mountain Vineyards, & more). There's more to do: do a tasting at B Cellars Vineyards and Winery.

To find where to stay, traveler tips, more things to do, and tourist information, refer to the Napa travel planner .

Traveling by car from Healdsburg to Napa takes 1.5 hours. Alternatively, you can do a combination of taxi and bus. In September, daily temperatures in Napa can reach 32°C, while at night they dip to 12°C. Wrap up your sightseeing on the 23rd (Mon) early enough to travel to New York City.

Things to do in Napa

Wineries Museums Shopping

Side Trips

St. Helena, Oakville, Glen Ellen, Rutherford, Schramsberg Vineyards
Highlights from your plan
Anderson's Conn Valley Vineyards ©
Anderson's Conn Valley Vineyards
Mumm Napa ©
Mumm Napa

5
nights
New York City

New York City ©
Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Museum-lovers will get to explore The Metropolitan Museum of Art and The Museum of Modern Art (MoMA). Give yourself a bit of retail therapy at Fifth Avenue and DM Weil Gallery. Next up on the itinerary: take in the pleasant sights at Times Square, look for gifts at Tiffany & Co., pause for some photo ops at 9/11 Memorial, and get a new perspective on nature at American Museum of Natural History.

For other places to visit, where to stay, ratings, and more tourist information, refer to the New York City trip planning tool .

Do a combination of bus, subway, and flight from Napa to New York City in 11.5 hours. Alternatively, you can do a combination of bus and flight; or drive. The time zone difference moving from Pacific Standard Time (PST) to Eastern Standard Time (EST) is 3 hours. Traveling from Napa in September, you can expect nighttime temperatures to be a bit warmer in New York City, with lows of 22°C. Wrap up your sightseeing on the 29th (Sun) to allow time to travel back home.

Things to do in New York City

Museums Shopping Parks

Side Trip

DM Weil Gallery
Highlights from your plan
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
American Museum of Natural History ©
The Museum of Modern Art
The Museum of Modern Art

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