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

Make it your trip
Fly
1
San Francisco
— 3 nights
Drive
2
Healdsburg
— 2 nights
Drive
3
Napa
— 3 nights
Fly
4
New York City
— 5 nights
Fly

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San Francisco

— 3 nights

City by the Bay

San Francisco is a top holiday destination featuring scenic beauty and great ethnic and cultural diversity.
Give yourself a bit of retail therapy at Ferry Building Marketplace and Ghirardelli Square. There's still lots to do: take in the waterfront at Fisherman's Wharf, get great views at Twin Peaks, wander the streets of Chinatown, and take in the views from Golden Gate Bridge.

To find where to stay, maps, and more tourist information, refer to the San Francisco trip itinerary site.

Auckland, New Zealand to San Francisco is an approximately 16-hour flight. Traveling from Auckland to San Francisco, you'll gain 20 hours due to the time zone difference. When traveling from Auckland in September, plan for warmer days in San Francisco, with highs around 28°C, while nights are about the same with lows around 17°C. Finish up your sightseeing early on the 18th (Wed) so you can go by car to Healdsburg.

Things to do in San Francisco

Neighborhoods · Shopping · Historic Sites · Childrens Museums

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 19th (Thu), take in the exciting artwork at Patrick Amiot, learn about winemaking at Stephen & Walker Winery, learn about winemaking at Jordan Vineyard & Winery, then learn about winemaking at Gracianna Winery, and finally stop by Petaluma Seed Bank. Here are some ideas for day two: get a taste of the local shopping with Sebastopol Center for the Arts, then do a tasting at Sapphire Hill Winery, then do a tasting at Bella Vineyards and Wine Caves, and finally tour the pleasant surroundings at Sonoma Coast State Beach.

To find where to stay, reviews, and tourist information, refer to the Healdsburg trip planner.

Getting from San Francisco to Healdsburg by car takes about 1.5 hours. Other options: fly; or do a combination of bus, train, and taxi. Traveling from San Francisco in September, you will find days in Healdsburg are a bit warmer (34°C), and nights are little chillier (12°C). Wrap up your sightseeing on the 20th (Fri) early enough to drive to Napa.

Things to do in Healdsburg

Wineries · Beaches · Parks · Outdoors

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.
Give yourself a bit of retail therapy at Oxbow Public Market and Imagery Estate Winery & Art Gallery. Appreciate the collections at The Hess Collection Winery & Art Museum and Mumm Napa. Change things up with these side-trips from Napa: Schramsberg Vineyards (in Calistoga), Benziger Family Winery (in Glen Ellen) and St. Helena (Anderson's Conn Valley Vineyards, Pride Mountain Vineyards, &more). There's still lots to do: do a tasting at B Cellars Vineyards and Winery.

For more things to do, traveler tips, maps, and other tourist information, read Napa itinerary maker website.

You can drive from Healdsburg to Napa in 1.5 hours. Other options are to take a bus; or do a combination of bus and train. In September in Napa, expect temperatures between 32°C during the day and 12°C at night. Cap off your sightseeing on the 23rd (Mon) early enough to travel to New York City.

Things to do in Napa

Wineries · Museums · Shopping

Side Trips

New York City

— 5 nights

Big Apple

Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Head to Fifth Avenue and Chelsea Marketfor some retail therapy. Appreciate the collections at The Metropolitan Museum of Art and 9/11 Memorial. Step out of New York City to go to New Paltz and see DM Weil Gallery, which is approximately 1h 45 min away. The adventure continues: take a stroll through Times Square, don't miss a visit to Statue of Liberty National Monument, learn more about the world around you at American Museum of Natural History, and admire the masterpieces at The Museum of Modern Art (MoMA).

To see traveler tips, ratings, more things to do, and other tourist information, refer to the New York City travel route builder site.

You can fly from Napa to New York City in 12 hours. Other options are to drive; or do a combination of bus and train. The time zone difference when traveling from Napa to New York City is 3 hours. Expect somewhat warmer evenings in New York City when traveling from Napa in September, with lows around 22°C. Finish your sightseeing early on the 29th (Sun) so you can travel back home.

Things to do in New York City

Museums · Parks · Shopping · Neighborhoods

Side Trip