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

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

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Route & dates

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

Start: Boston
Fly + bus:  3​h
1
New York City
— 12 nights
Fly + shuttle:  11​h
2
Monterey
— 4 nights
Drive:  3​h 15​min
3
St. Helena
— 7 nights
Drive:  1​h 30​min
4
San Francisco
— 11 nights
Fly:  7​h 15​min
End: Boston

12
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.
Go for a jaunt from New York City to Bronx to see Bronx Zoo about 36 minutes away. Next up on the itinerary: go for a walk through Central Park, enjoy breathtaking views from Empire State Building, get great views at Top of the Rock, and appreciate the history behind 9/11 Memorial.

Plan a New York City trip in moments using our itinerary builder.

Boston to New York City is an approximately 3-hour combination of flight and bus. You can also fly; or drive. June in New York City sees daily highs of 80°F and lows of 65°F at night. Wrap up your sightseeing on the 21st (Fri) early enough to travel to Monterey.

Things to do in New York City

Museums Parks Tours

Side Trips

Bronx Zoo, Brooklyn Botanic Garden
Highlights from your plan
Central Park ©
Central Park
Empire State Building ©
Empire State Building
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art

4
nights
Monterey

Monterey ©
Monterey is a city in the U.S. When in Monterey, make a side trip to see Henry Cowell Redwoods State Park in Felton, approximately 58 minutes away. There's still lots to do: immerse yourself in nature at Point Lobos, explore the landscape on two wheels at Monterey Peninsula Recreational Trail, admire nature's wide array of creatures at Monterey Bay Aquarium, and play a few rounds at Pebble Beach Golf Links.

Take the guesswork out of planning a Monterey vacation by using our trip itinerary maker.

Do a combination of flight and shuttle from New York City to Monterey in 11 hours. Alternatively, you can do a combination of bus, flight, and shuttle; or drive. The time zone changes from Eastern Standard Time to Pacific Standard Time, which is usually a -3 hour difference. Prepare for little chillier weather when traveling from New York City in June: high temperatures in Monterey hover around 68°F and lows are around 53°F. Finish up your sightseeing early on the 26th (Wed) so you can go by car to St. Helena.

Things to do in Monterey

Parks Outdoors Nature

Side Trips

Carmel, Pacific Grove, Pebble Beach Golf Links, Henry Cowell Redwoods State Park
Highlights from your plan
Point Lobos ©
Point Lobos
Pacific Grove Oceanview Boulevard ©
Pacific Grove Oceanview Boulevard
Monterey Bay Aquarium ©
Monterey Bay Aquarium

7
nights
St. Helena

St. Helena ©
The city of St.
Venture out of the city with trips to Healdsburg (Jordan Vineyard & Winery, Bella Vineyards and Wine Caves, & more), Sonoma (Simraceway Performance Driving Center, Mission San Francisco Solano, & more) and The Hess Collection Winery & Art Museum (in Napa). Dedicate the 27th (Thu) to wine at some of the top wineries in the area. There's lots more to do: learn about winemaking at Anderson's Conn Valley Vineyards, look for gifts at Oxbow Public Market, and immerse yourself in nature at Jack London State Historic Park.

To find traveler tips, other places to visit, maps, and other tourist information, read St. Helena online trip itinerary maker .

Getting from Monterey to St. Helena by car takes about 3.5 hours. Other options: do a combination of shuttle and flight; or fly. When traveling from Monterey in June, plan for somewhat warmer days in St. Helena, with highs around 83°F, while nights are about the same with lows around 51°F. Finish your sightseeing early on the 3rd (Wed) so you can drive to San Francisco.

Things to do in St. Helena

Wineries Tours Outdoors

Side Trips

Healdsburg, Napa, Oakville, Sonoma, Glen Ellen
Highlights from your plan
Anderson's Conn Valley Vineyards ©
Anderson's Conn Valley Vineyards
Wine Tours & Tastings
Simraceway Performance Driving Center ©

11
nights
San Francisco

San Francisco is a top holiday destination featuring scenic beauty and great ethnic and cultural diversity.
Dedicate the 8th (Mon) to wine at some of the top wineries in the area. Next up on the itinerary: snap pictures at Golden Gate Bridge, take in the waterfront at Fisherman's Wharf, take a stroll through SoMa, and buy something for everyone on your list at Ferry Building Marketplace.

To see maps, more things to do, traveler tips, and more tourist information, go to the San Francisco online holiday planner .

You can drive from St. Helena to San Francisco in 1.5 hours. Alternatively, you can do a combination of bus and subway; or take a bus. Traveling from St. Helena in July, you will find days in San Francisco are little chillier (73°F), and nights are about the same (57°F). Wrap up your sightseeing by early afternoon on the 14th (Sun) to allow time for travel back home.

Things to do in San Francisco

Neighborhoods Tours Museums
Highlights from your plan
Beer Tastings & Tours
Golden Gate Bridge ©
Golden Gate Bridge
Alcatraz Island ©
Alcatraz Island

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